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Tolchester Estates Homes for Sale

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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 serene living and vibrant community spirit, making it the perfect place to call home. With its lush landscapes and scenic views, Tolchester Estates provides an idyllic backdrop for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

Located in Kent County, Tolchester Estates is just a stone's throw from the historic downtown Chestertown, where you can explore quaint shops, delightful eateries, and cultural attractions. The nearby Chester River offers endless opportunities for outdoor recreation, from kayaking and fishing to leisurely strolls along the waterfront. The community is also conveniently situated near major highways, providing easy access to neighboring towns and cities.

Currently, there are a variety of homes for sale in Tolchester Estates, catering to diverse tastes and budgets. Whether you're looking for a cozy cottage or a spacious family home, you'll find properties that boast modern amenities, beautiful architectural designs, and expansive yards perfect for entertaining or simply enjoying the tranquility of nature.

Investing in a home in Tolchester Estates means embracing a lifestyle of comfort and community, where neighbors become friends and every day feels like a vacation. Don’t miss the opportunity to discover your dream home in this enchanting neighborhood—explore the listings today and take the first step toward your new beginning!

Newest Tolchester Estates Homes for Sale

8668 Elm Rd, Chestertown image
8668 Elm Rd, Chestertown $349,900

Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community o...

  • 4 Beds
  • 2 Baths
Courtesy of Kevin Dey Realty

Listing courtesy of Kevin Dey Realty. Contact:

8901 S Bayview Dr, Chestertown image
8901 S Bayview Dr, Chestertown $525,000

The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintai...

  • 3 Beds
  • 3 Baths
Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

21338 Virginia Ave, Chestertown image
21338 Virginia Ave, Chestertown $400,000

Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-st...

  • 2 Beds
  • 2 Baths
Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

8820 Cumberland St, Chestertown image
8820 Cumberland St, Chestertown $281,500 ▼

Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in ...

  • 3 Beds
  • 2 Baths
Courtesy of RE/MAX Advantage Realty

Listing courtesy of RE/MAX Advantage Realty. Contact:

8732 Elm Rd, Chestertown image
8732 Elm Rd, Chestertown $289,000

Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining...

  • 3 Beds
  • 2 Baths
Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

8630 Elm Rd, Chestertown image
8630 Elm Rd, Chestertown $419,900 ▲

Enjoy the Eastern Shore as your weekend retreat at 8630 Elm Road. Calling all boaters, fishers, hunters, beachgoers, nature and recreation lovers, investors, and resident...

  • 5 Beds
  • 3 Baths
Courtesy of Save 6, Incorporated

Listing courtesy of Save 6, Incorporated. Contact:

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