Refine Search
Map
Sort by
$1,595,000
4 Beds ⋅ 5 Baths
COMING SOON - expected on the market September 30th. Attractive Lower Eastport opportunity: beautifully updated, semi-detached home with a fully fenced backyard and detached cottage with proven rental income. Enjoy the charm and walkability of Lower Eastport from this thoughtfully updated 2007-built home on a peaceful, tree-lined street just two blocks from the harbor and close to parks, restaurants, shops and the waterfront. The property offers over 3000 square feet of living space between the main house and the cottage. Two dwellings make up a unique configuration that allows an exceptional degree of flexibility and privacy. Enter the main residence through a classic Eastport front porch, perfect for rocking chairs and enjoying views of the tree-lined street. The home features three bedrooms and three-and-a-half baths, a separate dining room, and an open kitchen adjoining a spacious living room. Sliding doors extend the living space to a covered porch overlooking the fenced backyard. Upstairs, the spacious primary suite overlooks the backyard and features a large walk-in closet and adjoining newly renovated bath. A second bedroom with its own hall bath provides privacy for family or guests. Custom plantation shutters throughout the main and top floors add a polished finish and privacy. About 800 square feet of living space on the lower level is currently configured as a family/TV room and third bedroom. Also downstairs are a full bath, laundry, and several storage spaces. This area can be accessed from the interior well as from its own door to the back yard, which allows for added privacy. At the rear of the property is the true standout: a stand-alone 670 square feet, one bedroom, one bath cottage licensed for full-time rental use. Extensively renovated in 2025, the cottage features LVP flooring, kitchen cabinetry, full-size appliances and an updated bathroom. Recently rented for $2,935 per month and garnering more than $35,000 annually, the cottage will be vacant at closing, giving the next owner the flexibility to rent it, use it for family or guests, create a private home office, or accommodate multigenerational living. The current owners have invested more than $100,000 in a property refresh over the past 18 months including new and updated baths; the cottage remodel; extensive electrical, lighting, and hardware upgrades; replacement A/C; interior and exterior painting; and landscaping. Ample street parking, with no parking fees for visitors, is available at this quiet residential end of Eastport. The property’s location between First and Second Streets is approximately two blocks from both Horn Point and Spa Creek. This offers the best of the neighborhood’s relaxed waterfront lifestyle while also remaining close to some of the best restaurants in Annapolis and just over the bridge from downtown Annapolis. This attractively updated Eastport home, complemented by a rentable cottage, presents a unique and appealing opportunity in one of Annapolis’s most popular neighborhoods.

123 Chesapeake Ave, Annapolis

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

$765,000
2 Beds ⋅ 2 Baths
Welcome to 312 Severn Avenue, Unit W308—a rarely available two-story, two-bedroom, two-bath condominium at The Tecumseh, one of Eastport’s most distinctive waterfront communities. Located on the third floor, this approximately 1,390-square-foot residence offers a unique two-level layout with plenty of opportunity to make it your own. The entry level features a welcoming foyer and a spacious bedroom with an en-suite bath. The lower level includes a second bedroom and full bath, kitchen, and a generous living and dining area with a wood-burning fireplace and access to a private balcony with beautiful views of downtown Annapolis, Spa Creek, and portion of the Naval Academy campus. While there is currently no washer and dryer within the unit, one can easily be added, and a community laundry room is conveniently located just down the hall. Set directly along Spa Creek, The Tecumseh offers a 72-slip private marina, waterfront swimming pool and deck, gated private parking, lobby, mailroom, conference room, and an on-site property manager. For the boater, ownership of W308 also includes an entitlement to a 29-foot boat slip. What truly sets this property apart is the lifestyle. Step outside and you’re moments from the water, just steps from Eastport’s Restaurant Row, and an easy walk across the bridge to downtown Annapolis. Rarely available, W308 presents a special opportunity to create your own home within a waterfront community cherished for its location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

312 Severn Unit W308, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$895,000
2 Beds ⋅ 3 Baths
Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 2-bedroom, 2.5-bathroom penthouse condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas, enhanced by a stunning spiral staircase that adds a touch of architectural flair. The living area is accentuated by cathedral ceilings. Natural light floods the space through skylights, creating an inviting atmosphere throughout. The flat was entirely upgraded by an interior design firm in 2024, featuring gleaming living room floors, new windows and a gourmet kitchen designed to elevate your culinary creations. This penthouse features an abundance of chic finishes including Spa-inspired luxury bathrooms. Of particular note is the upper level Master suite artfully designed and fashioned from what was a large open balcony. It features a private and cozy retreat with a luxurious ensuite bathroom. A home office has been thoughtfully designed with elegant built ins on the upper level. The main floor bedroom also offers ample space and privacy, making it ideal for guests. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the property offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

8 Spa Creek Lndg Unit A3, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$525,000
1 Beds ⋅ 2 Baths
Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 1-bedroom, 1.5-bathroom second floor condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas. Natural morning light floods the space through the kitchen creating an inviting atmosphere throughout. The flat has an upgraded refrigerator, new microwave, new washer&dryer, HVAC, heat pump and air handler all in aprox 2024. The home features gleaming living room floors, and a gourmet kitchen designed to elevate your culinary creations. The bedroom suite is a private and cozy retreat with a luxurious ensuite bathroom. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the community offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

13 Spa Creek Lndg Unit A2, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$1,395,000
4 Beds ⋅ 5 Baths
Highly desirable Eastport location—just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main‑level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage—ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

1030 Boucher Ave, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$995,000
2 Beds ⋅ 2 Baths
Highly Desirable Eastport Peninsula! Experience the best of the Eastport lifestyle in this charming home, ideally located in the heart of the peninsula. Relax on the inviting front porch and watch the world go by, or step out your door and walk to Eastport’s renowned restaurants, lively bars, boutique shopping, marinas, yacht clubs, and the water taxi to historic downtown Annapolis. Inside, beautiful heart pine floors add warmth and character. The spacious rear yard is a rare find in Eastport and offers plenty of room for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. The chef’s kitchen features Viking refrigerator and stainless steel appliances, creating a wonderful space for both everyday cooking and entertaining. Thoughtful improvements and major updates throughout the years make this home truly move-in ready while still offering the opportunity to add your own personal touches. Notable improvements include: * Pella rear sliding glass door — 2025 * Carrier first-floor HVAC — 2025 * Washer & dryer — 2024 * Viking refrigerator — 2024 * New roof — 2023 * First-floor bathroom remodeled — 2018 * Front porch replaced and metal roof added — 2018 * First-floor floors and stairs refinished by Beers — 2017 * Rinnai tankless water heater — 2016 * Upstairs bathroom and closet remodeled by Gate One Builders — 2011 * HardiePlank siding — 2009 * Fence — 2005 * Brick foundation repointed — 2004 * Shed — 2003 * Renovation and rear addition — 1998 A wonderful opportunity to own a piece of Eastport—move right in, enjoy the lifestyle, and make it your own.

412 Third St, Annapolis

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

$1,900,000
4 Beds ⋅ 4 Baths
***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

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

$750,000
3 Beds ⋅ 3 Baths
RARE OPPORTUNITY! TWO HOMES ON ONE LOT IN EASTPORT! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shops, waterfront, and attractions of Eastport and Downtown Annapolis, this property puts you close to everything while offering the flexibility of two separate living spaces. Notable recent improvements include: New roof and skylights (2023) New driveway (2022) Guest house electrical wiring (2022) New dishwasher (2024) Two homes. One lot. Endless possibilities. A unique opportunity in a highly desirable Annapolis location!

906 Jackson St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$1,875,000
4 Beds ⋅ 5 Baths
There is something unmistakably special about life in Eastport—and 820 Bay Ridge Ave captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence offers more than 4,000 square feet of sophisticated living across four beautifully finished levels, combining timeless architecture, thoughtful customization, and an effortless coastal sensibility just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and gracious brick front porch create a picture-perfect welcome. Inside, rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters establish a refined yet relaxed atmosphere. Unlike many homes in the community, this residence was thoughtfully customized during construction with numerous builder upgrades, enhanced electrical features, and details designed to improve both everyday living and long-term functionality. At the heart of the home, the beautifully appointed kitchen features honed granite countertops, premium appliances, abundant cabinetry, and a generous center island that opens seamlessly to the family room and its upgraded gas fireplace. The formal dining room, illuminated by a striking chandelier, is made for memorable dinners, while the adjoining sitting room or study is equally suited to a favorite book, working from home, or an evening bourbon. Outdoor living is woven beautifully into the home. Enjoy coffee on the charming front porch overlooking the flower garden, dinner in the private English courtyard, or cocktails on the second-floor terrace. Ceiling fans enhance both outdoor spaces, while a dedicated natural gas line makes grilling effortless and provides the opportunity for a future fire feature. Professionally enhanced landscaping and a thoughtfully improved yard complete this private outdoor retreat. The primary suite is serene and exceptionally spacious, with a custom walk-in closet, spa-inspired bath, and expansive private sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft provides additional inviting spaces for a home office, fitness studio, media room, and guest retreat. The finished lower level adds a large family room and full bath, creating remarkable flexibility for entertaining, overnight guests, or multigenerational living. The home was also designed with the future in mind, with a framed elevator shaft allowing for the addition of an elevator without compromising its architecture or thoughtful floor plan. And then there is the location. This is the kind of Annapolis address where so much of daily life can happen on foot. St. Mary’s School, City Dock, neighborhood cafés, restaurants, boutiques and shopping are all within walking distance, as are the Annapolis Yacht Club and Eastport Yacht Club. Stroll to Eastport’s waterfront restaurants and marinas, cross the Spa Creek Drawbridge into Historic Downtown Annapolis, or take the water taxi home after an evening downtown. The United States Naval Academy, galleries, parks, sailing, and the unmistakable energy of the Chesapeake are all part of the lifestyle. Morning coffee at a neighborhood café. An afternoon on the water. Dinner in Eastport. A walk across the bridge for ice cream at City Dock. School, sailing, dining, shopping and downtown Annapolis—all without having to get in the car. This is polished Eastport living at its best: gracious but never fussy, luxurious yet wonderfully livable, and perfectly positioned to enjoy one of Annapolis’ most sought-after neighborhoods. With more than 4,000 square feet, four finished levels, exceptional outdoor spaces, extensive custom upgrades, future elevator capability, and an enviable Sailor’s Quay address, 820 Bay Ridge Ave offers a rare opportunity to enjoy Annapolis exactly as it was meant to be lived.

820 Bay Ridge Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$575,000
3 Beds ⋅ 2 Baths
There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

1309 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$599,900
3 Beds ⋅ 1 Baths
Open House 10/11/26, 1 PM to 3 PM. Eastport! Eastport! Eastport! Corner lot that consists of 9,240 square feet. Off street parking and street parking. Stainless steel refrigerator, stacked washer and dryer, storage in lower level off kitchen. New 10 foot by 15 foot shed. Separate dining room. Back porch is 21 feet by 7 feet. Partially fenced back yard. Upstairs bedroom has unique wood ceiling. Freshly painted living room, 2 bedrooms, and dining room. Lot has room for expansion. Close to downtown, Quiet Waters Park, and Eastport Shopping Center. Easy access to main streets.

1311 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$325,000
2 Beds ⋅ 2 Baths
Fee-simple living in the Eastport area, minutes from downtown Annapolis — for less than a citywide condo. This bright, easy-living two-bedroom, two-full-bath home sits on its own 0.08-acre lot — no condo fee, no HOA — and features a new roof. The primary suite opens through full-size sliding glass doors straight onto a private patio and backyard, while the kitchen draws light from two exposures plus a skylight, with a pass-through eat-in counter perfect for morning coffee. A dedicated laundry center and off-street parking pad add everyday ease. Out back, a shed provides real storage for bikes, tools, and seasonal gear. Convenient to downtown Annapolis and the Eastport area's restaurants. Vacant and easy to show. Photos have been virtually staged. Open house Saturday and Sunday, 2–4 PM.

1136 Tyler Ave, Annapolis

Listing courtesy of Engel & Volkers Washington, DC. Contact:

$700,000
6 Beds ⋅ 3 Baths
Welcome to 1025 Hanson Street, offering nearly 2,880 sq. ft. of exceptionally flexible living space across three finished levels in the heart of Annapolis! Perfect for a multi-generational family. Thoughtfully improved and meticulously maintained, this turn-key home provides a rare combination of space, versatility, parking and major system upgrades. The main and upper levels feature 4 bedrooms, a full bath, a bright and open living area, an updated kitchen with granite countertops and tile backsplash, and dedicated laundry with front-loading washer and dryer, utility sink and additional storage. The fully finished ground level creates an incredible second living space featuring 2 additional bedrooms, a den/office, full bath, stunning secondary kitchen (minus stove/oven) with granite countertops, stainless steel appliances and tile backsplash, a second laundry setup with utility sink, and new LVP flooring throughout. A private side entrance, new fencing, paver walkway and patio access provide tremendous flexibility for multi-generational living, extended guests, a home office setup or simply additional space to spread out. Outside, you'll find features that are especially hard to come by in Annapolis—including dual driveways with parking for 6+ vehicles and/or boats, along with a two-story detached shed offering excellent storage and convenient yard and street access. Extensive improvements provide peace of mind, including a NEW 2025 roof on both the home and shed with transferable warranty, updated HVAC including heat pump and indoor coil, 60-gallon hybrid high-efficiency water heater, 200-amp electrical service, Tesla EV charger, French drain and stormwater management system, sump pump, updated attic insulation with spray foam, Nest thermostats, updated siding, additional ground-level egress, ceiling fans, fresh paint and much more. With three finished levels, two distinct living areas, exceptional parking and storage, and numerous major capital improvements already completed, 1025 Hanson Street offers the kind of versatility that's difficult to find in Annapolis. Whether you're looking for room for a growing household, multi-generational living, extended guests, midshipman sponsor hosting, or simply a home that provides plenty of space to live, work and entertain—this one is a 10/10!

1025 Hanson St, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

$1,875,000
6 Beds ⋅ 5 Baths
** Private first-look appointments are available. Contact the listing agent to schedule for a first-look. ** A rare find in Eastport: an oversized attached two-car garage, plus a driveway and additional off-street parking, in a walkable waterfront neighborhood where garages are hard to come by. Beyond the striking exterior is a brand-new, ground-up home spanning three expansive levels, featuring 6 bedrooms, 4.5 baths, a chef-inspired kitchen with an oversized island and walk-in pantry, a main-level bedroom, an impressive primary suite, upper-level laundry, and a third-floor loft ideal for an office, guest space, or studio. Outside, enjoy a fully fenced yard, patio, and covered front porch — all just a short walk from Eastport’s marinas, restaurants, waterfront lifestyle, and downtown Annapolis.

914 Van Buren St, Annapolis

Listing courtesy of Realty ONE Group Capital. Contact:

$750,000
3 Beds ⋅ 3 Baths
Welcome to Eastport. This three-bedroom and three-full-bath home, plus a lower-level den that easily serves as an on-suite; is a beautifully maintained, turn-key home offering over 2,000 square feet of fully finished living space. Originally transformed during a massive, studs-out 2017 remodel, this home offers ultimate peace of mind with entirely replaced core systems and premium finishes throughout. The chef’s kitchen is fully equipped with Saint Cecilia granite counter tops, an expansive island breakfast bar, premium stainless steel appliances, a mosaic tile back splash, and soft-close cabinetry. The open floor plan main level also includes 2 bedrooms and a full bathroom. Upstairs, a massive second-story addition houses a luxurious primary suite with a custom glass shower, a walk-in closet, and a sitting area. The lower level offers a family room with a storage area and a "DEN" with a full bath. No detail was spared in the renovation, which features gleaming new hardwood floors, energy-efficient double-pane tilt-in windows, and updated insulation. Enjoy worry-free living with a comprehensive HVAC setup including a gas furnace and central A/C, updated plumbing, new electrical panels, a new water heater, and a fully integrated, code-compliant interior fire sprinkler system. The exterior shines with architectural roof shingles, low-maintenance vinyl siding, new gutters, and a spacious gravel driveway. Outside, enjoy outdoor entertaining in the fully fenced, private backyard. Perfectly situated moments from historic downtown Annapolis, Eastport restaurants, and local waterways. Move right in and enjoy seamless coastal living!

907 Monroe St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

$749,999
3 Beds ⋅ 4 Baths
Welcome to this beautifully maintained townhome in Eastport’s sought-after Boucher Place community, where timeless design meets effortless, low-maintenance living. Built in 2013 and offering nearly 1,800 square feet of thoughtfully designed space, this home is tailored for both relaxing everyday comfort and vibrant entertaining. At the center of the main level is a bright, open kitchen anchored by a large island with seating. It seamlessly connects to a living space centered around a cozy gas fireplace, creating a warm, natural gathering spot for guests. Enjoy meals in the adjacent dining area, or step outside into your private outdoor oasis—a freshly landscaped rear patio lit by charming bistro lights, perfect for al fresco dining and evening relaxation. Rich hardwood floors run throughout the main living level, while brand-new carpet (2026) adds plush comfort upstairs. Coupled with fresh neutral interior paint (2026), the entire home delivers a crisp, move-in-ready feel. The upper two levels feature three generously sized bedrooms, highlighted by a serene primary suite complete with a walk-in closet and an en-suite bath featuring a deep soaking tub and separate walk-in shower. A dedicated second-floor laundry room adds essential daily convenience. For a true outdoor highlight, head up to the private rooftop deck- an ideal retreat for morning coffee or sunset drinks. Thoughtful exterior details and community perks make daily life a breeze. Practical highlights include a detached two-car garage with rear entry and a paved driveway, while a spacious community green sits just steps from your front door. The low-maintenance Boucher Place HOA covers lawn care, snow removal, and exterior building insurance for true lock-and-leave ease. Ideally located within walking distance of vibrant downtown shops, dining, and waterfront attractions, this exceptional Eastport property allows you to spend less time on upkeep and more time enjoying coastal living.

21 Boucher Pl, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$699,000
2 Beds ⋅ 2 Baths
Enjoy show-stopping sunsets and fabulous waterfront views of Spa Creek from this stunning condominium in the highly sought-after Shearwater complex in Eastport. This contemporary 2 bedroom condo is located on the second floor of building 6. From your private balcony, witness herons, egrets, ducks, and even the bald eagle in this bird and nature watchers’ paradise. Your view will feature a green valley that ends at the lagoon that leads directly to Spa Creek. In December, celebrate the famous EYC annual Parade of Lights in style by your wood-burning fireplace and in Spring/Summer enjoy the easy breeze with family and friends . The private community marina just steps away from your home, is the perfect place to dock your boat and store your kayak . It offers seamless access to Spa Creek, the Chesapeake Bay and beyond. Your luxury lifestyle also includes the choice to relax poolside, play tennis/pickleball on the courts, walk to town or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis waterfront dream has come true!

6 Spa Creek Lndg Unit B2, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$1,250,000
3 Beds ⋅ 3 Baths
Nestled in the heart of Eastport, this thoughtfully designed 3-bedroom, 2.5-bath home offers the perfect combination of comfortable living, modern updates, and one of Annapolis' most sought-after walkable locations. Complete with a rare detached two-car garage, this is an exceptional opportunity to enjoy the Eastport lifestyle in an established neighborhood that continues to attract significant investment and enduring demand. The main level features hardwood flooring throughout, a spacious living room, separate dining room, and an inviting family room with a wood-burning fireplace that opens directly to the kitchen—creating an ideal space for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, a gas cooktop, and a separate main-level laundry/mudroom for added convenience. A spacious three-season porch extends the living space and creates a wonderful transition to the beautifully landscaped backyard, complete with a flagstone patio, attractive stone retaining wall, and detached two-car garage—ideal for relaxing or entertaining. Upstairs, the spacious primary suite offers a walk-in closet and private bath, along with two additional bedrooms and a full bathroom. The unfinished lower level provides abundant storage, a dedicated workshop area, and exterior access to the rear yard. Recent improvements include a new HVAC system (2024), newer garage doors, and a low-maintenance composite front porch. Step outside and enjoy everything that makes Eastport one of the most desirable waterfront communities in the region. Walk or bike to neighborhood restaurants, coffee shops, marinas, the Annapolis Athletic Club, Spa Creek, multiple yacht clubs, and Historic Downtown Annapolis via the Eastport Bridge. Hop aboard the Water Taxi, spend afternoons on the waterfront, or simply enjoy the vibrant coastal lifestyle that surrounds you. Opportunities to purchase in established Eastport neighborhoods continue to become more limited as significant investment and redevelopment enhance the surrounding area. Whether you're looking for a wonderful place to call home or a long-term investment in one of Annapolis' most coveted communities, 1105 Boucher Avenue offers both lifestyle and lasting value.

1105 Boucher Ave, Annapolis

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

$1,750,000
4 Beds ⋅ 4 Baths
Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. This was a complete remodel in 2012! Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home, complete with a striking marble center island, black granite countertops, stainless steel appliances, a pantry, and an expansive dining area that seamlessly flows into the inviting living room. The main-level primary suite is a true retreat with a spa-inspired bath featuring a soaking tub, walk-in shower, and generous walk-in closet. Upstairs, you'll find two large bedrooms, that share a full bath and an additional bedroom with its own private full bath, and a versatile sun-drenched sitting area with a dramatic vaulted ceiling. The walk-out lower level includes a full bath and versatile space to suit your lifestyle. Outside, a private rear deck perfect for relaxing or entertaining and charming stone walkways and welcoming front porch add historic like charm. A private driveway is for convenient off-street parking, and a storage shed is perfect to house all of your outdoor needs. Ideally located within walking distance of historic downtown Annapolis, you'll enjoy easy access to waterfront dining, boutique shopping, historic landmarks, entertainment, and all the vibrant attractions this sought-after area has to offer. The Eastport lifestyle truly one of a kind!

219 Lockwood Ct, Annapolis

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

$565,000
3 Beds ⋅ 3 Baths
Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath residence offers approximately 1,600 finished square feet across two levels, combining a functional layout with quality finishes and extensive upgrades throughout. The main level features a bright living room and an updated kitchen with quartz countertops, shaker cabinetry, stainless steel appliances, and a dining area. A main-level bedroom and full bath provide flexibility for guests or a home office. A dedicated laundry and utility space leads to the rear addition, where the private primary suite includes vaulted ceilings, a walk-in closet, and an en-suite bath with double vanities, custom tile, and a walk-in shower. The upper level offers a finished attic suite with a third bedroom, full bath, and bonus flex space suitable for an office or additional living area. Interior features include durable flooring, recessed lighting, and a cohesive, modern design. Exterior highlights include a fully fenced backyard with new sod and a concrete patio, ideal for outdoor enjoyment. The property also features professional landscaping, a new asphalt driveway for off-street parking, and durable exterior materials including Hardie Plank siding, Andersen 200 Series windows, and a new architectural shingle roof. Major system upgrades include 200-amp electric service, new plumbing, dual-zone HVAC, and a whole-house sprinkler system. Conveniently located near restaurants, marinas, parks, downtown Annapolis, and Truxton Park.

1210 President St, Annapolis

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

$4,500,000
5 Beds ⋅ 4 Baths
There are places where you visit the water, and there are places where the water becomes part of your everyday life. Perfectly positioned along the shores of Spa Creek in the heart of Eastport, this exceptional waterfront residence offers a front-row seat to one of Annapolis' most coveted lifestyles. Imagine stepping from your back door onto your private pier, casting off for an evening cruise, a sunset sail, or a waterfront dinner in Annapolis Harbor just minutes away. Paddleboards and kayaks launch effortlessly from the floating dock, while the protected waters of Spa Creek become your backyard playground. Life here unfolds both on and off the water. Mornings begin with coffee on the balcony overlooking the creek as the masts in Annapolis Harbor come to life. Afternoons are spent entertaining friends across multiple waterfront terraces, watching sailboats glide past and city lights reflect across the water. Evenings conclude with a short stroll to Eastport's restaurants, marinas, yacht clubs, and waterfront gathering spots. Thoughtfully rebuilt and extensively updated, the home blends timeless craftsmanship with sophisticated coastal living. Wide-plank white oak flooring, custom millwork, designer finishes, and walls of glass frame breathtaking views from nearly every room. The open-concept living spaces flow seamlessly to the waterfront, creating an ideal setting for both intimate gatherings and large-scale entertaining. With a private 40-foot pier, 12,500-pound boat lift, floating dock, and direct access to the Chesapeake Bay, this is more than a waterfront home—it is an opportunity to embrace the Eastport lifestyle that draws people from around the world to Annapolis, . Properties that combine protected deep-water access, exceptional views, and walkability to Downtown Annapolis rarely become available. This is a home best experienced from the waterfront, where the views, the setting, and the lifestyle speak for themselves.

217 Lockwood Ct, Annapolis

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

$995,000
4 Beds ⋅ 4 Baths
Welcome to Eastport Estates at Griscom Square, a brand-new construction community of just 11 luxury single-family homes, located within one mile of downtown Eastport! Each residence showcases high-end finishes, spacious open-concept layouts, 9-foot ceilings, 4-5 Bedrooms, gourmet kitchen, modern baths, 2-car garages with private parking, and quality craftsmanship throughout, creating a truly well-built home. Inspired by its coastal setting, each home incorporates light-filled spaces and design elements that reflect Eastport’s nautical character. Enjoy effortless access to Eastport’s vibrant waterfront dining, live music, local marinas, yacht clubs, and scenic sunset views - or bike to or take the water taxi to City Dock, downtown Annapolis, and the United States Naval Academy. Luxury, lifestyle, and location - together in one place. This is a rare opportunity to build your own home this close to town. Lot and model options available!

105 Griscom Square Way, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: