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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
392
# of Listings
3
Avg # of Bedrooms
$454
Avg. $ / Sq.Ft.
$1,129,892
Med. List Price

Browse Annapolis Real Estate Listings

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392 Properties Found. Page 22 of 27.

Great Townhome at the Saltaire in Annapolis. 2 bedroom, 1.5 Bath with a fireplace and large back deck. Well priced in a popular community. Great investment, in an investor friendly community with long term tenants willing to stay for investors looking to continue to rent. Across the street from Truxton Park with includes "The Pip Moyer Recreation Center, ball fields, tennis and pickleball courts, a skateboard park, swim center and boat ramp are spread across the park. But what is often overlooked are the trails that wind through the park. To walk a two mile loop through the woods and along the creek, park behind the rec center near a fun new playground and look for a wooded trail head that is closer to the Salvation Army side. The trail is easy to follow. The path goes through the woods and down a slope until you see a pump station. The new pool is in the woods to your right. Continue on until you reach a driveable path coming from the direction of the pool. If you turn left you can cross a wooden bridge and walk on Silopanna until it reaches the Spa Creek Trail which passes the Chesapeake Children’s Museum and ultimately the trail that surrounds Bates Middle School. Following this trail can add significantly to your walk."
#MDAA2119606

ANNAPOLIS

290 HILLTOP LANE M

2 Beds

1 Baths

1,024 Sq.Ft.

$244,950

MLS#: MDAA2119606

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

Fantastic opportunity to build your dream home in Annapolis! This lot is conveniently located near stores, retaurants and route 50. Lot is owned by the house next door so they are currently using it as an extended yard.
#MDAA2103344

ANNAPOLIS

GILMER STREET

None Beds

None Baths

0.11 acres

$120,000

MLS#: MDAA2103344

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

*****Where Creek Road ends there are 8 lots, then this lot is available for purchase, then 8 more lots and Creek Road picks back up. This lot sits in the middle of 17 lots. All infrastructural would need to be completed by buyer. ****** This 0.41 acre lot is water privilege community with beach, boat dock, boat slips, boat ramp and more. Public sewer hook up available is available in the community . Well would be the water source, See disclosures for lot location.
#MDAA2064060

ANNAPOLIS

1227 CREEK DRIVE

None Beds

None Baths

0.41 acres

$79,900

MLS#: MDAA2064060

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

One-of-a-kind Waterfront Luxury in Annapolis, Maryland! Secluded on 2.59 lush, park-like acres along the shores of one of the Chesapeake Bay’s most serene and protected tributaries, this exceptional estate offers an unparalleled blend of privacy, elegance, and premier waterfront living rarely found in Annapolis. From the moment you arrive down the tree-lined drive, a sense of calm and sophistication sets in. With 185 feet of pristine shoreline, deep water, and a private pier with boat lift, this is more than a home, it’s a relaxing destination where every day feels like a retreat. Spanning over 12,000 square feet, this custom-built estate (main floor finished in 2014 by Pyramid Builders, lower level in 2019 by Bayview Builders) is crafted with the highest-quality materials and top-of-the-line features. Every detail has been curated with uncompromising quality to deliver a life of luxury, comfort, and effortless entertaining. This resort-like home is built to host—from elegant galas with ample onsite parking to relaxed family weekends. Inside, sunlit spaces and radiant-heated floors create a warm, welcoming atmosphere throughout the year. The grand two-story foyer with custom millwork ceiling opens to formal living and dining rooms, while the heart of the home—a soaring great room with fireplace—anchors the space with timeless beauty and comfort. A chef’s dream kitchen is equipped for both daily living and high-end entertaining, featuring Sub Zero refrigerators and wine cooler, Wolf stove/griddle and double ovens, dual dishwashers, warming drawers, catering entrance, ample custom cabinetry, and expansive granite countertops. Whether preparing an intimate dinner or a large event, this space delivers excellence. For gathering and unwinding, the custom mahogany bar with private balcony overlooking the waterfront and pool is located on the main floor and connects to the kitchen by the great room–perfect for serving pre-dinner cocktails or spreading out larger gatherings. A comfortable family room and sunroom off the kitchen overlook the waterfront and pool providing relaxing sunset views. A main-level guest suite with private balcony ensures both comfort and privacy for visitors while a sun-filled custom wood paneled office with fireplace provides an impressive and inspiring executive workspace at home. Ascend the stunning curved staircase to the primary suite for a serene escape with water views and attention to all your needs with sitting room, fireplace, dual dressing rooms, a private balcony, and a spa-like en-suite bath. Three additional en-suite bedrooms, a laundry room and an upper-level library offer generous, luxurious accommodations for family and guests. The newly finished walkout lower level feels like its own private coastal escape: game room, kitchenette, home gym, a 2nd laundry room, pool bath, sauna, and guest quarters with private entry—perfect for an au pair, in-laws, or long-term visitors. Step outside and discover a resort caliber setting: a heated saltwater pool and hot tub surrounded by travertine patios, Ipe decks, and outdoor dining areas that invite celebration and quiet reflection alike. Cruise effortlessly from your backyard to the Chesapeake Bay, South River, Annapolis Harbor and St. Michaels for waterfront dining or explore the many nearby creeks and coves. Whether you're boating, catching crabs off the dock, taking in the bald eagles during sunset, or paddling into calm morning waters, the connection to nature and the water here is effortless. Conveniently located just minutes from downtown Annapolis and within easy reach of commuter routes to Washington, D.C. and Baltimore, this extraordinary estate defines luxury living. This is more than a home—it’s an estate that offers a luxurious lifestyle immersed in nature, rooted in comfort, and ready to be shared. Embrace this rare opportunity to own an exclusive piece of Annapolis where luxury meets tranquility!
#MDAA2119272

ANNAPOLIS

840 CHILDS POINT ROAD

6 Beds

7 Baths

12,374 Sq.Ft.

$20,000

MLS#: MDAA2119272

Turnkey opportunity in the heart of historic Downtown Annapolis! Located on bustling Main Street just steps from City Dock, this beautifully renovated restaurant space offers prime visibility and unbeatable foot traffic. The interior features seating for 89 guests, with additional outdoor dining for 12, and all major updates completed 2022 - 2024, including a new grease interceptor, updated sanitary lines, and remodeled restrooms. Views of the harbor from all three levels. The bar area is the perfect setting to make locals feel at home and have visitors wishing they were locals! This versatile space is ready for your vision. Zoned C2 and surrounded by local shops, restaurants, and waterfront views, it’s the perfect spot to bring your concept to life in one of Maryland’s most charming and visited destinations. Also listed for sale.
#MDAA2118118

ANNAPOLIS

81 MAIN STREET

None Beds

None Baths

N/A

$13,850

MLS#: MDAA2118118

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.
#MDAA2114004

ANNAPOLIS

1856 SEVERN GROVE ROAD

5 Beds

5 Baths

5,930 Sq.Ft.

$10,000

MLS#: MDAA2114004

Professional photos coming soon. 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. An elevator serves all three levels, including 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. For even more flexibility, a private 1-bedroom, 1-bath guest suite with its own entrance, family room, and kitchenette is available for an additional $1,200/month—perfect for multigenerational living or an au pair. 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.
#MDAA2119906

ANNAPOLIS

174 ACTON ROAD

5 Beds

3 Baths

6,876 Sq.Ft.

$7,500

MLS#: MDAA2119906

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