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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

358

# of Listings

3

Avg # of Bedrooms

$480

Avg. $ / Sq.Ft.

$1,098,897

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

358 Properties Found. Page 21 of 24.

Vacant lot available in water access community on the Chesapeake Bay. Community has three marinas open to residents plus a boat ramp, fishing pier and private beach. This property is a 5 minute walk to the Oyster Harbor private community beach. Public sewer access at the street. Adjacent lot is available as well (see 1352 Fishing Creek Rd.). 15 minute drive to downtown Annapolis. Build your dream home now!

ANNAPOLIS

1350 FISHING CREEK ROAD

None Beds

None Baths

0.15 acres

$70,000

MLS#: MDAA2095012

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. )

ANNAPOLIS

319 6TH STREET SLIP #39

None Beds

None Baths

N/A

$70,000

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.

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

ANNAPOLIS

1848 MILVALE ROAD

5 Beds

5 Baths

5,855 Sq.Ft.

$25,000

MLS#: MDAA2074056

Now available for Rent or Sale. Fully Furnished Waterfront home available on sought-after Saltworks Creek. Bring your boats and water toys with plenty of space to accommodate up to a 46’ sailboat. Home features nearly 6,000 sq/ft luxury living, 5 bedrooms, 7 baths, situated on a stunning 3-acre private waterfront lot just off the Severn River yet close to everything Annapolis has to offer! The estate has a private 6’ deep-water dock with 2 boatlifts a short walk from the house. The rear of the home has a large custom-built outdoor terrace/patio area with a large hot tub for entertaining. This stunning property is the best of both worlds: located only a few miles from Route 50, downtown Annapolis, the Westfield Mall, the hospital, supermarkets, and stores, however, the secluded location feels like you're in the country!

There are 5 spacious bedrooms, each with its own full bathroom, including a separate 1 bedroom apartment with a kitchen and full bath on the Lower level perfect for live-in help or an Au pair. The Main floor's gorgeous Great Room with fireplace offers tall windows overlooking nature. The living room windows also have remote-controlled blinds that allow for perfect lighting. There is also a separate Living Room with a fireplace and a wet bar/butler's pantry. Work from home in the private, dedicated office space.

Enjoy cooking and gathering in the high-end fully equipped gourmet kitchen with custom wood cabinets, an island with a second sink, a breakfast bar with seating, top-of-the-line appliances including a new SubZero refrigerator and a Subzero wine fridge. The adjoining mud room with a separate entrance is outfitted with storage and a walk-in pantry. Just off the kitchen is a lovely dining room w/ beautiful light fixtures.

The Lower level boasts a stunning bar made from exotic wood, a sink, an icemaker, and built-in refrigeration storage system, and a seating area, and fireplace. A sliding glass door leads up to the stunning patio/terrace that is very private and perfect for large gatherings, with magical views of the lush estate and beyond to Salt Works Creek and the dock. The outdoor area is also accessible from the Main floor. Enjoy the beautiful, extra large Hot Tub.

Control 4 audio system provides high-quality sound throughout the home and the outdoor patio area. As well as operation of TV’s.

After sundown, built-in outdoor lighting beautifully illuminates the patio and the property.

Available for 12 or 24 Month Lease.
Contact listing agent for showings and more information.

ANNAPOLIS

1856 SEVERN GROVE ROAD

5 Beds

5 Baths

5,930 Sq.Ft.

$10,000

MLS#: MDAA2114004

Bay Ridge Coastal Retreat | Annapolis Waterfront Elegance
Welcome to one of the most coveted addresses in Annapolis, set in the sought-after waterfront community of Bay Ridge. This exceptional property rests on a level, manicured lot with sweeping views of the Chesapeake Bay — offering a front-row seat to some of the region’s most breathtaking scenery.
With sandy beach access just across the street, this non-riparian waterfront setting brings the Bay to your doorstep. Inside, the home features a thoughtfully remodeled kitchen and updated baths, a cozy fireplace for cooler evenings, and a spacious great room that captures panoramic water views. A dedicated home office adds convenience and flexibility, while an outdoor shower offers the perfect way to rinse off after a day on the beach or paddleboard.
The covered patio is a true extension of the living space — ideal for morning coffee as boats glide by, and peaceful evenings spent star-gazing over the water. The conditioned garage expands your options even further, ready to serve as a gym, studio, or anything your lifestyle demands.
Looking for a home that feels like a getaway? This treasured spot captures the essence of the coastal lifestyle — a place where the line between everyday living and vacation ease quietly disappears.
Bay Ridge is beloved for its active, connected community, where residents run, bike, paddle, and enjoy everything the Bay and Annapolis have to offer. This is a rare opportunity to experience waterfront living in one of the area's most desirable neighborhoods.

ANNAPOLIS

113 BAY DRIVE

3 Beds

2 Baths

1,836 Sq.Ft.

$7,500

MLS#: MDAA2113968

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

ANNAPOLIS

4 HUDSON STREET

None Beds

None Baths

N/A

$6,556

MLS#: MDAA2115160

None

ANNAPOLIS

1707 RITCHIE HIGHWAY

6 Beds

4 Baths

4,796 Sq.Ft.

$6,500

MLS#: MDAA2110352

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.

ANNAPOLIS

1707 GOVERNOR RITCHIE HIGHWAY RENTAL

6 Beds

4 Baths

6,196 Sq.Ft.

$6,500

MLS#: MDAA2110450

Escape to your own private Estate. 6000+ 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. Must Call the Agent to show.
Must be accompanied by agent.

All reasonable offers will be considered.

ANNAPOLIS

1707A GOVERNOR RITCHIE HIGHWAY

6 Beds

4 Baths

4,796 Sq.Ft.

$6,500

MLS#: MDAA2110358

Welcome to 200 Severn Avenue, a beautifully designed 3-bedroom, 3.5-bathroom home in the heart of Eastport, just steps from downtown Annapolis. Built in 2020, this modern coastal retreat offers 2,300 square feet of impeccably finished living space, combining contemporary elegance with thoughtful functionality. Inside, the open-concept main level boasts gleaming hardwood floors, a gourmet kitchen with granite countertops, high-end stainless steel appliances, a gas range, and a large island perfect for entertaining. The spacious living and dining areas flow seamlessly to a private Trex deck, ideal for outdoor relaxation. First floor is rounded out by an en suite bedroom offering the option for single - level living. Upstairs, the two additional en suite bedrooms offer comfort and privacy, while a versatile bonus space is perfect for a home office or reading nook. The home also features Lutron smart lighting, a WiFi-controlled HVAC system, and electronic locks for ultimate convenience. Situated in one of Eastport’s most desirable locations and offering 3 designated parking spots, this home is walkable to marinas, award-winning restaurants, shopping, Eastport Yacht Club and the Annapolis Yacht Club. Enjoy the vibrant waterfront lifestyle with easy access to boating, the Water Taxi, and year-round events like the famous Eastport vs. Annapolis Tug of War. This home is available for a long-term lease (2-3 years preferred).

ANNAPOLIS

200 SEVERN AVENUE

3 Beds

3 Baths

2,300 Sq.Ft.

$5,995

MLS#: MDAA2103290

Absolutely gorgeous fully remodeled light filled modern home! Two story sun drenched family room off kitchen w/ wood fireplace & 2 almost new sliding glass doors leading to the entertainers' dream stone patio! Main floor master suite w/ gorgeous master bathroom. Wake up every morning and sit on your stone patio as you enjoy the wildlife in your private, wooded backyard. Or watch a movie or sports while enjoying a cocktail. All the major components have been updated/replaced in this gorgeous home. Fine details throughout such as crown molding & wainscoting. Any gourmet chef's dream kitchen with granite counters, soft closing cabinets & drawers, almost new appliances, contrasting gray center island & tons of storage. Fully finished basement with media room, 6the bedroom! Also a 2 car oversized attached garage! Plus almost new roof, HVAC, water heater, water treatment system, carpet (in office, basement & living room ), appliances & much more! Windfern Forest community has a private pier w slips on a first come first served basis. Community also has a large gazebo, picnic tables & charcoal grills! Great place to call home! : )

ANNAPOLIS

513 POST OAK ROAD

5 Beds

4 Baths

3,568 Sq.Ft.

$5,900

MLS#: MDAA2113792

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-by-case.

PS current tenants are moving out 5/31

ANNAPOLIS

3730 THOMAS POINT ROAD

4 Beds

2 Baths

1,932 Sq.Ft.

$5,100

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.

ANNAPOLIS

1330 WASHINGTON DRIVE

3 Beds

2 Baths

1,584 Sq.Ft.

$5,000

MLS#: MDAA2113692

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-by-case.

ANNAPOLIS

3730 THOMAS POINT ROAD

4 Beds

2 Baths

1,932 Sq.Ft.

$5,000

MLS#: MDAA2114048

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