307 Washington Ave, Chestertown, MD 21620

Escape to Little Neck Farm, a 350-acre waterfront community with 29 total home sites on Maryland’s Eastern Shore, teaming with wildlife and serenity. This lightly used custom home is in move in condition featuring an open floor plan with gourmet center island kitchen, bright and lite hardwood floors, fireplace, 1st floor primary suite, large screen porch and deck, abundance of storage and much more. A brand new deep-water floating dock boat slip is included at the community waterfront park. The lot is 1.7 acres and is half wooded. Small storage shed included. Beautiful westerly sunsets!

108 N. Queen St, Chestertown, MD 21620

A wonderful spot to build your dream home on this fantastic 1-acre lot in Little Neck Farm. Nestled in a serene, water-oriented community, this property offers access to over 200 acres of common open space. Embrace the charm of Eastern Shore living with a location that combines country tranquility and natural beauty. This lot provides the ideal setting for your new home, allowing you to enjoy the best of both worlds—peaceful surroundings and convenient access to nearby amenities.

Carefree waterfront living within a short stroll or bike ride to Charming Historic Downtown Chestertown, Washington College and the Chester River Yacht and Country Club. This home offers some of the finest waterfront views in the entire Chester River Landing Community. Just imagine a front row seat to the annual Chestertown Fourth of July fireworks, broad views of the Schooner Sultana sailing to and from their Chester River port and the warm Chester River sunrises from all three floors of your home! The Chester River Landing Community offers a Relaxing Coastal Vibe with Community Pool, luscious flowering landscaping with oyster shell paths meandering through the community, deep water dockage ( slip #B-2 included in the sale) at the community marina, community firepit for cool spring and fall gatherings, and more. The home itself boasts 3 bedrooms, 2 1/2 Baths, two waterside decks with exceptional water views, spacious living level with marvelous kitchen, expansive dining area, comfortable living room, wood floors, fireplace, 2 car garage with 2 additional exterior parking spaces and 1st floor office or hobby room. This home and environment is ideal for retirement or weekend living close to several metropolitan areas including Philadelphia, Washington, DC. and Baltimore, Md. Come discover Chestertown and Maryland's Eastern Shore! Showings by appointment only.

1-acre vacant lot in Chesapeake Landing off of Buck Neck Rd. Not perc approved. You have access to the public boat ramp in Chesapeake Landing and possible deer hunting opportunities.

Welcome to your own private paradise nestled upon a picturesque 23.5-acre expanse along the edge of the peaceful Chesapeake Bay. Here you can enjoy an abundance of seasonal and local wildlife such as Bald Eagles, ospreys, Canada geese, ducks, bluebirds, turkey, and whitetail deer. There is an ideal blend of tillable and wooded acreage providing for an array of activities including hunting, farming, and gardening. Plenty of room to build a sizable barn for shop, livestock, or hobby use. The expansive 700' of waterfront is ideal for small watercraft, swimming, fishing kayaking and crabbing. The residence offers a rich blend of traditional style with coastal charm and commands breathtaking views of the shimmering Chesapeake Bay waters. Large and expansive windows ignite the bay’s gentle breeze and warming sunlight into every corner. Upon entering the home, you are greeted with an expansive open floor plan including beamed cathedral ceilings and airy light-filled atmosphere. The open kitchen and dining area provide the perfect gathering area for family and guests to enjoy the Chesapeake Bay views, the in-ground concrete pool, and the outside wrap around porch setting. The large loft area is ideal for converting to a second primary suite or as it is now, as a recreation room. This waterfront retreat offers conveniences to both Rock Hall and Chestertown with a perfect blend of tranquility, accessibility and privacy. Gorgeous sunsets add to the allure of this exceptional property!

5078 Grays Inn Creed Rd, Rock Hall, MD 21661

703 High St, Chestertown, MD 21620

Lot 142 & 142 - .34 +/- acre lot in Chesapeake Landing. Perc Approved, See documents for perc information. We suggest seeing Kent County Environmental Health for perc verification and further information. Perfect place to build your home or spec house! Located near public boat ramp and marina.

Welcome to Vicker’s Row in the heart of Downtown Historic Chestertown! This charming townhome is the epitome of turnkey living, offering a perfect blend of historic charm and modern convenience. With 2 bedrooms and 1.5 baths, this residence is an ideal haven for those seeking a low-maintenance lifestyle. Step inside and be greeted by the warmth of beautiful hardwood floors that seamlessly flow throughout the entire home. The living space is adorned with built-in bookshelves, adding a touch of character and providing a stylish solution for storage. Sunlight filters through the elegant plantation shutters, creating a cozy ambiance in every room. The bedrooms feature brand-new carpeting, ensuring comfort and a luxurious feel underfoot. The bathrooms boast tasteful tiling, marrying style and functionality seamlessly. Your convenience is further elevated with an additional private parking space located in the rear, eliminating the hassle of searching for street parking. A small exterior storage shed is included. Enjoy the convenience of being within walking distance to Washington College. Stroll to the nearby farmers market, explore charming shops, and savor culinary delights at the fine local restaurants, all just steps away from your front door. Seize the opportunity to make this Downtown Historic Chestertown townhome yours—where history meets modern comfort, and where the vibrant pulse of the community is right at your doorstep.

Welcome to 11719 St James Rd! Nestled on a serene one-acre parcel of land, this delightful Cape Cod-style has the perfect blend of comfort and character. Boasting 3 bedrooms, 1 full bath, a sun porch, and wood floors, this property exudes warmth and charm. With a unique vantage point overlooking unobstructed views of preserved farmland, this home offers the tranquility of rural living with all conveniences nearby. With new windows, a new roof, and a newer septic system, you can enjoy the benefits of improved efficiency. The properties generous one-acre lot, with room for a pole barn or pool, is great for gardening, outdoor activities, and more! You will also find a selection of marinas, schools, and the downtown areas of Chestertown and Rock Hall just a short drive away. One of the owner's of the home is a licensed realtor.