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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

357

# of Listings

3

Avg # of Bedrooms

$480

Avg. $ / Sq.Ft.

$1,092,577

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

357 Properties Found. Page 9 of 24.

Located just across from the Annapolis Library and minutes from the heart of downtown, this 1940s home blends preserved historic charm with prime land potential. Set on a large, flat lot, it offers original refinished pine floors, arched entryways, solid wood doors, and built-in features that speak to a level of craftsmanship rarely found today.

The main level includes two bedrooms and a full bath, a sun-filled living room with built-ins and a wood-burning fireplace, and a separate sunroom ideal for quiet mornings or flexible living space. Upstairs, three additional bedrooms and another full bath provide space for family, guests, or a home office setup.

A walk-up attic—recently insulated—offers the option to finish for added living space or use as-is for ample storage. The unfinished basement presents even more flexibility. Outside, a large, detached two-car garage sits at the rear of the lot, offering convenience and potential for future workshop or studio space.

The home has been freshly painted throughout and updated with modern lighting fixtures. Electrical systems have been fully updated, including GFCI protection and grounded outlets—bringing peace of mind without sacrificing the home's character.

This property caters to a range of possibilities. Ideal for those drawn to historic architecture and character-filled spaces, it’s also a strong contender as a land offering in an enviable location. Whether you’re envisioning a personal renovation, restoring and expanding on its original bones, or considering the lot for future development, the location—walkable to downtown and steps from the library—makes this a rare opportunity.

ANNAPOLIS

1411 WEST STREET

None Beds

None Baths

0.49 acres

$875,000

MLS#: MDAA2112956

Eastport Peninsula Opportunity. Easy access to Historic Annapolis, Naval Academy, restaurants, marinas, two blocks to the Maritime Museum. Situated on a corner lot, Second St and Chester, across the street from Leeward Market. Current layout offers 2 legal ; 2 bedroom/ 1 full bathroom apartments with decks . An added bonus is the 3 car detached garage accessed from Chester. This property offers you options : convert back to single family home, re-design or continue as a rental.
Make an appointment, take a look

ANNAPOLIS

544 SECOND STREET

4 Beds

2 Baths

1,512 Sq.Ft.

$875,000

MLS#: MDAA2101556

Eastport Peninsula Opportunity. Easy access to Historic Annapolis, Naval Academy, restaurants, marinas, two blocks to the Maritime Museum. Situated on a corner lot, Second St and Chester, across the street from Leeward Market. Current layout offers 2 legal ; 2 bedroom/ 1 full bathroom apartments with decks . An added bonus is the 3 car detached garage accessed from Chester. This property offers you options : convert back to single family home, re-design, or continue as a rental.
Make an appointment, take a look

ANNAPOLIS

544 SECOND STREET

4 Beds

None Baths

1,512 Sq.Ft.

$875,000

MLS#: MDAA2109572

This stunning, unique residence embraces all of the cornerstones of the ideal Annapolis home, with so much more. Ideally situated in picturesque Romar Estates, the home exudes quality and style. Walk to the community water frontage that offers boat dockage with 4’mlw, ramp, kayak rack and picnic area, on scenic grounds gently rolling to the water's edge of Aberdeen Creek.

8 Romar Drive basks in a light-filled, spacious, open floorplan. The residence is graced with too many improvements to mention, including fully renovated and freshly-painted interiors, a new portico over the front entrance, a new Douglas fir front door, new dimensional-shingle roof, gutters and downspouts, new windows throughout, new HVAC system, new water treatment system, new well pump, new water heater, new garage door, new driveway and front walkway hardscape, new firelit stone patio area, New Chicken Palace with electric, and new fencing. The sun-dappled day porch delights in garden views. The outdoor living spaces are equally exciting as the interiors... the property has been freshened with new plantings, with mature gardens and trees lovingly tended seasonally. 8 Romar Drive is a location ideally located near Downtown Annapolis, all commuting thoroughfares and town amenities.

ANNAPOLIS

8 ROMAR DRIVE

3 Beds

2 Baths

2,692 Sq.Ft.

$874,000

MLS#: MDAA2114830

New on site 1 day ago

Charming West Annapolis Home with Detached Studio in a Garden Setting.
Walk to the water & shops! Located on a quiet, tree-lined street in the heart of West Annapolis, this warm and welcoming cottage offers classic charm, flexible living spaces, lush gardens, and thoughtfully designed outdoor dining and seating areas. With two bedrooms and one-and-a-half baths in the main home (est. total square footage is 1900), plus a detached annex with its own kitchenette, shower, and bath, this property is ideal for those seeking a peaceful, walkable neighborhood in Annapolis.
Inside, you’ll find a cozy layout filled with natural light. A bright "sleeping sunporch", cheerful living and dining areas, and an updated kitchen make the main level both inviting and practical. Upstairs are two comfortable bedrooms and a beautifully renovated full bathroom. The unfinished basement offers additional space ready for your vision—whether storage, workshop, or future expansion.
A rare bonus is a detached garage (est 886 sq ft.), with a private annex, offering a flexible space perfect for guests, a home office, a creative studio, or a potential rental. Tucked behind mature landscaping for privacy, it adds value and versatility without interrupting the main home’s tranquility. This home and the detached annex offer proven short- and long-term rental income potential, with their charm and location making it attractive for visiting tenants or seasonal stays, including commissioning week. Showings can be scheduled today, but will start 6/3.

Outdoor Features
The outdoor spaces are a true highlight of this property, offering a perfect blend of beauty, function, and privacy:
*Partially fenced backyard *Wildflower garden with native plantings that attract pollinators and bloom throughout the seasons*Paver patios *Gravel walkways *Multiple outdoor seating and dining areas designed for both quiet moments and casual gatherings *Rain garden and three rain barrels provide sustainable water management *Vinyl storage shed on a concrete slab for tools, bikes, or garden gear

ANNAPOLIS

206 SHILEY STREET

2 Beds

1 Baths

1,308 Sq.Ft.

$850,000

MLS#: MDAA2114204

Welcome to this beautiful home in the sought out neighborhood of Eastport. This home is charming with beautiful hardwood floors and spacious back yard - perfect for entertaining. Ready for the next home owner to make it their own! Great water views of Seashell Marina and Butlers Marina. For the love of nature and water views you will be right at home! The home will need some TLC on the second floor and the attic. Don't miss your chance to own in this highly desirable community.

Cash offers require 10% EMD or $1,000 minimum, whichever is greater, and all financed offers require 1% minimum, whichever is greater. Offers will be reviewed as they are received.

Property sold as is.

ANNAPOLIS

316 CHESTER AVENUE

2 Beds

2 Baths

1,200 Sq.Ft.

$850,000

MLS#: MDAA2113318

4.625% Assumable mortgage!! Step into over 5,000 square feet of effortless style and comfort in this stunning 4-bedroom, 2.5-bath Colonial tucked away on a quiet cul-de-sac in the sought-after Bowen Manor community of Annapolis. With soaring ceilings, abundant natural light, and a flowing open layout, this home was made for both grand entertaining and easy everyday living. The main level features a gourmet kitchen with a large center island, double ovens, and a bright eat-in area that opens seamlessly to the family room with a cozy gas fireplace. Just off the kitchen, a sun-drenched sunroom offers the perfect space for morning coffee, casual dining, or relaxing with a good book. You'll also find a private home office behind French doors, along with formal living and dining rooms accented by detailed moldings and beautiful custom touches throughout. (Please note, some photos are renderings to allow for visualizing rooms with different paint colors)

Upstairs, the expansive primary suite is a true retreat, complete with a lighted tray ceiling, a massive walk-in closet, and a spa-inspired en-suite bath. Three additional generously sized bedrooms provide plenty of space for family and guests, served by a well-appointed full hall bathroom. A convenient upstairs laundry room adds everyday ease and efficiency.

The walk-out lower level features an additional family room, offering the perfect spot for casual lounging, movie nights, or playtime. With plenty of open space, this level also provides endless possibilities to customize — create a rec room, home gym, media room, or even a guest suite to suit your needs.

Enjoy evenings on the expansive deck overlooking a fully fenced backyard—perfect for summer barbecues, playtime, or peaceful relaxation. Minutes from major commuter routes, shopping, dining, and historic downtown Annapolis, this home delivers the space, location, and lifestyle you’ve been searching for. Don’t miss your chance to make this your next home!

ANNAPOLIS

229 BOWEN COURT

4 Beds

2 Baths

4,221 Sq.Ft.

$849,900

MLS#: MDAA2114420

Luxurious penthouse condo with tons of natural light and views overlooking the fountain and plaza! 1285 square feet of living space encompassing a spacious Living room with fireplace, Kitchen with granite counters and plenty of cabinet space and 2 spacious bedrooms with ensuite baths. Every room boasts views and sliding doors onto a juliet balcony, perfect for letting in the fresh air and the cool evening breeze. Neutral finishes throughout and recently new refrigerator (1.5 years old) and HVAC unit (2 years old) creates peace of mind and a move-in ready blank canvas. Simplify your life with easy lock and go living. Fabulous 24/7 live concierge services, secure and monitored building, designated parking space and storage area. Even bills are streamlined since most utilities are included in the monthly condo fee. Enjoy the plethora of amenities that the Residences at Park Place provides including outdoor pool, courtyard for entertaining and grilling, hot tub, dog park, party room with billiards table, fitness room and many social activities. Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

5 PARK PLACE 722

2 Beds

2 Baths

1,285 Sq.Ft.

$825,000

MLS#: MDAA2112456

Construction Has Started on This Home - Will Be Ready for an August / September Move-In!! Pricing is likely to increase as construction continues, and the builder makes decisions on the final options and finishes. Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful 9,000 square foot lot in the sought-after waterfront community of Cape St. Clare in Annapolis. (There are two lots at this location - One has already sold). *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. This exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor, granite countertops, upgraded cabinets, ceramic-clad baths and laundry room, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. Come home and enjoy the exciting amenities that this incredible water privileged community has to offer. Looking for Lifestyle? This water privileged community has all the lifestyle that you want including 3 community beaches, access to community docks, fishing / crabbing pier, picnic area, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, community clubhouse and outdoor pool (with membership). All Boats, Kayaks, Canoes and all watercraft are welcome! This location is a convenient commute to Baltimore and Washington DC. This is a rare opportunity for new construction in the Cape St. Claire community. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features available. Prices, terms, conditions, and availability are subject to change without prior written notice.

ANNAPOLIS

987 ST JOHNS DRIVE - TAFT MODEL

4 Beds

2 Baths

2,580 Sq.Ft.

$819,990

MLS#: MDAA2100510

Rarely available Eastport townhome offering direct water views and access to Spa Creek in a private, waterfront-style enclave on serene Hawkins Cove. Enjoy the Annapolis waterfront lifestyle without the waterfront taxes—this beautifully maintained home features over 2,000 sq. ft. of light-filled living space and three expansive balconies overlooking the waterfront. Perfect for kayakers or paddleboarders, the property is just steps from the private community dock and water access point. Inside, the sun-drenched primary suite feels like a sanctuary with vaulted ceilings, a cozy fireplace, and spa-inspired bath. Multiple stacked stone fireplaces add warmth and elegance throughout. Whether you're enjoying sunrise coffee overlooking the water or taking a water taxi to nearby restaurants and marinas, this home delivers the ultimate Eastport experience. Located in a quiet, hidden waterfront community with easy access to downtown Annapolis, this is a rare opportunity to live on the water’s edge—ideal as a year-round residence or lock-and-leave retreat.

ANNAPOLIS

1233 BOUCHER AVENUE

3 Beds

2 Baths

2,052 Sq.Ft.

$800,000

MLS#: MDAA2114452

#MDAA2109402

ANNAPOLIS

2801 RIVA ROAD

3 Beds

3 Baths

1,680 Sq.Ft.

$799,000

MLS#: MDAA2109402

Time for a Lifestyle Upgrade — Welcome to GrandView at Annapolis Town Center! Step into elegance with this spectacular "Everest" model on the 6th floor — a rare opportunity to own one of the most coveted floorplans in the building. This stunning, move-in-ready home shows like a designer model and boasts an array of luxurious upgrades designed for both comfort and style. Enjoy two spacious primary suites, a guest powder room, and a versatile office/den ideal for remote work or quiet relaxation. The open-concept living and dining area features soaring 10-foot ceilings, gleaming hardwood floors throughout (no carpet!) and custom lighting that create a sophisticated, yet warm atmosphere. The gourmet kitchen is a chef’s dream, equipped with granite countertops, high-end KitchenAid black stainless steel appliances, and rich cabinetry. Additional highlights include a large laundry room, large closets for optimal organization, a newer HVAC system, and a private balcony overlooking the vibrant boulevard — the perfect spot to enjoy a glass of wine and live music during the center’s summer concerts. Located on the highly sought-after retail side of the building, you’ll enjoy a true urban vibe with direct access to the best of Annapolis Town Center — Whole Foods, Target, top-rated restaurants, cafes, and boutique shops, all just steps from your door. GrandView amenities include: two assigned garage parking spaces, concierge service, state-of-the-art fitness center, rooftop pool with panoramic views and secure entry and elegant common spaces. Just minutes to Historic Downtown Annapolis, the Annapolis Mall, Anne Arundel Medical Center, and with easy access to Route 50 and I-97 for commuting to D.C. or Baltimore. Experience elevated living at GrandView — this is a MUST-SEE unit!

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 606

2 Beds

2 Baths

1,682 Sq.Ft.

$795,000

MLS#: MDAA2111666

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful 9,000 square foot lot in the sought-after waterfront community of Cape St. Clare in Annapolis. (There are two lots at this location - One has already sold). *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. This exciting Sussex J model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor, granite countertops, upgraded cabinets, ceramic-clad baths and laundry room, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,232 square feet of above grade living space to enjoy and plenty of room for expansion including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. Come home and enjoy the exciting amenities that this incredible water privileged community has to offer. Looking for Lifestyle? This water privileged community has all the lifestyle that you want including 3 community beaches, access to community docks, fishing / crabbing pier, picnic area, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, community clubhouse and outdoor pool (with membership). All Boats, Kayaks, Canoes and all watercraft are welcome! This location is a convenient commute to Baltimore and Washington DC. This is a rare opportunity for new construction in the Cape St. Claire community. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features available. Prices, terms, conditions, and availability are subject to change without prior written notice.

ANNAPOLIS

987 ST JOHNS DRIVE - SUSSEX MODEL

4 Beds

2 Baths

2,232 Sq.Ft.

$779,990

MLS#: MDAA2098272

#MDAA2116466

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 610

2 Beds

2 Baths

1,681 Sq.Ft.

$779,000

MLS#: MDAA2116466

Amazing opportunity to own a beautiful parcel of land on desirable Shot Town Road area where large estates abound. Build a sprawling estate or subdivision potential giving three smaller estates.

ANNAPOLIS

SHOT TOWN ROAD

None Beds

None Baths

7.83 acres

$750,000

MLS#: MDAA2113200

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