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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

266

# of Listings

3

Avg # of Bedrooms

$529

Avg. $ / Sq.Ft.

$1,357,478

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

108 Properties Found. Page 3 of 8.

**NEW PRICE, UPDATED SQUARE FOOTAGE + NEW PHOTOS ADDED — INCREDIBLE OPPORTUNITY!**

Boasting 1,549 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized 0.26-acre lot—offering space and flexibility nearly impossible to find this close to City Dock. While the main house charms with high ceilings, refinished hardwoods, and a light-filled 3-seasons wrap-around porch, the true crown jewel is the backyard oasis. Surrounded by stunning, mature trees, the sprawling lawn features an existing 1-car garage ripe for transformation. Bring your vision to easily rebuild this structure into a premier Accessory Dwelling Unit (ADU), income-producing apartment, or a private home office oasis. Walk to the Navy Stadium, local cafes, and the Poplar Trail. With room to grow, update, and build equity, this is a rare Annapolis footprint waiting for your personal touch!

Note on Square Footage: Finished square footage has been updated to 1,549 sq. ft. based on recent agent measurements. Public tax records currently reflect inaccurate historical data (1,442 sq. ft.) and do not fully capture the complete finished living area.

ANNAPOLIS

21 WOODLAWN AVENUE

3 Beds

2 Baths

1,549 Sq.Ft.

$819,000

MLS#: MDAA2144864

Love This HOME -- Briarwood – One of Anne Arundel County’s Finest Communities… Welcome to Rosebay Court!
A mature magnolia tree and inviting covered front porch set the stage for this beautifully updated/renovated brick colonial, ideally situated on a quiet cul-de-sac. Thoughtfully finished and move-in ready, this home is prepared to welcome its new owner.
Inside, a traditional layout blends seamlessly with an open-concept feel, offering both comfort and versatility for everyday living and entertaining. The main level features a welcoming living room, a formal dining room that opens to a light-filled kitchen complete with 42” white cabinetry, complementary granite countertops, a breakfast bar, pantry, and coffee nook. A Samsung appliance suite—including a five-burner stove and French door refrigerator—adds both style and functionality.
The adjoining "great room" is another space for family & friends to gather This room impresses with vaulted ceilings, skylights, and a cozy wood-burning fireplace—perfect ambience for crisp fall and winter evenings. At the heart of this space, the breakfast nook offers table space and easy access to the outdoors -- sliding glass doors that open to a new Trex deck, ideal for relaxing, entertaining, starting your day or ending your evening... . Neutral finishes throughout this home create a fresh look and feel
Upstairs, you’ll find four spacious bedrooms, including an owner’s suite with a private bath featuring dual vanities and walk-in closet. A well-appointed hall bath and ample closet space complete the upper level.
The finished lower level offers incredible flexibility, featuring a full bathroom and level walkout access to the backyard. Whether you envision an in-law suite, guest space, home office, gym, or additional living area, this level is ready to adapt to your needs. Step outside to a newly paved patio overlooking a serene green space, surrounded by nature.
Located in a sought-after school district and just minutes from Route 50, this home offers convenient access to shopping, waterfront dining, marinas, and scenic walking paths. Enjoy easy trips to the Eastern Shore and nearby beaches.
With all new mechanicals and updates ((detailed in the disclosures)), this home offers the perfect alternative to new construction—without the wait. Move in and start enjoying your dream home this summer!
*** please note disclosure: some photos have been enhanced with virtual staging/photography ***

ANNAPOLIS

1394 ROSEBAY COURT

4 Beds

3 Baths

2,252 Sq.Ft.

$809,900

MLS#: MDAA2140978

Private Contemporary Retreat in Annapolis! Tucked into one of the area’s most peaceful and private wooded settings, 1709 Point No Point Road offers a rare combination of total seclusion and unbeatable convenience. From the moment you arrive, the striking contemporary architecture, soaring skylights, and walls of windows connect you directly to nature, flooding the home with beautiful sunlight across all four seasons.

Inside, the flexible floor plan features 4 spacious bedrooms, 2.5 bathrooms, and multiple fireplaces designed for everyday comfort and effortless entertaining. The main living areas offer a natural flow with stunning wooded views, while the versatile lower level provides excellent additional space for a home office, recreation room, gym, or guest suite.

Outdoor living is a major highlight—maximize your indoor-outdoor lifestyle on the massive deck spanning the length of the home, surrounded by mature trees, serene landscaping, and a sense of calm that is hard to find. Complete with a 2-car garage and a premier location just minutes from Downtown Annapolis, the Naval Academy, shopping, dining, Route 50, and I-97. Schedule your tour today and step into your next chapter!

ANNAPOLIS

1709 POINT NO POINT DRIVE

4 Beds

2 Baths

2,464 Sq.Ft.

$800,000

MLS#: MDAA2148148

Welcome to this beautifully maintained custom built Tudor Style home in this small coastal community! NO HOA!! With a primary suite and full bath on the main level and another primary suite with full bath on the upper level, this home is perfect for multi-generational living and accessibility! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 bedroom and 1.5 bath; and the lower level has another full bath and several areas to make 2-3 additional bedrooms. The huge 1,100 sqft finished lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area; plus a family room or theatre room and private entrance! There is even space for a kitchenette! There are so many possibilities with this extra space including an apartment or in-law suite! The laundry is located on the main level in the mudroom off of the garage so you don't need to go to the basement to do laundry. Situated on almost a half of acre and only 2 blocks to the Chesapeake Bay! The backyard is fully fenced in and ready for summertime entertaining! The lot next to the home is a preserved wooded lot that offers privacy and attracts wildlife. This home is nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. Quiet Waters Park is only minutes away with walking trails, dog park/beach, concerts, ice skating, and so much more! The home has been well cared for and maintained. Recent updates include: HVAC, water heater, main level LVP floors that are very durable, trex deck and renovated front porch with tile, custom plantation shutters, renovated primary suite and luxury full bath, front load w/d, freshly painted epoxy floor in basement, professionally cleaned, professionally landscaped...and more! Sellers are motivated and ready for another family to make this their home! MOVE-IN READY AND A MUST-SEE! You won't find many homes with this lot size and location for this price. The lot offers extra space for parking a boat, RV..and more. Schedule your showing today! OPEN HOUSE SUN 1-3PM!

ANNAPOLIS

3280 ARUNDEL ON THE BAY ROAD

5 Beds

4 Baths

3,144 Sq.Ft.

$799,900

MLS#: MDAA2144206

Welcome to Eastport—just steps from downtown Annapolis. This charming duplex with rare two-car off-street parking offers the perfect blend of convenience, and coastal living. Freshly painted throughout, this meticulously maintained two-bedroom, 1.5-bath home features numerous updates, including new hardwood flooring throughout, new windows in the living room and kitchen, a new wood-burning stove, and a new A/C heat pump—making it move in ready. A generous deep lot offers excellent potential for future rear additions and expanded living space providing the opportunity to truly make this home your own. Whether you're looking for a full-time residence or the perfect weekend getaway, this Eastport gem has it all. Ideally located near the waterfront, you’ll enjoy easy walking access to marinas, top-rated restaurants, pubs, swim clubs, sailing clubs, and boutique shopping. Don't miss this turnkey offering in a prime location.

ANNAPOLIS

422 FIRST STREET

2 Beds

1 Baths

1,094 Sq.Ft.

$790,000

MLS#: MDAA2144296

BEAUTIFULLY RENOVATED EASTPORT GEM with MODERN COASTAL FINISHES! Perfect for a Primary Residence, 2nd Home or Rental Investment! ABOUT THE HOME: 3 levels of luxury living featuring 4 Bedrooms and 3.5 Bathrooms. Open-concept main level with New Hickory hardwood floors and designer lighting throughout. THE GOURMET KITCHEN: Custom white Shaker cabinetry, modern black hardware, Quartz countertops, oversized center island, and premium stainless appliances with gas cooking. THE PRIMARY SUITE: A rare main-level primary retreat with walk-in closet and spa-like bath featuring custom tile work and glass-enclosed shower. THE FLEXIBLE LOWER LEVEL: Fully finished walk-up basement with a 4th bedroom/office, family room with wood accent wall, and a custom full bath—perfect for a guest or in-law suite. THE EXTERIOR: Iconic white picket fence in front, with cozy front porch, and a private rear yard with beautiful wood privacy fence is expanded by an additional 736 SF (included in sale). New Black Andersen 100 series windows, Hardie Plank siding, and new hardscaped paths. PARKING: Private driveway with 4 off-street parking spaces. LOCATION: Unbeatable walkability to Downtown Annapolis, Maritime activities, and local favorites. See Annapolis City site for details on the Eastport Choice Neighborhood Initiative! Enjoy all that Eastport has to Offer! Don't Let This One Get Away! Make your Appointment Today!
Active Ring Camera on Property.

ANNAPOLIS

152 JEFFERSON STREET

4 Beds

3 Baths

2,282 Sq.Ft.

$785,000

MLS#: MDAA2142230

Amazing home at an amazing price point! Welcome home to this beautifully maintained transitional Craftsman in sought-after Clifford Estates, NO HOA! From the moment you arrive, you’re greeted by a spacious Trex front porch, the perfect place to sip your morning coffee, unwind after a long day, and wave to neighbors passing by. Step inside to discover an inviting, light filled interior featuring Brazilian cherry hardwood flooring, neutral tones, and a traditional, flowing layout designed for both everyday living and entertaining. The bright and airy living room offers abundant natural light, while the chef’s kitchen truly shines with granite countertops, updated backsplash, stainless steel appliances, a large island with additional storage, ample cabinetry, a pantry, and space for a breakfast table. A formal dining room provides the perfect setting for holiday gatherings or casual dinners, and a convenient main level powder room completes the space. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite featuring extra windows, a large walk-in closet, and an ensuite bath with dual vanities. An additional full hallway bath and bonus storage area add even more functionality.
The lower level offers incredible flexibility currently set up as a home gym, it’s ready for your vision. Finish it for additional living space, create guest quarters, or simply enjoy the storage. A cozy pellet stove adds warmth and charm as an additional heat source. Situated on a large corner lot, this home provides plenty of room to spread out. The rear Trex deck creates an ideal outdoor living space for entertaining or relaxing. With a detached garage, storage shed, attached three car garage, and a two car driveway, parking and storage are effortless. Additional highlights include a new roof (2025) for peace of mind. Enjoy a prime location just minutes from shopping, dining, and entertainment, including Annapolis Mall and the Maryland Renaissance Festival, with easy access to USNA, Fort Meade, Baltimore, Washington, DC, and BWI Airport.
This is the one you’ve been waiting for, schedule your private tour today.

ANNAPOLIS

92 CLIFFORD BOULEVARD

4 Beds

2 Baths

2,252 Sq.Ft.

$775,000

MLS#: MDAA2139188

Tucked just off Poplar Trail, 211 Pindell Avenue is a classic brick rancher that lives far larger than expected—4,497 square feet of light-filled, entertainer-ready space waiting to be enjoyed.

Inside, walls of oversized windows pour sunshine across hardwood floors and custom trim. The living room rises to a vaulted ceiling anchored by a wood-burning fireplace, while the dining room charms with a beamed ceiling and cozy woodstove. Multiple fireplaces throughout boast dramatic floor-to-ceiling brick fronts and hearths, adding warmth and character to every gathering.

The 2024-renovated kitchen is a true centerpiece, featuring stainless steel appliances, quartz countertops, a tile backsplash, high cabinetry, recessed lighting, and a center island with seating. A sunny Florida room and a great room with built-in bar extend the home's effortless flow.
Retreat to the primary bedroom, complete with refinished hardwood floors, a walk-in closet, sitting area, and en-suite bath. Downstairs, an expansive finished lower level features a den and bonus room —each with its own wood-burning fireplace and a game room.

Recent upgrades include new windows in 2023, a fence in 2024, a French drainage system, an EV charger, Ubiquiti WiFi, and fully rebuilt chimneys. A two-car garage and spacious paver driveway complete the package.

The location shines: close to Navy Stadium, downtown Annapolis, City Dock, the State House, and the Arts District. Boutiques and fine dining moments from your door. In close proximity to Washington, DC and Baltimore. This is Annapolis living at its best!

ANNAPOLIS

211 N PINDELL AVENUE

3 Beds

2 Baths

4,497 Sq.Ft.

$775,000

MLS#: MDAA2146688

Great historic home built in 1850 in the heart of downtown historic Annapolis. Completely renovated and remodeled in 2023. New kitchen, new bathroom, recessed lights, new ceiling fans, lighting. Stainless steel appliances. Original hardwood floors. Front bedroom has cathedral ceiling. Exterior home has been completely painted in 2025. New decking off rear of home with a patio. Walking distance to tons of restaurants, bars, banks, stores etc. Home is one block off Main Street. Easy access to Route 50, I-97 and Route 2. A must see to believe. Set up a showing and bring us an offer.

ANNAPOLIS

32 CORNHILL STREET

2 Beds

1 Baths

1,064 Sq.Ft.

$774,900

MLS#: MDAA2146252

PROFESSIONAL PHOTOS COMING FRIDAY! OPEN SATURDAY 6/27 AND SUNDAY 6/28 11-1! Nestled in the sought-after water-privileged community of Lindamoor, this beautifully updated home blends timeless character with modern comfort. Original hardwood floors complement a renovated kitchen featuring natural wood cabinetry, granite countertops, stainless steel appliances, and a raised breakfast bar with decorative glass accents. The private, tree-lined setting creates a serene backdrop for the screened porch and composite deck, perfect for relaxing or entertaining. The spacious primary suite offers a vaulted ceiling, oversized walk-in closet, and a luxurious bath with a Kohler air-jet tub, double vanity, separate shower, and cathedral ceiling. The lower level features durable flooring throughout the family room and fourth bedroom or office, complete with a wall of custom built-ins and convenient access to a full bath with jetted tub. A raised-hearth gas fireplace anchors the family room, which opens to a covered paver patio overlooking the backyard and wooded buffer. Additional highlights include a 3-4 car paver parking pad, abundant indoor storage, and a dedicated outdoor storage room with workbench. Voluntary Lindamoor Improvement Association membership ($150/year) provides access to community paths leading to Cove of Cork and the Severn River, a community pier, sandy beach and a mooring area.

ANNAPOLIS

59 SLEEPY HOLLOW ROAD

4 Beds

3 Baths

2,152 Sq.Ft.

$750,000

MLS#: MDAA2148920

New on site 2 days ago

You’ve experienced Eastport. You’ve admired the effortless ease of its residents, and now you’re ready to embrace that coveted, walkable, waterfront lifestyle. This enchanting, fully reimagined cottage offers it in abundance.

Storybook curb appeal? Effortlessly. A seamless blend of timeless character and refined modern luxury? Absolutely. A short stroll to coffee, cocktails, and the beloved Eastport-A-Rockin’ Festival? Naturally.

There is a reason the white picket fence endures as a symbol of the American dream. There is an undeniable allure to a home that feels as though it has been lifted from the pages of a classic novel. Set within Eastport’s sought-after Maritime District and enhanced by an owner’s discerning eye for elevated, thoughtfully curated finishes, this residence is as captivating as it is distinctive.

Inside, graceful curved archways, authentic hardwood floors, and sophisticated lighting create an atmosphere of understated elegance. Custom tilework, a beautifully appointed kitchen with travertine flooring, and bathrooms adorned with refined marble surfaces reflect a commitment to quality and design. Coastal charm and contemporary sensibility are artfully balanced, resulting in a home that feels both timeless and impeccably current.

Mornings unfold with quiet indulgence: a leisurely walk to Bakers & Co. for a chocolate almond croissant, followed by a scenic stroll to Oscar’s Coffee at Horn Point Marina. There, you linger over an iced coconut milk latte, exchanging greetings with neighbors before continuing on to Horn Point Park, where the shoreline invites both relaxation and play.

Eastport’s celebrated dining scene may beckon, but today is reserved for hosting. Friends arrive via water taxi from the Historic District, and your home becomes the gathering place. With three bedrooms, two full baths, and a heated and air-conditioned sunroom that effortlessly transforms into a charming sleeping porch, every guest is welcomed in comfort.

As evening settles in, conversation flows easily—perhaps around the fire pit beneath the stars, or within the enclosed rear sunroom, where sliding doors open wide to invite in music, laughter, and the gentle Chesapeake breeze.

The following morning begins with a simple pleasure: a walk across the street to Diehl’s Produce for fresh, seasonal ingredients. Brunch is served in the formal dining room, where everyone gathers once more before heading to the marina for an afternoon sail.

This is the essence of Eastport living—refined, relaxed, and richly rewarding. All that remains is your story.

ANNAPOLIS

1100 BAY RIDGE AVENUE

3 Beds

2 Baths

1,720 Sq.Ft.

$750,000

MLS#: MDAA2150422

Perched on the coveted south side of the 10th floor at GrandView Luxury Condominiums, Residence 1014 is more than a home—it is a private sanctuary above the treetops, where elegance, tranquility, and breathtaking views converge.
Boasting a rare, unobstructed southern exposure, this exceptional residence captures panoramic vistas stretching more than 20 miles into Southern Maryland. Whether enjoyed from the comfort of the living spaces or from the private balcony, the ever-changing landscape provides a spectacular backdrop from sunrise to sunset.
Meticulously maintained and thoughtfully enhanced, this two-bedroom, two-bathroom ensuite residence with a den showcases an impressive collection of recent upgrades, including a new hot water heater (2025), custom draperies in the primary suite (2025), and a complete KitchenAid appliance package—refrigerator, oven, dishwasher, and microwave (2026). Rich Swedish walnut hardwood flooring was installed throughout the living room, dining room, and den (2026), complemented by fresh paint in the dining room and den, new wall-to-wall carpeting in the primary bedroom, and coordinating luxury area rugs that beautifully unify the living and dining spaces (all completed in 2026).
Beyond these recent improvements, this residence stands apart from every other Everest model in the building. Custom draperies throughout, California Closets in every closet, and bespoke built-in cabinetry in the den reflect a level of craftsmanship and attention to detail rarely found. Every enhancement was selected with intention and care, creating a home that is both sophisticated and deeply inviting.
Residence 1014 offers a rare opportunity to experience elevated condominium living at its finest—where privacy, luxury, and spectacular views come together in perfect harmony.
Beyond your front door, the very best of Annapolis Town Center is just steps away. Whole Foods for groceries, Target for everyday essentials, CVS for prescriptions, and Bin 201 Wine & Spirits for a carefully selected bottle are all within a leisurely stroll from GrandView’s secure entrance. Whether enjoying a relaxed breakfast, a business lunch, happy hour with friends, or a celebratory dinner, an exceptional variety of restaurants and gathering places await without ever needing to start the car. Life at GrandView is not only beautiful—it is effortlessly convenient. Ideally located just minutes from historic downtown Annapolis and centrally positioned between Washington, D.C., Baltimore, and the beaches of Maryland’s Eastern Shore, this is luxury living with unmatched accessibility.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1014

2 Beds

2 Baths

1,672 Sq.Ft.

$750,000

MLS#: MDAA2147408

#MDAA2137262

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 102

3 Beds

2 Baths

1,853 Sq.Ft.

$742,425

MLS#: MDAA2137262

Open House Sunday, June 7th 2:30PM - 4PM. Modern and “like-new” townhome ideally located just minutes to Downtown Annapolis and Eastport, offering easy access to waterfront dining, marinas, and shopping! This nearly new construction home at 118 Treblis Way showcases modern style, thoughtful enhancements, and effortless living in a prime Annapolis location. This home (Largest Model / 4 Levels) has been meticulously improved by the current owners, featuring hardwood flooring on every level (excluding bedrooms) for a seamless and elevated look throughout. Freshly repainted from top to bottom, the interior feels bright, clean, and completely move-in ready. Designer wallpaper accents on three of the four levels add a custom, upscale touch that sets this home apart, with each space carefully curated to blend comfort and contemporary style. Ideally situated near Quiet Waters Park, enjoy easy access to scenic walking trails, dog parks, and outdoor recreation, all while being just minutes from the best of Annapolis living. With its like-new condition, stylish upgrades, and unbeatable location, this home is a standout opportunity you won’t want to miss.

ANNAPOLIS

118 TREBLIS WAY

3 Beds

3 Baths

2,348 Sq.Ft.

$739,000

MLS#: MDAA2141836

New on site 3 days ago

#MDAA2149918

ANNAPOLIS

708 SYDNEY TERRACE

3 Beds

3 Baths

2,836 Sq.Ft.

$738,000

MLS#: MDAA2149918

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