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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

$453

Avg. $ / Sq.Ft.

$1,135,816

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

392 Properties Found. Page 13 of 27.

Fully Renovated 2BR/3BA home in Heritage Harbour is back on the market.

This completely remodeled home offers a refined living experience within the highly sought-after 55+ community of Heritage Harbour. The interior has been improved with high-end finishes throughout, balancing clean design with everyday functionality.

Known for its extensive community offerings, residents of Heritage Harbour enjoy access to a golf course, indoor and outdoor pools, hot tub, sauna, Tennis and pickleball courts, fully equipped fitness center, exclusive community restaurant Wilder Fresh Kitchen, Boat slips, kayak launch & storage, an RV/boat storage lot, scenic walking trails, clubhouse events, and so much more. Schedule your tour today and discover all that Heritage Harbour has to offer!

ANNAPOLIS

2609 POINT LOOKOUT COVE

2 Beds

3 Baths

1,961 Sq.Ft.

$650,000

MLS#: MDAA2113432

PRIVATE WATER COMMUNITY! 5 BEDROOM 2.5 FULL BATH BRICK HOME SITS ON .42 ACRE LOT IN SOUGHT AFTER HILLSMERE ESTATES! FRESHLY PAINTED THROUGHOUT! UPPER LEVEL HARDWOOD FLOORS HAVE BEEN REFINISHED! UPDATED KITCHEN W/ SS APPLIANCES, QUARTZ COUNTER TOPS, TILED BACKSPLASH, TABLE SPACE W/ BREAKFAST BAR & RECESSED LIGHTING. LIVING ROOM HAS BRICK FIREPLACE AND MANTEL, HARDWOOD FLOORS, BAY WINDOW W/ PLANTATION SHUTTERS. DINING ROOM & BONUS SUNROOM IS SURROUNDED BY WINDOWS W/ PLANTATION SHUTTERS & 2 SETS OF FRENCH DOORS W/ ACCESS TO SIDE DECK AND EXT REAR PATIO. PRIMARY EN-SUITE HAS LIGHTED CEILING FAN, PRIVATE POWDER ROOM AND SLIDER DOOR W/ ACCESS TO REAR PATIO. 2 ADDITIONAL SPACIOUS BEDROOMS W/ HARDWOOD FLOORS. BEDROOM 3 HAS IN CLOSET AN ALL IN ONE WASHER/DRYER COMBO. THIS CAN BE REMOVED, BUT GIVES BUYER OPTION TO HAVE A RENTAL ON EACH LEVEL. HALLWAY BATHROOM W/ UPDATED TILED TUB SHOWER AND FLOORS. LOWER LEVEL HAS ADDITIONAL KITCHEN W/ TOASTER OVEN, MICROWAVE, SS REFRIGERATOR, MOVABLE ISLAND W/ CABINETS AND COUNTER TOP BURNERS. FAMILY ROOM HAS BRICK FIREPLACE AND MANTEL. TABLE SPACE . FULL BATHROOM W/ TUB SHOWER. 2 ADDITIONAL BEDROOMS AND LAUNDRY ROOM W/ BUILT IN CLOSET AND SHELVES. EXT SHED AND FENCED IN REAR YARD. FLAT ROOF 2025 AND EXT CHIMNEY REFINISHED. SWIMMING POOL AND SOCCER FIELD DIRECTLY ACROSS THE STREET. THIS COMMUNITY HAS AN OPTIONAL IMPROVEMENT ASSOCIATION FOR $25/YEAR BUT NOT REQUIRED. HILLSMERE COMMUNITY HAS LOTS OF AMMENITIES!

ANNAPOLIS

130 GREAT LAKE DRIVE

5 Beds

2 Baths

2,014 Sq.Ft.

$650,000

MLS#: MDAA2113704

Discover your slice of paradise in the heart of Annapolis! This exceptional property combines two complete homes with productive fruit trees, creating the ultimate in flexible living.

Main Home (3BR/2BA): Beautiful hardwood floors flows through the large living room and bedrooms, while the spacious kitchen with Island connects to a separate dining area - perfect fro daily living and entertaining. Three comfortable bedrooms and two full baths complete this well designed space.

In-Law suite Addition (1BR/2BA - 1200 sq ft): This isn't just and addition - It's a complete second home! Features include a large living room, Full eat-in kitchen, bedroom, two full baths, and generous laundry room. The crown jewel? An incredible 8x28 Sunroom with natural gas fireplace - your year round sanctuary with garden views. Separate entrance ensures complete privacy.

Step outside to your personal orchard featuring mature pear, apple, cherry, plum and chestnut trees, plus established grapevines. Imagine morning coffee in the sunroom or out the back patio surrounded by blooming fruit trees and harvesting your own fresh produce each season.

Entertaining made effortless with a sprawling 650 sq ft deck - perfect for everything from intimate dinners to large gatherings. The outdoor space flows seamlessly with nature's bounty at your fingertips.

Two separate driveways ensure privacy and convenience, with circular drive serving the main house (multiple car capacity) and a dedicated 4 - car driveway for the In-law suite.

Storage and workspace solved with a generous 12x24 detached garage and 8x14 shed - plenty of room for vehicles, tools, hobbies and seasonal storage.

Prime Annapolis location puts you in the heart of Maryland's historic capital where waterfront charm continues to fuel demand and properties remain strong. Just a mile from downtown Annapolis for all your dining and shopping needs. Walk to Truxtun park and the Pip Moyer center that houses a gym, basketball courts, and an indoor track. You can also walk to the newly renovated tennis court and Pickleball courts with lights. Around the corner is the Truxtun park pool, Public Boat ramp and fishing pier.

ANNAPOLIS

399 HILLTOP LANE

4 Beds

4 Baths

3,668 Sq.Ft.

$650,000

MLS#: MDAA2118498

Check out this charming, updated home in the water access neighborhood of Blackwalnut Cove! With 4 bedrooms and 3.5 bathrooms, it offers plenty of space and privacy, backing onto the woods. The main floor features an open kitchen and living area, plus a separate dining room. The finished basement includes an in-law suite with a kitchen, living room, and bedroom. Upstairs, you'll find 3 spacious bedrooms, including a primary bedroom with 2 large closets and an updated private bathroom. The back deck is perfect for cookouts, gatherings, or just relaxing. This gem won't last long! 🏡

ANNAPOLIS

1337 BLACKWALNUT COURT

4 Beds

3 Baths

2,500 Sq.Ft.

$649,999

MLS#: MDAA2115178

Welcome to The Element at Mill Creek, an exclusive 55+ community offering luxury, low-maintenance living just minutes from historic Annapolis. This stunning first-floor corner unit is filled with natural light from two sides, has 9-foot ceilings, and only one shared wall, creating a spacious and private living experience.

Designed for comfort and convenience, this two-bedroom, two-bath home plus a large study boasts modern finishes like Timberlake cabinetry with crown molding, stone countertops, recessed lighting, and Samsung stainless steel appliances. The spa-like bathrooms feature DalTile floor-to-ceiling wall tile with shower niches, and the living spaces showcase elegant plank flooring with customizable features such as LED mirrors and barn doors.

As part of The Element at Mill Creek, residents enjoy resort-style amenities, including a state-of-the-art fitness center, golf and sports simulator, walking trails, and multiple indoor and outdoor social areas. Pickleball courts and a dog park are coming in the upcoming months, adding even more to this vibrant community. Secure entry, optional garage parking, and proximity to downtown Annapolis further enhance the appeal .

Included with the sale is Garage Parking Space #31, a $19,500 value, offering added convenience and security.

Don’t miss this opportunity to own in one of Annapolis’ most sought-after 55+ communities.

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 101

2 Beds

2 Baths

N/A

$649,000

MLS#: MDAA2109922

May Delivery. Welcome to the Homes at River Birch. A luxury townhome community that celebrates the best of modern design and urban lifestyles. These farmhouse, attached homes are semi-custom with 4 bedroom options within two different floor plans. These homes boasts an abundance of features including wide plank LVP floors, gorgeous quartz countertops, stainless steel appliances, an attached garage, En Suite bath, custom wood cabinets, and an optional rooftop terrace perfect for entertaining. The unbeatable location is within walking distance of the finest shopping and restaurants Annapolis has to offer. Enjoy easy access to major commuting routes to D.C, Baltimore, the Bay Bridge and more! The Homes at River Birch are one of the recent crown jewels of Annapolis Development providing excellent modern craftsmanship and the finest conveniences at your fingertips.

ANNAPOLIS

2073 OLD ADMIRAL COURT

4 Beds

4 Baths

N/A

$644,900

MLS#: MDAA2109864

New List Price!! Great opportunity in West Annapolis! Discover the charm of 111 Clay St, a delightful 1940s Colonial offering a fantastic chance to own near Annapolis Downtown District. This home features a huge front porch, Large windows that brings in tons of natural light, to an open floor plan. Newly updated a few short years ago, this home features modern functionality and original charms. A 3 BR's, 1.5 BA's layout w/ a huge sunken tub and separate shower, just great for relaxing. This is a prime location offering so many things to do locally. You're walking distance to arts, entertainment, local shops, and restaurants. Even Navy Football and Basketball events are within close proximity. Take a look at this rare opportunity to call this wonderful place home!

ANNAPOLIS

111 CLAY STREET

3 Beds

1 Baths

1,568 Sq.Ft.

$635,000

MLS#: MDAA2111920

Welcome to The Element at Mill Creek, an exclusive 55+ community offering luxury, low-maintenance living just minutes from historic Annapolis. This stunning first-floor corner unit is filled with natural light from two sides, has 9-foot ceilings, and only one shared wall, creating a spacious and private living experience.

Designed for comfort and convenience, this two-bedroom, two-bath home plus a large study boasts modern finishes like Timberlake cabinetry with crown molding, stone countertops, recessed lighting, and Samsung stainless steel appliances. The spa-like bathrooms feature DalTile floor-to-ceiling wall tile with shower niches, and the living spaces showcase elegant plank flooring with customizable features such as LED mirrors and barn doors.

As part of The Element at Mill Creek, residents enjoy resort-style amenities, including a state-of-the-art fitness center, golf and sports simulator, walking trails, and multiple indoor and outdoor social areas. Pickleball courts and a dog park are coming in the upcoming months, adding even more to this vibrant community. Secure entry, optional garage parking, and proximity to downtown Annapolis further enhance the appeal.

Included with the sale is Garage Parking Space #31, now a $25,000 value, offering added convenience and security.

Don’t miss this opportunity. B4-Alt is said to be the most popular floor plan in the community and all 16 units of buildings 1C and 2B are sold out. This is also the largest of the 2-bedroom units. *Builder claims 1723 sqft though published taxed sqft is less. Buyer to confirm which may be accurate.

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 101

2 Beds

2 Baths

1,723 Sq.Ft.

$634,999

MLS#: MDAA2112868

Nestled in the gated waterfront condo community of Chesapeake Harbor, this home offers an array of resort-style amenities, including two pools, a private beach, two fishing piers, kayak storage, jogging paths, a gym, a marina, tennis and pickleball courts, and an on-site waterfront restaurant. Inside, you'll find a spacious primary bedroom featuring a cozy reading nook, a large walk-in closet, new carpet, and access to a private deck. The updated primary bathroom boasts a soaking tub and a separate shower. The open loft, complete with a closet and hardwood floors, offers versatility as a home office or can easily be used as a second bedroom. The living room features soaring ceilings, a gas fireplace, hardwood floors, and a wall of windows with a French door leading to a serene deck—all showcasing stunning water views of the marina and bay. The generous kitchen is equipped with updated stainless steel appliances, while the two-car garage, along with additional crawl space, provides ample storage. Additionally, the HVAC system and hot water heater were recently replaced. Conveniently located near public transportation and major commuter routes, this home offers easy access to downtown Annapolis, NSA/Fort Meade, Washington, D.C., Baltimore City, shopping, and recreational activities. Professional photos will be completed the first week of March.

ANNAPOLIS

2014 SAMS WAY 8A

2 Beds

2 Baths

1,923 Sq.Ft.

$624,900

MLS#: MDAA2104396

IMMEDIATE DELIVERY! Experience luxury living in this exquisite NEW CORNER UNIT bathed in natural light! GARAGE Parking Included! Delight in a true Chefs Kitchen with gorgeous cabinetry, gas cooktop and 11-foot peninsula. Large living & dining areas are perfect for entertaining and a sumptuous Primary Suite awaits... All in an amenity-rich 55+ community convenient to Rt. 50. Live minutes to downtown Annapolis, waterfront dining, shopping, Sandy Point and Bay Bridge. This home with private balcony enjoys a second floor elevation. Turnkey luxury includes window treatments and full-size washer & dryer. Virtual staging used to show space & layout.

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 112

2 Beds

2 Baths

1,621 Sq.Ft.

$624,410

MLS#: MDAA2095474

#MDAA2104116

ANNAPOLIS

14 DORSEY AVENUE A

None Beds

None Baths

0.12 acres

$600,000

MLS#: MDAA2104116

*TO BE BUILT / READY TO BE CUSTOMIZED. CONSTRUCTION STARTING SOON* Starting at a base price of $600k. Reach out to Chase Kincer today for customization options!
In addition to the builder's warranty, there is a 5-year roof warranty.
Listing Photos are just for representation purposes of the same spec house.

ANNAPOLIS

14 DORSEY AVENUE A

4 Beds

2 Baths

2,037 Sq.Ft.

$600,000

MLS#: MDAA2116188

Great SFH situated on flag lot in desirable location! Multiple living spaces on main level, open concept kitchen and family room with high ceilings and skylights. 2 generous sized bedrooms upstairs and spacious Primary Bedroom with private En Suite. Large basement with storage, exterior access, another bedroom and full bath. Garage was converted to additional space but can easily be converted back. Large, level fenced in backyard with in ground pool. Needs some work but priced accordingly. Sold ad-is. Buyer to pay all transfer and recordation taxes.

ANNAPOLIS

1809 LABROTT LANE

3 Beds

3 Baths

2,236 Sq.Ft.

$599,990

MLS#: MDAA2119690

2 Separate units. The house is not suitable to provide interior access to the Lower Level. The Lower unit is only rear accessible. The two units are 17A and 17B. Separate meters are in place. Three beds and one bath upper level. One bed and one bath lower level. Both levels have Kitchens. some updating needed

ANNAPOLIS

17 ELLIOTT ROAD

4 Beds

2 Baths

1,728 Sq.Ft.

$599,990

MLS#: MDAA2100582

Nestled in a tranquil corner of Annapolis, this expansive ¾-acre property offers a rare combination of privacy, natural beauty, and opportunity. With serene water views and a peaceful setting, the generous lot size may allow for subdivision—offering the flexibility to build a second home while retaining the existing residence or reimagine the space entirely. Ideally situated near local marinas and the Annapolis sailing school, this location is perfect for boating enthusiasts. Residents can enjoy the quiet surroundings while being just minutes from downtown Annapolis’ renowned dining, shopping, and waterfront attractions. A truly special offering in one of Maryland’s most desirable areas.

See residential listing. MLS is MDAA2108602. See property boundary maps and tons of title info in the document section.

ANNAPOLIS

7033 BEMBE BEACH ROAD

None Beds

None Baths

0.78 acres

$599,900

MLS#: MDAA2108878

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