Eastport Homes for Sale

Eastport Homes for Sale

Welcome to Eastport, a charming waterfront community nestled in the heart of Annapolis, Maryland. Known for its vibrant maritime culture, Eastport offers a unique blend of historic charm and modern convenience, making it an ideal place to call home. This picturesque neighborhood is bordered by the scenic waters of the Chesapeake Bay, providing residents with stunning views and easy access to boating, fishing, and other outdoor activities.

In Eastport, you'll find a variety of homes for sale that cater to diverse lifestyles. From quaint bungalows with character to contemporary waterfront properties boasting luxurious amenities, there’s something for everyone here. Many of the homes feature beautifully landscaped yards, inviting porches, and spacious interiors perfect for entertaining or relaxing with family. The community’s rich history is reflected in its architecture, with many homes dating back to the early 20th century, offering a glimpse into the area’s storied past.

Living in Eastport means embracing a vibrant community spirit. Residents enjoy a plethora of local shops, restaurants, and art galleries, all within walking distance. The annual Eastport-a-Rama festival and other community events foster a strong sense of belonging and celebration among neighbors.

With its prime location just minutes from downtown Annapolis, Eastport offers the perfect balance of tranquility and accessibility. Whether you’re drawn to the area for its stunning waterfront views, lively community, or the allure of historic homes, Eastport is a place where you can truly feel at home. Explore the homes for sale today and discover the charm of Eastport for yourself!

Newest Eastport Homes for Sale

$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:

$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:

$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:

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