Eastport Real Estate

Eastport Real Estate

Welcome to Eastport, a charming and vibrant subdivision nestled in the heart of Annapolis, Maryland. Known for its rich maritime heritage and picturesque waterfront views, Eastport offers a unique blend of coastal living and urban convenience. This historic neighborhood is situated just across the bridge from downtown Annapolis, making it an ideal location for those who appreciate the charm of a small town while still enjoying easy access to the bustling city life.

Eastport is renowned for its friendly community spirit and picturesque streets lined with beautifully maintained homes, many of which showcase stunning views of the Chesapeake Bay. Residents take pride in their neighborhood, where a mix of historic homes and modern architecture creates a delightful tapestry of styles. The area is perfect for families, young professionals, and retirees alike, offering a welcoming atmosphere for all.

One of Eastport’s standout features is its proximity to the water. With marinas, parks, and scenic walking trails, outdoor enthusiasts will find endless opportunities for sailing, kayaking, and fishing. The vibrant local scene is complemented by a variety of charming eateries, boutique shops, and art galleries, making every stroll through the neighborhood a delightful adventure.

Whether you're looking to settle down in a cozy waterfront cottage or a contemporary home with all the modern amenities, Eastport has something for everyone. Embrace the enchanting lifestyle that this Annapolis gem has to offer, where community, culture, and coastal beauty come together to create a truly exceptional living experience. Discover your dream home in Eastport today!

Newest Listings in Eastport

$1,595,000
4 Beds ⋅ 5 Baths
COMING SOON - expected on the market September 30th. Rare Lower Eastport opportunity: spacious townhome with a separately licensed one-bedroom detached cottage and 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 approximately 2,300 square feet of combined above-grade living space, including the 670-square-foot detached cottage, plus an additional 800 square feet of finished lower-level space in the main residence. This unique configuration combines generous living space with an exceptional degree of flexibility rarely found in Eastport. Enter the main residence through a charming raised covered porch that overlooks the tree lined street. This home offers three bedrooms and three and a half baths, with a separate dining room, open kitchen flowing into the living room and out onto a covered porch overlooking the fenced-in 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 private bath provides comfort and privacy for family or guests. Custom plantation shutters throughout the main and top floors add a polished finish and privacy. The finished lower level adds approximately 800 square feet of versatile living space and is currently configured as a family/TV room and third bedroom with a full bath, laundry, additional storage and private entrance to the back yard. 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 new LVP flooring, kitchen cabinetry, full-size appliances and an updated bathroom. Most recently rented for $2,935 per month, 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. Since purchasing the property in January 2025, the current owners have invested more than $100,000 in improvements. A full list of improvements is available from the listing agent. There is no off-street parking, however, ample street parking is available at this quiet end of Eastport. The property’s east of Second St. location is approximately two blocks from 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. A newer Eastport home, substantial finished living space, and a separate cottage with proven rental income of more than $35,000 annually – an opportunity that is difficult to replicate.

123 Chesapeake Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$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: 4102638686
$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: 4109724000
$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: (410) 280-5600
$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: 8888607369
$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: 4102638686
$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: 4102638686
$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: 4102638686
$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: tomspier1@gmail.com
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