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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
290
# of Listings
3
Avg # of Bedrooms
$449
Avg. $ / Sq.Ft.
$1,030,216
Med. List Price

Browse Annapolis Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

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$3M - $5M

Over $5M

290 Properties Found. Page 16 of 20.

Seize the opportunity to own a cleared, water-view lot in the community of Highland Beach, an incorporated municipality, Located just minutes from Downtown Annapolis, this lot provides easy access to schools, shopping, and dining. The community beach is only steps away, offering picturesque water views. Sewer hook-up is available at the street.
#MDAA2114238

ANNAPOLIS

3210 BRUCE

None Beds

None Baths

0.14 acres

$165,000

MLS#: MDAA2114238

Welcome to the sought-after community of Cape St. Claire! This lot is being offered as an addition to a home for sale. Please contact the county for possible development.
#MDAA2116560

ANNAPOLIS

1167 GREEN HOLLY DRIVE

None Beds

None Baths

0.21 acres

$165,000

MLS#: MDAA2116560

BUSINESS SALE ONLY- Fantastic opportunity to own this turnkey and well established restaurant in the heart of downtown Annapolis. Approximately 1500SF with 20 dine-in seat capacity. Fully equipped kitchen ready for any menu. Downtown Annapolis boasts a vibrant and diverse restaurant scene, seamlessly blending historic charm with modern culinary offerings. This location has excellent visibility on the popular Main St. Beer & Wine license available. Landlord approval of new tenant is required. Showings by appointment only.
#MDAA2105548

ANNAPOLIS

138 MAIN STREET

None Beds

None Baths

N/A

$150,000

MLS#: MDAA2105548

Level lot, 2017 perc evaluation indicated a possible home up to a 2,500 sq ft . Buyer to verify all information.
#MDAA455886

ANNAPOLIS

1012 CARRS ROAD

None Beds

None Baths

0.16 acres

$98,000

MLS#: MDAA455886

Boating season is just around the corner—embrace the maritime lifestyle with your very own waterfront slip at 319 6th Street, Annapolis, MD 21403. Boat size is limited to 34' length overall. Situated in the heart of Eastport, this sought-after marina places you in the Sailing Capital of the World, where boating isn’t just a pastime—it’s a way of life. Beyond the convenience of docking in a prime location, this slip comes with access to resort-style amenities, including a sparkling pool, fitness center, sauna, game and billiards room, and a party space for gathering with fellow boaters. One of the few marinas in Annapolis that allows liveaboards, this is the perfect opportunity for those looking to fully immerse themselves in the vibrant waterfront culture. With two gated parking spaces and easy in-and-out slip access, you'll enjoy seamless transitions from land to sea. Walk to downtown Annapolis, world-class yacht clubs, sailing schools, waterfront dining, and boutique shops, all while being part of a community that thrives on the water. Whether you’re setting sail for an adventure, cruising the Chesapeake, or simply soaking in the stunning harbor views, this slip offers a front-row seat to the best of Annapolis, including the iconic Eastport Lights Parade. Don’t just dock—live the Annapolis boating lifestyle year-round! (Contract will be contingent for 15 days as Condo bylaws require 15-day right of refusal to other unit owners-see disclosures. )
#MDAA2115754

ANNAPOLIS

319 6TH STREET SLIP #39

None Beds

None Baths

N/A

$65,000

MLS#: MDAA2115754

Excellent opportunity to fulfill your dream of constructing your own dream custom home. This lot is located in a beach community with lots of creeks. Enjoy the lazy days on or by the water with lots of activities. Make this a second home to just relax and enjoy being away from the hustle and bustle of city life.
#MDAA2111916

ANNAPOLIS

1221 CREEK DRIVE

None Beds

None Baths

0.26 acres

$55,000

MLS#: MDAA2111916

Welcome to 1848 Milvale located in the Saint Margarets area of Annapolis. As you enter the home you are struck by the beautiful wide views of Mill Creek, the open floor plan, and architectural details. The dining room and living room have gorgeous coffered ceilings, cherry hardwood floors, extensive millwork, floor-to-ceiling windows, and French doors that overlook the saltwater pool, spa, and creek. The kitchen offers a huge central island, wolf range, and custom cabinetry. Off the kitchen is the family room... it's striking with its vaulted barrel ceiling, custom built-ins, bar area, gas fireplace, and curved bank of windows centering again on the views of Mill Creek. The home has 2 main-floor bedroom suites with attached baths. The waterside bedroom has a poolside door and views of the creek while the front bedroom has serene views of the cornfields across the road facing East. One of the architectural highlights of the home is the stairwell tower with its impressive wide girth access to two distinct upper-level areas. Flooded with light, the high ceiling with clerestory windows first lands at the hall library-study. This cozy nook opens to a multi-purpose suite that can be used as a 3rd bedroom, a nursery, a 2nd family room, or an often-needed teen hangout area. The tower takes a turn to the left and accesses the primary bedroom and adjoining waterside office. The primary bedroom provides his and her walk-in closets, a huge spa bath with a soaking tub, heated floors, a walk-in shower, and laundry. Off of the primary bedroom is a handsome office with custom cabinets, a gas fireplace, and a deck to enjoy your morning coffee or a sunset cocktail. The lower level is the fifth-bedroom suite. This room is both the seller's workout room and wine cellar. The utility room has a wash sink, great for gardening, and houses the water treatment systems and 2 Geo-Thermal systems. The home has beautiful hardscaping with irrigation, and a rock garden water feature in the front of the home, and in the back, there is 148 ft of water frontage with a handsome Belgium stone seawall. The pier is "like new" with 2 slips, a 15,000 lb. boat lift, and 8 MLW. The pier is in a NO WAKE ZONE on weekends .. Located on one of the most sought-after roads in Annapolis and known for its privacy and country-like living, Milvale Road winds along the banks of Mill Creek in Saint Margarets surrounded by farmland and corn fields. A perfect place to unwind and enjoy the best sunsets around! Available from December 1, 2024-June 1, 2025
#MDAA2074056

ANNAPOLIS

1848 MILVALE ROAD

5 Beds

5 Baths

5,855 Sq.Ft.

$25,000

MLS#: MDAA2074056

Severn River Luxury Estate – 6-Month Furnished Rental in Annapolis. Available Fall 2025 through Spring 2026. Escape the chill of northern winters and enjoy the temperate beauty of the Mid-Atlantic from this luxurious waterfront estate in Annapolis, Maryland. Overlooking the Severn River and the iconic U.S. Naval Academy, this elegant retreat offers the perfect blend of relaxation, recreation, and refined living. Set on a private property with sweeping water views, this fully furnished home is ideal for a six-month stay, whether you're working remotely, entertaining guests, or simply recharging in a stunning setting. Enjoy pickleball on your private court, sunset walks along the water, dinners in downtown Annapolis just minutes away, or quiet mornings on one of the home's multiple verandas. Inside, you’ll find: * A grand formal dining room * Gourmet kitchen with top-of-the-line appliances, walk-in pantry, and dining area * Main-level office and cozy two-sided fireplace in family room * Multiple living and family rooms, including a club/game room over the garage * Private pier, in-ground pool, and outdoor entertaining space The second level features a luxurious primary suite with spa-like bath, water views, and a private veranda. Additional ensuite bedrooms and a spacious bonus room with balcony provide plenty of flexibility for guests, office space, or relaxation. A third-floor bedroom suite with sitting area and bath offers even more space and privacy, while the finished basement includes a bedroom, full bath, workout room, rec room, and walk-out access to the backyard. This is not just a rental—it’s a seasonal lifestyle upgrade in one of the East Coast’s most scenic and storied towns. Live well. Entertain often. Relax deeply. Welcome to your seasonal waterfront escape.
#MDAA2119338

ANNAPOLIS

1932 CARROLLTON ROAD

8 Beds

8 Baths

9,315 Sq.Ft.

$23,000

MLS#: MDAA2119338

Discover the magic of life on the water with this enchanting storybook home nestled along the serene Severn River. Breathtaking panoramic river views from nearly every room. Spacious light-filled living areas with timeless architectural charm. Lush landscaped gardens for outdoor entertaining. Wake up to the gentle sound of the river, sip morning coffee as sailboats drift by, and enjoy evenings with spectacular sunsets. Enter on the stoned and tree lined road that opens to a high bluff overlooking the Severn River. The perfect home for the discerning tenant. Hardwood floors and elegant finishes throughout. Open floor plan with a first-floor master, gourmet kitchen, enclosed porch, fireplace, and breathtaking views. Lower level boasts a private guest suite, family room and ample storage. Upper level houses 2 generously sized bedrooms that share a Jack-and-Jill bath. Privacy abounds with the spacious outdoor patio and expansive yard - all cared for by the landlord's contractor. Your only job is to enjoy this magnificent location. Close to the B&A bike trail and easy access to downtown Annapolis and major roadways. Minimum 2-year lease,
#MDAA2116104

ANNAPOLIS

5 WAVELAND FARMS ROAD

4 Beds

3 Baths

3,273 Sq.Ft.

$7,000

MLS#: MDAA2116104

Welcome to waterfront living at its finest. This stunning 5-bedroom, 3.5-bath custom home, built in 2018, offers expansive views of Spa Creek from every level. Perched on a generous 0.41-acre lot with a private deep-water boat slip (5’ MLW), this home is a rare rental opportunity in Annapolis. Inside, you'll find an open floor plan designed to take full advantage of the water views, featuring a gourmet kitchen with a dramatic waterfall island, high-end appliances, and walls of windows that fill the space with natural light. The main living level flows seamlessly from the kitchen to the dining and family rooms, perfect for both entertaining and everyday living. The light-filled walkout lower level that features floor-to-ceiling windows, a large recreation area, a bedroom, and full bath—ideal for use as an in-law or guest suite. Enjoy the serenity of Spa Creek from your backyard, launch your boat from your private slip, or simply take in the views from the comfort of your home. This is a rare rental offering that blends luxury, convenience, and waterfront charm. *Can be partially furnished if desired*
#MDAA2119906

ANNAPOLIS

174 ACTON ROAD

5 Beds

3 Baths

3,900 Sq.Ft.

$7,000

MLS#: MDAA2119906

Perfect for Automotive Repair Shop. Great Location in the heart of Annapolis.
#MDAA2115160

ANNAPOLIS

4 HUDSON STREET

None Beds

None Baths

N/A

$6,556

MLS#: MDAA2115160

Back on the Market! Escape to your own private Estate. 6100+ sqf of finished space with 2.2 acres of land in the most desirable location of Annapolis. 6 Bedrooms, 4.5 Bathrooms, with > 1000sqf for Master Suite. Two Fireplaces. Move-in condition. Potential for subdivision (check with engineer/county). A stone's throw to downtown without the city taxes. Across from B&A bike Trail & WWII Memorial. Direct access to Rt50 without any stoplights! BroadneckHS/Severn RiverMS/ArnoldES. Agent Owner. BRING YOUR OFFERS. All reasonable offers will be considered. Also open to reasonable allowance for prefered cosmetic updates to be completed prior to closing. Open to Owner Financing or leasing it at $6500/month. Property is now vacant on combo . Agent Owner.
#MDAA2110450

ANNAPOLIS

1707 GOVERNOR RITCHIE HIGHWAY

6 Beds

4 Baths

6,196 Sq.Ft.

$6,500

MLS#: MDAA2110450

Amazing waterfront residence on the Chesapeake Bay with almost 360 degree water views of the Chesapeake Bay, Fishing Creek, and South River. Enjoy a quiet and friendly neighborhood with private beaches and a pier for your boat across the street. Never hassle with bay bridge traffic and enjoy a unique location which is 5 miles to downtown Annapolis, 5 minutes to major retail and restaurants, and a 45 minute drive to downtown Baltimore and Washington DC. The open floor plan provides a great room with cathedral ceilings, hardwood floors, an updated gourmet kitchen, a dining area, and a wood burning fireplace all with panoramic bay views of the bay bride and Thomas Point Light House. A deck off the great room provides a perfect spot to enjoy the bay breeze, to watch the water life of the Chesapeake, and to see spectacular sights of the stars and moon over the bay at night. Up a few steps, you will find the large master bedroom with en-suite bath, large walk-in closet, and views of Fishing Creek through large windows. 2 additional bedrooms, a 2nd full bath, and laundry closet complete this level. Ground level foyer, 2-car attached garage, and storage shed complete the property. 2+ year lease preferred. See agent notes for Tenant responsibility.
#MDAA2117630

ANNAPOLIS

3563 NARRAGANSETT AVENUE

3 Beds

2 Baths

2,082 Sq.Ft.

$6,000

MLS#: MDAA2117630

Waterfront home in Oakwood Community w/ unsurpassed views of S. River and Bay. Newly renovated gourmet kitchen w/ island. Main level 2 BR 1 bath. Spacious open living area, F/R with wood-burning F/P. Hard wood FL through out. 2-Car garage w/ lots of workspace and storage. New 100 foot pier. Tranquil location, steps from Thomas Point Park. Pets case.
#MDAA2114138

ANNAPOLIS

3730 THOMAS POINT ROAD

4 Beds

2 Baths

1,932 Sq.Ft.

$5,050

MLS#: MDAA2114138

Views of the Great Chesapeake Bay come with this updated and upgraded Oyster Creek waterfront. Shared pier with a large boat slip, community beach and boat ramp for easy water access to the Bay. No smoking house and no pets allowed.
#MDAA2113692

ANNAPOLIS

1330 WASHINGTON DRIVE

3 Beds

2 Baths

1,584 Sq.Ft.

$5,000

MLS#: MDAA2113692

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