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906 Creek Dr, Annapolis
$6,200,000
4 Beds ⋅ 4 Baths
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.

289 State St Unit 4, 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.

313 Washington St, Annapolis
$2,965,000
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:

Selling Office: Long & Foster Real Estate, Inc..

219 Lockwood Ct, Annapolis
$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:

Selling Office: Coldwell Banker Realty.

122 Chesapeake Ave, Annapolis
$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.

912 Windsor Ave, Annapolis
$2,000,000
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:

Selling Office: Coldwell Banker Realty.

400 Chesapeake Ave Unit 2-101, Annapolis
$1,915,000
3 Beds ⋅ 4 Baths
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:

Selling Office: Long & Foster Real Estate, Inc..

526 Sixth St, Annapolis
$1,900,500
3 Beds ⋅ 3 Baths
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:

Selling Office: Coldwell Banker Realty.

712 Chesapeake Ave, Annapolis
$1,600,000
4 Beds ⋅ 3 Baths
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:

Selling Office: Long & Foster Real Estate, Inc..

619 Second St, Annapolis
$1,449,000
4 Beds ⋅ 4 Baths
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:

Selling Office: Coldwell Banker Realty.

1035 Boucher Ave, Annapolis
$1,399,000
4 Beds ⋅ 4 Baths
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:

Selling Office: Coldwell Banker Realty.

417 Chesapeake Ave, Annapolis
$1,380,000
3 Beds ⋅ 3 Baths
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.

1109 Boucher Ave, Annapolis
$1,350,000
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:

Selling Office: Coldwell Banker Realty.

4 Kelly Ct, Annapolis
$1,250,000
3 Beds ⋅ 4 Baths
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.

140 Jefferson St, Annapolis
$1,000,000
4 Beds ⋅ 3 Baths
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.

131 Eastern Ave, Annapolis
$900,000
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.

148 Jefferson St, Annapolis
$875,000
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.

818 Boucher Ave, Annapolis
$870,000
2 Beds ⋅ 1 Baths
Welcome to 818 Boucher Avenue in coveted Eastport—an exceptional opportunity to create your dream home in one of Annapolis’ most sought-after waterfront communities. Perfectly positioned on a prime oversized corner lot, this property offers captivating water views and endless potential for transformation. Nestled in the heart of Eastport, known for its vibrant maritime culture and walkable charm, this property invites you to bring your vision to life. Whether you imagine a stunning modern retreat or a timeless coastal residence, the setting provides the ideal canvas. Enjoy serene mornings with glistening water vistas and evenings filled with Chesapeake Bay breezes. Just moments from downtown Annapolis, marinas, dining, and boutique shopping, this location blends convenience with the tranquility of waterfront living. Opportunities like this—a premium lot with views in such a desirable neighborhood—are rare. Unlock the potential. Build your dream. Live the Eastport lifestyle.

818 Boucher Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

1116 Bay Ridge Ave, Annapolis
$835,000
4 Beds ⋅ 3 Baths
**Driveway parking in rear off of Jackson St.** This beautifully reimagined residence at 1116 Bay Ridge Avenue offers a sophisticated blend of classic Annapolis charm and high-end modern luxury. Located in a prime Eastport location, this home has been meticulously updated with a focus on quality craftsmanship and professional-grade amenities. The inviting exterior is defined by expert hardscaping and a welcoming stone walkway leading to a wide, sun-drenched entry foyer. Inside, the open-concept main level features durable engineered white oak flooring and a seamless flow designed for both daily living and grand-scale entertaining. The heart of the home is the gourmet chef’s kitchen, anchored by a center island with pendant lighting and premium quartz countertops. Culinary enthusiasts will appreciate the suite of stainless JennAir appliances, including a 6-burner gas range with griddle, a commercial-quality range hood, and custom soft-close cabinetry. The kitchen transitions easily into a spacious dining area and a stately "drawing room" living space, accented by architectural details like arched doorways and custom trim. The upper level boasts four generously sized bedrooms, including two with soaring vaulted ceilings that enhance the sense of scale and light. Modern essentials are integrated throughout, including a high-efficiency tankless gas water heater, upgraded shingle roof (less than 10 years old), and a dedicated mudroom with built-in shelving. Outdoor living is equally impressive, with a private fenced patio, professional landscaping, and a front wrap-around porch perfect for enjoying the coastal breeze. For the modern homeowner, the property is wired for an EV charger and features a rare, expansive driveway with off-street parking for up to four vehicles—a premium find in this area. Situated just moments from the waterfront wonders of Quiet Waters Park and the vibrant dining and shopping scene of Eastport and historic Downtown Annapolis, this home offers the quintessential Annapolis lifestyle. Whether you are walking to local boutiques or exploring the nearby Chesapeake Bay, 1116 Bay Ridge Ave provides an unparalleled opportunity to own a move-in-ready masterpiece in one of the city’s most sought-after corridors.

1116 Bay Ridge Ave, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

513 Fifth St, Annapolis
$825,000
2 Beds ⋅ 1 Baths
An exceptional opportunity to embrace the coveted Eastport lifestyle while planning and permitting your future dream home. Situated on a generously sized lot in one of Annapolis' most desirable waterfront communities, this property offers the rare chance to move in, enjoy, and thoughtfully design your long-term vision. The existing home is a contributing structure within the Eastport Overlay District, helping preserve the neighborhood's distinctive character and charm while offering potential for substantial expansion. Buyers are encouraged to conduct their own due diligence regarding future improvements, additions, and permitting requirements. The home features solid bones, off-street parking, and endless possibilities for customization. Perfectly positioned just moments from Safe Harbor Marina, Annapolis Yacht Club, Eastport Yacht Club, Lewnes' Steakhouse, waterfront dining, shopping, and downtown Annapolis. Start enjoying everything Eastport has to offer this summer and create a legacy property in one of the Chesapeake Bay's most sought-after locations. *The second photo is an AI concept*

513 Fifth St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: TTR Sotheby's International Realty.

1107 Brashears St, Annapolis
$800,000
5 Beds ⋅ 2 Baths
Discover the perfect blend of Annapolis charm and contemporary luxury at 1107 Brashears Street in desirable Eastport. Meticulously transformed and fully remodeled, this truly turn-key home presents 5 bedrooms and 2 full baths. Upon arrival, an inviting screened-in front porch welcomes you into a residence created for comfort. The main level is designed for modern living and entertaining, featuring an open floor plan anchored by a gourmet kitchen boasting a large center island and quality, stylish finishes that ensure a fresh, modern aesthetic. The layout offers maximum convenience with a valuable main-level bedroom and full bath. The comprehensive renovation inside and out showcasing stylish design and quality finishes throughout. The property is further enhanced by an expansive backyard, creating an outdoor retreat for the whole family to enjoy. The large paver-patio with fire pit, is ideal for entertaining, and family dinners. This Eastport gem perfectly balances premium convenience with exceptional comfort. This is your opportunity to own a like-new home in a prime location.

1107 Brashears St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: Long & Foster Real Estate, Inc..

1100 Bay Ridge Ave, Annapolis
$780,000
3 Beds ⋅ 2 Baths
You’ve experienced Eastport. You’ve admired the effortless ease of its residents, and now you’re . Embrace that coveted, walkable, waterfront lifestyle. This enchanting, fully reimagined cottage offers it in abundance. Storybook curb appeal? Effortlessly. A seamless blend of timeless character and refined modern luxury? Absolutely. A short stroll to coffee, cocktails, and the beloved Eastport-A-Rockin’ Festival? Naturally. There is a reason the white picket fence endures as a symbol of the American dream. There is an undeniable allure to a home that feels as though it has been lifted from the pages of a classic novel. Set within Eastport’s sought-after Maritime District and enhanced by an owner’s discerning eye for elevated, thoughtfully curated finishes, this residence is as captivating as it is distinctive. Inside, graceful curved archways, authentic hardwood floors, and sophisticated lighting create an atmosphere of understated elegance. Custom tilework, a beautifully appointed kitchen with travertine flooring, and bathrooms adorned with refined marble surfaces reflect a commitment to quality and design. Coastal charm and contemporary sensibility are artfully balanced, resulting in a home that feels both timeless and impeccably current. Mornings unfold with quiet indulgence: a leisurely walk to Bakers & Co. for a chocolate almond croissant, followed by a scenic stroll to Oscar’s Coffee at Horn Point Marina. There, you linger over an iced coconut milk latte, exchanging greetings with neighbors before continuing on to Horn Point Park, where the shoreline invites both relaxation and play. Eastport’s celebrated dining scene may beckon, but today is reserved for hosting. Friends arrive via water taxi from the Historic District, and your home becomes the gathering place. With three bedrooms, two full baths, and a heated and air-conditioned sunroom that effortlessly transforms into a charming sleeping porch, every guest is welcomed in comfort. As evening settles in, conversation flows easily—perhaps around the fire pit beneath the stars, or within the enclosed rear sunroom, where sliding doors open wide to invite in music, laughter, and the gentle Chesapeake breeze. The following morning begins with a simple pleasure: a walk across the street to Diehl’s Produce for fresh, seasonal ingredients. Brunch is served in the formal dining room, where everyone gathers once more before heading to the marina for an afternoon sail. This is the essence of Eastport living—refined, relaxed, and richly rewarding. All that remains is your story.

1100 Bay Ridge Ave, Annapolis

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

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

422 First St, Annapolis
$780,000
2 Beds ⋅ 2 Baths
Welcome to Eastport—just steps from downtown Annapolis. This charming duplex with rare two-car off-street parking offers the perfect blend of convenience, and coastal living. Freshly painted throughout, this meticulously maintained two-bedroom, 1.5-bath home features numerous updates, including new hardwood flooring throughout, new windows in the living room and kitchen, a new wood-burning stove, and a new A/C heat pump—making it move in ready. A generous deep lot offers excellent potential for future rear additions and expanded living space providing the opportunity to truly make this home your own. Whether you're looking for a full-time residence or the perfect weekend getaway, this Eastport gem has it all. Ideally located near the waterfront, you’ll enjoy easy walking access to marinas, top-rated restaurants, pubs, swim clubs, sailing clubs, and boutique shopping. Don't miss this turnkey offering in a prime location.

422 First St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

152 Jefferson St, Annapolis
$750,000
4 Beds ⋅ 4 Baths
BEAUTIFULLY RENOVATED EASTPORT GEM with MODERN COASTAL FINISHES! Perfect for a Primary Residence, 2nd Home or Rental Investment! ABOUT THE HOME: 3 levels of luxury living featuring 4 Bedrooms and 3.5 Bathrooms. Open-concept main level with New Hickory hardwood floors and designer lighting throughout. THE GOURMET KITCHEN: Custom white Shaker cabinetry, modern black hardware, Quartz countertops, oversized center island, and premium stainless appliances with gas cooking. THE PRIMARY SUITE: A rare main-level primary retreat with walk-in closet and spa-like bath featuring custom tile work and glass-enclosed shower. THE FLEXIBLE LOWER LEVEL: Fully finished walk-up basement with a 4th bedroom/office, family room with wood accent wall, and a custom full bath—perfect for a guest or in-law suite. THE EXTERIOR: Iconic white picket fence in front, with cozy front porch, and a private rear yard with beautiful wood privacy fence is expanded by an additional 736 SF (included in sale). New Black Andersen 100 series windows, Hardie Plank siding, and new hardscaped paths. PARKING: Private driveway with 4 off-street parking spaces. LOCATION: Unbeatable walkability to Downtown Annapolis, Maritime activities, and local favorites. See Annapolis City site for details on the Eastport Choice Neighborhood Initiative! Enjoy all that Eastport has to Offer! Don't Let This One Get Away! Make your Appointment Today! Active Ring Camera on Property.

152 Jefferson St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: RE/MAX Leading Edge.

1105 Van Buren St, Annapolis
$660,000
3 Beds ⋅ 2 Baths
Offer deadline Monday 27th at 5:00PM Seller reserves right to accept offer at anytime. Welcome to Colony Hills, one of Eastport's most coveted neighborhoods, where charm, convenience, and community come together with no HOA. This exceptionally stylish Cape Cod is full of character and timeless appeal, offering thoughtfully updated spaces inside and incredible outdoor living areas you'll enjoy year round. Step inside to discover a freshly painted interior accented by beautiful hardwood floors throughout the main level. Natural light pours into two inviting living spaces, creating a warm and welcoming atmosphere. The dining room is perfect for intimate dinners or entertaining family and friends and features two charming built ins that add both character and functionality. The beautifully updated kitchen is designed for gathering, complete with updated countertops, a large center island, stainless steel appliances, gas cooking, and exposed beams that create the perfect blend of warmth and style. Just beyond the kitchen, a spacious rear family room provides even more room to relax or entertain. The main level also features a generously sized bedroom and full bathroom, making it ideal for guests or flexible living. The bedroom offers two closets, including a unique bonus space that could easily serve as a small workshop, craft room, or creative studio. A full laundry room provides excellent storage and everyday convenience. Upstairs, you'll find the private primary suite and an updated bathroom, along with an additional bedroom. Charming nooks and architectural details throughout the upper level add to the home's undeniable character. The outdoor spaces truly set this home apart. Relax in the three season porch, soak in the brand new, top tier, hot tub on the expansive new Trex deck, or gather around the fire pit on crisp fall evenings, all with a fully fenced yard. Whether you're hosting friends or enjoying a quiet night at home, this backyard was designed for making memories. Don't miss the large shed, great for storing lawn and gardening equipment. Parking is a breeze with the large concrete driveway. Living in Colony Hills means you're just a short stroll to Eastport favorites like Vin 909, Adam's on Fourth, and Sammy's Italian Kitchen, or a quick bike ride to Historic Downtown Annapolis, Quiet Waters Park, and the Pip Moyer Recreation Center. Commuters will appreciate easy access to the U.S. Naval Academy, NSA Annapolis, Fort Meade, Baltimore, Washington, D.C., and BWI Airport. This is Eastport living at its finest. Don't miss your opportunity to call this special home your own, schedule your private showing today! *Updates include: Finished three season room/side porch (2025), Deck (2025), Hot Tub (2025), HVAC (2023), Crawl Space Encapsulation/Sump Pump/Dehumidifer (2023), Fence (2022), Roof/Siding/Windows (2021), Plantation Shutters (2021)

1105 Van Buren St, Annapolis

Listing courtesy of Compass. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty - OP.

7056 Bembe Beach Rd, Annapolis
$655,000
3 Beds ⋅ 3 Baths
Escape to coastal serenity at 7056 Bembe Beach Road, a beautifully maintained rancher offering the perfect blend of quiet, private living and premier access to the Annapolis waterfront. This immaculate, turn-key home is situated just a block from the water, providing a seamless transition from your front door to the shores of the Chesapeake. This residence is thoughtfully designed for comfort and longevity, featuring true Single-Level Living: The main floor hosts three spacious bedrooms, including a primary suite, two full baths, and a convenient laundry room. A versatile lower level offers a third full bath and ample space for a potential fourth bedroom, home office, or recreation area. Equipped with a Geothermal heating system and a brand-new roof featuring a 50-year transferable warranty for ultimate peace of mind. A stunning, large screened-in back porch comes complete with removable vinyl panels and a wood stove, transforming it into a cozy four-season retreat. The property is set on a sprawling landscaped yard that emphasizes privacy and peace. The large, lush yard offers plenty of room for gardening, entertaining, or simply enjoying the quiet neighborhood atmosphere. A high-quality, custom-built shed provides extra storage or a workshop space. Located in one of Annapolis's most sought-after pockets, you are surrounded by natural beauty and local favorites but you still enjoy the modern convenience of being on public water and sewer. Just a short walk to the new public Annapolis Carrs Beach and a single block from the water. Moments away from the Annapolis Maritime Museum & Park, a 12-acre waterfront "Park Campus" featuring hiking trails and public paddle-craft launches. Experience world-class boating facilities at Safe Harbor Port Annapolis and enjoy artisanal treats at the Black Market Bakers (formerly Black Market Cafe). A quick drive or bike ride connects you to local favorites like Annapolis Smokehouse & Tavern and the scenic Quiet Waters Park.

7056 Bembe Beach Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

1014 Van Buren St, Annapolis
$625,000
4 Beds ⋅ 2 Baths
Are you searching for the perfect home in Eastport, with a first-floor primary bedroom and a huge backyard? Look no further! This gorgeous Cape Cod, nestled in the sought-after Colony Hills community, has been lovingly restored, remodeled, and thoughtfully updated—and is truly move-in ready. Beautiful hardwood floors add warmth and character to the bright, airy interior, while the full basement provides plenty of additional space for storage. Outside, enjoy the spacious backyard and charming gazebo—perfect for relaxing, entertaining, or enjoying the Eastport lifestyle. The roof was replaced in 2017, offering added peace of mind. Ideally located near Eastport’s shops, restaurants, marinas, and waterfront attractions, with easy access to historic downtown Annapolis and major commuter and bus routes. Don’t miss your opportunity to make this wonderful Eastport home your own. **Schedule your showing today—this one won’t last long!

1014 Van Buren St, Annapolis

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

Selling Office: Compass.

1019 President St, Annapolis
$365,000
3 Beds ⋅ 2 Baths
* Price Drop! Don't miss out on this beautiful fully updated Eastport home for less than $400k! * Welcome to 1019 President St in the heart of Eastport—where charm, space, and modern upgrades come together just minutes from the water and Historic Annapolis. This beautifully renovated 3-bedroom, 2-bath home offers a rare combination of cozy living and exceptional outdoor space. Situated on an oversized lot with a classic white picket fence, the property features a huge yard, private parking for 4+ vehicles (a true rarity here), a welcoming front porch, and a spacious back patio—perfect for entertaining, relaxing, or simply enjoying the space that sets this home apart. Inside, the home has been completely transformed with top-to-bottom upgrades, including brand new central HVAC system, complete electric upgrades, new flooring throughout, a stunning modern kitchen with high-end finishes and appliances, and beautifully designed bathrooms. Natural light pours in on every level, highlighting the clean, fresh finishes, generous closet space, and an easy, functional layout. Located just a short walk to the water, nearby parks, and everything Eastport is known for—and only minutes to downtown Annapolis—this home offers a lifestyle that’s hard to match, blending comfort, convenience, and a truly standout setting.

1019 President St, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact:

Selling Office: Monument Sotheby's International Realty.

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