One of the most popular communities provided by {{page_data.agentName}}

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
266
# of Listings
3
Avg # of Bedrooms
$529
Avg. $ / Sq.Ft.
$1,357,478
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

266 Properties Found. Page 12 of 18.

Welcome to the gated community of Chesapeake Harbour, offering a stress-free lifestyle! This second-floor condo features two balconies. The large wrap-around balcony provides stunning views of the marina, while the second balcony, located off the kitchen, offers views of the bay. Inside, the main level features an open-concept living area and a spacious kitchen with stainless steel appliances and abundant cabinet and counter space. The primary suite is also located on this level. Up the beautiful spiral staircase, you will find a loft/bedroom and an additional sitting area. Chesapeake Harbour provides residents with a swimming pool, tennis courts, a beach, and much more. You are also within walking distance of the marina, shopping, and restaurants.
#MDAA2131544

ANNAPOLIS

2106 CHESAPEAKE HARBOUR DRIVE 202

2 Beds

2 Baths

1,688 Sq.Ft.

$624,900

MLS#: MDAA2131544

Welcome to 1365 Moyer Road, a beautifully renovated home offering the perfect blend of modern style, privacy, and convenience. Nestled just off Arundel on the Bay Road, this exceptional property is minutes from downtown Annapolis, Quiet Waters Park, and the Chesapeake Bay. The upper-level features three spacious bedrooms and two fully updated bathrooms, including a serene primary suite complete with an en-suite bath and balcony accessing secluded rear deck. The stunning kitchen showcases luxury finishes, while tastefully renovated bathrooms and upscale luxury plank flooring throughout add warmth and sophistication. Lower-level offers additional full-bathroom, rec space with a cozy fireplace, flex room perfect for a home office or playroom and plenty of storage space. Filled with natural light, the inviting sunroom opens to a brand-new rear deck, creating the ideal space for relaxing or entertaining. Set on a private, fully fenced 0.65-acre lot, this oversized home offers plenty of room to enjoy both indoors and out. A rare opportunity to own a move-in-ready retreat in an unbeatable location.
#MDAA2149760

ANNAPOLIS

1365 MOYER ROAD

3 Beds

3 Baths

1,814 Sq.Ft.

$615,000

MLS#: MDAA2149760

848 Deerwood Court offers a wonderful opportunity to enjoy life in Heritage Harbour, one of Annapolis' most sought-after active adult communities. Situated on a desirable corner lot at the end of a quiet cul-de-sac, this well-designed ranch-style home features three bedrooms, two full bathrooms, a spacious side addition, and a two-car garage. The home has been lovingly maintained over the years and offers a comfortable floor plan with generous living spaces, abundant natural light, and excellent flow for both everyday living and entertaining. The side addition provides valuable extra living space rarely found in many homes of this size, while the corner lot setting offers attractive curb appeal and additional privacy. This property presents an excellent opportunity for buyers to personalize a home to their own tastes and style while enjoying all that Heritage Harbour has to offer. Whether you're looking to make updates immediately or over time, the solid layout and desirable location provide a strong foundation for future improvements. Residents of Heritage Harbour enjoy an exceptional lifestyle with access to a community lodge, indoor and outdoor pools, fitness facilities, walking trails, waterfront amenities, clubs, activities, and countless opportunities to stay active and connected. Conveniently located near shopping, dining, downtown Annapolis, medical facilities, and major commuter routes, this home combines comfort, convenience, and community in one of the area's most desirable neighborhoods. Don't miss the opportunity to make this Heritage Harbour home your own and enjoy the active lifestyle that has made this community such a popular destination for buyers seeking the very best of Annapolis living.
#MDAA2146412

ANNAPOLIS

848 DEERWOOD COURT

3 Beds

2 Baths

1,900 Sq.Ft.

$605,000

MLS#: MDAA2146412

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.

$602,602

MLS#: MDAA2136300

Summer is here, and the time is right for moving into that new place to call your own! Tucked away on a quiet cul-de-sac just minutes from downtown Annapolis, this 2,000± square foot home offers the rare combination of privacy, meaningful upgrades, and everyday convenience. The shaded backyard is a summer favorite spot for your hammock or fire pit with s'mores. Since 2021, major improvements have already been handled for you, including a new roof, windows and sliders, vinyl siding with upgraded gutters, HVAC system, water heater, and fully updated kitchen and bathrooms... giving buyers confidence in both condition and long-term value. The layout offers 4 bedrooms and 2.5 baths with a flow that allows you to live comfortably day-to-day while still having that work-from-home dedicated bonus space without sacrificing an entire bedroom. Set on a manageable, low-maintenance lot with no HOA, this is an ideal fit for those who want space and freedom without added restrictions. Extend the driveway, add a garage, put in a swing set, or a tree-house. Heck, add both! This is a great place to make it exactly what you want it to be. With its location just minutes from downtown Annapolis dining, boutique shopping, water access, and commuter routes, the home delivers both accessibility and a tucked-away feel. This home is waiting for you! Turn key and ready to move in. Or consider it as an investment property and enjoy the fruits of the demand from the US Naval Academy, traveling nurses, or LTR.
#MDAA2141372

ANNAPOLIS

2 SILOPANNA COURT

4 Beds

2 Baths

2,000 Sq.Ft.

$599,900

MLS#: MDAA2141372

BIG $50K PRICE REDUCTION ON THIS BEAUTIFUL 2 BR UNIT! Look no further! This Chesapeake Harbour marina view condo, is available immediately in 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.

$599,900

MLS#: MDAA2136184

Price reduced!! Amazing opportunity! Situated in one of Annapolis’ most desirable waterfront communities, Oyster Harbor, 3328 Shore Drive offers a premier corner-lot location with beautiful second-floor water views. Enjoy the coastal lifestyle with easy access to marinas, parks, the community beach, local dining, and the charm of nearby historic Annapolis. This property presents an incredible opportunity for buyers looking to renovate, update, or create their dream home in a sought-after location. Don’t miss this rare chance to bring your vision to life!
#MDAA2144406

ANNAPOLIS

3328 SHORE DRIVE

3 Beds

2 Baths

1,824 Sq.Ft.

$599,000

MLS#: MDAA2144406

Welcome to easy waterfront living in the heart of Eastport. Rarely available and beautifully renovated, this top-floor 2-bedroom, 2-bath condominium in the sought-after Severn House community offers direct views of Back Creek, turnkey interiors, and effortless access to the Annapolis waterfront lifestyle. Inside, the residence has been thoughtfully updated with a clean, coastal feel and comfortable, move-in ready finishes throughout. The open-concept living spaces are bright, inviting, and designed for easy everyday living. The kitchen opens to the dining area and living room, creating a comfortable flow for entertaining, gathering, or simply enjoying the sense of space. From the main living area, sliding glass doors lead to a private balcony with direct views over Back Creek, adding a beautiful waterfront backdrop to the home. The primary suite features an ensuite bathroom and walk-in closet, while the second bedroom offers a gracious closet and utilizes the full hall bath. A washer/dryer combo unit adds everyday convenience. Severn House is one of Eastport’s most beloved waterfront communities, known for its relaxed atmosphere, mature landscaping, and exceptional amenities. Residents enjoy a waterfront pool with spacious patio and deck areas, an outdoor clubhouse pavilion, kayak, canoe, and paddleboard launch, bike storage, communal laundry, on-site management, and available water taxi access from the dock. Please note that pets are not allowed in this community (exception for support animals that are approved). Gas and water are included in the condo fees. Just minutes from downtown Annapolis, Eastport restaurants, shops, marinas, and local favorites, 774-F Fairview Avenue offers a rare turnkey opportunity in one of Annapolis’ most convenient waterfront communities. 30-foot boat slip being sold separately - reach out for details.
#MDAA2145660

ANNAPOLIS

774 FAIRVIEW AVENUE F

2 Beds

2 Baths

1,060 Sq.Ft.

$595,000

MLS#: MDAA2145660

Welcome to 2016 Quay Village Court, Unit T-2, located in one of Annapolis' most sought-after gated waterfront communities. Tucked away in a private and secluded setting, this beautifully updated 2-bedroom, 2-bath home offers a peaceful retreat that barely feels like condo living. The walk-out location and mature landscaping create a wonderful sense of privacy, while the thoughtfully designed interior is warm, inviting, and beautifully maintained. From the patio and primary bedroom, you'll enjoy year-round views of the Chesapeake Bay beyond a natural shoreline of cattails and native grasses. The scenery changes daily, offering a peaceful backdrop filled with wildlife, sailboats, and ever-changing skies. Residents of Chesapeake Harbour enjoy exceptional amenities including a heated pool with lap lanes, a Bayfront pool, tennis courts, pickleball courts, private beaches, kayak launch and storage areas, community grilling stations, a marina, and waterfront dining. Professional interior photography and additional details will be uploaded soon. Stay tuned for a closer look at this special home and the Chesapeake Harbour lifestyle. https://youtu.be/fo_7CwN9AR8 Y
#MDAA2147972

ANNAPOLIS

2016 QUAY VILLAGE COURT T2

2 Beds

2 Baths

1,282 Sq.Ft.

$595,000

MLS#: MDAA2147972

Experience Ultimate Flexibility with this Versatile and Spacious Contemporary Townhome offering Unique Zoning flexibility , 3 Finished levels with 3,016sf, and a Rare Live/Work Opportunity in Village Greens of Annapolis! Operate a boutique business, studio, or professional office right from your street-level commercial space with no commute - previously a boutique shop - with a convenient Kitchenette/Wet Bar area and Half Bath. Upstairs on the Main Living Level, discover an upscale, open-concept layout flooded with natural light and fabulous Designer Touches, Crown Molding, Plantation Shutters, Gorgeous Wood Floors and a Half Bath. The Beautiful Gourmet Kitchen features a large Island, Bright White Cabinets, Stainless Appliances and Quartz Counters in addition to the Spacious Dining area, and Inviting Living Room, Cozy Gas Fireplace and Deck create the perfect hub for Entertaining! Retreat to the Upper Level offering a Serene Primary Suite with Amazing Attached Bath and Walk-in Closet in addition to the 2 Spacious bedrooms, accompanied by another full bath and a den/flex space. This unit has been Meticulously maintained including a new AC unit (Oct 2025) and a freshly painted 2 Car Attached Garage featuring high-temp epoxy flooring and extra storage and plenty of parking. Located just minutes from historic downtown Annapolis, major commuter routes, dining, and the waterfront. Live, work, and play without compromise! Schedule Your Showing Today!
#MDAA2149460

ANNAPOLIS

709 SKIPPERS LANE

3 Beds

2 Baths

3,016 Sq.Ft.

$595,000

MLS#: MDAA2149460

Welcome to 1016 Timber Creek Drive, a well maintained home nestled in the sought-after Timber Creek community of Annapolis. Featuring 3 bedrooms, 3 full baths, and three levels of living space, this home offers the perfect blend of comfort, functionality, and style. The main level showcases hardwood floors, a gas fireplace with marble surround, and an updated kitchen remodeled by Realistic Builders . Off the kitchen, a spacious side deck provides the perfect spot for grilling or enjoying your morning coffee, while the private, partially fenced backyard with brick patio creates an inviting outdoor gathering space ideal for summer barbecues. Upstairs, the spacious primary suite is complemented by two additional bedrooms and a second full bath. The lower level offers a large family room, full bath, laundry area, and flexible space perfect for guests, a home office, or recreation room. Extensively updated over the years, improvements include the kitchen remodel (2012), installation of a gas line, gas furnace, central air conditioning, and gas fireplace (2012), replacement windows (2016), partial roof replacement (2020), tankless hot water heater (2021), new dishwasher and dryer (2023), new washer and dryer (2024), and fresh interior paint (2026). Conveniently located just minutes from Quiet Waters Park, Eastport, and historic downtown Annapolis, as well as shopping, dining, and commuter routes, this move-in-ready home offers easy access to everything Annapolis has to offer.
#MDAA2148944

ANNAPOLIS

1016 TIMBER CREEK DRIVE

3 Beds

3 Baths

1,730 Sq.Ft.

$589,000

MLS#: MDAA2148944

Don’t miss this beautifully updated, move-in-ready condo in the highly sought-after, amenity-rich community of Chesapeake Harbour, offering serene marina views and the perfect backdrop to relax and watch the boats drift by. This inviting home is bright and cheery and features neutral paint and carpeting. There are two spacious bedrooms with two full baths. The open-concept living and dining areas create an effortless flow for both everyday living and entertaining and opens up to a deck that overlooks the marina. The updated kitchen showcases granite countertops and ample cabinetry, while the cozy wood-burning fireplace adds warmth and charm to the living space. Chesapeake Harbour offers resort-style living with 24/7 gated security, two pools, tennis courts, a private sandy beach, and scenic walking paths. Enjoy the convenience of a water taxi to Historic Annapolis or dine waterside at The Beacon, located right within the community. Experience low-maintenance coastal living at its finest, this is the one you’ve been waiting for.
#MDAA2143832

ANNAPOLIS

7004 CHANNEL VILLAGE COURT 102

2 Beds

2 Baths

N/A

$575,000

MLS#: MDAA2143832

Welcome to 1424 Regent Street, where modern style meets everyday comfort. This beautifully updated home offers exceptional curb appeal with a spacious driveway, a brand-new sprinkler system, and a fully fenced backyard featuring a large deck—perfect for entertaining, relaxing, or enjoying outdoor living. Step inside to discover a stunning custom-designed living room highlighted by a striking gold and white accent wall that creates a warm, sophisticated focal point. The adjoining dining area flows seamlessly into the show-stopping custom kitchen, complete with stylish cabinetry, gorgeous quartz countertops, and designer finishes that make cooking and gathering a true pleasure. The spacious primary suite features its own en-suite bathroom featuring custom designer finishes. An additional beautifully renovated full bathroom upstairs offers both style and convenience for family and guests. Throughout the home, you'll find thoughtfully designed custom bathrooms and quality updates that create a move-in-ready experience. The lower level offer additional entertaining space with a stone fireplace, as well as a bedroom and a full bathroom. With its modern upgrades, designer touches, functional layout, and inviting spaces, 1424 Regent Street is a home you'll be proud to call your own.
#MDAA2149718

ANNAPOLIS

1424 REGENT STREET

4 Beds

3 Baths

1,560 Sq.Ft.

$575,000

MLS#: MDAA2149718

Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting, with seamless flow from the cozy living room to the dining area and updated kitchen. You'll love the thoughtful details, including hardwood floors, a fireplace for those cooler evenings, and scenic views that bring the outdoors in. This home is ideally located to enjoy watching the sunrise over Chase Pond and the Bay with your morning coffee or tea. Later in the day the oversized wrap-around deck invites you to relax, entertain, or simply soak in the tranquil surroundings and watch the sunset over the Marina. Chesapeake Harbour is a vibrant, amenity-rich community with access to 2 pools, 2 tennis and pickle ball courts, kayaking, walking trails and a marina, all just minutes from downtown Annapolis. Whether you're a boating enthusiast or simply crave the coastal lifestyle, this property checks all the boxes. Don’t miss your chance to own this one-of-a-kind retreat. Schedule your tour today and experience Chesapeake Harbour living at its finest!
#MDAA2138114

ANNAPOLIS

2110 CHESAPEAKE HARBOUR DRIVE 101

2 Beds

2 Baths

1,237 Sq.Ft.

$575,000

MLS#: MDAA2138114

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.

$574,000

MLS#: MDAA2138392

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Sellers resources
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