Chesapeake Harbour Real Estate

Chesapeake Harbour Real Estate

Welcome to Chesapeake Harbour, a picturesque waterfront subdivision nestled in the heart of Annapolis, Maryland. This enchanting community offers a unique blend of coastal charm and modern living, making it a coveted destination for those seeking a serene lifestyle by the water.

Chesapeake Harbour is renowned for its stunning views of the Chesapeake Bay, providing residents with a front-row seat to breathtaking sunrises and sunsets. With its meticulously landscaped grounds and well-maintained properties, the neighborhood exudes an inviting atmosphere that feels like a retreat from the hustle and bustle of everyday life.

The subdivision features a variety of housing options, including elegant townhomes and luxurious waterfront condos, ensuring there’s a perfect fit for everyone. Many homes boast private balconies or patios that allow residents to soak in the beautiful views and enjoy the gentle breezes that come off the bay.

Community amenities are abundant in Chesapeake Harbour. Residents have access to a private marina, making it easy to indulge in boating and sailing adventures. The community also offers walking trails, tennis courts, and a sparkling pool, providing ample opportunities for recreation and relaxation.

Located just a stone’s throw from historic downtown Annapolis, residents can enjoy a vibrant lifestyle filled with dining, shopping, and cultural experiences. With its rich history and charming streets, Annapolis is the perfect backdrop for your new home.

Discover the allure of Chesapeake Harbour, where waterfront living meets community spirit, and make this idyllic neighborhood your next home sweet home.

Newest Listings in Chesapeake Harbour

3 Beds ⋅ 3 Baths

Welcome to an amazing condo experience right here in Chesapeake Harbour in Annapolis, MD. Picture this waterfront dream nestled in the serene Chesapeake Harbour in Harbour Village Marina, where every morning starts with a stunning view of the marina right from your balcony. It's not just a place to live, it's a lifestyle. The condo is special with an unparalleled waterfront experience. Imagine stepping out and having a beach at your disposal, or choosing between a dip in the waterfront pool or a friendly match on the tennis or pickleball courts—talk about options! If you're a boating enthusiast, you're in for a treat. The marina is right at your doorstep, complete with a beacon to guide you in. It's perfect for someone who loves the water as much as we all love a sunny day. And for those evenings when cooking isn't on the agenda, the waterfront restaurant, Beacon Waterfront Galley, offers the perfect excuse to indulge a little. Trust me, it’s the local secret everyone loves to share. This coastal condo with three bedrooms and three baths is spacious enough for hosting guests yet cozy enough to feel like home sweet home. The gas fireplace in the living room and main bedroom adds a touch of coziness when the crisp air sets in—imagine sipping your favorite drink by the fire after a long day. It's modern living at its best, with balconies offering fabulous marina views, making morning coffees and sunset watches even more special. Need space for those extra toys? There's a two-car garage, complete with an EV hookup—eco-friendly and convenient. These condos cater beautifully to folks looking for a second home or those who are ready to enjoy a more relaxed, retired life. This condo will provide you Peace of Mind with the many upgrades the owners have provided...From the Enhanced Baths to the Updated Ktchen with Granite countertops and Stainless steel appliances to the Lutron/USB/C connector Outlets just to name a few of the many Customized Features. It's about soaking up the sun, the peace, and the joys of waterfront living. Chesapeake Harbour stands out…They are the only waterfront condos with a beach, marina and restaurant all within the community in Annapolis. That's a pretty sweet deal, right? It sets the standard and leaves the competition with a high tide to catch up with. The exclusivity of Chesapeake Harbour keeps the demand robust, especially for folks longing for that perfect blend of relaxation and activity by the water. Let’s make your waterfront dreams a reality. Hope to catch you at Chesapeake Harbour soon—where the beach meets the boat and every day feels like a get-a-way. Painted throughout, Newer Carpet, Newer Granite Countertops, Newer Engineered Hardwood Floors, New Electrical 1 1/2 yrs ago...15 Amp reciprocal outlets with USB and C connector, Lutron Wall Swiches, New LED flush mounted Ceiling Lights, New Vanities with Granite Tops in All of the Baths, Newer doors, brushed Bronze Hinges and Glass Door Knobs throughout the whole house.

7038 Clinton Ct Unit #11B, Annapolis

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

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:

3 Beds ⋅ 3 Baths

Open Friday, July 10th from 4-6:30 PM! Vacation every day in your stunning two-level condo with exceptional views and amazing privacy! Wonderful open floor plan and walls of glass make you feel like you are on a boat and create outstanding views from every room. Exceptional features include smart technology throughout, a wood-burning fireplace, soaring ceilings, GE Cafe appliances (new in 2024), electric blinds, separate dining area with a glass wall that beautifully reflects the water and accentuates the gorgeous natural light. Designer-selected tones throughout the home reflect the changing moods of the outdoors — soft greys and grey blues echo the water and sky, while subtle sunrise-inspired oranges and purples bring warmth and character to the interiors. Cherry wood floors and rich wood accents create a seamless connection between indoor living and the surrounding waterfront setting. The unit has been redesigned to increase the storage, creating ample closet space. Every day is a new opportunity to experience an incredible sunrise over the Chesapeake Bay Bridge and Eastern Shore, follow the tankers and watch the boat races. Chesapeake Harbour is a gated waterfront resort with outstanding water access, including private beaches, boat launch, and great piers for gathering with friends and neighbors to watch the races or cast a fishing line. Choose which of the two waterside community pools suits your mood (one is heated), enjoy a game of tennis on the multiple available courts, or launch your boat or board from the sandy beach and glide across the water. Take one of the many community paths to the marina (slips at Chesapeake Harbour Marina are available for a fee and NOT part of the HOA) or stop in for drinks or dinner at The Beacon harborside restaurant. Better still, stay home where you have the best view in the community and just relax. This amazing haven is located within a few short minutes of fun Eastport, Downtown Annapolis and its many offerings, dozens of scrumptious close-by neighborhood restaurants, 5 minutes from multiple breathtaking parks (Quiet Waters, Thomas Point, EO Moyer, Carr's), and it truly feels like a world away from it all! Bonus-100% turnkey-furniture included! Ask for more details!

2127 Beach Village Ct Unit #202, Annapolis

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

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

1 Beds ⋅ 1 Baths

OPEN Sunday, 12-3. === 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:

1 Beds ⋅ 2 Baths

Welcome to 2004 Quay Village Ct #T1, located in the sought-after waterfront community of Chesapeake Harbour in Annapolis. This well-maintained 1-bedroom, 1.5-bath condominium offers comfortable, low-maintenance living with abundant natural light, spacious living areas, and two covered patios that seamlessly extend the living space outdoors. Residents enjoy access to an exceptional collection of resort-style amenities, including a private marina, kayak facilities, sandy beach access along the Chesapeake Bay, outdoor waterfront pools, tennis and pickleball courts, walking paths, picnic areas, and beautifully maintained common grounds. Trident Marina, located at the heart of the community, offers boat slips for lease accommodating yachts from approximately 30 to 120 feet, making it an ideal home base for boating enthusiasts. One of the community's most cherished traditions is gathering at the beach and waterfront common areas to watch the Wednesday Night Sailing Races, a long-standing Annapolis tradition featuring some of the region’s top sailors. Residents also enjoy front-row views of the annual Blue Angels Air Show, with spectacular aerial performances often visible directly from the community's waterfront vantage points. Additional conveniences include an on-site restaurant and pub, assigned parking, and gated entry with 24-hour security. The condominium association fee includes common area maintenance, exterior building maintenance, lawn care, pool and recreation facility access, security gate services, snow removal, and trash collection. Ideally situated near downtown Annapolis, major commuting routes, shopping, dining, and waterfront attractions, this property offers a unique opportunity to experience the best of Chesapeake Harbour’s waterfront lifestyle, combining boating, recreation, community events, and stunning Chesapeake Bay views in one exceptional setting. IMPORTANT TAX CORRECTION: the assessed value listed in SDAT is incorrect. Call co-listing agent with any questions.

2004 Quay Village Ct Unit #T1, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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

3 Beds ⋅ 4 Baths

Set elegantly along the marina within the prestigious Chesapeake Harbour, this waterfront townhouse presents a refined composition of craftsmanship, material integrity, and coastal elegance. Moments from the historic charm of Annapolis and the open horizon of the Chesapeake Bay, the residence captures a rare harmony between luxury living and a serene waterfront setting. The interiors reveal a meticulous approach to design, where every finish and fixture has been elevated to a standard of quiet sophistication. Expanses of beautifully refinished hardwood flooring provide warmth and continuity, while a dramatic fireplace clad in striking natural stone serves as a focal point—both sculptural and inviting. Thoughtfully layered lighting and custom window treatments create a seamless interplay of mood and light, enhancing both day-to-day living and evening ambiance. The kitchen is a study in precision and restraint, defined by custom-crafted cabinetry of exceptional quality and a layout designed for both function and visual clarity. A statement waterfall island anchors the space, complemented by premium-grade appliances discreetly integrated into the millwork. Every detail—from the refined hardware to the subtle display elements—reflects a commitment to elevated design and effortless usability, creating a setting equally suited for culinary pursuits and elegant entertaining. In the private quarters, the primary suite offers a tranquil retreat shaped by texture, proportion, and thoughtful innovation. Custom storage solutions and integrated shading systems enhance both comfort and privacy. The ensuite bath unfolds as a spa-like sanctuary, where heated flooring, high-caliber fixtures, tailored cabinetry, and curated lighting come together in a composition that is both indulgent and serene. Guest accommodations continue the narrative of quality and intention, featuring bespoke closets, refined finishes, and bathrooms appointed with elevated materials, heated surfaces, and carefully selected fixtures that mirror the home’s overarching design language. The lower level extends the living experience with equal attention to detail—incorporating custom built-ins, ambient lighting, and seamless access to a landscaped patio that opens directly to the waterfront. Outdoor spaces are thoughtfully integrated into the home’s overall design. Multiple expansive decks invite uninterrupted views of the marina and surrounding waters, while the ground-level terrace, framed by manicured landscaping and soft lighting, offers an intimate setting for relaxation or gathering. These outdoor environments function as natural extensions of the interior, blurring the boundary between indoors and out. Beyond its aesthetic appeal, the residence is underpinned by extensive structural and mechanical enhancements, ensuring lasting performance and modern efficiency. Every improvement has been executed with an emphasis on durability and long-term quality. Life within this gated waterfront community offers a distinctive blend of privacy and resort-style living, with access to marina facilities, waterfront amenities, and a setting defined by coastal beauty. This home is a quiet expression of luxury—where superior materials, exceptional craftsmanship, and a remarkable waterfront location come together in seamless balance.

2186 Chesapeake Harbour Dr E, Annapolis

Listing courtesy of Coldwell Banker Realty - Washington. Contact: 2023876180

3 Beds ⋅ 3 Baths

Now is your chance to call this HOME! Welcome to 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

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

2 Beds ⋅ 2 Baths

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.

2106 Chesapeake Harbour Dr Unit #202, Annapolis

Listing courtesy of Keller Williams Realty. Contact: 3028467839

2 Beds ⋅ 2 Baths

The Seasons change the views. Tremendous price reduction. See the virtually staged photos of the living room. A great opportunity just before the summer. Quiet tranquil setting for this 2 bedroom 2 bath unit with a view of the Bay in the distance, Windows in second bedroom replaced in 2024. To be sold in As-is condition. Enjoy the community amenities - 24 hour security, swimming pools, tennis courts, a beach and walking trails. Bay Ridge Rd. to Route 50 and 97 to DC and Baltimore. Easy to show, just call Showings to log in.

2010 Quay Village Ct Unit #101, Annapolis

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

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