Chesapeake Harbour Real Estate

Chesapeake Harbour Real Estate

Welcome to Chesapeake Harbour, a picturesque waterfront subdivision nestled in the heart of Annapolis, Maryland, within Anne Arundel County. This charming community offers a unique blend of coastal living and suburban comfort, making it an ideal place for families, retirees, and everyone in between.

Chesapeake Harbour is renowned for its stunning views of the Chesapeake Bay, where residents can enjoy breathtaking sunsets and the soothing sounds of the water. With a variety of homes ranging from elegant townhouses to luxurious waterfront estates, there’s a perfect fit for every lifestyle. Many properties feature private balconies, spacious decks, and direct access to the marina, allowing you to embrace the nautical lifestyle to its fullest.

The community is also equipped with top-notch amenities, including a private beach, swimming pools, and well-maintained walking trails that wind through lush green spaces. For those who love to stay active, the nearby marina offers opportunities for sailing, kayaking, and fishing, making it easy to enjoy the great outdoors.

Chesapeake Harbour is conveniently located just minutes from downtown Annapolis, where you can explore historic sites, boutique shops, and a vibrant dining scene. The area is also known for its excellent schools and family-friendly atmosphere, making it a sought-after destination for those looking to settle down.

Experience the charm and serenity of Chesapeake Harbour, where coastal elegance meets community spirit. Discover your dream home in this idyllic setting today!

Newest Listings in Chesapeake Harbour

$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:

$595,000
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
$575,000
2 Beds ⋅ 2 Baths
This is a sought after MAIN FLOOR, END UNIT*** Look at the floor plan (first shot in the photos) and see the difference***Light and open, this home has been completely remodeled and feels very different from other condos***Yes, Chesapeake Harbour has the two pools, one right on the bay. It has 'miles' of walkable private community beachfront. It has tennis and pickleball and beachside kayak, paddle board and canoe storage, and a launch area. It has a fully manned 24 hour security entry gate & on-site security personal, walking paths, a private marina and highly rated, marina side, restaurant and bar*** LOOK AT THE PHOTOS***WATCH THE VIDEO***It's all quite glorious . And the unit itself will sell itself. You open either of your 2 new sliding glass doors, and walk right outside (with or without your dog) out to your huge private patio. There is the marina. Walk down to the water. Walk to either pool. Walk down along the beach past the many community piers and out by the pond. Take your dog out on your kayak (with his life vest on). Sit down to views of the Bay Bridge at dusk*** Main Floor- End Unit! All those windows, that cherry flooring and that privacy, check it out!

7048 Harbour Village Ct Unit #T2, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$685,000
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:

$625,000
2 Beds ⋅ 3 Baths
Welcome to the sought-after waterfront community of Chesapeake Harbour! This beautiful 2-bedroom, 2.5-bath end unit condo offers a spacious, light-filled floor plan with a rare combination of features. Transom windows above sliding doors and windows in the living and dining rooms adds even more light. The updated kitchen is designed for both everyday living and entertaining, showcasing granite countertops, a center island, stainless steel appliances, under cabinet lighting, and a built-in wine fridge. Expansive living room with vaulted ceiling has an electric fireplace for added ambiance. The loft, complete with custom built-in shelves, provides the perfect space for a home office, family room, or guest retreat. The half bath in the loft area is a great plus. Primary bedroom with huge walk-in closet and primary bath with double vanity & large walk in shower. Enjoy outdoor living on the expansive wraparound deck, ideal for morning coffee, outdoor dining, or simply relaxing. Located in one of Annapolis' premier gated waterfront communities, Chesapeake Harbour offers exceptional amenities, including a private beach, two swimming pools, tennis & pickleball courts, walking trails, a marina, and the popular Beacon Waterfront Galley & Bar, all just minutes from Historic Downtown Annapolis. Outdoor enthusiasts will appreciate the opportunity to join the Canton Kayak Club, offering convenient access to kayaks and launch sites throughout the region, including a resident-access launch within Chesapeake Harbour.

7048 Harbour Village Ct Unit #202, 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
$650,000
1 Beds ⋅ 1 Baths
=== WATERFRONT= ONE BEDROOM "C" FLOOR PLAN = EXTRA WIDE CONDO: Four pane sliders in living room and there are 4 glass pane windows in master bedroom == Master has a private exit door to a beach front patio == Front row seats for the Blue Angels flyover and weekly regatta races ... Amenities galore with two community pools / pool house complexes - one directly on the bay == two community sports courts - one by Chase Pond. Onsite Gourmet Cafe - the 'Beacon' overlooking a privately owned 200 slip Marina and just an oyster shell path stroll to the private 1600-foot sandy bayfront beach with a small craft storage area... The front entrance is secured 24/7/365 and the security team walks the premises daily... HOA and CONDO fees are very affordable compared to other areas. Direct entrance walkway already in place from car park for handicap adaptable--- can further level entrance steps to kitchen... Life's a Beach !!

2020 Quay Village Ct Unit #T1, Annapolis

Listing courtesy of Coastal Realty Maryland. Contact:

$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
$610,000
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
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