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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

$506

Avg. $ / Sq.Ft.

$1,384,240

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

276 Properties Found. Page 14 of 19.

Stunning Oyster Harbor – Coastal Charm Meets Comfort

This gorgeous property blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat ramp, and storage racks for kayaks and paddle boards, creating the ultimate waterfront lifestyle just minutes from downtown Annapolis.

The home itself is designed for both entertaining and everyday enjoyment. An enormous screened-in porch and a spacious, fully fenced backyard provide plenty of room to garden, relax in a hammock, or host gatherings. After a day at the beach, the outdoor shower is the perfect convenience.

Inside, the property features three bedrooms, two full bathrooms, and hardwood floors throughout the main level.

Don’t miss the opportunity to live in this beautiful home and vibrant waterfront community—where comfort, charm, and lifestyle come together seamlessly.

ANNAPOLIS

1252 CREEK DRIVE

3 Beds

2 Baths

1,555 Sq.Ft.

$565,000

MLS#: MDAA2145374

Location Location location!!
Modern rancher style home located near everything Annapolis has to offer! It's just minutes to Downtown Annapolis. The House is much bigger than it looks. A beautiful fenced in backyard with a composite decking awaits for outdoor entertaining. This house also features 5 bedrooms and two full bath. This home is almost 2,000 sf. finished. Entire home was fully renovated in 2025. The finished basement features a laundry room, family room, 2 spacious bedrooms, and one full bathroom. The whole top level features 3 bedrooms, one full bath, open concept style kitchen with island that opens to the dining space and large living room. New HVAC, plumbing and electrical system. Move-in ready, fully furnished!! This home really offers a wonderful opportunity to enjoy Annapolis living — just minutes from shopping, dining, and commuter routes.

ANNAPOLIS

1002 TYLER AVENUE

5 Beds

2 Baths

1,920 Sq.Ft.

$550,000

MLS#: MDAA2130284

Opportunity awaits in sought-after St. Margarets! This 3-bedroom, 1-bath home with hardwood floors, situated on a gorgeous 1-acre lot offering plenty of space and potential. Solid built home they don't make houses like this any longer, needs updating, making it the perfect chance to bring your ideas and renovate to your personal taste. Most major systems updated within last 10 years. Whether you are looking for an investment opportunity or a property to create your dream home, this one has endless possibilities. Home is being sold strictly “AS IS.” Home warranty included.

ANNAPOLIS

1509 DUVALL ROAD

3 Beds

1 Baths

1,512 Sq.Ft.

$550,000

MLS#: MDAA2144750

Beautifully updated and filled with thoughtful improvements, this Cape Cod in Annapolis combines model-like interiors, a recently finished lower level, and inviting outdoor living just minutes from the Chesapeake Bay. Blooming perennial landscaping and a covered front porch create a warm welcome, while inside, a deceptively spacious open concept floor plan showcases hardwood flooring, recessed lighting, and a soft neutral palette that carries throughout the home.
The living room is bright and airy, highlighted by a partial vaulted ceiling accented with skylights that fill the space with natural light. Just beyond, the renovated kitchen blends style and function with stainless steel appliances, a tile backsplash, abundant cabinetry, roll-out shelving, and a swing-out pantry designed for effortless organization. A dedicated dining area with a modern light fixture completes the main living space with a polished touch.
The main level includes a spacious bedroom with a walk-in closet featuring a built-in organization system. Also on this level is a beautifully renovated full bath complete with a double sink vanity, stylish finishes, and a tiled tub and shower surround. Nearby, the laundry room provides storage shelving and convenient access to the backyard.
Upstairs, two generously sized bedrooms share an updated full bath with a tiled shower enclosed by frameless glass. One of the upper level bedrooms is enhanced by a charming shiplap accent wall and a cozy window seat, adding character and a tucked-away place to relax. The recently finished lower level expands the living space with a comfortable family room featuring durable wood-look tile flooring, a versatile bonus room, and a sizable storage area.
Outdoor spaces are equally inviting, with a deck and patio overlooking the spacious backyard, creating room to entertain, relax, or enjoy the surrounding greenery. A storage shed with a garage door adds functionality, while major updates including the roof and water heater offer additional peace of mind.
This location places you moments from some of Annapolis’ most scenic waterfront recreation, including Sandy Point State Park with its sandy beach, marina, fishing and crabbing access, and sweeping Chesapeake Bay Bridge views. Jonas Green Park, Quiet Waters Park, and Thomas Point Park are also nearby, offering trails, kayaking, waterfront overlooks, and endless opportunities to enjoy the natural beauty of the Annapolis area. Hop on the Broadneck Peninsula Trail across the street and head to Sandy Point Park or connect to the B&A Trail.

ANNAPOLIS

1470 LOG INN ROAD

3 Beds

2 Baths

1,465 Sq.Ft.

$550,000

MLS#: MDAA2145366

Welcome to Village Greens — Where Annapolis Living Reaches Its Full Potential. Tucked along a tree-lined streetscape that delivers that quintessential Annapolis vibe, this stunning 3 BR, 2.5 BA luxury townhome checks every box. Step inside to an open concept main level where rich hardwood floors flow beneath soaring ceilings, plantation shutters grace every window, and modern updated lighting plus freshly painted spaces adds a polished, contemporary feel throughout. Upstairs, vaulted ceilings continue to impress. The primary suite is a true retreat — custom walk-in closet, soaring ceilings, walk-in shower, soaking tub, and a double bowl owner's vanity. Gorgeous LVP flooring runs throughout the upper level, combining beauty with durability. A true basement with windows sets this home apart — bright and full of possibilities, with a plumbing rough-in already in place for a future bath. Outside, gated rear access leads to private resident parking pads and garages, keeping the neighborhood's gorgeous streetscape beautifully uninterrupted. Minutes to Route 50 puts Baltimore, D.C., and the Eastern Shore within easy reach — yet you're squarely in the heart of Annapolis, minutes from world-class waterfront dining, the iconic City Dock, Quiet Waters Park, and everything that makes this city so beloved. Fresh crabs, sailing, brick streets, and the Naval Academy — this is the Annapolis lifestyle, beautifully lived. Schedule your tour today!

ANNAPOLIS

607 S CHERRY GROVE AVENUE

3 Beds

2 Baths

2,008 Sq.Ft.

$550,000

MLS#: MDAA2145726

HERITAGE HARBOUR! It's the perfect size! 2 Bedrooms. 2 full Baths. Den. Sun Room Addition. Deck (2025). HVAC (2025). Architectural Shingle Roof (2021). HHCA's site touts the community as... an established community in Annapolis, offering beautiful wooded lots and featuring a wide variety of recreational, cultural, social, and educational activities for its residents. Residents can participate in over 90 activities, clubs and committees. The center of community activities is the Lodge, which features a welcoming atrium, an auditorium, indoor and outdoor pools, fitness center, library, boutique, activities room, woodwork shop, game rooms, coffee corner and meeting rooms. Behind the Lodge, residents enjoy a picnic area, horseshoes, bocce ball and kayaking on our waterfront on the South River. We also offer multiple tennis and pickleball courts, a nine-hole golf course, a pro shop, a clubhouse dining room, a pier with boat slips and RV and boat storage on a lot in the community. Residents enjoy the convenience of regular bus trips to shopping centers and special bus trips to cultural destinations, as well as volunteer drivers for medical appointments. Our pet-friendly community of active residents always welcomes newcomers!

ANNAPOLIS

2550 GOLFERS RIDGE ROAD

2 Beds

2 Baths

1,661 Sq.Ft.

$550,000

MLS#: MDAA2143166

#MDAA2134520

ANNAPOLIS

102 VANGUARD LANE

4 Beds

3 Baths

2,000 Sq.Ft.

$549,999

MLS#: MDAA2134520

This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaking panoramic views and an abundance of natural light from its sunny southern exposure. Featuring two generously sized bedrooms with expansive closets, this upscale residence combines comfort and style. Inside, you’ll find beautiful hardwood floors (no carpet), soaring 10-foot ceilings, elegant granite countertops throughout and NEW appliances. The freshly painted interiors are complemented by custom window treatments that add both privacy and sophistication. Step outside to your private balcony and enjoy sweeping views of the surrounding area. Two assigned parking space for convenience. Building Amenities: Rooftop pool with panoramic vistas. State-of-the-art fitness center. Elegant club rooms for gatherings and relaxation. Concierge service for a luxurious living experience Ideally located in the vibrant Annapolis Town Center, this condo puts you within walking distance of premier shopping, dining, and entertainment options. Whether you're enjoying a meal at one of the area's finest restaurants or exploring local boutiques, everything you need is just moments away. This is a must-see home that blends modern living with the best of Annapolis! Don't miss out on the chance to call this spectacular property yours.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 513

2 Beds

2 Baths

1,485 Sq.Ft.

$549,000

MLS#: MDAA2139908

Motivated seller! New price reflects home and pool "as is."
This spacious split-level home offers an exceptional combination of comfort and functionality.

The main level features an updated kitchen with adjoining dining area, creating a welcoming space for meals and gatherings. A stunning 400-square-foot sunroom addition provides year-round enjoyment and opens directly to an expansive 400-square-foot composite deck, perfect for entertaining or relaxing outdoors. The primary suite includes a private ensuite bathroom, while two additional bedrooms and a full hall bath complete the upper level.

The walk-out lower level offers incredible flexibility with a spacious family room, a separate living room featuring a wood-burning fireplace, two additional bedrooms, and a convenient half bath—ideal for guests, a home office, or multi-generational living.

Outside, you'll find driveways on both sides of the house, with parking for up to four vehicles. There are two storage sheds for all your tools and equipment, and a portable generator that conveys with the property and is capable of powering approximately three-quarters of the home.

Pool, pool equipment and home convey "as is."

Mortgage savings may be available for buyers of this listing.

ANNAPOLIS

1115 SKYWAY DRIVE

5 Beds

3 Baths

1,480 Sq.Ft.

$540,000

MLS#: MDAA2146744

Nestled in the sought-after Southwoods community just off West Street, this beautifully updated single-family home offers the perfect blend of comfort, style, and convenience with easy access to everything Annapolis has to offer. Inside, luxury vinyl plank flooring flows throughout the inviting two-story floor plan featuring arched entryways, a cozy fireplace, and flexible living spaces designed for today’s lifestyle. The updated kitchen shines with white cabinetry, Corian countertops, stainless steel appliances, pantry storage, and a convenient breakfast bar with seating, all opening to a sunny morning room and family room ideal for everyday living and entertaining. A main-level office or flex space, along with a powder room, adds versatility and function. Upstairs, the spacious primary suite features a private bath, while two additional bedrooms share a well-appointed hall bath. Enjoy outdoor living with a welcoming front porch, private backyard, deck, and off-street driveway parking — all in a location that puts shopping, dining, Historic Annapolis, commuter routes, and waterfront attractions just moments away.

ANNAPOLIS

1529 RITCHIE LANE

3 Beds

2 Baths

1,524 Sq.Ft.

$539,000

MLS#: MDAA2146440

Seller Says SELL!!! Welcome to penthouse living at Element at Mill Creek, one of Annapolis’ most stylish and thoughtfully designed 55+ communities. This 2 bed + Den, 2 bath top-floor residence with in-home laundry offers the privacy and quiet you’ll appreciate, paired with the elevated finishes and upgrades that truly make it better than new construction. From the moment you enter, you’ll notice the difference. Since purchasing, the owner has enhanced the home with carefully selected upgrades—refined lighting, custom touches, and elevated finishes that go beyond the builder’s base offerings. The result is a move-in-ready home with personality, warmth, and polish already in place. No waiting on construction timelines, no post-settlement projects—just effortless living from day one. This penthouse unit enjoys abundant natural light and peaceful views, along with the convenience of an assigned parking space in a secure garage—providing comfort and ease year-round. Life at Element at Mill Creek is designed for connection, wellness, and enjoyment. Residents enjoy a beautifully appointed clubhouse featuring indoor and outdoor dining spaces, a state-of-the-art fitness center, gathering rooms, and even a golf simulator for year-round play. Outdoors, you’ll find pickleball courts, scenic walking trails, and a dedicated dog park—perfect for staying active and social while enjoying the thoughtfully landscaped grounds. The community’s modern coastal architecture and easy layout create a fresh, welcoming neighborhood atmosphere that feels both intimate and sophisticated. Located just minutes from downtown Annapolis, you’ll have easy access to everything that makes the area so special—waterfront dining, boutique shopping, art galleries, live music, and year-round festivals. Spend afternoons strolling along City Dock, catching a sailboat race on the Chesapeake Bay, or enjoying dinner at one of the many acclaimed local restaurants. The charm, history, and vibrant lifestyle of Annapolis are right at your doorstep. And unlike many new construction purchases—where buyers are often responsible for the majority of closing costs—this resale offers a more traditional and balanced approach, with costs typically shared between buyer and seller. Title insurance discount also available. Stylish, upgraded, and ideally located, this penthouse at Element at Mill Creek offers the perfect blend of low-maintenance luxury, active living, and the best of Annapolis just moments away.

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 409

2 Beds

2 Baths

1,210 Sq.Ft.

$530,000

MLS#: MDAA2137136

Welcome home to 530 Samuel Chase Way — a fantastic end-unit townhome in the heart of Tidewater Colony! This home was designed for today's lifestyle, the flexible entry level features a private bedroom, full bath, and family room with wet bar— both rooms ideal for hosting guests, creating a dedicated home office, or enjoying additional living and recreation space. Upstairs, the open-concept main level is equally suited for everyday living and entertaining, showcasing a kitchen with quartz countertops, stainless steel appliances, and abundant natural light. The adjoining dining area and spacious living room create an inviting gathering space, while the large deck extends the living area outdoors for dining, relaxing, or entertaining. Oversized windows on three sides fill this level with natural light and creates an airy, welcoming feeling throughout.
The upper level offers two generously sized bedrooms, including a private owner's suite, an additional full bath, and conveniently located laundry. Perfectly positioned just outside Annapolis city limits with direct access to US-50, you're minutes from Downtown Annapolis, the waterfront, Annapolis Mall, and Parole Town Center. Community amenities include walking trails, tennis courts, an outdoor pool, fitness center, clubhouse, and playgrounds. Seller is purchasing a buyer home warranty through CINCH Home Services. Schedule your tour today and come experience living in Tidewater Colony!

ANNAPOLIS

530 SAMUEL CHASE WAY

3 Beds

3 Baths

2,408 Sq.Ft.

$530,000

MLS#: MDAA2147202

OPEN SATURDAY 6/6_ 12-2 and SUNDAY 6/7_ 1-3 Come enjoy the ease of single-level living, secure community, and the unmatched lifestyle of waterfront. The warm and inviting living room opens to sweeping Spa Creek Views, while a dazzling kitchen with a picturesque window makes creating a meal a delight...with a wood-buring fireplace and engineered hardwoods. Step outside through sliding doors to a relaxing deck enjoying the sunsets. Extra storage on the deck and in the basement for all your needs. There are boat slips available, depending on size and water depth. Shearwater is one of Annapolis's most coveted gated communities know for its lush landscaping, amenities, and easy access to downtown. Here, you enjoy the best of both worlds-resort-style living while being minutes away from restaurants, shops, and the charm of Historic Annapolis. Enjoy an abundance of nature, blue herons, osprey, and wild fowl. The Shearwater community offers a private waterfront pool with sun deck, pickleball, regulation racketball court, tennis, kayak and dinghy rack/storage, a deep water marina, walking paths-all within a gated community. Enjoy a nice walk, bike, ride, or the water taxi will pick you up at the marina dock and take you downtown. All the fun activities in Eastport are right at your back yard. The Eastport Yacht Club parade of lights in December makes it's final turn right in front of Shearwater. Rare opportunity to combine waterfront access and the timeless Annapolis Lifestyle.

ANNAPOLIS

8 SPA CREEK LANDING 8A2

1 Beds

1 Baths

1,100 Sq.Ft.

$525,000

MLS#: MDAA2146120

Location, lifestyle, and charm come together at 216 Parker. This picture-perfect Annapolis rancher offers easy one-level living just moments from some of the city's favorite local destinations. Start your mornings with a walk to Black Market Bakers, spend weekends cheering on the Midshipmen at Navy-Marine Corps Memorial Stadium, and enjoy effortless access to commuter routes connecting you to Baltimore, Washington, D.C., and beyond.
While the main level provides comfortable everyday living, the finished lower level significantly expands the home's functionality, creating space for a recreation room, home office, guest suite, gym, or whatever fits your lifestyle best. It's the perfect balance of manageable size and flexible living space.
Cute as can be and ideally located, this home offers the rare opportunity to enjoy a true Annapolis lifestyle with convenience at every turn. Whether you're exploring downtown, meeting friends for dinner, or simply relaxing at home, you'll love having the best of Annapolis right outside your door.

ANNAPOLIS

216 PARKER AVENUE

4 Beds

3 Baths

2,389 Sq.Ft.

$525,000

MLS#: MDAA2145968

Priced to sell, and taking into account the need for some paint and a little TLC. Please remove shoes or use shoe covers the floors were just refinished.

ANNAPOLIS

1248 HILLTOP DRIVE

4 Beds

3 Baths

1,940 Sq.Ft.

$525,000

MLS#: MDAA2142150

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