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Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.

One of the most popular communities provided by Maryland Sandbox

361

# of Listings

3

Avg # of Bedrooms

$481

Avg. $ / Sq.Ft.

$1,098,732

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

361 Properties Found. Page 5 of 25.

Experience Historic Charm & Modern Elegance in the Heart of Annapolis.

Nestled in the heart of downtown Annapolis, this stunning historic Federal-style home offers the perfect blend of timeless character and modern sophistication. Located on the iconic Duke of Gloucester Street, this residence places you just steps away from the waterfront, top-tier dining, boutique shopping, and the rich history that defines Annapolis.

From the moment you step inside, you’re welcomed by pristine hardwood floors, soaring ceilings, and an abundance of natural light that fills every room. The spacious and thoughtfully updated interior seamlessly combines historic charm with contemporary convenience, featuring custom millwork, built-ins, and an elegant fireplace that creates an inviting atmosphere.

The gourmet kitchen is a chef’s dream—offering premium appliances, custom cabinetry, and a layout designed for both entertaining and daily living. Enjoy your morning coffee in the sun-drenched breakfast nook or step outside to the private courtyard, a peaceful retreat perfect for al fresco dining or evening gatherings.

The primary suite is a sanctuary of its own, offering ample closet space and a spa-inspired ensuite bath. Additional bedrooms provide comfort and flexibility for guests, a home office, or creative spaces.

Beyond its breathtaking interiors, the true magic of this home lies in its location—walk to the U.S. Naval Academy, Maryland State House, and City Dock, or simply enjoy the vibrant energy of downtown life.

This is more than a home; it’s an opportunity to own a piece of Annapolis's history with all the conveniences of modern luxury. Don’t miss your chance to experience it firsthand—schedule your private showing today!

Short term rental numbers are remarkable.Seller willing to share upon request.

ANNAPOLIS

146 DUKE OF GLOUCESTER STREET

4 Beds

3 Baths

3,042 Sq.Ft.

$1,549,000

MLS#: MDAA2108604

A Rare Find in the Heart of Eastport! Built in 2006 with timeless Eastport charm, this beautifully maintained home offers the perfect blend of traditional style and modern convenience. Enjoy off-street parking for 2 cars and a host of high-end features throughout. Step inside to discover hardwood flooring on all 3 levels, radiant floor heat, and zoned heating and cooling – including a private AC control in the primary suite. The spacious layout includes three full baths with stone tile details, a whirlpool tub and 2-person shower in the primary bath, and a soaking tub in the guest bath.
The primary bedroom features skylights with rain sensors and remote-controlled shades, as well as his and hers closets. Enjoy a full-size washer & dryer on the second floor. The large 3rd level loft can be used as a 4th bedroom. On the main level there is a pantry/mudroom, separate side entry leads you to step to the unfinished basement with 8' ceilings. Designed with safety and comfort in mind, this home includes ceiling sprinklers on all levels, enhanced fire-rated walls, and a top-rated corner for a wood stove. Outdoor living is just as impressive with rain gardens in the front and back, Leaf Filter gutter guards, outdoor water and electric access, and dimmable lighting on the front porch as well as inside kitchen/dining areas. Additional highlights: Updated interior paint throughout (2024); New refrigerator (2024); dishwasher (2023); and microwave with stove exhaust (2025). Security system with front door camera. Included in the fenced rear yard is a permanent exclusive 5’ rear easement for added privacy.
Enjoy the best of Eastport living in a home designed for comfort, efficiency, and peace of mind.

ANNAPOLIS

541 SECOND STREET

4 Beds

3 Baths

2,341 Sq.Ft.

$1,549,000

MLS#: MDAA2114340

Welcome to 816 Bay Ridge Avenue, a beautifully maintained 4-bedroom, 4.5-bath home located in Eastport’s coveted Sailor’s Quay community. Offering over 3,300 square feet of refined living space, this home blends modern coastal style with everyday convenience—just minutes from downtown Annapolis, marinas, and top-rated restaurants. Built in 2012, the home features an open-concept layout with hardwood floors throughout, fresh paint, premium trim, and a gourmet kitchen with granite countertops, stainless steel appliances, and a gas cooktop. The spacious main level is ideal for both casual living and entertaining. One of only a few homes in the community with a full-size ELEVATOR servicing all three levels, this residence is ideal for those seeking long-term comfort and accessibility. The oversized primary suite includes two large walk-in closets and a spa-like bath. A second en suite bedroom on the upper level—located next to the elevator—offers a convenient option for guests or multi-generational living. The finished lower level includes a full bath and is pre-plumbed for a future beverage center. An adjacent unfinished area is ready for a 5th bedroom, home gym, or office. Additional features include a 2-car garage, extra parking, Hardie plank siding, multiple decks, excellent storage, and great natural light throughout. Low-maintenance living with a $150/month HOA—this is Eastport living at its finest.

ANNAPOLIS

816 BAY RIDGE AVENUE

4 Beds

4 Baths

3,374 Sq.Ft.

$1,510,000

MLS#: MDAA2114914

Settled into a quiet corner of Eastport and surrounded by beautiful homes, this 4-bedroom, 2.5-bath house sits on just over a third of an acre (14,615 sq ft) with a spacious front and back yard, flower beds bursting with potential, and plants that are already doing their part to make this place feel like home.

Set along the tranquil waters of Back Creek, this property offers peaceful water views, free from boat traffic and city noise—just enough to remind you why you chose the maritime life.. It’s tucked just far enough off the main path that it feels like a bit of a secret, yet you’re still minutes from downtown Annapolis.

Inside, you’ll find a house full of charm, character, and space that’s just waiting for a little love to shine again. The vintage kitchen comes complete with a classic double wall oven, cooktop, dishwasher, and even a retro under-cabinet tuner because every kitchen needs a soundtrack. There's also a serving hatch to the family room that makes meals, snacks, and conversation flow easier. The space is well lit, with two overhanging lights and perimeter in-set lighting that wraps almost all the way around. Yes, the wallpaper and backsplash are original, and they have a whole personality if you're ready to lean into their allure.

Even the powder room has something to say, with a classic yet unique pedestal sink that adds just the right amount of traditional comfort and style. And if you find yourself needing a little creative inspiration while making a quick trip to the loo—well, this might just be the place for it. It’s got that kind of charisma!

Just around the corner, The family room is anchored by a cozy wood-burning fireplace insert, creating an inviting spot to gather when the weather turns cool. Hardwood floors run throughout the home, offering a warm foundation for whatever expression or design you bring to life.

Moving past the stairs and down the hallway toward the bedrooms, you’ll find a large dedicated laundry room complete with a utility sink and counter space making it easy to fold towels or stash those things you’d rather not tackle immediately. Steps away, the primary bathroom offers generous built-in storage, giving you even more space to keep things neat and out of sight.

Heading downstairs to finish the tour of the interior, the unfinished basement offers a few already-framed bonus areas ideal for storage, hobbies, or even that future rec room or guest suite you've been imagining.

Outside, a white vinyl picket fence surrounds three sides of the property and a private driveway offers convenient off-street parking for one vehicle with plenty of room for guests or extra vehicles nearby. And if you decide to purchase Lot 115 next door, you'll have a fully fenced yard that wraps around both properties—perfect for gardens, gatherings, or simply room to roam.

So whether you’re ready to bring this home to life with a refresh or dream of starting from scratch, 703 Glendon Avenue is full of potential in a neighborhood that truly feels like home.

For all those wondering, Eastport is known for its strong sense of community, walkability, and a laid-back spirit best summed up by its motto: “Fun With a Purpose.” You’ll find that energy in the local restaurants and watering holes—Vin909, Lewnes Steakhouse, Davis’ Pub, Boatyard Bar & Grill, Chart House, Black Wall Hitch and more—all just a short stroll or bike ride away.

According to the President of the Park Wood Association: The Parkwood Civic Association (PCA) is a voluntary group (not an HOA) with $100 annual dues used to maintain community areas like Parkwood & Short Street Park, Hoffman Park, and the docks, as well as fund a fall picnic. PCA membership is required to apply for a dock slip. Applicants must own the boat, registered to their Parkwood address. A waitlist, based on boat size, is managed by the dock master. Slip fees are additional—about $800 for large and $550 for small slips.

ANNAPOLIS

703 GLENDON AVENUE

4 Beds

2 Baths

2,654 Sq.Ft.

$1,500,000

MLS#: MDAA2109762

OPEN, SATURDAY, MAY 31th...12:00-2:00 A rare gem in a peaceful oasis in the heart of Eastport. This classic 1930's home is set in among an enclave of seven homes that are nestled along the shores of Spa Creek. A charming gravel drive winds through the cluster of homes that access a private path down to the new marina, built in April 2025. The lush front yard and mature trees lead to the classic front porch that offers the ideal place to greet your neighbors or relax in the shade. The traditional wood floors flow throughout first and second floors. Formal dining is perfect for dinners with family or friends. The island kitchen offers casual entertaining space, tons of cabinets and access to the back deck and private yard. A direct path to the two-car garage will make it easy to bring in groceries right into the kitchen! The living room has loads of light and a fireplace for the chilly nights. The landing with bookcase leads to wide steps to the second floor. The primary suite is large with two sinks and a glass walk-in shower. The guest bedroom offers additional closet space and has its own full bath. The laundry is located on the second floor. Stair leads to an attic that could be expanded for more sleeping areas. All the charm of Eastport access with restaurants and shops within walking distance. A private marina with new docks and finger piers for your sail or power boat, kayak or paddle board...summer fun awaits! This peaceful private neighborhood offers a rare opportunity for the ideal Annapolis lifestyle...

ANNAPOLIS

97 QUARTER LANDING RD ROAD

2 Beds

2 Baths

1,920 Sq.Ft.

$1,500,000

MLS#: MDAA2114754

New on site 2 days ago

Step into timeless charm and refined living in the heart of Eastport. This beautifully maintained 3-bedroom, 2-bathroom Craftsman-style home offers over 3,400 square feet of versatile living space and an unbeatable location just three blocks from the water. Originally built in 1925 and thoughtfully updated, this residence effortlessly blends classic architectural detail with modern luxury. Inside, you'll find gleaming hardwood floors, 9-foot ceilings, and natural light pouring through large windows. The gourmet kitchen is a chef’s dream, featuring stainless steel appliances, a commercial-grade stove, and generous prep space—perfect for entertaining or crafting everyday meals. Both full bathrooms have been stylishly updated, reflecting a blend of historic charm and contemporary design. The converted garage offers a flexible space ideal for a gym, studio, or home office—adaptable to fit your lifestyle needs. Outside, enjoy a landscaped, fenced yard and a welcoming front porch that invites quiet mornings and evening gatherings. Located in one of Annapolis’s most sought-after waterfront communities, this Eastport gem is just moments from marinas, local restaurants, and community beach access. Whether you’re kayaking on Spa Creek or walking to downtown Annapolis, the Eastport lifestyle is unmatched. This home is perfect as a primary residence for those who value walkability, character, and coastal living. Don’t miss the opportunity to own a slice of historic Eastport with all the conveniences of modern luxury.

ANNAPOLIS

313 CHESAPEAKE AVENUE

3 Beds

2 Baths

2,576 Sq.Ft.

$1,500,000

MLS#: MDAA2109252

Discover amazing coastal charm in this stunning craftsman-style residence nestled in the heart of Eastport. Situated just a few houses from the waters of Back Creek, this exceptional property offers over 4,200 finished square feet of meticulously designed living space, blending sophisticated style with the relaxed ease of Annapolis living. You'll be immediately captivated by the luxury designer finishes found around every corner of this remarkable home. The main level offers a traditional yet open floor plan, seamlessly connecting the chef-inspired kitchen to the great room where the fireplace offers a warm ambiance and elegant tray ceilings add architectural interest and height. The formal dining and sitting rooms are perfect for entertaining both great parties or more intimate gatherings. Culinary enthusiasts will delight in the gourmet kitchen, featuring breathtaking quartzite countertops, sleek white cabinetry, and top-of-the-line stainless steel appliances. The home offers four generously sized bedrooms and three and a half bathrooms. The primary suite is a true sanctuary with a spa like bathroom complete with luxurious fixtures and finishes and generously sized walk in closet. A bedroom level walk in laundry room offers function and convenience. Ideal for multi-generational living or accommodating guests, the lower level features a thoughtfully designed in-law or au pair suite with a separate entrance for ultimate privacy, offering a kitchenette, living room, full bathroom and spacious bedroom plus separate laundry. The detached two-car garage provides coveted off-street parking and offers an abundance of storage space above. Embrace the quintessential Eastport lifestyle with effortless access to vibrant restaurants, shops and plentiful festivals all just a leisurely stroll away. Eastport's water privileged Parkwood neighborhood offers residents a marina with slips, ramp, kayak storage racks and a picnic area all overlooking Back Creek, just a few houses away! Schedule your private tour today!

ANNAPOLIS

718 SPRINGDALE AVENUE

4 Beds

3 Baths

3,954 Sq.Ft.

$1,495,000

MLS#: MDAA2112510

First time on the market in 40 years! This is a rare and special opportunity to own a detached home with both a garage and driveway in The Historic District of Downtown Annapolis. This elegant home seamlessly blends gorgeous original details with modern updates on three finished levels. Wrought iron fence frames the home which is ideally set back on the lot and leads to the inviting and spacious front porch. Entrance hall with its original staircase opens to the living room with built in shelves surrounding the gas fireplace. The large living and dining rooms have oversized windows flooding the home with natural light and pocket doors which can separate the large open spaces. The sunny kitchen and attached family rooms have been updated with a bar area, cherry cabinets, powder room and exotic granite making it the ideal place to gather around the gas fireplace. Step into the sunroom from the kitchen for dining or lounging and admire the landscaped backyard that big enough to host a nice-sized party. 2nd and 3rd floors have spacious bedrooms and include an en-suite primary. All of this just a few short blocks to Main Street and a picturesque waterfront park where you can sit and read a book, hop on the water taxi or drop your kayak in Spa Creek. The perfect home for your perfect Annapolis life!

ANNAPOLIS

138 CHARLES STREET

4 Beds

2 Baths

3,100 Sq.Ft.

$1,495,000

MLS#: MDAA2111466

#MDAA2051918

ANNAPOLIS

2644 CLAIBOURNE ROAD

6 Beds

4 Baths

3,702 Sq.Ft.

$1,484,000

MLS#: MDAA2051918

Back on the market with a DRAMATIC price improvement!! Welcome to your truly turnkey 3-unit investment property in the HEART of Annapolis!! All 3 units come FULLY furnished, down to the spoons and forks!! Literally STEPS away from the Naval Academy main gate and downtown Annapolis!! Unit 1 is a 1 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. You will immediately notice that all 3 units are a perfect blend of nicely updated without losing an ounce of the original charm we all love about Annapolis. You will also see the amazing space in all the units and rooms - the floor plans are perfectly executed, and the space and function are on point! Unit 1 has direct access to the outdoor rear patio. Unit 2 is a 2 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. The 2 bedrooms are wonderfully separated from the family room and kitchen, and both are primary-sized bedrooms, but the true primary is an extra special retreat with its own sitting area. Unit 2 also has direct access to the rear outdoor patio. Unit 3 is a 1 bedroom, 1 bathroom unit with a family room, dining area, and a full kitchen (no dishwasher). The unique feature that you will notice about Unit 3 is that it, too, has tall ceilings, unlike the upper levels of many downtown Annapolis homes. So many different investment options, live in one, rent the others, rent them all, wonderful short-term rental opportunity. Full 2 year rental history available in the document sections. Showings are by appointment only and limited due to high occupancy rate of the units, reach out early to arrange a time to see this rarely available Annapolis gem!! Don't hesitate, it won't last long at this new, aggressive price!!

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

3 Baths

2,649 Sq.Ft.

$1,475,000

MLS#: MDAA2112630

Back on the market with a DRAMATIC price improvement!! Welcome to your truly turnkey 3-unit investment property in the HEART of Annapolis!! All 3 units come FULLY furnished, down to the spoons and forks!! Literally STEPS away from the Naval Academy main gate and downtown Annapolis!! Unit 1 is a 1 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. You will immediately notice that all 3 units are a perfect blend of nicely updated without losing an ounce of the original charm we all love about Annapolis. You will also see the amazing space in all the units and rooms - the floor plans are perfectly executed, and the space and function are on point! Unit 1 has direct access to the outdoor rear patio. Unit 2 is a 2 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. The 2 bedrooms are wonderfully separated from the family room and kitchen, and both are primary-sized bedrooms, but the true primary is an extra special retreat with its own sitting area. Unit 2 also has direct access to the rear outdoor patio. Unit 3 is a 1 bedroom, 1 bathroom unit with a family room, dining area, and a full kitchen (no dishwasher). The unique feature that you will notice about Unit 3 is that it, too, has tall ceilings, unlike the upper levels of many downtown Annapolis homes. So many different investment options, live in one, rent the others, rent them all, wonderful short-term rental opportunity. Full 2 year rental history available in the document sections. Showings are by appointment only and limited due to high occupancy rate of the units, reach out early to arrange a time to see this rarely available Annapolis gem!! Don't hesitate, it won't last long at this new, aggressive price!!

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

None Baths

2,649 Sq.Ft.

$1,475,000

MLS#: MDAA2112408

#MDAA2106136

ANNAPOLIS

9 RUSTY RED DRIVE

5 Beds

4 Baths

5,062 Sq.Ft.

$1,389,000

MLS#: MDAA2106136

Ready to build your dream home?

Buyer Fell through. Priced to sell fast!

This project is mostly demo'ed and ready for you to take over and make it your own. You can run with our plans as rended in the pictures or make your own.

****NO Walking on the property without an appointment. Showings by appointment with hold harmless signed as the property is gutted***

Current structure is a pretty much a shell. What makes this an amazing opportunity is what is existing. For an example the concrete structure on the main part of the house that could easily be reused to build an awesome modern home. The left side of the home has a large pool inside that if you were to build large glass doors could overlook / open up to the rear water views. There is an existing boat house which you would not be able to make today. There is a ton of impervious surface area and parking for all your needs. The double lot that we had to have joined.

The plans we drafted up are over 10,000 sq feet including a 2 wide 2 deep garage, large kitchen with walk in cold room, lots of glass and openness, elevator, and more. This home would be the perfect weekend get away to entertain.

Note: the sale is for the project AS-IS and not a new finished home. We will include our plans if you like for free and happy to show you what we envisioned. ** bedroom / bath count etc are based off plans and not existing. **Listing Agent is co-owner.

ANNAPOLIS

1254 WASHINGTON DRIVE

6 Beds

8 Baths

11,350 Sq.Ft.

$1,350,000

MLS#: MDAA2042774

Discover the perfect blend of comfort and convenience in this rare 3-bedroom, 2.5-bath condo located in the desirable Park Place community. With three deeded parking spaces, you’ll never have to worry about parking in this vibrant area.

Step inside to find a spacious and inviting layout, featuring upgraded appliances that make both everyday living and entertaining a breeze. The open-concept living area flows seamlessly into a modern kitchen, perfect for culinary enthusiasts. Enjoy the ease of maintenance and stylish design throughout, with ample storage and natural light enhancing every room.

The primary suite offers a private retreat, complete with an en-suite bathroom for added luxury. Two additional bedrooms provide flexibility for guests, a home office, or family.

Take advantage of the community amenities, including beautifully landscaped grounds and convenient access to local shops, dining, and parks. pool, party room, dog park, outdoor patio in the back of the building with grills. Front desk is staffed 24/7 for your convenience. A vibrant community that is perfectly located in town.

Experience the charm of Park Place living!

ANNAPOLIS

5 PARK PLACE 428

3 Beds

2 Baths

1,822 Sq.Ft.

$1,350,000

MLS#: MDAA2097498

Embrace the opportunity to create your dream waterfront retreat on this expansive 10,072 sq ft (0.24-acre) property, strategically located on the tranquil shores of Chesapeake Ave in the coveted Venice Beach area. This combined offering includes Lots 3 & 4 Block C (Tax #020288602739800), providing a unique canvas for your architectural vision.
Whether you choose to renovate the existing structure or start fresh with a custom build, you'll enjoy breathtaking and expansive water views, perfect for soaking up the serene coastal ambiance. This property is a paradise for water enthusiasts, featuring direct access to boating, fishing, and crabbing from your own private pier.
Sold strictly "AS-IS," this property offers an unparalleled chance to invest in prime real estate in a prestigious area, with endless potential to craft a personalized sanctuary tailored to your lifestyle.
Bullets-
*Single-family waterfront home with outstanding views
*Prime waterfront location on Chesapeake Ave in Venice Beach
*Combined lots offer 10,072 sq ft (0.24-acre) of potential
*Ideal for new construction or renovation with expansive water views
*Private pier for boating, fishing, and crabbing
*Sold "AS-IS" for maximum flexibility in development plans
Explore the boundless possibilities of this prime waterfront property and create a legacy home that will be cherished for generations.
SEE SELLER'S Renderings / Drawing for a potential buildout

ANNAPOLIS

1407 CHESAPEAKE AVENUE

3 Beds

1 Baths

964 Sq.Ft.

$1,350,000

MLS#: MDAA2114466

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