Tolchester Estates Real Estate

Welcome to Tolchester Estates, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers a unique blend of serene living and vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle.

Tolchester Estates is strategically located near the scenic banks of the Chester River, providing residents with breathtaking views and easy access to a variety of outdoor activities. Whether you enjoy kayaking, fishing, or simply strolling along the waterfront, this delightful community has it all. The lush landscapes and well-maintained parks invite you to explore nature and unwind in the fresh air.

The homes in Tolchester Estates exude warmth and character, with a range of architectural styles that cater to diverse tastes. Each property is thoughtfully designed, featuring spacious layouts, modern amenities, and beautiful outdoor spaces perfect for entertaining or relaxing. With a strong sense of community, neighbors often come together for seasonal events and gatherings, fostering lasting friendships and creating a welcoming atmosphere.

Conveniently located just a short drive from the historic downtown Chestertown, residents can enjoy an array of local shops, restaurants, and cultural attractions. The town is known for its rich history and vibrant arts scene, offering plenty of opportunities for exploration and engagement.

If you’re looking for a peaceful retreat with a strong sense of community, Tolchester Estates is the perfect place to call home. Discover the charm of this lovely subdivision and experience the best of Maryland living!

Newest Listings in Tolchester Estates

$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:

Start Your Search