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2104 Chesapeake Harbour Dr E Unit 202, Annapolis

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.

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

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!

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

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!

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:

$619,000

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!

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:

7004 Channel Village Ct Unit 102, Annapolis

$575,000

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.

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

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!

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

$565,000

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.

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:

2010 Quay Village Ct Unit 101, Annapolis

$490,000

Good Pride Reduction. See the virtually staged photos of the living room. Seller converting the fireplace to electric and adding a new washer/dryer. With the leaves falling the view to the bay is improving. 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.

2 Beds ⋅ 2 Baths

Good Pride Reduction. See the virtually staged photos of the living room. Seller converting the fireplace to electric and adding a new washer/dryer. With the leaves falling the view to the bay is improving. 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: