Tolchester Estates Homes for Sale

Welcome to Tolchester Estates, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision, located in Kent County, offers a unique blend of serene living and vibrant community life, making it an ideal choice for families, retirees, and anyone in search of a peaceful retreat.

Tolchester Estates is renowned for its spacious homes and beautifully landscaped properties, providing an inviting atmosphere for residents and visitors alike. The architecture reflects a harmonious blend of modern amenities and classic design, ensuring that each home exudes warmth and character. With a variety of homes for sale, prospective buyers can find options that suit their lifestyle, whether you're looking for a cozy cottage or a larger family residence.

One of the standout features of Tolchester Estates is its close-knit community feel. Residents enjoy access to a range of recreational activities, including nearby parks, walking trails, and water access to the Chesapeake Bay. The area is perfect for outdoor enthusiasts, offering opportunities for boating, fishing, and exploring the scenic beauty of Maryland’s Eastern Shore.

In addition to its natural charm, Tolchester Estates is conveniently located just a short drive from the historic downtown Chestertown, where you can indulge in local shops, restaurants, and cultural events. With a rich history and a vibrant arts scene, Chestertown is a delightful place to call home.

If you’re in the market for a new home, Tolchester Estates has a selection of properties that may be just what you’re looking for. Discover the perfect blend of tranquility and community in this enchanting subdivision today!

Newest Tolchester Estates Homes for Sale

$289,900

2 Beds ⋅ 2 Baths

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

21146 Montana Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$320,000

3 Beds ⋅ 2 Baths

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

8706 Elm Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

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