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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
208
# of Listings
3
Avg # of Bedrooms
$517
Avg. $ / Sq.Ft.
$1,092,296
Med. List Price

Browse Annapolis Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

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$3M - $5M

Over $5M

208 Properties Found. Page 8 of 14.

Welcome to 1576 St. Margaret’s Road, a meticulously rebuilt rancher set on a peaceful 1.89-acre level lot. If you’ve been searching for single-level living with room to breathe, this is the one. The spacious layout offers a seamless flow between the living and dining areas, creating the perfect setting for both everyday living and entertaining. With two bedrooms and a full bath on each side of the home, the design provides ideal privacy for owners and guests alike. The current owner completed a comprehensive rebuild in 2009, replacing all major systems, including: roof, HVAC, windows, septic, electrical, plumbing, insulation, kitchen, and hall bathroom. The kitchen features custom cabinetry, granite countertops, stainless steel appliances, and ceramic tile flooring. In 2010, a 950-square-foot addition expanded the home to include an additional living area, a primary suite with an en suite full bath, an additional bedroom, a two-car garage, and new siding across the entire exterior. Step outside to a beautiful deck and screened-in patio (completed in 2020) overlooking the expansive backyard — perfect for relaxing, entertaining, or simply enjoying the privacy of your surroundings. The unfinished, waterproofed basement offers endless potential for future living space, a home gym, workshop, or storage. This home offers the confidence of modern infrastructure paired with timeless charm, while still providing the lot size and privacy that are increasingly hard to find. Set well back from the road on a quiet street, this property delivers exceptional seclusion while still being just minutes from downtown Annapolis, major commuter routes, shopping, dining, and the Chesapeake Bay. Located within one of the county’s top-performing school districts, this home is the perfect blend of location, lifestyle, and long-term value. This is the total package!
#MDAA2140372

ANNAPOLIS

1576 SAINT MARGARETS ROAD

4 Beds

2 Baths

1,792 Sq.Ft.

$690,000

MLS#: MDAA2140372

This rarely available 4-story luxury townhome offers over 2,600 square feet of beautifully designed living space in one of Annapolis’ most sought-after communities. Highly desirable for their open floor plans and exceptional parking, these end-unit townhomes rarely come to market. This property offers four private parking spaces—two in the garage and two in the driveway—an uncommon find for townhome living. Inside, you'll find gorgeous hardwood floors, soaring ceilings, upgraded trim and doors, and abundant natural light throughout. The designer kitchen is a true centerpiece featuring quartz countertops, a massive island perfect for gathering, double ovens for the home chef, and upgraded KitchenAid appliances, all complemented by stylish fixtures and finishes. This spacious home includes four generously sized bedrooms and five bathrooms, with a bathroom conveniently located on every level for ultimate functionality. The primary suite is a true retreat, complete with a dream walk-in closet and spa-like bath. Additional highlights include epoxy-coated garage floors and an EV charger that conveys, blending luxury with modern convenience. The crown jewel of the home is the private rooftop deck—perfect for summer evenings, entertaining guests, or enjoying breathtaking sunset views. Ideally positioned within Admirals Square, the home is tucked away for optimal privacy. The community is known for its unbeatable location—minutes from downtown Annapolis, premier shopping, restaurants, and major commuter routes including I-97 and Route 50. This is a rare opportunity to own one of Admirals Square’s most desirable townhome styles - one you don't want to miss!
#MDAA2139692

ANNAPOLIS

218 WESLEY BROWN LANE

4 Beds

3 Baths

2,652 Sq.Ft.

$675,000

MLS#: MDAA2139692

Look no further! Welcome to Chesapeake Harbour, one of Annapolis' most sought after waterfront communities. This beautifully renovated 2 BR | 2 BA | 1200 SF condo on the second level is truly turn key offering over $100K in high end improvements crafted with top of the line materials throughout. Enjoy stunning tranquil marina views from your deck and living space, creating a peaceful coastal retreat. The sumptuous Primary Suite features access to deck, a spa inspired Bath with an impressive walk in shower and custom closet with built-ins. Recent updates include new carpet throughout and a new oversized water heater, ensuring comfort and peace of mind. Residents of Chesapeake Harbour enjoy an exceptional lifestyle with front entrance security , waterfront dining at the Beacon Waterfront Bar, marina access, waterfront pools, tennis, private beach and walking trails and just minutes to Downtown Annapolis.
#MDAA2136184

ANNAPOLIS

7022 CHANNEL VILLAGE COURT 101

2 Beds

2 Baths

1,200 Sq.Ft.

$675,000

MLS#: MDAA2136184

New on site 1 day ago
Now is your chance to call this HOME! Welcome to this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. Whether you're looking for a worry-free vacation spot or a serene place to call home, this 3-bedroom, 3 full bath sanctuary with a gourmet kitchen and totally updated baths has you covered with over 1,700 square feet of style and comfort. This Bayfront community allows you to vacation at home year round. Take a stroll around the marina or decide if you want to lounge at one of the 2 pools, play tennis or pickle ball, or take your kayak out and watch the sunrise over the Bay Bridge, the choices are endless. Enjoy visiting The Beacon where you can grab a drink at the outdoor bar, Proud Mary's or go inside for brunch or dinner as you watch the boats bob in the marina. Looking for more options? Historic downtown Annapolis's fantastic restaurants and shopping are just a stone's throw away making every day feel like a vacation. Enjoy the tranquility of a pet-friendly environment and embrace the best of both a coastal retreat and vibrant city life!
#MDAA2140810

ANNAPOLIS

2108 CHESAPEAKE HARBOUR DRIVE E 201

3 Beds

3 Baths

1,700 Sq.Ft.

$675,000

MLS#: MDAA2140810

Experience the pinnacle of downtown Annapolis living at Park Place, the city’s most coveted luxury condominium address. This exquisite 2-bedroom, 2-bath residence offers a refined blend of sophistication, comfort, and effortless urban living—just steps from the waterfront, historic streets, acclaimed dining, boutiques, and cultural landmarks that define this remarkable city. Designed for a lifestyle of ease and indulgence, Park Place delivers an unmatched suite of amenities: a resort-style in-ground pool, state-of-the-art fitness center, dog park, and dedicated office and meeting spaces, all within a vibrant mixed-use community featuring its own restaurants, shops, and service-oriented businesses. Residents enjoy the peace of mind and convenience of a 24-hour concierge, security, package pickup, and dry-cleaning drop off services, elevating everyday living to something truly exceptional. This unit also comes with 2 garage parking spaces and a storage unit. More than just a condominium, Park Place is a lifestyle—where luxury, location, and convenience converge. This is not simply a place to live, but a place to thrive, offering the very best of Annapolis living in one premier, impeccably curated setting.
#MDAA2135262

ANNAPOLIS

5 PARK PLACE 102

2 Beds

2 Baths

1,208 Sq.Ft.

$669,000

MLS#: MDAA2135262

Cape St. Claire Home sold with Extra Lot included! This lovely Cape St. Claire property boasts an extra lot, offering more space for your family to enjoy. Build a detached garage with extra living space or possible ADU. Upon entering the home, you’ll immediately feel at ease. The spacious living room, which could also serve as a formal dining area, features a cozy fireplace. The kitchen, with its wall of windows, brings the outdoors in, providing an abundance of natural light. The first-floor bedroom is perfect for a variety of needs, and the entryway to the family room creates an ideal space for a child’s play or reading area, or simply another comfortable living space. Just a few steps away, the family room invites you to relax or step outside onto the patio, where you can take in the beauty of the natural rear yard. Upstairs, you’ll find an additional roomy bedroom as well as the 17x15 primary bedroom, which comes with its own upgraded private bath, huge bow window and double closets. This 3-bedroom, 2-bath home has undergone numerous upgrades, including new flooring, fresh paint, granite countertops, stainless steel appliances, and updated bathrooms. Other recent improvements include new sidewalks, a new water softener system, and a newer roof. The attached 2-car garage completes this perfect package!
#MDAA2103730

ANNAPOLIS

1165 GREEN HOLLY COURT

3 Beds

2 Baths

2,218 Sq.Ft.

$650,000

MLS#: MDAA2103730

This 2 bedroom, 2 bath condo is move-in ready! Freshly painted, and brand new carpet in bedrooms. Park Place boasts numerous amenities that make it one of the best places to live in Annapolis. With an ideal location, you can walk everywhere in town to restaurants and shopping. When you enter the lobby, you will be greeted by the 24/7 staff at the front desk. The party room is perfect for larger gatherings and meetings with friends and neighbors. The Social Committee organizes plenty of events to join in and have fun with your neighbors if you feel like it. s. Grab a book from the library and relax on the back patio. The pool is fabulous, and there is a lifeguard on duty during the season. The dog park is perfect for your pet. Grills for your convenience are also located on the back patio! Walk to the Naval Academy Stadium minutes away and enjoy the lively Football season. Come and see why Park Place is the perfect place to call home!
#MDAA2122622

ANNAPOLIS

5 PARK PLACE 626

2 Beds

2 Baths

1,314 Sq.Ft.

$649,999

MLS#: MDAA2122622

Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and living areas—perfect for everyday living and entertaining. Just off the living room, enjoy an enclosed deck that adds extra flexible space and a great place to relax or entertain. This level also includes three spacious bedrooms and an updated full bathroom. Downstairs, the home continues to impress with tiled flooring throughout, heated floors, and a large primary suite with a private full bathroom, plus walkout access to an enclosed patio featuring a heated exercise pool or hot tub. Outside, the property offers a large cleared lot with beautiful landscaping, an irrigation system, and a shed for additional storage. Hillsmere Shores is known for its exceptional community amenities including a marina, multiple boat ramps and kayak launches, a beach, playground, and access to Quiet Waters Park, with the Key School conveniently located right across the street. An electric vehicle charger is also included, adding even more value and convenience—this move-in ready home is a rare opportunity to enjoy a renovated property and an unmatched Annapolis lifestyle.
#MDAA2126696

ANNAPOLIS

100 CARROLL DRIVE

4 Beds

2 Baths

1,935 Sq.Ft.

$649,000

MLS#: MDAA2126696

Welcome to brand-new luxury living at Element at Mill Creek, a new construction community of modern condominiums designed for style, comfort, and convenience. This spacious, light-filled home offers southern exposure and a private balcony with serene views of lush forest retention—perfect for relaxing or entertaining. Inside, enjoy a chef-inspired kitchen with quartz countertops, upgraded cabinetry, stainless steel appliances, and a large center island. The open-concept living and dining areas create a warm, inviting atmosphere ideal for gatherings or quiet evenings. The primary suite features a generous walk-in closet and a spa-style bath with high-end finishes. Additional features include a full-size washer and dryer, included window treatments, ample storage, and reserved parking. As part of the new Element at Mill Creek community, you’ll enjoy low condo fees, resort-style amenities, and the ease of low-maintenance living in a brand-new home. Inquire today about available floor plans and pricing—your perfect new home is waiting!
#MDAA2137264

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 310

2 Beds

2 Baths

1,558 Sq.Ft.

$632,400

MLS#: MDAA2137264

Welcome to this beautifully updated 3-bedroom, 2.5-bath Colonial nestled in the highly sought-after Arundel on the Bay community in Annapolis. This sun-drenched home features a bright and open floor plan with contemporary doors and trim, new replacement windows, and gleaming hardwood floors throughout the main level. The gourmet kitchen is a chef’s delight, showcasing 42" white shaker cabinets, absolute black countertops, brand-new stainless-steel appliances, and direct access to a screened-in porch—perfect for relaxing or entertaining. Upstairs, you'll find three spacious bedrooms and two updated full baths. The primary suite offers a beautifully appointed custom shower designed for comfort and style. Located in a waterfront community, Arundel on the Bay provides an array of amenities including a private pier, boat slips, beach access, boat ramps, playground, and scenic walking trails. Enjoy a serene yet convenient lifestyle just minutes from downtown Annapolis, shopping, and top-rated restaurants, with easy commutes to Washington, D.C., and Baltimore.
#MDAA2127094

ANNAPOLIS

3410 NEWPORT AVENUE

3 Beds

2 Baths

1,654 Sq.Ft.

$630,000

MLS#: MDAA2127094

Motivated Sellers!! Price Just Improved!! Rare Opportunity in an Amazing Annapolis Neighborhood! Welcome to 79 Windwhisper. A beautiful 4 bedroom, 2500 sq foot, 3.5 bath home with an office, located in one of Annapolis’ most desirable neighborhoods. This well-maintained property offers numerous recent updates, including new carpet, hardwood flooring on main level, updated bathrooms, flooring, fresh paint interior and exterior, a new refrigerator, and a new dishwasher, making it move-in ready. The home features a fully finished basement, providing plenty of additional living or entertainment space, along with the convenience of a garage. Enjoy the Chesapeake lifestyle with a private neighborhood marina just a short walk away, perfect for kayaking and paddleboarding. Outdoor lovers will also appreciate being less than 2 miles from Quiet Waters Park, offering trails, waterfront views, and year-round recreation. Ideally located near the U.S. Naval Academy and just 3 miles from Historic Downtown Annapolis, you’ll have easy access to waterfront dining, shopping, and local events. Professional landscaping is already scheduled and fully paid for, with improvements to be completed in April, adding even more curb appeal to this wonderful property. Don’t miss this rare opportunity to own in an exceptional Annapolis location!
#MDAA2138392

ANNAPOLIS

79 WINDWHISPER LANE

4 Beds

3 Baths

2,560 Sq.Ft.

$629,999

MLS#: MDAA2138392

Recently Refreshed and Brand-New Roof to be installed by seller prior to closing!!! Ready for showings this week!! Welcome to 40 Windwhisper Lane, Updated 4 bedroom and 2.5 bath home, including a bedroom and half bath conveniently located on the main level. Enjoy an updated kitchen and numerous renovations throughout, complemented by fresh new paint, lighting, and moldings. Other updates include the upper-level primary bathroom, New HVAC & Hot Water Heater. Outside, you’ll love the fully fenced backyard, back deck, and stone patio—perfect for entertaining, pets, or peaceful outdoor enjoyment. An unfinished lower level provides ample storage and future potential. Located just a short distance to private marinas / water access and downtown Annapolis! Enjoy easy access to waterfront dining, shops, local parks, the U.S. Naval Academy, and all the charm the historic district has to offer.
#MDAA2134390

ANNAPOLIS

40 WINDWHISPER LANE

4 Beds

2 Baths

1,855 Sq.Ft.

$629,000

MLS#: MDAA2134390

Welcome to this beautifully updated 3-bedroom, 2-bath single-family home in the highly sought-after, amenity-rich Heritage Harbour community in Annapolis. Thoughtfully designed for comfortable main-level living, this home features a spacious primary suite with a gorgeous updated bath and walk-in closet, along with a second bedroom, 2nd updated full bath, and convenient main-level laundry. The gorgeous light-filled kitchen is a showstopper, showcasing crisp white cabinetry, brushed gold hardware, black stainless steel appliances, luxury vinyl plank flooring, offering table space framed by a charming bay window. Entertain with ease in the separate dining room and inviting living room with a cozy fireplace, or unwind in the den—perfect for a home office or quiet reading retreat. The sunroom provides an additional light-filled living space to enjoy year-round. Freshly painted throughout, the home also features new flooring and carpet on both levels. The walk-out lower level offers a versatile third bedroom or flex space, along with abundant unfinished storage. Step outside to the rear deck backing to trees—an ideal setting for relaxing or entertaining in a peaceful, private setting. Residents of Heritage Harbour enjoy an unmatched lifestyle with access to the community lodge, featuring a dramatic atrium, indoor and outdoor pools, fitness center, library, boutique, activity rooms, woodworking shop, game rooms, coffee corner, and meeting spaces. Outdoor amenities include a picnic area, bocce ball, horseshoes, kayaking on the South River, tennis and pickleball courts, a nine-hole golf course with pro shop, clubhouse dining, a pier with boat slips, and RV/boat storage. Experience resort-style, active adult living at its finest. Schedule your private showing today and discover all that Heritage Harbour has to offer!
#MDAA2133750

ANNAPOLIS

860 WOODMONT ROAD

3 Beds

2 Baths

1,623 Sq.Ft.

$629,000

MLS#: MDAA2133750

WELCOME HOME!This beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip A 54 & Waterfront Pool.This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring butcher-block countertops, stainless-steel appliances, gas range with vent hood, built-in microwave, and designer recessed lighting throughout the home. Custom built-ins include a butler’s pantry and laundry cabinetry for smart, hidden storage.A full wall of sliding glass doors opens to a spacious deck offering peaceful seasonal views of Back Creek. The residence also includes a large deeded basement storage unit.Enjoy exclusive ownership of a deeded deep water 30+ foot boat slip—one of the few in Annapolis with direct vehicle access, allowing you to drive right to the dock for easy loading and unloading.Located in the heart of Eastport, Severn House offers a waterfront pool, beautifully maintained grounds, and the area’s most protected deep-water marina. Sidewalks lead to Downtown Annapolis, the U.S. Naval Academy, and the city’s famed restaurants and shops.This turnkey waterfront condo perfectly balances luxury, comfort, and location—schedule your private showing today.
#MDAA2136172

ANNAPOLIS

755 FAIRVIEW AVENUE 755 D

3 Beds

2 Baths

1,295 Sq.Ft.

$619,950

MLS#: MDAA2136172

Welcome to brand-new luxury living at Element at Mill Creek, a new construction community of modern condominiums designed for style, comfort, and convenience. This spacious, light-filled home offers southern exposure and a private balcony with serene views of lush forest retention—perfect for relaxing or entertaining. Inside, enjoy a chef-inspired kitchen with quartz countertops, upgraded cabinetry, stainless steel appliances, and a large center island. The open-concept living and dining areas create a warm, inviting atmosphere ideal for gatherings or quiet evenings. The primary suite features a generous walk-in closet and a spa-style bath with high-end finishes. Additional features include a full-size washer and dryer, included window treatments, ample storage, and reserved parking. As part of the new Element at Mill Creek community, you’ll enjoy low condo fees, resort-style amenities, and the ease of low-maintenance living in a brand-new home. Inquire today about available floor plans and pricing—your perfect new home is waiting!
#MDAA2136300

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 112

2 Beds

2 Baths

1,621 Sq.Ft.

$614,900

MLS#: MDAA2136300

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