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 offers a unique blend of coastal living and suburban tranquility, making it one of the most sought-after neighborhoods in Anne Arundel County.

Chesapeake Harbour is renowned for its stunning views of the Chesapeake Bay, providing residents with a daily dose of natural beauty. The community features a variety of housing options, from elegant townhomes to luxurious waterfront properties, each designed to maximize the breathtaking vistas and enhance your living experience. With meticulously landscaped grounds and serene walking paths, you’ll find plenty of opportunities to enjoy the outdoors right at your doorstep.

For those who appreciate an active lifestyle, Chesapeake Harbour boasts an array of amenities, including a private marina, swimming pools, and tennis courts. The community is also conveniently located near the vibrant downtown Annapolis, where you can explore charming boutiques, indulge in gourmet dining, and immerse yourself in the rich history of the area.

Families will appreciate the top-rated schools and family-friendly atmosphere that Chesapeake Harbour offers. With a strong sense of community and numerous social events throughout the year, residents quickly feel at home here.

Whether you’re looking for a peaceful retreat or an active lifestyle, Chesapeake Harbour is the perfect place to call home. Discover the beauty and charm of this exceptional Annapolis community, where waterfront living meets modern convenience. Come and experience the best of Maryland living at Chesapeake Harbour!

Newest Listings in Chesapeake Harbour

$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:

$775,000
2 Beds ⋅ 2 Baths
There is something special about life on the Chesapeake Bay, and this exceptional end-unit residence captures it beautifully. Ideally positioned where the Channel meets the Marina, the home enjoys an unobstructed view up the Channel toward the Chesapeake Bay and Bay Bridge, with expansive water vistas from nearly every room. A waterside wraparound patio, abundant green space, and fabulous interior upgrades further distinguish this unique waterfront setting. Morning begins with the sun rising over the Bay, visible from the primary bedroom and throughout the residence, while the ever-changing waterfront provides a spectacular backdrop to everyday life. From Wednesday night sailing races and Blue Angels flyovers to fireworks, passing boats, and expansive rainbows over the water, there is always something memorable to take in. Inside, the home feels bright, comfortable, and beautifully connected to its waterfront surroundings. The spacious living room is filled with natural light from an abundance of windows framing the incredible views. The electric fireplace provides a warm, relaxing atmosphere for quiet evenings or gathering with friends. Two bedrooms and two full baths provide a comfortable and versatile floor plan, whether used as a full-time residence, weekend retreat, or easy lock-and-leave Annapolis getaway. Just beyond the living room, the covered wraparound patio extends the living space outdoors and overlooks both the water and a large grassy area, an unexpected luxury in condominium living. A second patio off the kitchen offers its own highly sought-after private, no-stair walkway, allowing access to the beautifully appointed kitchen with an immediate view right out to the Bay Bridge. Together with the surrounding green space and multiple outdoor living areas, the residence offers a wonderful sense of privacy and lives much more like a single-family home than a traditional condo. Beyond the front door, Chesapeake Harbor offers a lifestyle centered around the water. Spend summer days at one of two swimming pools, including the waterfront pool, launch a kayak from the community beach, play tennis or pickleball, or follow the walking trails along the shoreline. When the day winds down, stroll to The Beacon for waterfront dining and return home as the evening light settles over the Bay. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, world class dining, shopping, and historic attractions, this exceptional residence also offers convenient access to Washington, DC, Baltimore, and BWI Airport. Whether as a full-time residence or lock-and-leave waterfront retreat, this is a rare opportunity to experience Chesapeake Harbor from a truly special vantage point.

7026 Channel Village Ct Unit #T2, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$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:

$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: (410) 429-7425
$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: (410) 429-7425
$849,000
3 Beds ⋅ 3 Baths
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:

$549,900
2 Beds ⋅ 2 Baths
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

2016 Quay Village Ct Unit #T2, Annapolis

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

$1,119,000
3 Beds ⋅ 3 Baths
Experience one of Annapolis' most extraordinary Chesapeake Bay waterfront homes. This is true waterfront living—not a distant glimpse of a creek or narrow shoreline, but an ever-changing front-row seat overlooking the Chesapeake Bay, the mouth of the Severn River, the Bay Bridge, and the shipping channel. From spectacular sunrises to moonlit evenings, enjoy an ever-changing panorama of sailboats, Wednesday night races, cruising yachts, commercial ships, abundant wildlife, and the beauty of every season from the comfort of your own home. Designed to evoke the feeling of living aboard your own yacht, walls of glass immerse the main living spaces in breathtaking water views from virtually every room. This exceptional three-bedroom, three-bath residence features soaring ceilings, an open floor plan, rich cherry wood floors, a wood-burning fireplace, smart lighting, electric blinds, and new GE Café smart appliances (2024). The home has also been thoughtfully redesigned to provide extraordinary storage rarely found in waterfront condominiums, with expanded closets and additional storage areas that make everyday living as practical as it is beautiful. Uniquely positioned within Chesapeake Harbour, this residence enjoys one of the community's most private waterfront settings. Unlike many waterfront condominiums where decks overlook one another or are visible from common areas, this spacious waterfront deck is tucked into a remarkably private location, allowing you to enjoy the panoramic Bay views with an exceptional sense of peace and seclusion. Chesapeake Harbour is one of Annapolis' premier gated waterfront communities, offering a true resort lifestyle just minutes from historic downtown Annapolis, Eastport, Quiet Waters Park, Thomas Point Park, and numerous waterfront restaurants, while remaining within approximately an hour of Washington, Baltimore, and three major airports. Community amenities include two waterfront swimming pools (one heated), tennis and pickleball courts, a private beach with kayak storage and launch area, scenic walking and biking trails, picnic and barbecue areas, and an on-site marina (slips available separately), The Beacon waterfront restaurant and tiki bar, electric vehicle charging, and ample guest parking. What truly sets this home apart is an experience that cannot be remodeled or recreated. Kitchens, bathrooms, and finishes can always be updated, but an irreplaceable waterfront setting like this endures forever. Every day brings a different view, a different sky, and a different parade of boats across the Chesapeake Bay—yet the sense of tranquility never changes. Now offered unfurnished at $1,119,000, with furnishings available separately. Join us for our Waterfront Sunset Preview on Friday, August 7, from 5:00–7:30 PM, and experience firsthand why this remarkable home offers one of the most captivating waterfront lifestyles in Annapolis.

2127 Beach Village Ct Unit #202, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$619,000
2 Beds ⋅ 3 Baths
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: (410) 280-5600
$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: 8888607369
$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: (410) 429-7425
$565,000
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: (410) 429-7425
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