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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

$475

Avg. $ / Sq.Ft.

$1,078,449

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

389 Properties Found. Page 22 of 26.

Welcome to 38 Pleasant St! This renovated 2-bedroom, 1-bath townhome is located in downtown Annapolis and could be the perfect starter home or investment property. Renovations in 2021 included a new kitchen with stainless steel GE appliances, new flooring, HVAC, and a hot water heater. The main level features a living room, dining room, and kitchen that leads out to a fenced-in yard. The upper level includes 2 bedrooms, a full bath, and a laundry room. Windows have been replaced.

This home is centrally located in downtown Annapolis, within close proximity to the USNA, St. John's College, the cultural district, the City Dock, waterfront, shops, restaurants, and government buildings. Whether you're looking for an affordable home in Annapolis or considering a weekend getaway, this is the perfect choice.

This townhouse is not part of an HOA or condo association and is completely move-in ready. Don't wait!

ANNAPOLIS

38 PLEASANT STREET

2 Beds

1 Baths

840 Sq.Ft.

$259,900

MLS#: MDAA2105312

Welcome to 204 Victor Parkway in the fairwinds condo community in Annapolis, This move-in ready 2 bed 2 bathroom condo is spacious and functional, this home has been meticulously maintained and offers a blend of simple living while maximizing your location needs. This condo is on the second level and has its own balcony, The primary bedroom host an en suite bathroom plus a modern vanity that can be used for various ideas. The Fairwinds community provides an abundance of amenities, including a large outdoor pool, tennis courts, multiple playgrounds, picnic areas, and expansive open spaces for residents to enjoy. Ideally located just minutes from Quiet Waters Park, local shopping centers, marinas, and Downtown Annapolis, you'll have easy access to all the best that Annapolis has to offer, including a short drive to the U.S. Naval Academy.
*Condo includes water & gas utilities. *

ANNAPOLIS

204 VICTOR PARKWAY G 204G

2 Beds

2 Baths

970 Sq.Ft.

$250,000

MLS#: MDAA2111984

Open House Sunday, May 18th, 1-3 pm. 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 with a community pool, across from the Annapolis Recreation Center.

ANNAPOLIS

290 HILLTOP LANE M

2 Beds

1 Baths

1,024 Sq.Ft.

$249,950

MLS#: MDAA2115488

New on site 2 days ago

This beautiful second-floor condo truly has it all—an open floor plan with a contemporary flair, a private den, and a spacious balcony. Located in The Landing at Spa Creek, this home offers the perfect balance of comfort, convenience, and resort-style living. The private den makes an ideal home office or guest space, adding flexibility to your lifestyle. Tucked along Spa Creek, this community is minutes from Historic Downtown Annapolis, the U.S. Naval Academy, Annapolis Towne Centre, and the West Street corridor. Condo fees cover water, gas, trash pick-up, exterior maintenance, and access to incredible amenities: Clubhouse with lounge, sundeck and outdoor pool and fitness center with locker rooms. Truxtun Park is conveniently located across the street and offers a pier, boat ramp, canoe/kayak storage, walking trails with beautifully landscaped grounds, tennis/pickleball courts and renovated pool facility. Pip Moyer rec center is close by and offers a 80,000 sq. ft. indoor rec center featuring a three-court gym, indoor track, rock-climbing wall, fitness center, and indoor playground. Whether you love being near the water, crave walkable recreation, or want a low-maintenance lifestyle with top-tier amenities, this is the place to be.

ANNAPOLIS

1136 COVE ROAD 202

1 Beds

1 Baths

819 Sq.Ft.

$247,000

MLS#: MDAA2116766

Welcome to the heart of downtown Annapolis, where city living meets historic charm! This 3-bedroom, 1 Full and 1 Half-bathroom, townhome offers an incredible opportunity to be just 2 blocks away from the Capitol building, shopping, restaurants, and the picturesque waterfront filled with boats. Convenience is key with parking included, allowing you to explore the vibrant downtown area with ease. Kitchen appliances are also included in the sale, making this property quicker for you to move in and enjoy. Don't miss this rare opportunity to own a piece of Annapolis for under $250,000! This charming townhome is your ticket to experiencing the vibrant downtown lifestyle Annapolis has to offer or add another rental property to your portfolio.

ANNAPOLIS

63 TOWN PINES COURT

3 Beds

1 Baths

1,037 Sq.Ft.

$215,000

MLS#: MDAA2112570

New on site 1 day ago

Charming One-Bedroom Condo in Prime Annapolis Location! Welcome to 211 B Victor Parkway, a
beautifully maintained one-bedroom, one-bath condo offering exceptional value in the heart of
Annapolis. Nestled in a convenient location near Quiet Waters Park, this home provides easy
access to all the shopping, dining, and cultural attractions the city has to offer. Step inside to
discover a bright and inviting living space, enhanced by large windows and a sliding patio door
that flood the interior with natural light. The open layout flows seamlessly into a private backyard
area, perfect for relaxing or entertaining. Enjoy the convenience of a stacking washer and dryer,
and appreciate the thoughtful touches throughout this well-kept home. Whether you're a first-time buyer, downsizing, or seeking a smart investment, this condo is a rare find in a sought-after
community. Don’t miss your chance to own this light-filled gem in an unbeatable location

ANNAPOLIS

211 VICTOR PARKWAY B B

1 Beds

1 Baths

673 Sq.Ft.

$205,000

MLS#: MDAA2116434

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.

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.

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.

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.

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.

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.

ANNAPOLIS

1227 CREEK DRIVE

None Beds

None Baths

0.41 acres

$79,900

MLS#: MDAA2064060

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 1350 Fishing Creek Rd.). 15 minute drive to downtown Annapolis. Build your dream home now!

ANNAPOLIS

1352 FISHING CREEK ROAD

None Beds

None Baths

0.15 acres

$70,000

MLS#: MDAA2095014

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

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Buyers resources

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Getting a Mortgage To Buy a Home

Home Hazards Awareness

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8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

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Selling Your Home for More $$

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