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Tolchester Estates Real Estate

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Tolchester Estates Real Estate

Welcome to Tolchester Estates, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers a perfect blend of tranquility and community, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle surrounded by nature.

Tolchester Estates is strategically located near the scenic Chesapeake Bay, allowing residents to enjoy breathtaking waterfront views and a plethora of outdoor activities. The area is rich in history, with Chestertown being one of Maryland’s oldest towns, featuring beautifully preserved colonial architecture and a vibrant arts scene. Residents can stroll along the quaint streets, explore local shops, and dine at delightful eateries that showcase the region’s culinary talents.

The subdivision itself boasts well-maintained homes, spacious lots, and an inviting atmosphere. With an emphasis on community, Tolchester Estates hosts various events throughout the year, encouraging neighbors to connect and create lasting friendships. Whether you’re taking a leisurely walk, biking along the nearby trails, or enjoying a picnic at one of the local parks, you’ll find that the community’s charm is truly unmatched.

Families will appreciate the proximity to reputable schools and recreational facilities, ensuring that children have access to quality education and activities. For those who enjoy boating or fishing, the nearby marinas provide easy access to the waterways, making it a perfect spot for water enthusiasts.

Discover the enchanting lifestyle that Tolchester Estates has to offer—where comfort, community, and natural beauty come together in perfect harmony. Your dream home awaits in this idyllic Maryland subdivision!

Newest Listings in Tolchester Estates

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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