Chesapeake Landing Real Estate

Chesapeake Landing Real Estate

Welcome to Chesapeake Landing, an exquisite subdivision nestled in the heart of Maryland, where the charm of suburban living meets the allure of waterfront tranquility. This community offers a unique blend of picturesque landscapes, modern amenities, and a vibrant neighborhood atmosphere, making it the perfect place to call home.

Chesapeake Landing is strategically located near the stunning shores of the Chesapeake Bay, providing residents with easy access to a variety of outdoor activities, including boating, fishing, and scenic strolls along the waterfront. The lush greenery and beautifully landscaped parks within the subdivision create a serene environment, ideal for families and nature enthusiasts alike.

The homes in Chesapeake Landing showcase a delightful mix of architectural styles, each designed to cater to diverse tastes and lifestyles. From cozy single-family homes to spacious townhouses, the properties are thoughtfully crafted with modern features and finishes, ensuring comfort and style. Many homes boast stunning views, spacious backyards, and proximity to community amenities such as playgrounds, walking trails, and picnic areas.

Living in Chesapeake Landing means embracing a lifestyle enriched by a strong sense of community. Residents enjoy a calendar filled with neighborhood events, from seasonal festivals to summer barbecues, fostering connections and friendships. Additionally, the subdivision is conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

Experience the perfect blend of relaxation and community spirit at Chesapeake Landing—where your dream home awaits! Come explore this hidden gem in Maryland and discover why so many are proud to call it home.

Newest Listings in Chesapeake Landing

$1,525,000
3 Beds ⋅ 4 Baths ⋅ MDAA2155110 MLS ⋅ Chesapeake Landing Condo BLDG.
Spectacular water-view home nestled at the tip of the Eastport Peninsula in coveted Chesapeake Landing, a premier gated community. Set within the vibrant Maritime Republic of Eastport, deeply rooted in sailboat racing and pleasure-boating traditions. 23 Chesapeake Landing offers an exceptional blend of comfort, convenience and the Annapolis waterfront lifestyle. Residents treasure the neighborhood’s walkability, with an array of restaurants, pubs, boutiques, historic City Dock and Downtown Annapolis just steps from your door! Take a water taxi across Spa Creek to downtown or lauch a kyak or paddleboard from nearby Horn Point Park. Well maintained and freshly painted, this thoughtfully designed end-unit townhome, providing an abundance of natural light is equally suited to relaxed everyday living and effortless entertaining. The kitchen features sleek stainless-steel appliances, granite countertops, custom cabinetry and abundant storage. A casual dining area encourages relaxed gatherings, while the adjoining deck is perfectly positioned for outdoor grilling. Overlooking the living room and the water views beyond, the separate dining room provides an elegant setting for more formal occasions. The inviting living room is enhanced with taller ceilings, hardwood flooring and a wood-burning fireplace that adds warmth and ambience during the cooler months. Expansive sliding glass doors, fitted with plantation shutters, open to one of three newly rebuilt and expanded decks providing an ideal setting for savoring the water views or relaxing with your favorite beverage. This remarkable vantage point also provides front-row views of Fourth of July and New Year’s Eve fireworks, the annual Blue Angels Airshow and the ever-changing parade of sailboats, powerboats, regattas, naval vessels and the occasional pirate ship. The generously sized owner’s suite welcomes you with dramatic vaulted ceilings, abundant natural light, an en-suite bath and a private deck for even more water viewing pleasure. A second bedroom, full bath and laundry area complete the bedroom level. The loft level offers tremendous flexibility and may be adapted as additional bedroom space, a home office, art studio, fitness room or whatever best complements your lifestyle. The ground floor level, warmed by a second fireplace and enhanced by updated luxury vinyl plank flooring provides additional comfortable living space with exceptional flexibility, including its own private entrance. A full bath provides the perfect setup as an additional guest suite. French doors open to a private patio overlooking the beautifully landscaped grounds. Designed for easy lock-and-leave living, this home allows you to travel with peace of mind. The Annapolis Maryland Capital Yacht Club owns and manages the marina, pool and clubhouse. For the boating enthusiast, marina slips available for lease provide easy access to the Chesapeake Bay and its many waterfront destinations including use of the pool and clubhouse. Just outside your door, The Maritime Republic of Eastport combines the charm of a coastal village with the energy of a thriving maritime community - all just across Spa Creek from the U. S. Naval Academy and the culture, history and amenities of downtown Annapolis. Don't miss an opportunity to make this exceptional Eastport residence your home!

23 Chesapeake Lndg, Annapolis
$349,900
3 Beds ⋅ 3 Baths ⋅ MDKE2006980 MLS
Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today.

23208 Buck Neck Rd, Chestertown
$269,000
3 Beds ⋅ 2 Baths ⋅ MDKE2006880 MLS ⋅ Chesapeake Landing BLDG.
Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown
$260,000
3 Beds ⋅ 2 Baths ⋅ MDCC2022570 MLS
Welcome to 83 Starboard Court. Easy to move in. Freshly painted throughout and brand new carpet. Updated windows 2024. Heat Pump 2018. Spacious kitchen and dining area with ceramic tile, appliances and large pantry, main level laundry, half bath and large family room on main level. Sliding door access to rear 12x 9 patio, attached storage shed and large flat fenced yard. Upstairs a large primary suite with walk in closet. Clean full bathroom and 2 additional bedrooms. Lots of extra storage area in the attic. Convenient location close to schools, shopping, I-95, APG, MARC and AMTRAK trains. Only 1 hour to Phila and BWI airports.

83 Starboard Ct, Perryville
$429,900
4 Beds ⋅ 3 Baths ⋅ MDKE2006640 MLS
Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

10781 Fermoy Rd, Chestertown
$40,000
MDKE2005564 MLS
Lots 287 and 288 on Tonopah Rd. in Chestertown. 15,000 sq/ft, .344 acres. Approved perc site on file. The HO Association is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community.

Tonopah Rd., Chestertown
$5,000
MDKE2005260 MLS
Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

Kinglet Rd, Chestertown
$38,000
MDKE2002844 MLS

Spinnaker Rd, Chestertown
$10,000
MDKE2001692 MLS
Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

Sheldrake Dr, Chestertown
Start Your Search