Tolchester Estates Homes for Sale

Welcome to Tolchester Estates, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers a unique blend of tranquility and community spirit, making it the perfect place for families, retirees, and everyone in between. Surrounded by the natural beauty of Kent County, Tolchester Estates is just a stone's throw away from the serene waters of the Chesapeake Bay, providing residents with endless opportunities for outdoor adventures.

As you explore the homes for sale in Tolchester Estates, you'll discover a variety of architectural styles and layouts that cater to diverse tastes and needs. From cozy single-family homes to spacious properties with modern amenities, each residence reflects the warmth and charm of this inviting community. Many homes feature beautifully landscaped yards, perfect for summer barbecues or peaceful evenings under the stars.

Tolchester Estates is not just about stunning homes; it’s about a vibrant lifestyle. Residents enjoy easy access to local parks, walking trails, and recreational facilities, ensuring that there’s always something to do. The nearby historic downtown Chestertown offers a delightful mix of boutique shops, art galleries, and delicious dining options, fostering a sense of connection and community.

With homes for sale in this sought-after subdivision, now is the perfect time to explore the possibilities of making Tolchester Estates your new home. Experience the perfect blend of comfort, convenience, and natural beauty in this idyllic Maryland community. Come and discover why Tolchester Estates is more than just a place to live; it's a place to thrive!

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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