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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

276

# of Listings

3

Avg # of Bedrooms

$515

Avg. $ / Sq.Ft.

$1,434,627

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

127 Properties Found. Page 3 of 9.

#MDAA2145808

ANNAPOLIS

7 GERMAN STREET

3 Beds

2 Baths

1,764 Sq.Ft.

$839,000

MLS#: MDAA2145808

#MDAA2144296

ANNAPOLIS

422 FIRST STREET

2 Beds

1 Baths

1,094 Sq.Ft.

$835,000

MLS#: MDAA2144296

Welcome home to this one of a kind three bedroom, two and a half bath rancher on a double lot in sought after Cape St Claire. One level living at it's finest, with a huge sunroom with vaulted ceiling on one wing, and the bedrooms on the other wing of this sprawling rancher. This property has been lovingly maintained by the owners, with the addition of the sunroom, powder room, laundry room, and part of the garage in more recent years. The 600 square foot light filled sunroom is the focal point of the house now, with wonderful built in bookshelves and entertainment center. The original family room has a wood burning fireplace, and makes a cozy den or office. Stainless appliances and table space in the kitchen with French doors leading to the stone patio out back. The living room and dining room have ample space for gatherings. In the bedroom wing of the house find the primary bedroom with an attached full bath and two more ample bedrooms share the hall full bath. Recent updates include; in 2020 - Fast Care Floor System installed in garage & driveway resurfaced, in 2023 a new roof, in 2025 new well pump, updated electric to code, one new air conditioner, new stainless steel liner in fireplace , & new oil tank, and in 2026 - new faucets in kitchen and master bath****** Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to Ft Meade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore

ANNAPOLIS

1047 LITTLE MAGOTHY VIEW

3 Beds

2 Baths

2,892 Sq.Ft.

$825,000

MLS#: MDAA2146800

Love This HOME at the NEW PRICE!! 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.

$825,000

MLS#: MDAA2140978

Open House Sunday 12-2 Welcome to Winchester On The Severn. One of Annapolis's most established waterfront community's. This home provides mature landscaping with a canopy of lovely trees and bushes both in the front and rear yard. Covered front porch! You will be pleased to enter a spacious foyer. Main level bedroom with a full bath to the left. A few steps up to the open floor plan with spacious living room that feeds into the dining room. Be prepared to enjoy the screened porch off the dining room. A wonderful spot to relax and enjoy the back yard. The eat in kitchen is filled with light! Comfortable family room is complimented with a wood burning fireplace. And you can also walk out from the family room to the back yard! The basement is dry and has a new 2025 heat pump. The 3 additional bedrooms have fresh paint. The larger bedroom is en-suite. Ready to know about the neighborhood? Amenities include private beach on the Severn River, marina, boat ramp, multiple piers, dog beach, beach pavilion, and the Chase Creek swim club. Nearby is the B&A trail. You may not want to leave the home but if you do it is a short ride to Annapolis and all major routes. Welcome. Enjoy

ANNAPOLIS

1518 WINCHESTER ROAD

4 Beds

3 Baths

2,249 Sq.Ft.

$825,000

MLS#: MDAA2147986

The sellers are offering $10,000.00 towards purchasers closing costs.
Phenomenal home at a great price! This is a must see!
Nestled in the highly desirable Annapolis Roads community on the mouth of Lake Ogleton, this distinctive home offers exceptional indoor and outdoor living spaces, timeless architectural details, and access to some of Annapolis' most sought-after waterfront amenities. Private spaces abound. From the beautiful screened family room, to the covered deck, ivy covered brick walled patio, sun room, there is always a quiet area to relax.
The many windows provide natural light throughout.
Major systems and appliances recently updated include the furnace (3 years), dishwasher, two air conditioning units( approximately 9 years), washer and dryer. Updated windows.
Extensive hardscaping surrounds the property, creating multiple inviting outdoor spaces. The sunroom is a standout feature, showcasing hand-hewn beams, custom built-in cabinetry, and a wall of Cape Cod-style windows that fill the space with natural light.
Throughout the home include custom lighting highlights built-in shelving, cabinetry, and workspaces. The spacious primary suite features an ensuite bath with a jetted tub, walk-in closet, and an additional shoe closet. A second jetted tub is located in the upper-level hall bath.
Residents enjoy access to Annapolis Roads' exceptional amenities, including a private beach, bayfront pavilion, playground, fire pit, community pier, kayak/SUP storage, boat ramp, hiking trails, and a variety of neighborhood events throughout the year.
A unique opportunity to enjoy the charm, character, and community lifestyle that make Annapolis Roads such a special place to call home.

ANNAPOLIS

2644 QUEEN ANNE CIRCLE

3 Beds

3 Baths

3,000 Sq.Ft.

$820,000

MLS#: MDAA2146714

Nestled in the charming Boucher Place community, this exquisite end-of-row townhouse offers a perfect blend of coastal and traditional architectural styles, creating a warm and inviting atmosphere. Built in 2013, this residence boasts 1,800 square feet of thoughtfully designed living space, ideal for those seeking comfort and elegance. The kitchen is a chef's dream, featuring upgraded countertops, a spacious island, and high-end stainless steel appliances, including a gas range and built-in microwave. The combination of hardwood on the main level, throughout adds a touch of sophistication, while plush carpeting in the bedrooms ensures a cozy retreat. The home features three generously sized bedrooms, each designed with comfort in mind. The primary suite is a true sanctuary, complete with a walk-in closet and a luxurious en-suite bathroom featuring a tub shower. Enjoy the warmth of the gas fireplace in the family room, creating a perfect ambiance for relaxation. Thoughtful details such as ceiling fans and window treatments enhance the home's comfort and style. Step outside to your private outdoor oasis, where a roof top balcony, deck, and patio await, perfect for enjoying morning coffee or evening gatherings. The beautifully landscaped courtyard view adds to the serene atmosphere, making it an ideal spot to unwind. This property also includes a detached two-car garage with rear entry, ensuring convenience and ample storage. The paved driveway and well-maintained sidewalks enhance the overall appeal of the home. As part of the Boucher Place community, residents benefit from included association services such as lawn maintenance, snow removal, and insurance, allowing for a low-maintenance lifestyle. Experience the perfect blend of luxury and comfort in this stunning townhouse, where every detail has been carefully curated to create a welcoming home. Embrace the exclusive lifestyle that awaits you in this beautiful property. New Roof in 2024 and new hardwoods in 2025.

ANNAPOLIS

19 BOUCHER PLACE

3 Beds

3 Baths

1,800 Sq.Ft.

$819,000

MLS#: MDAA2142690

New on site today

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

Discover the perfect blend of Annapolis charm and contemporary luxury at 1107 Brashears Street in desirable Eastport. Meticulously transformed and fully remodeled, this truly turn-key home presents 5 bedrooms and 2 full baths. Upon arrival, an inviting screened-in front porch welcomes you into a residence created for comfort. The main level is designed for modern living and entertaining, featuring an open floor plan anchored by a gourmet kitchen boasting a large center island and quality, stylish finishes that ensure a fresh, modern aesthetic. The layout offers maximum convenience with a valuable main-level bedroom and full bath. The comprehensive renovation inside and out showcasing stylish design and quality finishes throughout.

The property is further enhanced by an expansive backyard, creating an outdoor retreat for the whole family to enjoy. The large paver-patio with fire pit, is ideal for entertaining, and family dinners. This Eastport gem perfectly balances premium convenience with exceptional comfort. This is your opportunity to own a like-new home in a prime location.

ANNAPOLIS

1107 BRASHEARS STREET

5 Beds

2 Baths

1,800 Sq.Ft.

$799,999

MLS#: MDAA2142894

RENOVATED EASTPORT GEM With MODERN COASTAL FINISHES! Perfect for a main 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 Andersen 100 series windows, Hardie Plank siding, and new hardscaped paths. PARKING: Private driveway with 2 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.

$799,900

MLS#: MDAA2142230

Welcome to this beautifully maintained custom built Tudor Style home! 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! 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

Property offers off street parking, with an additional concrete pad for a boat. Eastport living is all about energy and convenience, this charming coastal home has it in abundance. Enjoy a rare double lot complete with new wood fencing creating a private outdoor space, new roof, windows, interior upgrades and thoughtful finishes. Additional upgrades include a tankless water heater, for an endless supply. You'll find a light filled space and recently refinished gleaming hardwood floors throughout.
Outside you're across from The Annapolis Athletic Club and a few blocks to restaurants, pubs, Historic Annapolis and The Naval Academy. Where character and comfort come together. Easy commute to Washington DC and major airports.

*Four bedroom, with the fourth being a flex space office/guest room*

ANNAPOLIS

1100 BAY RIDGE AVENUE

4 Beds

2 Baths

1,720 Sq.Ft.

$799,000

MLS#: MDAA2141488

This charming downtown Annapolis home is located in the most desirable neighborhood of Murray Hill. Walk out your door and access everything Annapolis has to offer - restaurants, stores, Naval Academy, Stadium, etc. This property was completely renovated recently. The kitchen offers stainless steel appliances, quartz countertops and engineered wood flooring throughout! The property also includes a large backyard and ample parking - a rare find in downtown Annapolis! As you walk into your new home you will notice the open kitchen/living room area has plentiful lighting with white cabinetry, Kitchen Aid appliances, an island with extra storage, and a subway tile backsplash. The main level also offers two spacious bedrooms and a large deck off of the kitchen with lots of sunlight. The lower level of the home offers the primary bedroom and private bathroom, along with a den area that includes a beautiful brick fireplace surrounded by bookshelves and cabinets, a 1/2 bath and front load washer & dryer! There is plenty of storage and a door to access the large backyard where you can enjoy the playground & picking crabs while your kids run around in the fenced in backyard! Murray Hill features water access at the end of many streets where it is easy to launch a kayak/stand up paddle board or hop on the water taxi! It is also very close proximity to the Navy stadium which makes walking to the games an easy short walk! Come enjoy the best of Annapolis life in a charming home and the perfect location!

ANNAPOLIS

57 SPA ROAD

3 Beds

2 Baths

1,555 Sq.Ft.

$799,000

MLS#: MDAA2146170

New on site 1 day ago

Lovingly maintained by the original owners since 1986, this classic colonial is ready for its next chapter. Tucked away on a peaceful cul-de-sac, this home offers a wonderful setting with a spacious lot, mature trees, established gardens and a backyard that was thoughtfully designed and professionally landscaped over the years. Enjoy the changing seasons from the impressive 18x16 sunroom addition featuring walls of windows overlooking the beautiful backyard, or step outside onto the adjoining deck for outdoor entertaining and relaxation.

The main level offers a traditional layout with formal living and dining rooms, while the kitchen, family room and sunroom create a spacious gathering area in the heart of the home. The large kitchen features granite countertops, abundant cabinet space and a center island with plenty of room for meal preparation and casual seating. A convenient half bathroom and attached two-car garage complete this level.

Upstairs, you will find three generously sized bedrooms including the primary suite with an attached bathroom featuring a soaking tub, separate walk-in shower and dual vanity. The primary bedroom also offers excellent closet space along with a versatile adjoining sitting room/walk-in closet area that could easily be converted back into an additional bedroom. An additional walk-in closet within the primary bedroom includes a convenient second-level laundry area while still providing functional closet space. Two additional spacious bedrooms and a full hall bathroom complete the upper level.

The unfinished walk-up lower level provides additional storage, a second laundry area and plenty of possibilities for future living space. With updated HVAC (2026),new siding(2025) wonderful additions and a beautiful established homesite, this special property offers the opportunity to make lasting memories for years to come.

ANNAPOLIS

2802 AUTUMN CHASE RUN

4 Beds

2 Baths

2,612 Sq.Ft.

$785,000

MLS#: MDAA2148962

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

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