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Chaplin, CT Houses for Sale

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  • 60 Chaplin St, Chaplin, CT 06235
    60 Chaplin St, Chaplin, CT 06235
    60 Chaplin St, Chaplin, CT 06235
    /40

    $350,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,438 Sq Ft

    60 Chaplin St, Chaplin, CT 06235

    Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places.

    Agent Photo

    Stephen Daly

    KW Legacy Partners

    60 Chaplin St, Chaplin, CT 06235
  • 13 Bates Rd, Chaplin, CT 06235
    13 Bates Rd, Chaplin, CT 06235
    13 Bates Rd, Chaplin, CT 06235
    /36

    $419,900

    $30K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,887 Sq Ft

    13 Bates Rd, Chaplin, CT 06235

    Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra

    Kristen Merrill Countryside Realty

    13 Bates Rd, Chaplin, CT 06235
  • 21 Linkkila Ln, Chaplin, CT 06235
    21 Linkkila Ln, Chaplin, CT 06235
    21 Linkkila Ln, Chaplin, CT 06235
    /40

    $579,000

    • 5 Beds
    • 4 Baths
    • 2,604 Sq Ft

    21 Linkkila Ln, Chaplin, CT 06235

    Set on nearly 4 private acres, 21 Linkkila Lane offers the space, flexibility, and peaceful setting that make country living feel special. Start your morning with coffee on the deck while taking in the surrounding landscape and watching the horses at the neighboring horse farm. Inside, this beautifully updated log home strikes the perfect balance between cozy character and clean, modern updates.

    Amanda Polansky RE/MAX Coast and Country

    21 Linkkila Ln, Chaplin, CT 06235
  • 222 Tower Hill Rd, Chaplin, CT 06235
    222 Tower Hill Rd, Chaplin, CT 06235
    222 Tower Hill Rd, Chaplin, CT 06235
    /23

    $379,000

    $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,610 Sq Ft

    222 Tower Hill Rd, Chaplin, CT 06235

    Beautifully set on 4.02 scenic acres in Chaplin, Connecticut, this charming 3-bedroom, 2-bath home offers the perfect blend of character, privacy, and versatility. Featuring approximately 1,600 square feet, the home showcases soaring vaulted ceilings, stunning exposed beams, and an inviting open-concept kitchen, dining, and living area filled with natural light. The finished lower level offers a

    Lisa Therecka Therecka & Associates LLC

    222 Tower Hill Rd, Chaplin, CT 06235
Connecticut Windham County

Houses for Sale in Chaplin, CT

Why Live in Chaplin

Chaplin, nestled in the rolling hills of northeastern Connecticut, provides a rural lifestyle with the Natchaug River running through its center. This small Windham County community, home to fewer than 2,200 residents, is surrounded by state-owned forests, offering a peaceful setting. Properties in Chaplin are spacious, often covering several acres, and feature a variety of home styles including ranch-style homes, Cape Cods, farmhouses, and historic 19th-century houses in the Chaplin Historic District. The crime risk in Chaplin is lower than the national average. For higher education, the University of Connecticut and Eastern Connecticut State University are less than 10 miles away. Outdoor activities abound with Edward Garrison Park, which includes a playground, baseball diamond, and disc golf course, as well as Hubbard Sanctuary and Agnes’ Pasture with nearly 2 miles of trails. Diana’s Pool, a popular spot along the Natchaug River, and Mansfield Hollow State Park, just over 5 miles away, offer additional recreational opportunities. Dining options in Chaplin include The Baker’s Dozen and Blondie’s Country Diner, while shopping needs are met in nearby Windham, about 7 miles away. Chaplin is accessible via State Route 198 and U.S. Route 6, with regional bus services and a park-and-ride lot available for commuters.

Learn more about living in Chaplin

Single Family Home Prices in Chaplin, CT

The median price for single family homes in Chaplin is $356,250, and there are 4 single family home listings available for sale.

Single Family Home Price Trends

Median Home Price
$356,250
Median 3-Bedroom Home Price
$356,250
Median 4-Bedroom Home Price
$346,250
Median 5-Bedroom Home Price
$499,450
How to Buy a Home How to Finance a Home How to Sell a Home

In Chaplin, there are currently 4 houses for sale, offering an array of options for potential buyers. With houses priced between $350,000 to $579,000, there's a range to accomodate every budget. As of August, 2026 the median home price in Chaplin is $349,900, while the average sale price is $367,946, offering insights into the local housing market. On average, houses spend 55 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chaplin, CT and find the perfect place to call home.

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