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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
389
# of Listings
3
Avg # of Bedrooms
$474
Avg. $ / Sq.Ft.
$1,078,320
Med. List Price

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389 Properties Found. Page 10 of 26.

New on site 4 days ago
Charming West Annapolis Home with Detached Studio in a Garden Setting. Walk to the water, Tucker St. boat ramp, & 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. Please note the 2nd full bath is in the detached office. 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
#MDAA2114204

ANNAPOLIS

206 SHILEY STREET

2 Beds

2 Baths

1,308 Sq.Ft.

$850,000

MLS#: MDAA2114204

If you're looking for a charming home in the sought out neighborhood of Eastport. This home has 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. Seller is sharing their architectural designs but due to unforeseen circumstances they did not move forward. Don't miss your chance to own in this charming home in the highly desirable community of Eastport! 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.
#MDAA2113318

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!
#MDAA2114420

ANNAPOLIS

229 BOWEN COURT

4 Beds

2 Baths

4,221 Sq.Ft.

$849,900

MLS#: MDAA2114420

New on site 2 days ago
Welcome to 1381 Sunwood Terrace — a nicely maintained brick-front Colonial tucked away on a 0.87-acre flag lot in the highly desirable Rosewood community on the Broadneck Peninsula. Built in 1994 and lovingly maintained by its original owners, this spacious home offers approximately 4,000 square feet of finished living space with 4 bedrooms, 3.5 bathrooms, and a flexible, flowing layout perfect for everyday living and entertaining. The updated eat-in kitchen (2010) features rich cherry cabinetry, granite countertops, island with storage, a beverage center, stainless steel appliances (2024), and a pantry — all opening effortlessly to the inviting family room with newer carpet (2020), a wood-burning fireplace, with mantle, and twin French doors that lead to a large deck overlooking the backyard. Upstairs, the expansive primary suite offers a vaulted ceiling, oversized sitting area, large walk-in closet, and a luxurious ensuite bath. Three additional bedrooms — two with walk-in closets — and a beautifully updated hall bath (2020) complete the upper level. On the main floor, you'll find a formal living room, a spacious dining room with a charming bay bump-out, chair rail, and crown molding, as well as a dedicated home office with recessed lighting. Additional features include: 2-car garage with epoxy flooring, Freshly paved private driveway (2025), Architectural roof with 40–50-year shingles (2021), Gutter Relief System (2011), Fresh main-level paint (2021), Newer dryer (2023), Underground sprinkler system (sold as-is). Ideally located on a cul-de-sac in the sought-after Broadneck school district, with a low annual HOA fee ($350/year) AND NO FRONT FOOT FEE - FULLY PAID! Just minutes from downtown Annapolis, Broadneck's new walking/bike trail, parks, shopping, restaurants, hospitals, and major commuter routes to DC, Baltimore, and downtown Annapolis. Book a Showing appointment today! Don’t miss the chance to own this hidden gem in one of Annapolis’ most coveted neighborhoods!
#MDAA2116898

ANNAPOLIS

1381 SUNWOOD TERRACE

4 Beds

3 Baths

4,036 Sq.Ft.

$849,900

MLS#: MDAA2116898

New on site 2 days ago
Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. Make this Home Your Own! USE YOUR IMAGINATION! Great Location within STEPS to the Private Community Beaches etc.! 3,084 Total Sq Footage, .21 acre. lot size. THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE COMMUNITY BEACHES! & THE BIG WOODS "BAY RIDGE CONSERVATION AREA” W/TRAILS AND ACCESS TO BLACKWALNUT CREEK, A TRUE GEM! WALK TO COMMUNITY MARINA,W/BOAT RAMP, MOORING BALLS & SLIPS, PLAYGROUND, BASKETBALL/PICKEL BALL COURT, KAYAK RACKS , Kass Park: BASEBALL/SOCCER, LACROSSE FIELD!! WHETHER YOU'RE A BOATER, SUP ENTHUSIAST, DOG WALKER, RUNNER, HIKER (PRIVATE TRAILS IN THE BIG WOODS), RUNNER, THIS NEIGHBORHOOD HAS IT ALL! JOINING THE BAY RIDGE CIVIC ASSOCIATION IS VOLUNTARY. Home is being SOLD STRICTLY AS-IS! DO NOT WALK ON SIDE DECK ENTRY AND DECK OFF MASTERBEDROOM!
#MDAA2116136

ANNAPOLIS

13 LAWRENCE AVENUE

3 Beds

3 Baths

1,980 Sq.Ft.

$849,000

MLS#: MDAA2116136

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!
#MDAA2112456

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.
#MDAA2100510

ANNAPOLIS

987 ST JOHNS DRIVE - TAFT MODEL

4 Beds

2 Baths

2,580 Sq.Ft.

$819,990

MLS#: MDAA2100510

New on site 1 day ago
Sought-After Broadneck Area! This spacious Colonial offers 3 finished levels, 4 bedrooms, and 3.5 baths, perfectly situated in a desirable community with Broadneck schools. The upper level features 4 bedrooms, including an updated primary suite, hall bath and convenient laundry area. The main level boasts a formal living room and dining room, an updated kitchen with a breakfast area, a cozy family room, a powder room and mud room. Featuring hardwood flooring. The fully finished basement includes a second family room with fireplace, a bedroom, and a full bath — ideal for guests or multi-generational living. Outdoor living shines with a screened porch, deck, gazebo, and a peaceful backyard that backs to trees. Additional highlights include a 2-car garage and a 2-zone HVAC system featuring a high-efficiency geothermal heat pump. Enjoy easy access to commuter routes, Sandy Point State Park, and Podickory Point Yacht & Beach Club.
#MDAA2113440

ANNAPOLIS

2104 HARBOR DRIVE

5 Beds

3 Baths

2,240 Sq.Ft.

$799,000

MLS#: MDAA2113440

New on site 1 day ago
Welcome to 2772 Gingerview Lane in the desirable Riva Trace community! This beautifully updated home features over $100K in recent upgrades, including a stunning primary bath remodel, new Bosch 21 SEER HVAC, 2 gas fireplaces, water heater, fresh paint, and more. There’s even a flexible main-level space that could easily serve as a sixth bedroom, office, or guest suite. While the sellers have poured their hearts into this home, life’s path led them in a different direction. After relocating from Gambrills, MD to Poland in July 2024 to pursue a career opportunity and run a handmade jewelry business abroad, unexpected challenges brought them back to Maryland just a few months later. They quickly fell in love with the charm, peacefulness, and natural beauty of Riva Trace and knew they had found their place. But in May 2025, Seller 1 was offered a dream position in Seattle—an opportunity too good to pass up. As reluctant as they are to leave, they hope the next owner will appreciate the love and upgrades they’ve invested. The home offers stunning finishes, serene surroundings, a safe and quiet street, and access to walking trails, water amenities, and all that Riva Trace has to offer. This is more than a house—it’s a home ready to welcome its next chapter.
#MDAA2117354

ANNAPOLIS

2772 GINGERVIEW LANE

5 Beds

3 Baths

3,852 Sq.Ft.

$799,000

MLS#: MDAA2117354

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!
#MDAA2111666

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.
#MDAA2098272

ANNAPOLIS

987 ST JOHNS DRIVE - SUSSEX MODEL

4 Beds

2 Baths

2,232 Sq.Ft.

$779,990

MLS#: MDAA2098272

Welcome to Grandview, an exceptional condo nestled in the vibrant Annapolis Towne Center! This unique unit offers a fantastic layout with two primary bedrooms, each boasting its own private ensuite bathroom, providing ultimate comfort and convenience. You'll also appreciate the thoughtful addition of a separate hall bathroom, ensuring guests have their own dedicated space. The spacious kitchen is a delight, featuring all brand new appliances ready for your culinary adventures. Elegant French doors open from the main living area into a versatile den, perfect for a home office, media room, or cozy retreat. The inviting living room is enhanced by a sophisticated tray ceiling and features a slider that opens to your private balcony, offering lovely views of the surrounding area. Practicality meets luxury with a separate laundry room complete with a brand new washer and dryer and ample cabinet space. This unit feels fresh and modern, having been newly painted throughout and showcasing upgraded light fixtures. Enjoy the beauty of newly installed wood flooring that flows seamlessly through the main living spaces. For added comfort and well-being, the HVAC system is equipped with an air purifier. Forget the parking hunt! This condo comes with a prime parking space conveniently located on the concierge level, #70, as well as an additional parking space, #287. For your storage needs, you'll find a dedicated storage unit, #17. Grandview amenities include concierge services, fitness center, roof top pool and lounge, club & library rooms, and a secure entry. Experience the best of Annapolis living with unparalleled convenience and a truly distinctive floor plan at Grandview!
#MDAA2116466

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 610

2 Beds

2 Baths

1,681 Sq.Ft.

$779,000

MLS#: MDAA2116466

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—this beautifully maintained home features over 2,000 sq. ft. of light-filled living space and three expansive balconies overlooking the waterfront. Community dock and water access is perfect for small craft. Inside, the sun-drenched primary suite feels like a sanctuary with vaulted ceilings, a cozy fireplace, and spa-inspired bath. Three stacked stone fireplaces add warmth and elegance throughout. Whether you're enjoying morning coffee overlooking the water or walking 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.
#MDAA2114452

ANNAPOLIS

1233 BOUCHER AVENUE

3 Beds

2 Baths

2,052 Sq.Ft.

$775,000

MLS#: MDAA2114452

****PRICE IMPROVEMENT***Welcome to this beautifully maintained Cape Cod nestled on a private and serene .94-acre lot—a rare gem offering the perfect blend of peaceful seclusion and unbeatable convenience. Located in the heart of Annapolis, this home provides quick access to premier shopping, dining, downtown Annapolis, the Naval Academy, Navy Stadium, and more! ****OPEN HOUSE 5/20 12-2***** Step inside to an Artisan eat-in kitchen featuring a picturesque bay window with views of the lush, professionally landscaped perennial garden. The true showstopper is the main-level primary suite, boasting a soaring vaulted wood ceiling, generous layout, and a beautifully updated en-suite bath. Enjoy indoor-outdoor living with a brand new spacious deck, a 6-person hot tub, and a cozy screened-in porch just off the kitchen—ideal for relaxing or entertaining year-round. This community offers amenities galore with no HOA fee: tennis courts, tot lot, walking paths, community pier, and kayak/boat storage racks. This Property also presents an exceptional short-term rental opportunity, thanks to it's private hot tub, spacious acreage and prime location near the Naval Academy and all the downtown Annapolis has to offer. Proven rental history available upon request. Move-in ready and truly one-of-a-kind, this home combines character, charm, and location. Don’t miss your chance—
#MDAA2109402

ANNAPOLIS

2801 RIVA ROAD

3 Beds

3 Baths

1,680 Sq.Ft.

$759,900

MLS#: MDAA2109402

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.
#MDAA2113200

ANNAPOLIS

SHOT TOWN ROAD

None Beds

None Baths

7.83 acres

$750,000

MLS#: MDAA2113200

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