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An Eastport waterfront home located on Spa Creek set on a prominent .165-acre site once part of a historic city park, this property offers approximately 3000 above grade finished living space thoughtfully designed to capture waterviews of the creek. Built in 2009 and designed by Alt Breeding Schwarz with a landscape plan by Forested Creative Ecology. The exterior showcases cedar shake siding, Azek trim, Marvin aluminum-clad windows, a 30-year architectural shingle roof, and a 2-car garage with designer doors. Modern amenities include public water and sewer, natural gas, electric car charger, whole-house surge protection, owned solar panels, generator, and a robust 400-amp electrical service. Enjoy approximately 76 feet of bulkheaded waterfront with a resurfaced pier offering 6+ feet of water depth, a 10,000-pound boat lift, electric and plumbing at the dock, kayak storage, and lounge netting. A stone wall built from original Main Street cobblestones adds historic character at the water’s edge. Inside, the home features a dramatic two-story entry, white oak hardwood floors, custom millwork, three gas fireplaces, built-ins, and an open layout ideal for both daily living and entertaining. The gourmet kitchen is equipped with Wolf, Sub-Zero, and KitchenAid appliances, granite countertops, and custom Mouser cabinetry. Four/five bedrooms and four baths include a main-level bedroom, an expansive primary suite with spa-like bath, upper-level laundry, and a finished lower level with bedroom/office, full bath, library shelving, and custom bar. Outdoor living is enhanced decking, a bluestone patio overlooking Spa Creek, and a low-maintenance permaculture landscape installed in 2023 featuring fruit trees, berries, herbs, and native plantings. Additional highlights include a fenced yard, irrigation system, exterior lighting, security system, and private driveway with pavers. A rare opportunity to own a distinctive, energy-efficient waterfront home just minutes from downtown Annapolis, offering deep water access, refined craftsmanship, and unparalleled Eastport waterfront living.

906 Creek Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Cummings & Co. Realtors.

$5,950,000

South Annapolis Yacht Center is located on Spa Creek overlooking the beautiful skyline of Historic Annapolis. This award winning residence features an elegant interior design that brings the feel of the adjoining waterway into the living area. Patrick Sutton thoughtfully did the interior design and Bret Anderson of Pyramid Builders constructed this magical 3 bedroom, 3 bath waterfront residence. A bright open floor plan, perfect for entertaining, connects to the wrap around deck overlooking the water. The kitchen features a six burner La Cornue range with matching hood, Sub-Zero refrigerator with custom freezer draws, wine cooler and a large luxe marble center island all overlooking the water. The Primary Suite enjoys beautiful views of Spa Creek & Annapolis, a large dressing room with rosewood cabinets and a luxurious spa like bath. The Primary suite walls are fully upholstered with a wool herringbone material and braided leather trim giving the space a warm comfortable feel. There are 2 additional ensuite bedrooms with one doubling as a den/in home office. There are 2 gas fireplaces, one in the main living area and one on the waterfront deck. There is a rented 1 car garage (across the street, $700/mo) and a storage unit in the lower level of the building. Access to this fabulous residence is via an elevator that opens directly into the unit. Enjoy watching the Christmas Boat Parade, Commissioning Week Blue Angels Show and the 4th of July Fireworks from the waterfront deck. The adjoining world class marina not only is a perfect spot to keep your boat but a great view to watch some of the most beautiful yachts on the East Coast. The prime Spa Creek location, the quality of construction and the award winning interior design puts this property in a league of its own.

South Annapolis Yacht Center is located on Spa Creek overlooking the beautiful skyline of Historic Annapolis. This award winning residence features an elegant interior design that brings the feel of the adjoining waterway into the living area. Patrick Sutton thoughtfully did the interior design and Bret Anderson of Pyramid Builders constructed this magical 3 bedroom, 3 bath waterfront residence. A bright open floor plan, perfect for entertaining, connects to the wrap around deck overlooking the water. The kitchen features a six burner La Cornue range with matching hood, Sub-Zero refrigerator with custom freezer draws, wine cooler and a large luxe marble center island all overlooking the water. The Primary Suite enjoys beautiful views of Spa Creek & Annapolis, a large dressing room with rosewood cabinets and a luxurious spa like bath. The Primary suite walls are fully upholstered with a wool herringbone material and braided leather trim giving the space a warm comfortable feel. There are 2 additional ensuite bedrooms with one doubling as a den/in home office. There are 2 gas fireplaces, one in the main living area and one on the waterfront deck. There is a rented 1 car garage (across the street, $700/mo) and a storage unit in the lower level of the building. Access to this fabulous residence is via an elevator that opens directly into the unit. Enjoy watching the Christmas Boat Parade, Commissioning Week Blue Angels Show and the 4th of July Fireworks from the waterfront deck. The adjoining world class marina not only is a perfect spot to keep your boat but a great view to watch some of the most beautiful yachts on the East Coast. The prime Spa Creek location, the quality of construction and the award winning interior design puts this property in a league of its own.

287 State St Unit 2, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$3,310,000

Exceptional Waterfront and Beachfront living on Horn Point in coveted Eastport. Launch your kayak or SUP after morning coffee, and watch the sailboat races from your deck, yard, and beach later that day. This elegant charmer is the Perfect place to watch the Blue Angels without leaving home! The home was completely re-built in 2009 (all that remains is the original garage floor) and has been meticulously maintained. Upon your first steps inside, you'll be drawn to spectacular views of the Severn River as you walk through an open floor plan adorned with rich Brazilian hardwood flooring and abundant natural light. The main level offers a great room with a perfectly blended family room, dining area with a gas fireplace, a second sitting area, a gourmet kitchen and private deck. A separate hall leads you to 2 spacious bedrooms and full bath. The gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a generous island perfect for entertaining. Dining and relaxing on your private deck overlooking the yard and beach is steps away from the kitchen. Privately located behind the kitchen the home gym with vaulted ceilings and water views can be converted to a home office, play area, an additional sitting room, and more. The main level laundry room and hallway to the garage also lead you to a bonus work-room attached to the garage. This room could easily become a creative space, painting studio, she-shed, or additional home office. The beautiful floating staircase complements the great room and leads you to the upper level. The primary suite is all about the view! Breathtaking Severn River and Chesapeake Bay- front views and a spa-like bathroom with a jetted tub and walk-in, steam shower. The primary suite would not be complete without a large dressing room with access to a separate home office / sitting room with water views, and private deck. The fourth bedroom with en suite is on the upper level, with a walk in closet and access to attic storage. The exterior is equally impressive, showcasing a yard and private beach on the Severn River. Relax on the balcony or deck, surrounded by lush landscaping and exterior lighting that enhances the ambiance. The property also includes an attached garage with attic storage above it and ample driveway space for convenience. A generator is included and a pier is an option for your buyer. With a prime bayside location, this home offers not just a residence but a lifestyle of luxury and tranquility. Experience the perfect blend of modern amenities and natural beauty, making every day feel like a vacation. Don't miss the opportunity to call this remarkable property your own!

Exceptional Waterfront and Beachfront living on Horn Point in coveted Eastport. Launch your kayak or SUP after morning coffee, and watch the sailboat races from your deck, yard, and beach later that day. This elegant charmer is the Perfect place to watch the Blue Angels without leaving home! The home was completely re-built in 2009 (all that remains is the original garage floor) and has been meticulously maintained. Upon your first steps inside, you'll be drawn to spectacular views of the Severn River as you walk through an open floor plan adorned with rich Brazilian hardwood flooring and abundant natural light. The main level offers a great room with a perfectly blended family room, dining area with a gas fireplace, a second sitting area, a gourmet kitchen and private deck. A separate hall leads you to 2 spacious bedrooms and full bath. The gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a generous island perfect for entertaining. Dining and relaxing on your private deck overlooking the yard and beach is steps away from the kitchen. Privately located behind the kitchen the home gym with vaulted ceilings and water views can be converted to a home office, play area, an additional sitting room, and more. The main level laundry room and hallway to the garage also lead you to a bonus work-room attached to the garage. This room could easily become a creative space, painting studio, she-shed, or additional home office. The beautiful floating staircase complements the great room and leads you to the upper level. The primary suite is all about the view! Breathtaking Severn River and Chesapeake Bay- front views and a spa-like bathroom with a jetted tub and walk-in, steam shower. The primary suite would not be complete without a large dressing room with access to a separate home office / sitting room with water views, and private deck. The fourth bedroom with en suite is on the upper level, with a walk in closet and access to attic storage. The exterior is equally impressive, showcasing a yard and private beach on the Severn River. Relax on the balcony or deck, surrounded by lush landscaping and exterior lighting that enhances the ambiance. The property also includes an attached garage with attic storage above it and ample driveway space for convenience. A generator is included and a pier is an option for your buyer. With a prime bayside location, this home offers not just a residence but a lifestyle of luxury and tranquility. Experience the perfect blend of modern amenities and natural beauty, making every day feel like a vacation. Don't miss the opportunity to call this remarkable property your own!

513 Horn Point Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

A new standard of waterfront living unfolds at the South Annapolis Yacht Centre, a boutique enclave of just eleven luxury residences rising along the edge of Spa Creek where Eastport’s maritime heritage meets modern design. Set within this celebrated marina village, Residence #4 is a rare two-level duplex that captures the beauty of the water and the energy of downtown Annapolis from every vantage point. The residence blends architectural precision with coastal ease. The main level welcomes guests through an elegant entry hall leading to a great room featuring gorgeous wood floors, ample seating around a gas fireplace, a huge island with Quartzite counter, and incredible views down and across Spa Creek. The door to the waterfront deck folds back to create a seamless transition between inside and out; even in colder weather, the number of windows and the size of the doors bring the views of the city’s spires in full focus. The chef’s kitchen includes a double Wolf range and Sub-Zero refrigerator with custom freezer drawers, and there’s plenty of room for multiple chefs to work together! The floor plan also includes an office area with powder room, and the owners installed a beautiful bar with beverage refrigerator and ice machine. The spacious bedroom suite offers a luxurious ensuite bath, and the large walk-in closet has a full-size washer and dryer. Descend via the elevator to the lower level, where a second bedroom suite opens to an enchanting waterside deck. There’s a spa-inspired bathroom, walk-in closet, and wet bar with mini-fridge, creating a self-contained sanctuary ideal for visiting friends or family. Every element of the home reflects the craftsmanship and intent that define the South Annapolis Yacht Centre—an award-winning waterfront community designed by ABS Architects and constructed by Pyramid Builders. The property integrates modern architecture with the rhythms of marina life, offering 74 deep-water slips, a private boardwalk, and access to the full-service marina’s amenities. Anchored in Eastport’s vibrant waterfront district, the South Annapolis Yacht Centre celebrates the best of Chesapeake Bay living — where sailing heritage, walkable streets, and panoramic water views converge into an atmosphere of understated elegance. 289 State Street, Residence #4 offers more than a home; it offers a lifestyle defined by craftsmanship, connection, and the timeless allure of Annapolis.

$3,000,000

2 Beds ⋅ 3 Baths

A new standard of waterfront living unfolds at the South Annapolis Yacht Centre, a boutique enclave of just eleven luxury residences rising along the edge of Spa Creek where Eastport’s maritime heritage meets modern design. Set within this celebrated marina village, Residence #4 is a rare two-level duplex that captures the beauty of the water and the energy of downtown Annapolis from every vantage point. The residence blends architectural precision with coastal ease. The main level welcomes guests through an elegant entry hall leading to a great room featuring gorgeous wood floors, ample seating around a gas fireplace, a huge island with Quartzite counter, and incredible views down and across Spa Creek. The door to the waterfront deck folds back to create a seamless transition between inside and out; even in colder weather, the number of windows and the size of the doors bring the views of the city’s spires in full focus. The chef’s kitchen includes a double Wolf range and Sub-Zero refrigerator with custom freezer drawers, and there’s plenty of room for multiple chefs to work together! The floor plan also includes an office area with powder room, and the owners installed a beautiful bar with beverage refrigerator and ice machine. The spacious bedroom suite offers a luxurious ensuite bath, and the large walk-in closet has a full-size washer and dryer. Descend via the elevator to the lower level, where a second bedroom suite opens to an enchanting waterside deck. There’s a spa-inspired bathroom, walk-in closet, and wet bar with mini-fridge, creating a self-contained sanctuary ideal for visiting friends or family. Every element of the home reflects the craftsmanship and intent that define the South Annapolis Yacht Centre—an award-winning waterfront community designed by ABS Architects and constructed by Pyramid Builders. The property integrates modern architecture with the rhythms of marina life, offering 74 deep-water slips, a private boardwalk, and access to the full-service marina’s amenities. Anchored in Eastport’s vibrant waterfront district, the South Annapolis Yacht Centre celebrates the best of Chesapeake Bay living — where sailing heritage, walkable streets, and panoramic water views converge into an atmosphere of understated elegance. 289 State Street, Residence #4 offers more than a home; it offers a lifestyle defined by craftsmanship, connection, and the timeless allure of Annapolis.

289 State St Unit 4, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: TTR Sotheby's International Realty.

$2,965,000

Unparalleled excellence in design and attention to detail in the heart of Eastport. This elegant and inviting home is so tastefully designed that it fits right in with the historic homes of Eastport and Murray Hill. Built in 2020, the elevated quality and attention to fit and finish take it to another level! Over 3800 square feet in the main house with 5 bedrooms and 5.5 baths along with another bedroom, bathroom, and sitting room in the charming Guest House with 800 square feet and a one car garage. The owner-builder spared no expense when filling the home with quality components: solid brass handles, WaterWorks plumbing fixtures, over $50k in high end lighting fixtures integrated into a Lutron system, Sonos audio, European character-grade, live sawn white oak floors, a standing seam metal roof with traditional hemmed seems, a full brick masonry wood burning fireplace, gas-fed lanterns at the front porch, oiled mahogany porch floors, SubZero appliances, two laundry rooms, a home gym, blue-stone rear patio, and so much more. The private driveway offers additional parking and the blue-stone patio and back yard provide a haven for entertaining. This home is central to everything you want to enjoy in Eastport and Downtown Annapolis!

5 Beds ⋅ 6 Baths

Unparalleled excellence in design and attention to detail in the heart of Eastport. This elegant and inviting home is so tastefully designed that it fits right in with the historic homes of Eastport and Murray Hill. Built in 2020, the elevated quality and attention to fit and finish take it to another level! Over 3800 square feet in the main house with 5 bedrooms and 5.5 baths along with another bedroom, bathroom, and sitting room in the charming Guest House with 800 square feet and a one car garage. The owner-builder spared no expense when filling the home with quality components: solid brass handles, WaterWorks plumbing fixtures, over $50k in high end lighting fixtures integrated into a Lutron system, Sonos audio, European character-grade, live sawn white oak floors, a standing seam metal roof with traditional hemmed seems, a full brick masonry wood burning fireplace, gas-fed lanterns at the front porch, oiled mahogany porch floors, SubZero appliances, two laundry rooms, a home gym, blue-stone rear patio, and so much more. The private driveway offers additional parking and the blue-stone patio and back yard provide a haven for entertaining. This home is central to everything you want to enjoy in Eastport and Downtown Annapolis!

313 Washington St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Simultaneously Listed and SOLD

$2,800,000

Simultaneously Listed and SOLD

422 Third St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Experience the very best of the Eastport lifestyle, where sweeping views of Spa Creek, Historic Annapolis, and the Annapolis Harbor create an ever-changing backdrop to daily life. Thoughtfully designed to maximize its remarkable setting, the residence features a reverse floor plan, placing the main living spaces at the top level to fully capture the water views and vibrant harbor activity. The heart of the home is an expansive, light-filled open floor plan where walls of windows and doors frame the water and seamlessly connect the interior to an oversized deck, an ideal setting for entertaining or quiet moments overlooking the Creek. The gourmet kitchen is both refined and functional, flowing effortlessly into the dining and living areas. Throughout the home, meticulous attention to detail is evident with rich hardwood flooring, upgraded lighting, and beautifully curated finishes. Designed with flexibility and comfort in mind, the layout offers multiple living spaces, including an additional family room on the entry level, along with a thoughtfully arranged bedroom layout. The home features a luxurious primary suite complete with a cozy fireplace, and its own access to the extensive deck. The entry level bedroom suite and additional well-appointed bedrooms and bath comfortably accommodate family and guests. The unfinished lower level with walkout stairs to the backyard offers exceptional potential for future living space, recreation, or storage, allowing the next owner to tailor the home to their specific needs. Outdoor living is equally compelling, with spacious entertaining area and multiple vantage points to take in the water views and surroundings. The covered deck, grass yard and stone paved sitting areas allow for enjoying the setting all year long. This property is in the perfect location to stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and street-end parks with hidden treasures. Not to mention you are merely steps away from downtown Annapolis and Naval Academy by either walking across the Spa Creek drawbridge or motoring in a water taxi. You are also close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. Annapolis/Eastport offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft.Meade/NSA and Washington, DC. Welcome Home!

$2,595,000

4 Beds ⋅ 5 Baths

Experience the very best of the Eastport lifestyle, where sweeping views of Spa Creek, Historic Annapolis, and the Annapolis Harbor create an ever-changing backdrop to daily life. Thoughtfully designed to maximize its remarkable setting, the residence features a reverse floor plan, placing the main living spaces at the top level to fully capture the water views and vibrant harbor activity. The heart of the home is an expansive, light-filled open floor plan where walls of windows and doors frame the water and seamlessly connect the interior to an oversized deck, an ideal setting for entertaining or quiet moments overlooking the Creek. The gourmet kitchen is both refined and functional, flowing effortlessly into the dining and living areas. Throughout the home, meticulous attention to detail is evident with rich hardwood flooring, upgraded lighting, and beautifully curated finishes. Designed with flexibility and comfort in mind, the layout offers multiple living spaces, including an additional family room on the entry level, along with a thoughtfully arranged bedroom layout. The home features a luxurious primary suite complete with a cozy fireplace, and its own access to the extensive deck. The entry level bedroom suite and additional well-appointed bedrooms and bath comfortably accommodate family and guests. The unfinished lower level with walkout stairs to the backyard offers exceptional potential for future living space, recreation, or storage, allowing the next owner to tailor the home to their specific needs. Outdoor living is equally compelling, with spacious entertaining area and multiple vantage points to take in the water views and surroundings. The covered deck, grass yard and stone paved sitting areas allow for enjoying the setting all year long. This property is in the perfect location to stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and street-end parks with hidden treasures. Not to mention you are merely steps away from downtown Annapolis and Naval Academy by either walking across the Spa Creek drawbridge or motoring in a water taxi. You are also close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. Annapolis/Eastport offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft.Meade/NSA and Washington, DC. Welcome Home!

219 Lockwood Ct, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Perfectly sited on over a quarter-acre gated lot on Second Street, this meticulously maintained Eastport estate offers 4,500+ square feet of luxurious living space and extensive oak flooring in one of Annapolis’ most coveted neighborhoods. Enjoy the tranquility of suburban-style privacy with the walkability of downtown living - just steps to water access, acclaimed restaurants, shopping, and marina life. Inside, generous proportions define the main level. A spacious living room and elegant formal dining room open to the expansive deck and pool area, while a chef’s kitchen boasts a quartzite island, high-end appliances, and a casual eat-in space. The main level also features an updated laundry room, chic powder room, and a dramatic family room with vaulted wood ceilings, gas fireplace, and sliding doors to the outdoor oasis. Upstairs, the serene primary suite features vaulted ceilings, a walk-in closet, and a spa-inspired bath with heated floors, a rainfall shower, double vanity, and heated towel rack. Three additional oversized bedrooms and a stylish hall bath complete the second floor. The third level offers breathtaking views of Historic Annapolis and the Naval Academy from the rooftop balcony - perfect for fireworks or Blue Angel flyovers - and includes a family room, kitchenette, full bath, and bedroom. The fully finished lower level is made for entertaining, with a rec room, custom bar (complete with kegerator and refrigerated drawers), a flexible bonus room ideal for a wine cellar or storage, and a workshop. Step outside to your private resort: a heated in-ground pool and spa with motorized cover, a pergola with adjustable louvers, lush landscaping, and a park-like front yard. Additional features include Hardie siding, composite decking, updated windows and gutters (all completed in 2019), a two-car garage, and a gated driveway. This is a rare Eastport offering where timeless elegance, thoughtful updates, and premier location come together. Welcome Home!

$2,555,000

5 Beds ⋅ 4 Baths

Perfectly sited on over a quarter-acre gated lot on Second Street, this meticulously maintained Eastport estate offers 4,500+ square feet of luxurious living space and extensive oak flooring in one of Annapolis’ most coveted neighborhoods. Enjoy the tranquility of suburban-style privacy with the walkability of downtown living - just steps to water access, acclaimed restaurants, shopping, and marina life. Inside, generous proportions define the main level. A spacious living room and elegant formal dining room open to the expansive deck and pool area, while a chef’s kitchen boasts a quartzite island, high-end appliances, and a casual eat-in space. The main level also features an updated laundry room, chic powder room, and a dramatic family room with vaulted wood ceilings, gas fireplace, and sliding doors to the outdoor oasis. Upstairs, the serene primary suite features vaulted ceilings, a walk-in closet, and a spa-inspired bath with heated floors, a rainfall shower, double vanity, and heated towel rack. Three additional oversized bedrooms and a stylish hall bath complete the second floor. The third level offers breathtaking views of Historic Annapolis and the Naval Academy from the rooftop balcony - perfect for fireworks or Blue Angel flyovers - and includes a family room, kitchenette, full bath, and bedroom. The fully finished lower level is made for entertaining, with a rec room, custom bar (complete with kegerator and refrigerated drawers), a flexible bonus room ideal for a wine cellar or storage, and a workshop. Step outside to your private resort: a heated in-ground pool and spa with motorized cover, a pergola with adjustable louvers, lush landscaping, and a park-like front yard. Additional features include Hardie siding, composite decking, updated windows and gutters (all completed in 2019), a two-car garage, and a gated driveway. This is a rare Eastport offering where timeless elegance, thoughtful updates, and premier location come together. Welcome Home!

417 Second St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Engel & Volkers Annapolis.

$2,375,000

There is nothing else in Eastport like this beautiful, one floor living, attached garage, home with 4 bedrooms, 3 baths, large finished lower level and separate guest house with a 5th bedroom, 4th full bath. Built in 2014 on two lots with 10 foot ceilings, 8 foot doors (18 inches taller than the standard door), in a Montecito west coast style with incredible proportions and finishes, this home's design makes a strong statement in addition to its unique combination of features for Eastport. The main living area is a great room with huge window in the front facing kitchen and 34 feet of glass doors opening to a 34-foot-long screen porch with vaulted ceiling, five skylights and a gas fireplace. The bedroom layout is for the sophisticated owner. There is a separate two bedroom guest suite with its own foyer off the entry hall, linens storage and full bath to the design standard of primary bath with walk-in shower, finishes and lighting. The large primary bath has an outer room with free standing tub and double sinks. This room has two tall thin windows framing the tub mosaic wall and two skylights. The second room of the primary bathroom has an oversized walk-in shower with rain shower and wall showerheads in addition to a third skylight. Both the tub and the shower walls have beautiful mosaic tile floor to ceiling back walls dramatically lit from above by recessed lights. The large walk-in closet is what you would expect in a home designed to this standard and there is a second closet in the primary suite. There is another bedroom or office on the opposite side of the great room, and like the primary bedroom, looks out on the large landscaped backyard mosaic tile wall. The windows are proportionally large for the 10-foot ceilings. The design of the kitchen reflects the space that a single floor, double lot home provides. Ample storage below counters in drawers with hidden utensil drawers and expansive counterspace in the kitchen, provide a clean, contemporary feel. The Melie separate refrigerator and freezer are completely hidden behind the cabinet doors completing the sophisticated contemporary design. A large square island with two ovens, seating for 6, and surface area is the center of this entertaining kitchen. The front hall leads to the living area that is centered on a long, glass sealed fireplace that is both practical and striking. The two-car garage is part of the home, directly entering on a side hallway. It is large enough for two of the largest SUVs and has a finished storage loft above. There is also a finished lower level with a gym, surround sound entertainment system, pool table, separate large workshop, and a 14x14 storage room, all with 9 foot ceilings. THE HVAC as well as hot water are all geothermal, cost effective with no noisy outside systems. The separate guest house has a cathedral ceiling and full bath. The HVAC in the guest house is a high efficiency Mitsubishi split system. The front landscaping includes stone wall and gardens as well as a pergola swing and small patio with Adirondak chairs for when you want outdoors to be social. Illuminated brick sidewalk and mahogany stairs lead to the large entry doors. Privacy is in the large backyard where landscaping accentuates the beauty and utility of an impressive entertaining space. Brick sidewalks and a large stone patio under the shade of 4 red bud trees with outdoor kitchen and firepit. Landscape lighting and irrigation complete and match the look.

There is nothing else in Eastport like this beautiful, one floor living, attached garage, home with 4 bedrooms, 3 baths, large finished lower level and separate guest house with a 5th bedroom, 4th full bath. Built in 2014 on two lots with 10 foot ceilings, 8 foot doors (18 inches taller than the standard door), in a Montecito west coast style with incredible proportions and finishes, this home's design makes a strong statement in addition to its unique combination of features for Eastport. The main living area is a great room with huge window in the front facing kitchen and 34 feet of glass doors opening to a 34-foot-long screen porch with vaulted ceiling, five skylights and a gas fireplace. The bedroom layout is for the sophisticated owner. There is a separate two bedroom guest suite with its own foyer off the entry hall, linens storage and full bath to the design standard of primary bath with walk-in shower, finishes and lighting. The large primary bath has an outer room with free standing tub and double sinks. This room has two tall thin windows framing the tub mosaic wall and two skylights. The second room of the primary bathroom has an oversized walk-in shower with rain shower and wall showerheads in addition to a third skylight. Both the tub and the shower walls have beautiful mosaic tile floor to ceiling back walls dramatically lit from above by recessed lights. The large walk-in closet is what you would expect in a home designed to this standard and there is a second closet in the primary suite. There is another bedroom or office on the opposite side of the great room, and like the primary bedroom, looks out on the large landscaped backyard mosaic tile wall. The windows are proportionally large for the 10-foot ceilings. The design of the kitchen reflects the space that a single floor, double lot home provides. Ample storage below counters in drawers with hidden utensil drawers and expansive counterspace in the kitchen, provide a clean, contemporary feel. The Melie separate refrigerator and freezer are completely hidden behind the cabinet doors completing the sophisticated contemporary design. A large square island with two ovens, seating for 6, and surface area is the center of this entertaining kitchen. The front hall leads to the living area that is centered on a long, glass sealed fireplace that is both practical and striking. The two-car garage is part of the home, directly entering on a side hallway. It is large enough for two of the largest SUVs and has a finished storage loft above. There is also a finished lower level with a gym, surround sound entertainment system, pool table, separate large workshop, and a 14x14 storage room, all with 9 foot ceilings. THE HVAC as well as hot water are all geothermal, cost effective with no noisy outside systems. The separate guest house has a cathedral ceiling and full bath. The HVAC in the guest house is a high efficiency Mitsubishi split system. The front landscaping includes stone wall and gardens as well as a pergola swing and small patio with Adirondak chairs for when you want outdoors to be social. Illuminated brick sidewalk and mahogany stairs lead to the large entry doors. Privacy is in the large backyard where landscaping accentuates the beauty and utility of an impressive entertaining space. Brick sidewalks and a large stone patio under the shade of 4 red bud trees with outdoor kitchen and firepit. Landscape lighting and irrigation complete and match the look.

1004 Moss Haven Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Introducing 122 Chesapeake Avenue, a beautifully constructed Eastport residence offering refined coastal living with elevated design throughout. Built in 2014, this luxury Craftsman showcases a seamless blend of clean architectural lines, modern functionality, and high-end finishes across all three levels. The main level is designed for effortless living and entertaining, featuring an open layout with rich hardwood flooring, detailed millwork, coffered ceilings, and a gas fireplace framed by custom built-ins. The kitchen serves as the centerpiece of the home with a substantial island, professional-grade gas range, walk-in pantry, and a well-appointed butler’s pantry complete with a wet bar and beverage cooler. Indoor and outdoor living connect seamlessly with access to a spacious screened porch, patio, and fully fenced yard. A flexible main-level office with an adjacent full bath offers the option for a guest suite or fifth bedroom. Upstairs, the primary suite is both bright and inviting, featuring vaulted ceilings, a gas fireplace, dual walk-in closets, and a spa-inspired bath with a freestanding soaking tub and double vanity. Two additional bedrooms each include private en-suite baths, along with a conveniently located upper-level laundry room. The finished lower level, renovated in 2024, provides a generous secondary living area with a gas fireplace, an additional bedroom and full bath, a separate flex room, and multiple storage areas. Complete with professionally landscaped grounds, hardscaping, a built-in outdoor grill, and private driveway parking, this home is ideally positioned near Eastport’s waterfront, marinas, and just minutes to downtown Annapolis. A turnkey offering combining thoughtful design, comfort, and location.

$2,275,000

4 Beds ⋅ 5 Baths

Introducing 122 Chesapeake Avenue, a beautifully constructed Eastport residence offering refined coastal living with elevated design throughout. Built in 2014, this luxury Craftsman showcases a seamless blend of clean architectural lines, modern functionality, and high-end finishes across all three levels. The main level is designed for effortless living and entertaining, featuring an open layout with rich hardwood flooring, detailed millwork, coffered ceilings, and a gas fireplace framed by custom built-ins. The kitchen serves as the centerpiece of the home with a substantial island, professional-grade gas range, walk-in pantry, and a well-appointed butler’s pantry complete with a wet bar and beverage cooler. Indoor and outdoor living connect seamlessly with access to a spacious screened porch, patio, and fully fenced yard. A flexible main-level office with an adjacent full bath offers the option for a guest suite or fifth bedroom. Upstairs, the primary suite is both bright and inviting, featuring vaulted ceilings, a gas fireplace, dual walk-in closets, and a spa-inspired bath with a freestanding soaking tub and double vanity. Two additional bedrooms each include private en-suite baths, along with a conveniently located upper-level laundry room. The finished lower level, renovated in 2024, provides a generous secondary living area with a gas fireplace, an additional bedroom and full bath, a separate flex room, and multiple storage areas. Complete with professionally landscaped grounds, hardscaping, a built-in outdoor grill, and private driveway parking, this home is ideally positioned near Eastport’s waterfront, marinas, and just minutes to downtown Annapolis. A turnkey offering combining thoughtful design, comfort, and location.

122 Chesapeake Ave, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: Monument Sotheby's International Realty.

$2,200,000

Welcome to Eastport living at its finest—where timeless coastal design meets understated luxury just one block from the water. Perfectly situated on the highly sought Eastport Pennisula, this elegant two-story home blends craftsmanship, comfort, and walkable charm in one of Annapolis’s most desirable neighborhoods. Inside, soaring ceilings, coffered detailing, and recessed lighting tucked behind crown molding create a warm, sophisticated ambiance. The open-concept kitchen—with gorgeous Cambria Quartz counters, GE Café appliances, an expansive bar and dining area—flows seamlessly into the living room for easy entertaining. Extra-wide flat-board trim, rich hardwood floors, and designer finishes throughout reflect thoughtful quality at every turn. Upstairs, each bedroom enjoys a private ensuite bath and California Closets storage. The primary suite and a second bedroom open to private verandas with marina and sailboat-mast views. Two fireplaces—one wood-burning in the family room and one gas in the primary suite—add warmth and ambiance. The home is also equipped with a Bose whole-house sound system and central audio hub, all conveying. Outdoor living is equally inviting: a front porch perfect for greeting neighbors, and a private fenced rear veranda and brick patio ideal for gatherings or summer crab feasts, tucked between the home and the detached two-car garage—a rare Eastport feature. As an added bonus, the garage is equipped with a Level 2 EV Charging Station. Located adjacent to Safe Harbor Marina (formerly Mears Marina, Swim and Tennis Club) and close to Eastport Democratic Club (social not political club) as well as Sixth Street Beach on Back Creek. Launch a kayak or paddleboard steps from your home or walk just blocks to Annapolis and Eastport Yacht Clubs, Severn Sailing Association and countless local marinas, restaurants, and coffee shops. Come see what the Eastport Lifestyle is all about!

Welcome to Eastport living at its finest—where timeless coastal design meets understated luxury just one block from the water. Perfectly situated on the highly sought Eastport Pennisula, this elegant two-story home blends craftsmanship, comfort, and walkable charm in one of Annapolis’s most desirable neighborhoods. Inside, soaring ceilings, coffered detailing, and recessed lighting tucked behind crown molding create a warm, sophisticated ambiance. The open-concept kitchen—with gorgeous Cambria Quartz counters, GE Café appliances, an expansive bar and dining area—flows seamlessly into the living room for easy entertaining. Extra-wide flat-board trim, rich hardwood floors, and designer finishes throughout reflect thoughtful quality at every turn. Upstairs, each bedroom enjoys a private ensuite bath and California Closets storage. The primary suite and a second bedroom open to private verandas with marina and sailboat-mast views. Two fireplaces—one wood-burning in the family room and one gas in the primary suite—add warmth and ambiance. The home is also equipped with a Bose whole-house sound system and central audio hub, all conveying. Outdoor living is equally inviting: a front porch perfect for greeting neighbors, and a private fenced rear veranda and brick patio ideal for gatherings or summer crab feasts, tucked between the home and the detached two-car garage—a rare Eastport feature. As an added bonus, the garage is equipped with a Level 2 EV Charging Station. Located adjacent to Safe Harbor Marina (formerly Mears Marina, Swim and Tennis Club) and close to Eastport Democratic Club (social not political club) as well as Sixth Street Beach on Back Creek. Launch a kayak or paddleboard steps from your home or walk just blocks to Annapolis and Eastport Yacht Clubs, Severn Sailing Association and countless local marinas, restaurants, and coffee shops. Come see what the Eastport Lifestyle is all about!

600 Sixth St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

$2,000,000

Welcome to 912 Windsor Ave — The only ground up new construction home that is move in ready within city limits located right in the heart of coveted Eastport, Annapolis! With inspiration from a traditional four-square style home, this thoughtfully designed residence spans three finished levels and offers 3,029 square feet of refined finished living space offering 5 bedrooms and 4.5 bathrooms. Step inside into a welcoming foyer with a custom built-in bench and 9” wide wood floors. The open floor plan unfolds beneath a 9-foot tall shiplap ceiling with stained accent-beams. The gourmet kitchen is a showstopper — premium quartz countertops, an oversized island with seating, monogram stainless steel appliances, and a walk-in pantry. The family room features a gas fireplace, built-in shelving, and an 8-foot tall Pella quad glass slider which opens to a Trex deck overlooking the spacious fully fenced backyard. The main floor bedroom with an ensuite bath provides future flexibility with it currently set up as an office but providing the option for main floor living if needed. Upstairs, the luxurious primary suite boasts scalloped walnut wainscoting, a shiplap tray ceiling, and a large walk-in closet with built-ins. The ensuite bath dazzles with a fully tiled backsplash double vanity and walk in shower which includes a bench, rain head, and handheld fixtures. Two additional bedrooms with walk in closets share a beautifully appointed hall bath, while an upper-level laundry room offers convenience. The fully finished basement elevates entertaining with a wine bar, beverage fridge, and display wine rack — perfect for hosting. Outside, enjoy a manicured lawn with full irrigation, Sonos integrated outdoor speakers, and a firepit paver patio. Just a walk from the Annapolis Yacht Club, City Dock, iconic restaurants, and the U.S. Naval Academy, this is Annapolis living at its finest. Easy access to Washington, DC & Baltimore. Come see this gem in person to experience all the amenities it has to offer before it is gone!

5 Beds ⋅ 5 Baths

Welcome to 912 Windsor Ave — The only ground up new construction home that is move in ready within city limits located right in the heart of coveted Eastport, Annapolis! With inspiration from a traditional four-square style home, this thoughtfully designed residence spans three finished levels and offers 3,029 square feet of refined finished living space offering 5 bedrooms and 4.5 bathrooms. Step inside into a welcoming foyer with a custom built-in bench and 9” wide wood floors. The open floor plan unfolds beneath a 9-foot tall shiplap ceiling with stained accent-beams. The gourmet kitchen is a showstopper — premium quartz countertops, an oversized island with seating, monogram stainless steel appliances, and a walk-in pantry. The family room features a gas fireplace, built-in shelving, and an 8-foot tall Pella quad glass slider which opens to a Trex deck overlooking the spacious fully fenced backyard. The main floor bedroom with an ensuite bath provides future flexibility with it currently set up as an office but providing the option for main floor living if needed. Upstairs, the luxurious primary suite boasts scalloped walnut wainscoting, a shiplap tray ceiling, and a large walk-in closet with built-ins. The ensuite bath dazzles with a fully tiled backsplash double vanity and walk in shower which includes a bench, rain head, and handheld fixtures. Two additional bedrooms with walk in closets share a beautifully appointed hall bath, while an upper-level laundry room offers convenience. The fully finished basement elevates entertaining with a wine bar, beverage fridge, and display wine rack — perfect for hosting. Outside, enjoy a manicured lawn with full irrigation, Sonos integrated outdoor speakers, and a firepit paver patio. Just a walk from the Annapolis Yacht Club, City Dock, iconic restaurants, and the U.S. Naval Academy, this is Annapolis living at its finest. Easy access to Washington, DC & Baltimore. Come see this gem in person to experience all the amenities it has to offer before it is gone!

912 Windsor Ave, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Embrace the ease of true coastal living in this beautifully appointed home, ideally situated just a short stroll from the waterfront and the bustling center of Downtown Annapolis. Blending classic seaside charm with refined finishes, this meticulously curated home features stunning interiors, where every detail reflects superior craftsmanship and thoughtful design. Rich hardwood flooring, custom moldings, and plantation shutters in the living room establish a sophisticated ambiance throughout. The formal living room, anchored by a gas fireplace, offers an inviting yet polished setting for both intimate evenings and gracious entertaining. At the heart of the home, the gourmet kitchen is impeccably appointed with professional-grade Thermador appliances, an expansive Silestone center island, and a custom-designed polished nickel pot rack by Ann Morris—a striking statement of artistry and function. Step out to the covered patio overlooking the thoughtfully designed gardens, creating a seamless transition between refined interiors and serene outdoor living. The primary suite is a sanctuary of comfort and privacy, featuring two substantial walk-in closets, a spa-inspired bath and a private balcony. A separate den on the primary suite level with its own balcony provides space for a study or a quiet reading room. The third level features two additional ensuite bedrooms both with vaulted ceilings, one offers a private balcony and the other a French balcony - both bathed in natural light and architectural character. Completing this exceptional offering is a detached two-car garage with unfinished storage above and the added exclusivity of private gated parking. The large unfinished lower level is perfect for extra storage! Perfectly positioned within walking distance to Downtown Annapolis’ acclaimed restaurants, boutiques, and cultural attractions, this home presents a rare opportunity to experience coastal living with grace, sophistication, and enduring style.

400 Chesapeake Ave Unit 2-101, Annapolis

$1,915,000

Embrace the ease of true coastal living in this beautifully appointed home, ideally situated just a short stroll from the waterfront and the bustling center of Downtown Annapolis. Blending classic seaside charm with refined finishes, this meticulously curated home features stunning interiors, where every detail reflects superior craftsmanship and thoughtful design. Rich hardwood flooring, custom moldings, and plantation shutters in the living room establish a sophisticated ambiance throughout. The formal living room, anchored by a gas fireplace, offers an inviting yet polished setting for both intimate evenings and gracious entertaining. At the heart of the home, the gourmet kitchen is impeccably appointed with professional-grade Thermador appliances, an expansive Silestone center island, and a custom-designed polished nickel pot rack by Ann Morris—a striking statement of artistry and function. Step out to the covered patio overlooking the thoughtfully designed gardens, creating a seamless transition between refined interiors and serene outdoor living. The primary suite is a sanctuary of comfort and privacy, featuring two substantial walk-in closets, a spa-inspired bath and a private balcony. A separate den on the primary suite level with its own balcony provides space for a study or a quiet reading room. The third level features two additional ensuite bedrooms both with vaulted ceilings, one offers a private balcony and the other a French balcony - both bathed in natural light and architectural character. Completing this exceptional offering is a detached two-car garage with unfinished storage above and the added exclusivity of private gated parking. The large unfinished lower level is perfect for extra storage! Perfectly positioned within walking distance to Downtown Annapolis’ acclaimed restaurants, boutiques, and cultural attractions, this home presents a rare opportunity to experience coastal living with grace, sophistication, and enduring style.

400 Chesapeake Ave Unit 2-101, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

A rare opportunity to own a beautifully reimagined residence in the heart of Eastport, where timeless architecture meets modern comfort. Rich in history and craftsmanship, the home showcases an antique fireplace mantel with a hand-carved frieze, artisan wrought iron banister and fencing created by a metalsmith and co-founder of the renowned Niermann Weeks design atelier, and wide lintels that reflect the character of a bygone era. A thoughtfully designed 1986 renovation introduced a two-story addition and reconfigured the home around a central hallway, creating the exceptional floor plan enjoyed today while preserving its historic charm. The kitchen was beautifully renovated in 2022 by designer Nicole Rauzi of Chroma Kitchens, featuring updated custom cabinetry, fixtures, appliances, and a 6-burner Wolf range, blending contemporary function with classic style. Plantation shutters throughout the home add timeless elegance and privacy. French doors open from the living room to a newly completed screened porch (2026), overlooking a private garden filled with mature perennials and seasonal blooms, creating an inviting extension of the home's living space. Rarely found in Eastport, the property provides a two-car garage and three off-street parking spaces. Above the garage, the finished living space with a full bath and its own mini-split HVAC system (2022), offers flexibility as a guest suite, private office, studio and more. Additional home improvements include Hardie Plank siding (2020), washer and dryer (2022), and irrigation system (2017). Previously featured on the prestigious Annapolis Home & Garden Tour, this exceptional residence places you just moments from Eastport's celebrated restaurants, marinas, boutiques, galleries, and waterfront parks, with easy access across the Spa Creek Bridge to Historic Downtown Annapolis. A home where historic character, thoughtful updates, and an unmatched Eastport lifestyle come together in one extraordinary offering.

$1,900,500

A rare opportunity to own a beautifully reimagined residence in the heart of Eastport, where timeless architecture meets modern comfort. Rich in history and craftsmanship, the home showcases an antique fireplace mantel with a hand-carved frieze, artisan wrought iron banister and fencing created by a metalsmith and co-founder of the renowned Niermann Weeks design atelier, and wide lintels that reflect the character of a bygone era. A thoughtfully designed 1986 renovation introduced a two-story addition and reconfigured the home around a central hallway, creating the exceptional floor plan enjoyed today while preserving its historic charm. The kitchen was beautifully renovated in 2022 by designer Nicole Rauzi of Chroma Kitchens, featuring updated custom cabinetry, fixtures, appliances, and a 6-burner Wolf range, blending contemporary function with classic style. Plantation shutters throughout the home add timeless elegance and privacy. French doors open from the living room to a newly completed screened porch (2026), overlooking a private garden filled with mature perennials and seasonal blooms, creating an inviting extension of the home's living space. Rarely found in Eastport, the property provides a two-car garage and three off-street parking spaces. Above the garage, the finished living space with a full bath and its own mini-split HVAC system (2022), offers flexibility as a guest suite, private office, studio and more. Additional home improvements include Hardie Plank siding (2020), washer and dryer (2022), and irrigation system (2017). Previously featured on the prestigious Annapolis Home & Garden Tour, this exceptional residence places you just moments from Eastport's celebrated restaurants, marinas, boutiques, galleries, and waterfront parks, with easy access across the Spa Creek Bridge to Historic Downtown Annapolis. A home where historic character, thoughtful updates, and an unmatched Eastport lifestyle come together in one extraordinary offering.

526 Sixth St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

EXCITING PRICE IMPROVEMENT! SELLER HAS REDUCED THE PRICE-DON'T MISS THIS GREAT OPPORTUNITY. Immerse yourself in the quintessential Eastport lifestyle with this inviting Craftsman-style residence, ideally located just moments from the water access at Davis Park and the vibrant offerings of Eastport and downtown Annapolis. This beautifully maintained home spans three thoughtfully designed levels and features four bedrooms, three and a half baths, an elevator, and comfortable sitting areas on every floor. Highlights include a gourmet kitchen, warm living spaces with a fireplace, rich wood flooring, a generous dining area, and a reverse floor plan that captures light, views, and a relaxed coastal feel—making every day feel like a getaway. The entry level is perfect for hosting family and friends, offering three bedrooms, including a private ensuite with direct access to the deck and hot tub, plus two additional bedrooms served by a hall bath. The second level is devoted to the primary retreat, featuring an open sitting area overlooking the level below, a spacious bedroom, a private deck with peaceful backyard views, and a luxurious spa-inspired bath. The top level serves as the heart of the home, complete with an expansive partially covered balcony where you can enjoy seasonal glimpses of Back Creek from an exceptionally private setting. Outdoor spaces are equally impressive, with a welcoming front porch and a large, fenced rear yard featuring a deck, hot tub, and pergola—ideal for entertaining, grilling, or simply soaking in the Eastport vibe. A detached garage with driveway provides rare and valuable off-street parking for multiple vehicles. Above the garage, a finished space with a separate entrance offers endless flexibility for guests, a home office, studio, or rental opportunity. This property also presents excellent potential as a VRBO or Airbnb, offering year-round income possibilities in one of Annapolis’s most sought-after neighborhoods. Buyer should check current licensing regulations for Annapolis. Enjoy leisurely strolls through Eastport’s artistic, maritime streets to acclaimed restaurants, pubs, and charming street-end parks, one is right next door. Downtown Annapolis and the Naval Academy are just steps away via the Spa Creek drawbridge or a quick ride on the water taxi. From here, you’re also close to premier cruising and fishing waters, with easy access to destinations like Baltimore’s Inner Harbor, St. Michaels, Oxford, and Solomon’s Island. Conveniently located approximately five miles from Routes 50 and 97, with direct access to Baltimore, BWI, Fort Meade/NSA, and Washington, DC, this home offers the perfect blend of coastal charm, walkable convenience, and sophisticated living. Welcome to Eastport living at its best.

$1,730,000

EXCITING PRICE IMPROVEMENT! SELLER HAS REDUCED THE PRICE-DON'T MISS THIS GREAT OPPORTUNITY. Immerse yourself in the quintessential Eastport lifestyle with this inviting Craftsman-style residence, ideally located just moments from the water access at Davis Park and the vibrant offerings of Eastport and downtown Annapolis. This beautifully maintained home spans three thoughtfully designed levels and features four bedrooms, three and a half baths, an elevator, and comfortable sitting areas on every floor. Highlights include a gourmet kitchen, warm living spaces with a fireplace, rich wood flooring, a generous dining area, and a reverse floor plan that captures light, views, and a relaxed coastal feel—making every day feel like a getaway. The entry level is perfect for hosting family and friends, offering three bedrooms, including a private ensuite with direct access to the deck and hot tub, plus two additional bedrooms served by a hall bath. The second level is devoted to the primary retreat, featuring an open sitting area overlooking the level below, a spacious bedroom, a private deck with peaceful backyard views, and a luxurious spa-inspired bath. The top level serves as the heart of the home, complete with an expansive partially covered balcony where you can enjoy seasonal glimpses of Back Creek from an exceptionally private setting. Outdoor spaces are equally impressive, with a welcoming front porch and a large, fenced rear yard featuring a deck, hot tub, and pergola—ideal for entertaining, grilling, or simply soaking in the Eastport vibe. A detached garage with driveway provides rare and valuable off-street parking for multiple vehicles. Above the garage, a finished space with a separate entrance offers endless flexibility for guests, a home office, studio, or rental opportunity. This property also presents excellent potential as a VRBO or Airbnb, offering year-round income possibilities in one of Annapolis’s most sought-after neighborhoods. Buyer should check current licensing regulations for Annapolis. Enjoy leisurely strolls through Eastport’s artistic, maritime streets to acclaimed restaurants, pubs, and charming street-end parks, one is right next door. Downtown Annapolis and the Naval Academy are just steps away via the Spa Creek drawbridge or a quick ride on the water taxi. From here, you’re also close to premier cruising and fishing waters, with easy access to destinations like Baltimore’s Inner Harbor, St. Michaels, Oxford, and Solomon’s Island. Conveniently located approximately five miles from Routes 50 and 97, with direct access to Baltimore, BWI, Fort Meade/NSA, and Washington, DC, this home offers the perfect blend of coastal charm, walkable convenience, and sophisticated living. Welcome to Eastport living at its best.

215 Chester Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$1,660,000

Step into the heart of Eastport, where charm and convenience meet in this beautifully renovated Cape Cod. Just a short stroll from the water’s edge and downtown Annapolis, this home embodies the Eastport lifestyle — vibrant, nautical, and effortlessly welcoming. From the moment you enter, natural light pours through every window, illuminating three levels of thoughtfully designed living space. Classic details — arched doorways, hardwood floors, custom built-ins, and rich millwork — blend seamlessly with modern updates, creating a home that feels both timeless and fresh. The inviting floor plan offers room for every occasion. A serene primary suite with its own fireplace provides a private retreat, while the main-level office doubles as a guest room or den. Formal living room with fireplace and gorgeous dining room set the stage for elegant entertaining The family room invites casual gatherings with another fireflace and access to the screened porch. The updated kitchen is a true centerpiece, with fresh cabinetry, stylish countertops, and a backsplash that ties it all together. Upstairs, a spiral staircase leads to a sunlit loft with a private balcony — perfect for a creative nook, playroom, or quiet reading space. Outside, the screened porch, fenced yard, and welcoming front porch create effortless indoor-outdoor living, ideal for relaxing or hosting friends. The basement was recently waterproofed. Practical touches like a mudroom with laundry and off-street parking make everyday life easy. Beyond the walls, Eastport beckons. Launch your kayak from Horn Point Park, wander streets lined with art and history, or cross the Spa Creek drawbridge to downtown Annapolis and the Naval Academy. From this location, the Chesapeake Bay is your playground — with cruising and fishing destinations like Baltimore’s Inner Harbor, St. Michael’s, Oxford, and Solomon’s Island all within reach. Annapolis offers the perfect balance of small-town charm and cosmopolitan sophistication, and this Eastport jewel places you right at the center of it all. With quick access to Rt. 50 and 97, Baltimore, BWI, Ft. Meade/NSA, and Washington, DC are just a drive away. This is more than a home — it’s a lifestyle. Welcome to Eastport.

Step into the heart of Eastport, where charm and convenience meet in this beautifully renovated Cape Cod. Just a short stroll from the water’s edge and downtown Annapolis, this home embodies the Eastport lifestyle — vibrant, nautical, and effortlessly welcoming. From the moment you enter, natural light pours through every window, illuminating three levels of thoughtfully designed living space. Classic details — arched doorways, hardwood floors, custom built-ins, and rich millwork — blend seamlessly with modern updates, creating a home that feels both timeless and fresh. The inviting floor plan offers room for every occasion. A serene primary suite with its own fireplace provides a private retreat, while the main-level office doubles as a guest room or den. Formal living room with fireplace and gorgeous dining room set the stage for elegant entertaining The family room invites casual gatherings with another fireflace and access to the screened porch. The updated kitchen is a true centerpiece, with fresh cabinetry, stylish countertops, and a backsplash that ties it all together. Upstairs, a spiral staircase leads to a sunlit loft with a private balcony — perfect for a creative nook, playroom, or quiet reading space. Outside, the screened porch, fenced yard, and welcoming front porch create effortless indoor-outdoor living, ideal for relaxing or hosting friends. The basement was recently waterproofed. Practical touches like a mudroom with laundry and off-street parking make everyday life easy. Beyond the walls, Eastport beckons. Launch your kayak from Horn Point Park, wander streets lined with art and history, or cross the Spa Creek drawbridge to downtown Annapolis and the Naval Academy. From this location, the Chesapeake Bay is your playground — with cruising and fishing destinations like Baltimore’s Inner Harbor, St. Michael’s, Oxford, and Solomon’s Island all within reach. Annapolis offers the perfect balance of small-town charm and cosmopolitan sophistication, and this Eastport jewel places you right at the center of it all. With quick access to Rt. 50 and 97, Baltimore, BWI, Ft. Meade/NSA, and Washington, DC are just a drive away. This is more than a home — it’s a lifestyle. Welcome to Eastport.

3 Chester Ave, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Perfectly positioned in the heart of Eastport, this outstanding turnkey residence captures the essence of the Annapolis lifestyle, where charming neighborhood streets, waterfront parks, marinas, acclaimed restaurants, coffee shops, and downtown Annapolis are all just moments from your front door. Lovingly cared for throughout the years, the home blends timeless character with the comfort and functionality today’s buyers desire. Designed for both everyday living and effortless entertaining, the spacious kitchen flows seamlessly into the inviting family room, where French doors open to a beautiful screened porch ideal for relaxing after a day on the water or gathering with friends on warm summer evenings. The luxurious primary suite offers a peaceful retreat with a tray ceiling, custom spa-like bath, and oversized walk-in closet. Three additional bedrooms provide charm and flexibility, while the finished third level with hardwood flooring creates the perfect bonus space for a home office, playroom, studio, or guest overflow. Additional highlights include second-floor laundry, plantation shutters throughout, beautifully landscaped grounds, and an oversized fenced backyard with a paver patio that extends the living space outdoors. Rare off-street parking for three cars adds exceptional convenience in this highly walkable Eastport location. Life in Eastport is all about embracing the charm and energy of Annapolis’ treasured waterfront lifestyle. Stroll the artful, nautical streets lined with acclaimed restaurants, lively pubs, yacht clubs, marinas, and tucked-away waterfront parks, or make your way into downtown Annapolis and the Naval Academy by crossing the Spa Creek drawbridge or hopping aboard the water taxi. Whether enjoying waterfront dining, launching a paddleboard, attending local events, or simply taking in the vibrant harbor atmosphere, this location offers an unmatched blend of coastal charm and walkable convenience. For boating enthusiasts, some of the Chesapeake Bay’s best cruising and fishing destinations await just beyond your dock, with easy access to celebrated waterfront towns including St. Michaels, Oxford, Solomons, and Baltimore’s Inner Harbor. Perfectly positioned just minutes from Routes 50 and 97, commuting to Baltimore, BWI, Ft. Meade/NSA, and Washington, DC is equally effortless. Welcome Home!

$1,600,000

Perfectly positioned in the heart of Eastport, this outstanding turnkey residence captures the essence of the Annapolis lifestyle, where charming neighborhood streets, waterfront parks, marinas, acclaimed restaurants, coffee shops, and downtown Annapolis are all just moments from your front door. Lovingly cared for throughout the years, the home blends timeless character with the comfort and functionality today’s buyers desire. Designed for both everyday living and effortless entertaining, the spacious kitchen flows seamlessly into the inviting family room, where French doors open to a beautiful screened porch ideal for relaxing after a day on the water or gathering with friends on warm summer evenings. The luxurious primary suite offers a peaceful retreat with a tray ceiling, custom spa-like bath, and oversized walk-in closet. Three additional bedrooms provide charm and flexibility, while the finished third level with hardwood flooring creates the perfect bonus space for a home office, playroom, studio, or guest overflow. Additional highlights include second-floor laundry, plantation shutters throughout, beautifully landscaped grounds, and an oversized fenced backyard with a paver patio that extends the living space outdoors. Rare off-street parking for three cars adds exceptional convenience in this highly walkable Eastport location. Life in Eastport is all about embracing the charm and energy of Annapolis’ treasured waterfront lifestyle. Stroll the artful, nautical streets lined with acclaimed restaurants, lively pubs, yacht clubs, marinas, and tucked-away waterfront parks, or make your way into downtown Annapolis and the Naval Academy by crossing the Spa Creek drawbridge or hopping aboard the water taxi. Whether enjoying waterfront dining, launching a paddleboard, attending local events, or simply taking in the vibrant harbor atmosphere, this location offers an unmatched blend of coastal charm and walkable convenience. For boating enthusiasts, some of the Chesapeake Bay’s best cruising and fishing destinations await just beyond your dock, with easy access to celebrated waterfront towns including St. Michaels, Oxford, Solomons, and Baltimore’s Inner Harbor. Perfectly positioned just minutes from Routes 50 and 97, commuting to Baltimore, BWI, Ft. Meade/NSA, and Washington, DC is equally effortless. Welcome Home!

712 Chesapeake Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

A Rare Find in the Heart of Eastport! Built in 2006 with timeless Eastport charm, this beautifully maintained home offers the perfect blend of traditional style and modern convenience. Enjoy off-street parking for 2 cars and a host of high-end features throughout. Step inside to discover hardwood flooring on all 3 levels, radiant floor heat, and zoned heating and cooling – including a private AC control in the primary suite. The spacious layout includes three full baths with stone tile details, a whirlpool tub and 2-person shower in the primary bath, and a soaking tub in the guest bath. The primary bedroom features skylights with rain sensors and remote-controlled shades, as well as his and hers closets. Enjoy a full-size washer & dryer on the second floor. The large 3rd level loft can be used as a 4th bedroom. On the main level there is a pantry/mudroom, separate side entry leads you to step to the unfinished basement with 8' ceilings. Designed with safety and comfort in mind, this home includes ceiling sprinklers on all levels, enhanced fire-rated walls, and a top-rated corner for a wood stove. Outdoor living is just as impressive with rain gardens in the front and back, Leaf Filter gutter guards, outdoor water and electric access, and dimmable lighting on the front porch as well as inside kitchen/dining areas. Additional highlights: Updated interior paint throughout (2024); New refrigerator (2024); dishwasher (2023); and microwave with stove exhaust (2025). Hardwood floors refinished (2025). Security system with front door camera. Included in the fenced rear yard is a permanent exclusive 5’ rear easement for added privacy. Enjoy the best of Eastport living in a home designed for comfort, efficiency, and peace of mind.

$1,470,000

A Rare Find in the Heart of Eastport! Built in 2006 with timeless Eastport charm, this beautifully maintained home offers the perfect blend of traditional style and modern convenience. Enjoy off-street parking for 2 cars and a host of high-end features throughout. Step inside to discover hardwood flooring on all 3 levels, radiant floor heat, and zoned heating and cooling – including a private AC control in the primary suite. The spacious layout includes three full baths with stone tile details, a whirlpool tub and 2-person shower in the primary bath, and a soaking tub in the guest bath. The primary bedroom features skylights with rain sensors and remote-controlled shades, as well as his and hers closets. Enjoy a full-size washer & dryer on the second floor. The large 3rd level loft can be used as a 4th bedroom. On the main level there is a pantry/mudroom, separate side entry leads you to step to the unfinished basement with 8' ceilings. Designed with safety and comfort in mind, this home includes ceiling sprinklers on all levels, enhanced fire-rated walls, and a top-rated corner for a wood stove. Outdoor living is just as impressive with rain gardens in the front and back, Leaf Filter gutter guards, outdoor water and electric access, and dimmable lighting on the front porch as well as inside kitchen/dining areas. Additional highlights: Updated interior paint throughout (2024); New refrigerator (2024); dishwasher (2023); and microwave with stove exhaust (2025). Hardwood floors refinished (2025). Security system with front door camera. Included in the fenced rear yard is a permanent exclusive 5’ rear easement for added privacy. Enjoy the best of Eastport living in a home designed for comfort, efficiency, and peace of mind.

541 Second St, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

This exceptional 4 bedroom, 2 full baths, 2 half bath Coastal Contemporary residence captures the essence of Eastport living, where walkability, water access, and a vibrant coastal lifestyle come together seamlessly. Ideally situated just moments from marinas, restaurants, shopping, and the charm of downtown, the home is surrounded by the waterways that define this coveted location, offering effortless access to everything that makes Eastport so special. Inside, soaring ceilings, beautiful hardwood flooring, and an open, light-filled floor plan create an inviting and functional living environment. The well-appointed kitchen features quality cabinetry, quartz countertops, JennAir appliances, and custom built-ins that blend everyday convenience with elevated design. A thoughtfully integrated dumbwaiter enhances ease between levels, while heated floors in the entryway and guest bath add a subtle layer of comfort. Outdoor living is equally compelling, with a spacious wraparound deck designed for entertaining and a wine balcony off the primary suite that embodies relaxation and captures serene water views—perfect for quiet mornings or evening relaxation. The landscaped yard offers a peaceful retreat, highlighted by a pond with a cascading waterfall that adds both ambiance and privacy. Additional features include a reverse osmosis water filtration system, multiple gas fireplaces, and efficient, well-maintained systems that support comfortable, low-maintenance living. Rounding out the property is the rare advantage of a 2-car garage with built-in storage above, along with a private driveway—an invaluable feature in Eastport where parking is often at a premium. Combining location, lifestyle, and thoughtful design, this residence presents a unique opportunity to enjoy the best of Annapolis living. Welcome Home!

$1,449,000

This exceptional 4 bedroom, 2 full baths, 2 half bath Coastal Contemporary residence captures the essence of Eastport living, where walkability, water access, and a vibrant coastal lifestyle come together seamlessly. Ideally situated just moments from marinas, restaurants, shopping, and the charm of downtown, the home is surrounded by the waterways that define this coveted location, offering effortless access to everything that makes Eastport so special. Inside, soaring ceilings, beautiful hardwood flooring, and an open, light-filled floor plan create an inviting and functional living environment. The well-appointed kitchen features quality cabinetry, quartz countertops, JennAir appliances, and custom built-ins that blend everyday convenience with elevated design. A thoughtfully integrated dumbwaiter enhances ease between levels, while heated floors in the entryway and guest bath add a subtle layer of comfort. Outdoor living is equally compelling, with a spacious wraparound deck designed for entertaining and a wine balcony off the primary suite that embodies relaxation and captures serene water views—perfect for quiet mornings or evening relaxation. The landscaped yard offers a peaceful retreat, highlighted by a pond with a cascading waterfall that adds both ambiance and privacy. Additional features include a reverse osmosis water filtration system, multiple gas fireplaces, and efficient, well-maintained systems that support comfortable, low-maintenance living. Rounding out the property is the rare advantage of a 2-car garage with built-in storage above, along with a private driveway—an invaluable feature in Eastport where parking is often at a premium. Combining location, lifestyle, and thoughtful design, this residence presents a unique opportunity to enjoy the best of Annapolis living. Welcome Home!

619 Second St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Welcome to Eastport, one of Annapolis most sought-after waterfront communities! This newer construction home offers the perfect blend of modern convenience, functional living, and an unbeatable location, complete with the rare convenience of a two-car garage and full-sized driveway, all within walking distance to the very best of Eastport and Downtown Annapolis. Perfectly positioned to enjoy the Eastport lifestyle, this home is just moments from beloved local restaurants, coffee shops, marinas, waterfront parks, and shopping, with easy access across the Spa Creek Bridge to Historic Downtown Annapolis, City Dock, and the Naval Academy. Inside, the thoughtfully designed floor plan blends comfort and functionality with stylish finishes throughout. The gourmet kitchen opens seamlessly to the main living spaces and is complemented by a wet bar, gas fireplace, hardwood flooring, and abundant natural light. A versatile front room offers flexibility for a sitting room, home office, playroom, or additional living space. 3 Full and 1 half bathrooms, plus hardwood flooring throughout! Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite, along with the convenience of upper-level laundry. Finished stairs lead to an expansive lower level with high ceilings, walk-out access, and rough-in plumbing for a future bath, offering endless possibilities for a recreation room, gym, guest suite, or additional living space tailored to your needs. Outdoor living is equally inviting with a fenced backyard and rear deck spanning the width of the home perfect for dining, entertaining, or relaxing after a day in town. Enjoy the best of Eastport living with waterfront charm, walkability, and Downtown Annapolis just moments away.

$1,399,000

Welcome to Eastport, one of Annapolis most sought-after waterfront communities! This newer construction home offers the perfect blend of modern convenience, functional living, and an unbeatable location, complete with the rare convenience of a two-car garage and full-sized driveway, all within walking distance to the very best of Eastport and Downtown Annapolis. Perfectly positioned to enjoy the Eastport lifestyle, this home is just moments from beloved local restaurants, coffee shops, marinas, waterfront parks, and shopping, with easy access across the Spa Creek Bridge to Historic Downtown Annapolis, City Dock, and the Naval Academy. Inside, the thoughtfully designed floor plan blends comfort and functionality with stylish finishes throughout. The gourmet kitchen opens seamlessly to the main living spaces and is complemented by a wet bar, gas fireplace, hardwood flooring, and abundant natural light. A versatile front room offers flexibility for a sitting room, home office, playroom, or additional living space. 3 Full and 1 half bathrooms, plus hardwood flooring throughout! Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite, along with the convenience of upper-level laundry. Finished stairs lead to an expansive lower level with high ceilings, walk-out access, and rough-in plumbing for a future bath, offering endless possibilities for a recreation room, gym, guest suite, or additional living space tailored to your needs. Outdoor living is equally inviting with a fenced backyard and rear deck spanning the width of the home perfect for dining, entertaining, or relaxing after a day in town. Enjoy the best of Eastport living with waterfront charm, walkability, and Downtown Annapolis just moments away.

1035 Boucher Ave, Annapolis

Listing courtesy of Compass. Contact:

This exceptional 3-bedroom, 2.5-bath sun-drenched contemporary home sits on a spacious Eastport corner lot. Enjoy the vibrant Eastport lifestyle from your newly updated, well-maintained oasis featuring warm hardwood floors and generous living, dining, and kitchen areas. The open layout complements the coastal Eastport vibe, while the inviting wraparound porch is great for morning coffee or an evening cocktail. The living room’s focal point is a gas fireplace that reflects off the beautiful wood floors and opens to the gourmet kitchen and newly designed dining area. The second level is dedicated entirely to the spacious primary spa-inspired suite with an oversized walk-in closet, custom built-ins, and an updated sublime bath with walk-in shower and heated floors. A hidden laundry room adds convenience. The private east-facing deck overlooks the rear yard, offering stunning sunrises to start your day. The third level features two bedrooms and an elegant shared bath, with one bedroom enjoying winter water views. The fourth-floor loft can serve as a bedroom, office, or exercise space. The expansive back patio and side yard are ideal for BBQs and soaking in the Eastport atmosphere. Two highly coveted off-street parking spaces are a rare find. Stroll Eastport streets, dine at five-star restaurants, enjoy cozy pubs, or watch boating activity from street-end parks. You’re moments from yacht clubs and marinas. Downtown Annapolis and the Naval Academy are close by via the charming Spa Creek drawbridge or the iconic water taxi. The Eastport peninsula is flanked by two creeks with quick access to the Severn River and Chesapeake Bay. Annapolis offers charm and sophistication with colleges, music venues, galleries, street fairs, acclaimed boat shows, and proximity to two major cities. Much of the home was updated to a high standard in 2024–25. Located just 5 miles from Route 50 and 97, you’ll have direct access to BWI and Washington, DC. Welcome home to your Eastport dream!

$1,380,000

This exceptional 3-bedroom, 2.5-bath sun-drenched contemporary home sits on a spacious Eastport corner lot. Enjoy the vibrant Eastport lifestyle from your newly updated, well-maintained oasis featuring warm hardwood floors and generous living, dining, and kitchen areas. The open layout complements the coastal Eastport vibe, while the inviting wraparound porch is great for morning coffee or an evening cocktail. The living room’s focal point is a gas fireplace that reflects off the beautiful wood floors and opens to the gourmet kitchen and newly designed dining area. The second level is dedicated entirely to the spacious primary spa-inspired suite with an oversized walk-in closet, custom built-ins, and an updated sublime bath with walk-in shower and heated floors. A hidden laundry room adds convenience. The private east-facing deck overlooks the rear yard, offering stunning sunrises to start your day. The third level features two bedrooms and an elegant shared bath, with one bedroom enjoying winter water views. The fourth-floor loft can serve as a bedroom, office, or exercise space. The expansive back patio and side yard are ideal for BBQs and soaking in the Eastport atmosphere. Two highly coveted off-street parking spaces are a rare find. Stroll Eastport streets, dine at five-star restaurants, enjoy cozy pubs, or watch boating activity from street-end parks. You’re moments from yacht clubs and marinas. Downtown Annapolis and the Naval Academy are close by via the charming Spa Creek drawbridge or the iconic water taxi. The Eastport peninsula is flanked by two creeks with quick access to the Severn River and Chesapeake Bay. Annapolis offers charm and sophistication with colleges, music venues, galleries, street fairs, acclaimed boat shows, and proximity to two major cities. Much of the home was updated to a high standard in 2024–25. Located just 5 miles from Route 50 and 97, you’ll have direct access to BWI and Washington, DC. Welcome home to your Eastport dream!

417 Chesapeake Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$1,350,000

Living the Eastport lifestyle - This is what upscale, modern urban living is all about! It's an easy walk to downtown shops, restaurants and marinas from this centrally located 13 year old Craftsman style home. Light filled rooms include the upper level bedrooms, one currently used as an office and one with a balcony. The lower level offers a full bath and separate entry with flexible space that could accommodate relatives or visitors, a media or exercise room, or additional office space. There is a two car garage off a rear alley that can accommodate 3-4 additional vehicles. Professionally designed, year round gardens and outdoor living spaces are perfect for entertaining. Play with the kids and walk your pets in the common green space (maintained by the Boucher Place HOA) behind the house. Downsizing there is ample storage! Moving up? The flexible floorplan will perfectly accommodate your changing lifestyle. Come see for yourself.

4 Beds ⋅ 5 Baths

Living the Eastport lifestyle - This is what upscale, modern urban living is all about! It's an easy walk to downtown shops, restaurants and marinas from this centrally located 13 year old Craftsman style home. Light filled rooms include the upper level bedrooms, one currently used as an office and one with a balcony. The lower level offers a full bath and separate entry with flexible space that could accommodate relatives or visitors, a media or exercise room, or additional office space. There is a two car garage off a rear alley that can accommodate 3-4 additional vehicles. Professionally designed, year round gardens and outdoor living spaces are perfect for entertaining. Play with the kids and walk your pets in the common green space (maintained by the Boucher Place HOA) behind the house. Downsizing there is ample storage! Moving up? The flexible floorplan will perfectly accommodate your changing lifestyle. Come see for yourself.

1109 Boucher Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Enjoy living in the heart of Eastport, where charming streets, waterfront parks, and a vibrant dining scene create one of Annapolis' most coveted lifestyles. This inviting home on a private cul-de-sac with just 4 houses combines comfortable living spaces with exceptional indoor-outdoor flow, all within walking distance of local shops, restaurants, marinas, and downtown Annapolis. Thoughtfully designed, the main level offers a wonderful balance of open gathering spaces and cozy retreats. The combined living and dining room is filled with natural light from high ceilings and skylights and opens directly to the expansive deck overlooking the backyard. At the heart of the home, the kitchen with center island flows seamlessly into the family room, where a fireplace creates a warm ambiance and easy access to the large screened porch and deck encourages effortless indoor-outdoor living. A newly renovated powder room provides privacy and convenience for family and guests. Upstairs, the primary suite provides a peaceful retreat featuring an ensuite bath with skylight, walk-in shower, and walk-in closet. Two additional bedrooms share a hall bath and are bathed in natural light, with one showcasing soaring ceilings. The lower level offers exceptional versatility with a spacious recreation room centered around a countertop area with full-size refrigerator, making it ideal for movie nights, game days, or hosting. A full bath, stackable laundry area, and a bonus room that makes an excellent office, or hobby space complete this level. Outside, the fenced backyard provides privacy and space for gatherings with family and friends, while the expansive deck and screened porch create inviting spaces to relax and enjoy the seasons. Stroll the artful and nautical streets to five-star restaurants, neighborhood pubs, and hidden street-end parks. You'll find yourself just moments from downtown Annapolis and the Naval Academy. Eastport and Annapolis offer the perfect balance of small-town charm and world-class sophistication, with convenient access to Routes 50 and 97 for easy commuting to Baltimore, BWI Airport, Fort Meade, NSA, and Washington, D.C. Welcome Home!

$1,250,000

Enjoy living in the heart of Eastport, where charming streets, waterfront parks, and a vibrant dining scene create one of Annapolis' most coveted lifestyles. This inviting home on a private cul-de-sac with just 4 houses combines comfortable living spaces with exceptional indoor-outdoor flow, all within walking distance of local shops, restaurants, marinas, and downtown Annapolis. Thoughtfully designed, the main level offers a wonderful balance of open gathering spaces and cozy retreats. The combined living and dining room is filled with natural light from high ceilings and skylights and opens directly to the expansive deck overlooking the backyard. At the heart of the home, the kitchen with center island flows seamlessly into the family room, where a fireplace creates a warm ambiance and easy access to the large screened porch and deck encourages effortless indoor-outdoor living. A newly renovated powder room provides privacy and convenience for family and guests. Upstairs, the primary suite provides a peaceful retreat featuring an ensuite bath with skylight, walk-in shower, and walk-in closet. Two additional bedrooms share a hall bath and are bathed in natural light, with one showcasing soaring ceilings. The lower level offers exceptional versatility with a spacious recreation room centered around a countertop area with full-size refrigerator, making it ideal for movie nights, game days, or hosting. A full bath, stackable laundry area, and a bonus room that makes an excellent office, or hobby space complete this level. Outside, the fenced backyard provides privacy and space for gatherings with family and friends, while the expansive deck and screened porch create inviting spaces to relax and enjoy the seasons. Stroll the artful and nautical streets to five-star restaurants, neighborhood pubs, and hidden street-end parks. You'll find yourself just moments from downtown Annapolis and the Naval Academy. Eastport and Annapolis offer the perfect balance of small-town charm and world-class sophistication, with convenient access to Routes 50 and 97 for easy commuting to Baltimore, BWI Airport, Fort Meade, NSA, and Washington, D.C. Welcome Home!

4 Kelly Ct, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Compass.

$1,175,000

Beautifully Appointed Eastport Home. Conveniently located in the heart of Eastport, Annapolis, this newer home offers the perfect blend of style, comfort, and walkability. Set on a premium corner lot, the property features a desirable detached garage and wonderful curb appeal. The main level showcases an open floor plan anchored by a gourmet kitchen with granite countertops, stainless steel appliances, and custom cabinetry with crown molding. A private office provides the perfect space for working from home, while the formal dining room is ideal for hosting dinners. The sitting room across from the office offers an inviting retreat—perfect for curling up with your favorite book or simply unwinding in comfort. A spacious family room with a gas fireplace is the perfect gathering space, complemented by a full bathroom for added convenience. Gleaming wood floors run throughout, tying the spaces together with warmth and elegance, while a wet bar and expansive deck extend the home’s entertaining potential outdoors. Upstairs, the luxurious primary suite boasts a sitting area and spa-like bath, offering a private retreat at the end of the day. Two additional ample-sized bedrooms and another full bathroom provide comfort and flexibility for family or guests, while the conveniently located upper-level laundry makes everyday living a breeze. An unfinished basement with rough in could be finished with a recreation room, bedroom and a full bathroom. Endless possibilities. With easy access to Eastport’s vibrant restaurants and just a short walk to downtown Annapolis, this home is a must-see for those seeking both convenience and elegance.

Beautifully Appointed Eastport Home. Conveniently located in the heart of Eastport, Annapolis, this newer home offers the perfect blend of style, comfort, and walkability. Set on a premium corner lot, the property features a desirable detached garage and wonderful curb appeal. The main level showcases an open floor plan anchored by a gourmet kitchen with granite countertops, stainless steel appliances, and custom cabinetry with crown molding. A private office provides the perfect space for working from home, while the formal dining room is ideal for hosting dinners. The sitting room across from the office offers an inviting retreat—perfect for curling up with your favorite book or simply unwinding in comfort. A spacious family room with a gas fireplace is the perfect gathering space, complemented by a full bathroom for added convenience. Gleaming wood floors run throughout, tying the spaces together with warmth and elegance, while a wet bar and expansive deck extend the home’s entertaining potential outdoors. Upstairs, the luxurious primary suite boasts a sitting area and spa-like bath, offering a private retreat at the end of the day. Two additional ample-sized bedrooms and another full bathroom provide comfort and flexibility for family or guests, while the conveniently located upper-level laundry makes everyday living a breeze. An unfinished basement with rough in could be finished with a recreation room, bedroom and a full bathroom. Endless possibilities. With easy access to Eastport’s vibrant restaurants and just a short walk to downtown Annapolis, this home is a must-see for those seeking both convenience and elegance.

412 Jefferson St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Keller Williams Select Realtors of Annapolis.

$1,057,600

Experience the Eastport Lifestyle in a Beautifully Rebuilt Home Don’t miss this exceptional opportunity — a previous contract fell through due to circumstances beyond the seller’s control, making this stunning Eastport home available once again. Completely gutted, expanded, and rebuilt in 2023, this residence seamlessly blends modern luxury with timeless charm. Every major system has been replaced, offering true peace of mind and move-in-ready living. The chef’s kitchen is a standout, featuring a 36-inch Bertazzoni range with gas burners and electric oven, custom hood, built-in refrigerator and dishwasher with cabinetry panels, and a wine refrigerator — all designed for a sleek, cohesive look and effortless entertaining. The main level offers an open family room and dining area with direct access to the rear deck and yard. A first-floor primary suite provides exceptional convenience and includes a spa-like bath with a walk-in shower. Upstairs are two generously sized bedrooms and a stylish full bath, also with a walk-in shower. The lower level adds flexible living space with a cozy wood-burning fireplace, workshop area, abundant storage, an additional refrigerator, and a triple-safe sump pump system. Outside, enjoy a large yard with access from both the front and rear streets, plus off-street parking in the rear. Architectural plans are available for a two-car garage or a garage with an accessory dwelling unit above (buyer to verify with the City of Annapolis regarding permits and approvals). Additional features include underground irrigation for the front yard and flower beds, as well as a fully encapsulated crawl space for enhanced comfort and efficiency. All major components — including roof, HVAC, mini-splits, plumbing, electrical, insulation, windows, doors, flooring, bathrooms, and appliances — were replaced in 2023. The home was taken down to the studs and a second level was added during the rebuild. Ideally located just moments from Eastport’s restaurants, shops, and downtown Annapolis. Appraisal in hand at $1,085,000.

Experience the Eastport Lifestyle in a Beautifully Rebuilt Home Don’t miss this exceptional opportunity — a previous contract fell through due to circumstances beyond the seller’s control, making this stunning Eastport home available once again. Completely gutted, expanded, and rebuilt in 2023, this residence seamlessly blends modern luxury with timeless charm. Every major system has been replaced, offering true peace of mind and move-in-ready living. The chef’s kitchen is a standout, featuring a 36-inch Bertazzoni range with gas burners and electric oven, custom hood, built-in refrigerator and dishwasher with cabinetry panels, and a wine refrigerator — all designed for a sleek, cohesive look and effortless entertaining. The main level offers an open family room and dining area with direct access to the rear deck and yard. A first-floor primary suite provides exceptional convenience and includes a spa-like bath with a walk-in shower. Upstairs are two generously sized bedrooms and a stylish full bath, also with a walk-in shower. The lower level adds flexible living space with a cozy wood-burning fireplace, workshop area, abundant storage, an additional refrigerator, and a triple-safe sump pump system. Outside, enjoy a large yard with access from both the front and rear streets, plus off-street parking in the rear. Architectural plans are available for a two-car garage or a garage with an accessory dwelling unit above (buyer to verify with the City of Annapolis regarding permits and approvals). Additional features include underground irrigation for the front yard and flower beds, as well as a fully encapsulated crawl space for enhanced comfort and efficiency. All major components — including roof, HVAC, mini-splits, plumbing, electrical, insulation, windows, doors, flooring, bathrooms, and appliances — were replaced in 2023. The home was taken down to the studs and a second level was added during the rebuild. Ideally located just moments from Eastport’s restaurants, shops, and downtown Annapolis. Appraisal in hand at $1,085,000.

1007 Park Ave, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: Northrop Realty.

$1,000,000

Open House Saturday 2-4PM & Sunday 12-2PM. Welcome to your own Eastport retreat, where the inviting outdoor living spaces set the stage for everything this exceptional home has to offer. Located within walking distance to waterfront restaurants, marinas & yacht clubs, the fully fenced backyard is perfect for entertaining, morning coffee, gathering with friends, or simply relaxing on warm summer evenings. Inside, this beautifully updated 4-bedroom, 3-bath home offers a versatile floor plan with two bedrooms and one full bath on the main level, plus two spacious upper-level bedrooms and two additional full baths. The thoughtfully curated design feels straight out of a Serena & Lily magazine, featuring designer lighting, stylish finishes, and a light, airy coastal aesthetic throughout. Additional highlights include a stone driveway/landing providing extra parking or flexible storage space. The unfinished basement offers exceptional storage for bikes, paddleboards, boating gear, lawn and garden equipment, or the potential to create a workshop, hobby room, or creative space tailored to your needs. Just moments from the heart of Eastport, this home delivers the perfect blend of coastal charm, comfort, and lifestyle in one of Annapolis’ most sought-after waterfront communities.

Open House Saturday 2-4PM & Sunday 12-2PM. Welcome to your own Eastport retreat, where the inviting outdoor living spaces set the stage for everything this exceptional home has to offer. Located within walking distance to waterfront restaurants, marinas & yacht clubs, the fully fenced backyard is perfect for entertaining, morning coffee, gathering with friends, or simply relaxing on warm summer evenings. Inside, this beautifully updated 4-bedroom, 3-bath home offers a versatile floor plan with two bedrooms and one full bath on the main level, plus two spacious upper-level bedrooms and two additional full baths. The thoughtfully curated design feels straight out of a Serena & Lily magazine, featuring designer lighting, stylish finishes, and a light, airy coastal aesthetic throughout. Additional highlights include a stone driveway/landing providing extra parking or flexible storage space. The unfinished basement offers exceptional storage for bikes, paddleboards, boating gear, lawn and garden equipment, or the potential to create a workshop, hobby room, or creative space tailored to your needs. Just moments from the heart of Eastport, this home delivers the perfect blend of coastal charm, comfort, and lifestyle in one of Annapolis’ most sought-after waterfront communities.

140 Jefferson St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Engel & Volkers Annapolis.

$900,000

Experience the pinnacle of Annapolis living in this expertly restored 1920s masterpiece. Situated in the sought-after Eastport peninsula, this residence offers a rare blend of historic charm and contemporary high-end luxury, boasting serene views of Back Creek and the Eastern Shore. The open concept interior is anchored by gleaming hardwood floors that transition seamlessly into a gourmet kitchen featuring premium stainless steel appliances and stunning Calcutta Gold countertops. The primary suite features soaring cathedral ceilings that create an expansive, sun-drenched atmosphere, which is complemented by a walk-in closet with views of the Creek and Shore. All systems have been replaced for total owner confidence: all-new plumbing, new electrical, and a high-efficiency HVAC system under warranty. The home features new windows and a new roof, with insulation brought entirely up to 2026 standards. This is more than a renovation; it is a total transformation that honors its 1920s roots while delivering the performance and luxury of a brand-new home, within walking distance to the local marinas and dining that define the Eastport lifestyle.

2 Beds ⋅ 2 Baths

Experience the pinnacle of Annapolis living in this expertly restored 1920s masterpiece. Situated in the sought-after Eastport peninsula, this residence offers a rare blend of historic charm and contemporary high-end luxury, boasting serene views of Back Creek and the Eastern Shore. The open concept interior is anchored by gleaming hardwood floors that transition seamlessly into a gourmet kitchen featuring premium stainless steel appliances and stunning Calcutta Gold countertops. The primary suite features soaring cathedral ceilings that create an expansive, sun-drenched atmosphere, which is complemented by a walk-in closet with views of the Creek and Shore. All systems have been replaced for total owner confidence: all-new plumbing, new electrical, and a high-efficiency HVAC system under warranty. The home features new windows and a new roof, with insulation brought entirely up to 2026 standards. This is more than a renovation; it is a total transformation that honors its 1920s roots while delivering the performance and luxury of a brand-new home, within walking distance to the local marinas and dining that define the Eastport lifestyle.

131 Eastern Ave, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$875,000

Brand New Construction Completed and ready for move in! Price reduction and the home is ready for its very first owner. Perfectly positioned in Eastport, Annapolis, just moments from downtown, this brand-new home places you in the heart of it all: boat shows, waterfront dinners, parades, morning coffee walks, and sunset strolls along the harbor. Leave the car behind and lean into the Annapolis lifestyle. Inside, the home blends modern design with thoughtful flexibility. With 5 bedrooms and 3 full baths, including two bedrooms on the main level, you have options, guest space, multigenerational living, or the ideal home office. Upstairs, the primary suite offers a private retreat with a walk-in shower, double-sink vanity, and elevated finishes. Two additional bedrooms share a well-appointed hall bath with a tub. Gold accents throughout the kitchen and bathrooms add warmth and character, while oak-toned flooring and windows on every side allow natural light to pour throughout the home. The kitchen is the centerpiece, expansive island, generous prep space, and seamless access to the backyard through sliding glass doors, with an additional rear entry for convenience. There is even potential for a deck installation prior to closing, offering flexibility for the next owner. Outdoor living is just as intentional. A rare front yard in Eastport is framed by a half fence and gate, while the fully fenced backyard creates a private setting for cookouts, gatherings, or quiet evenings at home. A welcoming front porch completes the picture. This is not just a new build. It is an opportunity to live fully connected to everything Annapolis has to offer, with the comfort of a rare brand-new construction.

5 Beds ⋅ 3 Baths

Brand New Construction Completed and ready for move in! Price reduction and the home is ready for its very first owner. Perfectly positioned in Eastport, Annapolis, just moments from downtown, this brand-new home places you in the heart of it all: boat shows, waterfront dinners, parades, morning coffee walks, and sunset strolls along the harbor. Leave the car behind and lean into the Annapolis lifestyle. Inside, the home blends modern design with thoughtful flexibility. With 5 bedrooms and 3 full baths, including two bedrooms on the main level, you have options, guest space, multigenerational living, or the ideal home office. Upstairs, the primary suite offers a private retreat with a walk-in shower, double-sink vanity, and elevated finishes. Two additional bedrooms share a well-appointed hall bath with a tub. Gold accents throughout the kitchen and bathrooms add warmth and character, while oak-toned flooring and windows on every side allow natural light to pour throughout the home. The kitchen is the centerpiece, expansive island, generous prep space, and seamless access to the backyard through sliding glass doors, with an additional rear entry for convenience. There is even potential for a deck installation prior to closing, offering flexibility for the next owner. Outdoor living is just as intentional. A rare front yard in Eastport is framed by a half fence and gate, while the fully fenced backyard creates a private setting for cookouts, gatherings, or quiet evenings at home. A welcoming front porch completes the picture. This is not just a new build. It is an opportunity to live fully connected to everything Annapolis has to offer, with the comfort of a rare brand-new construction.

148 Jefferson St, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Samson Properties.

$875,000

*** A must-see opportunity in the desirable Eastport Peninsula! This unique property features two attached dwellings in one, offering exceptional flexibility and income potential. The original dwelling, once a charming church, has been thoughtfully converted into a 2-bedroom, 1.5-bath home with an open-concept main level full of character and charm. The second dwelling, located at the rear, is a cozy cottage complete with 1 bedroom, loft, and kitchen —perfect for rental income, guests, or extended family. A truly special property with endless possibilities—don’t miss it!