Eastport Real Estate

Eastport Real Estate

Welcome to Eastport, a charming and vibrant subdivision nestled in the heart of Annapolis, Maryland. Known for its picturesque waterfront views and a rich tapestry of history, Eastport offers a unique blend of coastal living and urban convenience, making it a coveted destination for homebuyers and investors alike.

As you stroll through the tree-lined streets of Eastport, you’ll discover a delightful mix of historic homes and modern residences, each exuding character and charm. The community is renowned for its friendly atmosphere, where neighbors become friends and local businesses thrive. With a variety of boutiques, cafes, and restaurants just a stone’s throw away, residents enjoy a lifestyle that balances relaxation with the excitement of city living.

One of Eastport's standout features is its proximity to the Chesapeake Bay. Outdoor enthusiasts will relish the numerous opportunities for sailing, kayaking, and fishing, all while taking in breathtaking sunsets over the water. The nearby parks and walking trails provide ample space for family outings, picnics, and leisurely strolls.

Eastport is also conveniently located just minutes from downtown Annapolis, where you can immerse yourself in the rich maritime history and culture that the city is known for. From the historic State House to the bustling City Dock, there's always something to explore.

Whether you’re looking for a serene retreat or an active community, Eastport offers the perfect blend of both. Discover your dream home in this enchanting neighborhood and experience all that Eastport has to offer!

Newest Listings in Eastport

513 First St, Annapolis
$2,100,000
4 Beds ⋅ 3 Baths
Homes this charming and inviting located on Horn Point in Eastport don't come on the market that often! This delightful home exudes classic elegance and modern comfort. Updates are already completed so you don't have to do a thing but move right in. The open floor plan with immaculate hard wood flooring invites you to relax or entertain. The kitchen and family room "great room" and gas fireplace overlook the private patio and gardens. A huge bonus is the large, primary bedroom suite on the main level. Loads of natural light everywhere in this home. Beautiful renovation with four spacious bedrooms and two and a half baths, the layout is designed for both relaxation and entertaining. The heart of the home features a family room that flows seamlessly into the kitchen, complete with an inviting island and upgraded countertops. Enjoy cozy evenings by the fireplace, adorned with glass doors and a classic mantel. The hardwood floors throughout add warmth, while built-ins provide both style and functionality. The unfinished basement offers potential for customization, with walkout stairs leading to the landscaped yard, perfect for outdoor gatherings. This urban gem is just blocks from the Severn River, where you can enjoy leisurely walks or hop on a boat and enjoy the Chesapeake Bay. The community is vibrant, with local parks, shops, and dining options that foster a friendly atmosphere. There's ample space for gardening or play. Parking is a breeze with a driveway and on-street options. This home is not just a property; it's a place where memories are made, surrounded by a welcoming community that truly feels like home.

513 First St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

316 Chester Ave, Annapolis
$450,000
2 Beds ⋅ 2 Baths
SIMULCAST AUCTION. Online pre-bidding begins November 17, 2026 at 10:00 AM ET. Live bidding begins November 19, 2026 at 1:00 PM ET, both on-site at 316 Chester Ave and online through the Ashland Auction Group bidding platform. List price is the suggested opening bid. A 10% buyer’s premium will be added to the high bid. On-site bidders must bring a $10,000 cashier’s check. Online bidders must register and complete the required credit card authorization. Pre-auction offers may be accepted. Built in 1920, this detached Eastport home offers 2 bedrooms and 2 full bathrooms. Inside, the home features a living room, dining room, hardwood floors, and an interior staircase. The outdoor space includes a patio and rear yard on approximately 0.07 acres. Butler’s Marina is nearby on Chester Avenue, and the Annapolis Maritime Museum’s waterfront campus is on Second Street. Eastport’s restaurants and marinas are nearby, with downtown Annapolis and City Dock across the Spa Creek Bridge. The property needs updates and is sold as-is.

316 Chester Ave, Annapolis

Listing courtesy of Ashland Auction Group LLC. Contact:

1136 Tyler Ave, Annapolis
$315,000
2 Beds ⋅ 2 Baths
Own your own land in the Eastport area with no condo fee, no HOA, and no pet restrictions. This single-level, two-bedroom, two-full-bath home has a new roof, central air, and a private patio and backyard just outside the sliding glass doors of the primary bedroom. The kitchen is bright from two sides plus a skylight, with a pass-through and eat-in counter for coffee or casual meals. Wood floors, ceiling fans, and a main-floor laundry make daily life easy, and an off-street parking pad and a shed for bikes, tools, and seasonal gear add storage and convenience. At 800 square feet, it’s a manageable, low-upkeep step from a condo or rental into homeownership, about 10 minutes from downtown Annapolis. Photos have been virtually staged.

1136 Tyler Ave, Annapolis

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

1010 Park Ave, Annapolis
$1,298,000
4 Beds ⋅ 4 Baths
Skip the renovations and settle right into this Eastport gem. From top to bottom, flawlessly turnkey in every detail, this home invites you to immediately embrace the coveted downtown lifestyle. Custom-built in 2021, this 3200 sq ft home perfectly blends modern luxuries with classic Eastport charm. Fine finishes, 9-foot ceilings, stunning millwork, and gorgeous white oak floors set the tone. The heart is the chef’s kitchen with a show-stopping center island and granite counters. The kitchen is open to the light-filled family room, flanked by a cozy gas fireplace and custom built-ins. A versatile 4th bedroom or office, full bath, and chic beverage center complete the main level. Upstairs features a convenient laundry room, three spacious bedrooms—including a vaulted primary suite—and two beautifully appointed bathrooms with modern tile and granite vanities. The fully finished lower level adds a large recreation area, another full bath and ample storage. For outdoor living, the amazing 300-square-foot screened porch will quickly become a favorite spot. Step off the porch and enjoy the crafted stone patio, firepit and a fully fenced, grassy backyard. Perfectly positioned, you are just moments from Eastport's celebrated restaurants, marinas, and waterfront parks, with an easy stroll across the Spa Creek Bridge to Historic Downtown Annapolis. This exceptional turn-key offering delivers the best of Eastport living in a flawless package. Check out the Interactive Floor Plan!

1010 Park Ave, Annapolis

Listing courtesy of Compass. Contact:

830 Chester Ave, Annapolis
$1,795,000
4 Beds ⋅ 4 Baths
Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

830 Chester Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

100 Severn Ave Unit 507, Annapolis
$1,250,000
1 Beds ⋅ 1 Baths
A Serene Retreat with Unforgettable Scenery... Enjoy breathtaking, unobstructed water views from every window in this inviting condominium, where peaceful surroundings meet comfortable living. Thoughtfully designed for relaxation and everyday convenience, this home offers a wonderful opportunity to wake up to beautiful scenery and unwind beside the water at the end of the day. Front-row balcony viewing of Blue Angels practice and show dates in May for Commissioning Week; Parade of Lights; Fireworks on 4th July and New Year’s Eve. Daily activity in the Annapolis Harbor. • Overlooking Spa Creek, Ego Alley, U.S. Naval Academy, Eastport Bridge, Severn River, Annapolis skyline. • Elevator • Secured Condo and Garage Building • The open-plan living, dining, and kitchen area is flooded with natural light. • A chef’s kitchen flanks the 10 ft island, maximized with new cabinet storage. • Appliances: Sub-Zero, Miele, Bertazzoni, Whirlpool • Kitchen and bath cabinets: natural Hickory and off-white flat-panel • The large walk-in closet and in-unit laundry connect the bedroom to the Kohler spa-like bath and separate vanity area. • Built-in cabinet for TV and electric fireplace • Walking distance to shops, pubs, and restaurants. • Water taxi 1 block away. • Local marinas, shopping, restaurants, pubs, and cafes within walking distance Whether you are looking for a full-time residence, a weekend getaway, or an investment opportunity, this condominium offers an exceptional setting and a lifestyle centered on the view. Come experience tranquility and charm for yourself.

100 Severn Ave Unit 507, Annapolis

Listing courtesy of Coastal Realty Maryland. Contact:

531 Second St, Annapolis
$1,199,000
2 Beds ⋅ 3 Baths
This charming historic Eastport home was built in the early 1900s and moved to Second Street in 1937. David Fogle, renowned preservationist architect and professor, purchased the home in 1970s and designed the light-filled addition featuring Palladium windows and architectural angles. The home bridges the integrity of the past to the present with its original Heart Pine floors on the main level. The current owners did a full kitchen renovation to include custom-built Heartwood cherry cabinets, dry/wet bar, and granite countertops with plenty of room for food prep and entertaining! The combined living room/dining room area is spacious and open while the comfortable family room opens to the front porch and overlooks a lovely flower garden. The family room opens to a brick patio and a large partially- fenced backyard that is ideal for warm weather entertaining. Lots of custom bookshelves throughout, and there are two gas fireplaces on the main level for added charm and ambiance in the cold weather! Full bathroom on the first floor. The spacious bright primary bedroom on the second floor features skylights and windows that offer views of the private backyard. Second bedroom is perfect for an office/guest room with Murphy bed. The coveted off-street parking accommodates four cars. The house is located in the heart of Eastport's historic maritime neighborhoods where watermen made a living from fishing, crabbing, and oystering. The front porch on this friendly street is the perfect spot for impromptu gatherings with neighbors and friends. Easy walk to marinas on Back and Spa Creeks, the Maritime Museum, yacht clubs, restaurants, pubs and shops; access to seasonal water taxi transport to downtown Annapolis. Eastport charm at its best!

531 Second St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

827 Bay Ridge Ave, Annapolis
$869,000
3 Beds ⋅ 3 Baths
Enjoy the convenience and charm of Eastport living at 827 Bay Ridge, just a short walk to local restaurants, shops, marinas, parks, and downtown Annapolis. This updated and well-maintained 3-bedroom, 3-full-bath home offers comfortable, flexible living space. The main level features two bedrooms and two full baths, inviting living areas, hardwood floors, and an updated kitchen with white cabinetry, granite countertops, and stainless steel appliances. Just off the living and dining areas, the screened porch overlooks the private backyard, creating the perfect spot to relax or entertain. The lower level provides additional living space with a third bedroom and full bath, ideal for guests, a private retreat, or a home office. Outdoor features include a welcoming front porch, rear patio, private backyard, and a driveway conveniently located behind the home, along with a storage shed. Whether you’re looking for a full-time residence or a weekend getaway, this turnkey home has everything that makes coastal living so desirable!

827 Bay Ridge Ave, Annapolis

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

123 Chesapeake Ave, Annapolis
$1,595,000
4 Beds ⋅ 5 Baths
Exceptional Lower Eastport property: tastefully updated, semi-detached home with a detached one-bedroom cottage with proven rental income. Enjoy the charm and walkability of Lower Eastport from this 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 neighborhood. 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 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 as well as from its own entrance 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 is now vacant, 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 property upgrades 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:

312 Severn Unit W308, Annapolis
$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:

8 Spa Creek Lndg Unit A3, Annapolis
$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:

13 Spa Creek Lndg Unit A2, Annapolis
$506,000
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:

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