Chesapeake Harbour Real Estate

Chesapeake Harbour Real Estate

Welcome to Chesapeake Harbour, a picturesque waterfront community nestled in the heart of Annapolis, Maryland. This charming subdivision is a hidden gem in Anne Arundel County, offering a perfect blend of serene living and vibrant coastal lifestyle. With its stunning views of the Chesapeake Bay and proximity to the historic charm of Annapolis, Chesapeake Harbour is an ideal destination for those seeking both relaxation and adventure.

As you stroll through the beautifully landscaped streets, you’ll discover a variety of exquisite homes that reflect the coastal architecture of the region. Many residences feature spacious layouts, private balconies, and modern amenities, making them perfect for families and retirees alike. The community is designed to foster a sense of belonging, with friendly neighbors and a welcoming atmosphere.

Chesapeake Harbour is not just about beautiful homes; it’s also about an active lifestyle. Residents enjoy access to a range of amenities, including private docks, a marina, and a community pool. The nearby walking and biking trails along the waterfront provide the perfect setting for outdoor enthusiasts, while the stunning sunsets over the bay offer a daily reminder of the natural beauty that surrounds you.

Living in Chesapeake Harbour means being just minutes away from the vibrant downtown Annapolis, where you can explore a rich tapestry of history, dining, and shopping. Whether you’re sailing on the bay, enjoying a meal at a waterfront restaurant, or attending local festivals, there’s always something to do in this enchanting community.

Experience the best of Maryland living at Chesapeake Harbour, where every day feels like a vacation. Your dream home awaits!

Newest Listings in Chesapeake Harbour

2121 Beach Village Ct Unit 102, Annapolis
$600,000
2 Beds ⋅ 2 Baths
Tucked away in a serene, private setting, this rarely available 2 bedroom, 2 bathroom mid level residence delivers effortless Annapolis waterfront living. Designed with an open floor plan, the home features an updated kitchen complete with a built in desk area and rear balcony access. A separate dining area flows naturally into a welcoming living room anchored by a wood-burning fireplace, opening out to a private balcony overlooking the Chesapeake Bay and Chase Pond. Wake up to water views in the primary suite, which boasts an en suite bathroom, a generously sized walk in closet, and direct balcony access. A spacious second bedroom, a full hall bath, and a full-size in-unit laundry complete this turnkey home. Chesapeake Harbour offers an unmatched resort lifestyle with 24/7 gated security, private community beach, pools, tennis & pickleball courts, walking trails, marina access, and on-site dining, all just minutes from downtown Annapolis and Eastport.

2121 Beach Village Ct Unit 102, Annapolis

Listing courtesy of Compass. Contact:

7010 Channel Village Ct Unit 102, Annapolis
$674,000
2 Beds ⋅ 2 Baths
Beautiful Views of Chesapeake Bay and Chesapeake Harbour Marina immediately capture your attention in this stunning 2-bedroom, 2-bathroom waterfront condo at Chesapeake Harbour. Bright, open, and filled with natural light, this spacious home offers just over 1,200 square feet of comfortable living space with an inviting floor plan that is perfect for both everyday living and entertaining. The Tuscan-style kitchen opens seamlessly to the dining and living areas, creating an easy flow throughout the main living space. A wood-burning fireplace adds warmth and character to the living room, while large windows and doors bring the beautiful waterfront surroundings into the home. One of the most exceptional features is the expansive balcony accessible from both the living room and primary bedroom. This wonderful outdoor space offers breathtaking panoramic views of the Chesapeake Bay and Chesapeake Harbour Marina, along with a clear view of the Bay Bridge. Whether you're starting your day with coffee on the balcony, settling in with a good book, watching sailboats make their way across the Bay, or enjoying the excitement of Annapolis' Wednesday and Thursday evening races, the ever-changing scenery makes every moment feel special. The setting is also spectacular during the Blue Angels air show and fireworks. An additional balcony off the kitchen provides another inviting spot to enjoy the outdoors and take in the peaceful surroundings. Chesapeake Harbour offers a resort-like lifestyle in a welcoming, pet-friendly community with an impressive array of amenities and activities throughout the year. Enjoy tennis and pickleball courts, 2 swimming pools, a private sandy beach, community piers for fishing, a marina, picnic areas with grills, and walking and jogging paths around scenic Chase Pond. Residents enjoy a variety of gatherings and activities throughout the year, creating a wonderful sense of connection and camaraderie. A 24-hour attended gatehouse provides added security and peace of mind. The Chesapeake Harbour Marina also features a restaurant with outdoor dining and live music on weekends, making it easy to enjoy waterfront dining and entertainment close to home. Ideally located just minutes from Historic Downtown Annapolis, Eastport, waterfront dining and shopping, and the U.S. Naval Academy, Chesapeake Harbour offers a peaceful setting while keeping you close to everything Annapolis has to offer. Washington, DC, Baltimore, and BWI Airport are all easily accessible. Whether you're looking for a year-round residence or a weekend retreat, this special condo offers the opportunity to enjoy the beauty and lifestyle of Chesapeake Harbour every day. Come experience the views, the amenities, the friendly atmosphere, and the relaxed waterfront setting for yourself. Welcome to your new home!

7010 Channel Village Ct Unit 102, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

2123 Quay Village Ct Unit 202, Annapolis
$850,000
2 Beds ⋅ 2 Baths
Experience waterfront living in sought-after Chesapeake Harbour, where sweeping marina and Chesapeake Bay views create a beautiful backdrop for this thoughtfully renovated 2-bedroom, 2-bath condo with a magnificent view. Freshly updated with brand-new flooring, newly renovated kitchen (new cabinets, countertops, wine fridge), fresh paint throughout, custom shutters, walk in closet in primary bedroom and 2 elegant bathrooms featuring Carrera marble. The spacious interior offers high ceilings with thoughtfully placed skylights that add to the open, light-filled feel, while the large loft provides flexible additional living space and excellent storage. A private storage unit in the loft provides even more convenience. Beyond your front door, enjoy the quintessential Chesapeake Harbour lifestyle with two swimming pools, including a heated pool and a waterfront pool, private community beach, tennis and pickleball courts, kayak launch and storage, fishing piers, shoreline walking trails, marina access, electric charging stations and waterfront dining at The Beacon. Gated community with 24-hour security, all just minutes from Downtown Annapolis, Eastport, and the Naval Academy. Whether you're looking for a full-time residence, weekend escape, or lock-and-leave waterfront retreat, this is an exceptional opportunity to enjoy the best of Annapolis waterfront living.

2123 Quay Village Ct Unit 202, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

2104 Chesapeake Harbour Dr E Unit 202, Annapolis
$669,000
3 Beds ⋅ 2 Baths
Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and high-end upgrades from top to bottom. The open, light-filled layout features stylish new LVP flooring (Oct 2024) and contemporary lighting throughout (2024). Cook and entertain in the updated kitchen with custom cabinetry and quartz countertops (Dec 2024), plus brand-new appliances (Jan 2025). Relax in the primary suite with its custom Closet America walk-in closet (Sept 2025). Living in Chesapeake Harbour gives you direct access to a deep-water marina, private beach, pools, tennis courts, 24/7 security, and an on-site waterfront restaurant, all just minutes from historic Downtown Annapolis.

2104 Chesapeake Harbour Dr E Unit 202, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

2123 Beach Village Ct Unit T2, Annapolis
$565,000
2 Beds ⋅ 2 Baths
Direct, unobstructed views of Chesapeake Bay define this terrace-level home in Chesapeake Harbour. The two-bedroom, two-bath condominium features an open living and dining area centered around a fireplace, plus a kitchen with granite countertops, a subway-tile backsplash, and white cabinetry. A patio at the front and another at the rear provide two distinct outdoor spaces. The primary bedroom is well-appointed and includes direct patio access and a generously sized walk-in closet. A second bedroom, a full hall bath, and in-unit laundry complete the interior. The current floor plan measures approximately 1,267 square feet of finished interior space. Chesapeake Harbour is a gated waterfront community with 24-hour security and convenient access to downtown Annapolis. Amenities include a private beach, marina, two pools, tennis and pickleball courts, walking paths, kayak access and storage, and waterfront dining within the community. Few homes in this community see the water this directly. This home offers sweeping views of the Chesapeake Bay from the living room to the patio. This breathtaking view awaits you at 2123 Beach Village Ct, Unit T2. Welcome Home!

2123 Beach Village Ct Unit T2, Annapolis

Listing courtesy of Compass. Contact:

2102 Chesapeake Harbour Dr E Unit 202, Annapolis
$675,000
3 Beds ⋅ 3 Baths
Welcome to coastal living at its finest in Annapolis’ gated Chesapeake Harbour community! Enjoy sweeping marina views, fantastic people watching, and resort style amenities including 2 pools, tennis/pickleball courts, kayak access, walking trails, beaches, cocktails and entertainment at the dock bar and waterfront dining at The Beacon Restaurant. This sun drenched 3 bedroom, 3 full bath condo boasts high ceilings and a seamless floor plan made for entertaining. The upper level loft doubles as a flexible 3rd bedroom or home office, offering an airy, open concept layout that overlooks the main living area to maximize light and space. Don't miss this coastal gem!

2102 Chesapeake Harbour Dr E Unit 202, Annapolis

Listing courtesy of Compass. Contact:

7038 Clinton Ct, Annapolis
$800,000
3 Beds ⋅ 3 Baths
NEW PRICE FOR AN EXCEPTIONAL PROPERTY !!! Experience the ultimate waterfront lifestyle in the prestigious Harbour Village Marina at Chesapeake Harbour, where panoramic marina views and exceptional amenities create one of Annapolis' most sought-after communities. This beautifully updated 3 bedroom 3 bath waterfront condominium offers an inviting blend of elegance, comfort, and coastal charm. Wake each morning to tranquil marina views from your private balcony, spend your afternoons enjoying the private sandy beach, waterfront pool, tennis and pickleball courts, or simply watch the boats come and go from one of the area's premier marinas. Whether you're an avid boater or simply appreciate life on the water, this is waterfront living at its finest. Inside, the spacious floor plan is designed for both everyday living and effortless entertaining. The living room and primary suite each feature a gas fireplace, creating warm and inviting spaces to unwind. Multiple balconies capture beautiful marina vistas, while the updated kitchen showcases granite countertops, stainless steel appliances, and generous workspace for preparing meals or gathering with family and friends. Thoughtful upgrades throughout the home provide both style and peace of mind, including fresh interior paint, engineered hardwood flooring, updated granite countertops, designer bathroom vanities with quartz countertops, newer interior doors with brushed bronze hardware and glass door knobs, LED ceiling lighting, Lutron switches, modern 15-amp outlets with USB and USB-C charging ports, and numerous electrical improvements. The oversized two-car garage with EV charging capability adds convenience for today's lifestyle. Residents of Chesapeake Harbour enjoy an unmatched collection of waterfront amenities, including a private beach, marina, waterfront swimming pools, tennis and pickleball courts, walking paths, and the popular Beacon Waterfront Galley & Bar...all within the gated community. No other condominium community in Annapolis offers this unique combination of waterfront recreation, boating, dining, and resort-style living. Whether you're searching for a full-time residence, an elegant weekend retreat, or the perfect lock and leave waterfront home, this exceptional condominium offers a rare opportunity to enjoy the Chesapeake Bay lifestyle in one of Annapolis' most exclusive waterfront communities.

7038 Clinton Ct, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

2002 Dakota Pl Unit 2A, Annapolis
$619,000
2 Beds ⋅ 3 Baths
NEWLY ENHANCED AND WORTH A SECOND LOOK! A beautifully enclosed second bedroom transforms this residence into a true 2-bedroom, 2.5 bath home, offering added privacy, versatility, and an even more appealing living experience. Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an attached 2 car garage with interior access and additional parking out front, a rare and coveted amenity in the neighborhood. The entry level features an eat-in kitchen with white cabinets and counters, powder room and laundry room with a few steps up to the living room. The thoughtfully designed split-level layout creates a natural separation between the home’s functional spaces and its main entertaining areas, allowing gatherings to flow effortlessly while keeping day-to-day tasks discreetly tucked away. The dramatic living area where soaring ceilings, gas fireplace with custom built-ins, and walls of windows fill the space with natural light while framing the harbor views. Step outside to the expansive full-width waterside deck, the perfect setting for morning coffee, evening cocktails, or simply enjoying the marina activity and views stretching toward the Chesapeake Bay. Upstairs, the spacious primary suite offers a balcony, an ensuite bath with new cabinet and drawer fronts, and a peaceful retreat for relaxing after a long day. A loft-style flex space overlooks the living room below and can easily function as a second bedroom, home office, or additional lounge area, complemented by a full hall bath. Life in Chesapeake Harbour feels like a year-round vacation with an unmatched collection of resort-style amenities, including two waterfront pools, a private sandy beach, exclusive fitness center for a small enclave of residents, tennis and pickleball courts, fishing piers, walking and jogging paths, picnic areas with grills, scenic Chase Pond, and the security of a 24-hour attended gatehouse. The newly opened waterfront marina restaurant adds to the vibrant atmosphere with outdoor dining and live music on weekends. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, waterfront dining, shopping, and historic attractions, this exceptional residence also offers easy access to Washington, DC, Baltimore, and Baltimore/Washington International Thurgood Marshall Airport. Whether you are searching for a full-time residence or a lock-and-leave waterfront retreat, this home offers the very best of the Annapolis waterfront lifestyle. Welcome Home!

2002 Dakota Pl Unit 2A, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

7004 Channel Village Ct Unit 102, Annapolis
$575,000
2 Beds ⋅ 2 Baths
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.

7004 Channel Village Ct Unit 102, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

2108 Chesapeake Harbour Dr Unit 201, Annapolis
$599,999
3 Beds ⋅ 3 Baths
Dramatic Price Reduction just taken on this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. This 2nd Village location provides the perfect short walk to Chase Pond, the Bay View pool, the kayak beach, tennis and pickleball courts and both community piers on Chesapeake Bay, no car needed. When the autumn leaves fall you have even more of a water view until they bloom again in April, though you are surrounded by expansive lawns and lush landscaping year-round. 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!

2108 Chesapeake Harbour Dr Unit 201, Annapolis

Listing courtesy of Compass. Contact:

2110 Chesapeake Harbour Dr Unit 101, Annapolis
$560,000
2 Beds ⋅ 2 Baths
AMENITY RICH LOCATION!!! Welcome to this beautiful 2 bedroom, 2 bath coveted, spacious and serene 2nd floor end unit condo, located in Second Village just steps away from all of the amenities found in Chesapeake Harbour. Imagine yourself enjoying the Bay front swimming pool, the sandy beach, kayaks, grills, picnic tables, fishing/crabbing piers, jog/walking paths, pickleball and tennis courts, and the EV charging station. Chesapeake Harbour is a gated community which provides a guarded 24-hour security entrance, has a private marina with available deep-water slips, direct bay access, and a gourmet restaurant with a waterfront tiki bar - all just minutes from downtown Annapolis. This spotless home offers the perfect blend of privacy, natural light, and lush greenery surrounding it on all sides. With a winter water view of Chesapeake Bay and Chase Pond from the kitchen’s center island, you can enjoy the additional square footage not found with interior units. The open floor plan is bathed in sunlight from floor to ceiling windows and invites the outside in. The living spaces are airy and inviting, with a seamless flow from the cozy living room to the dining area and updated kitchen, including hardwood and tiled floors, a fireplace for those cooler evenings, and a large wraparound deck, available only on end units, where relaxing or entertaining outside can be enjoyed. Whether you are a boating enthusiast, enjoy all the historical small-town charm that Annapolis offers, 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 the perfect blend of adventure and relaxation that living in Chesapeake Harbour offers. Priced to make it your own.

2110 Chesapeake Harbour Dr Unit 101, Annapolis

Listing courtesy of Compass. Contact:

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