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North Windham, CT Homes for Sale with Acreage

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  • /35

    $579,000

    $20K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,220 Sq Ft

    21 Linkkila Ln, Chaplin, CT 06235

    Private Country Retreat with In-Law Suite on Nearly 4 Acres. Welcome to 21 Linkkila Lane in Chaplin, Windham County, Connecticut-a beautifully updated log home offering exceptional privacy, flexible living space, and modern upgrades on nearly four picturesque acres. The main residence features three spacious bedrooms and three full bathrooms, highlighted by an extensively renovated kitchen,

    Derek Greene Derek Greene

    21 Linkkila Ln, Chaplin, CT 06235
  • /36

    $429,900

    $20K 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
  • /2

    $335,000

    • Land
    • 62.27 Acres
    • $5,380 per Acre

    0 Scotland Rd Unit 24160798, Chaplin, CT 06235

    **Builders Take Notice** This is a beautiful 62.273 acres with subdivision opportunities. A-2 Survey is available. Owner financing is available.

    Sherry Borgeson Berkshire Hathaway NE Prop.

    0 Scotland Rd Unit 24160798, Chaplin, CT 06235
  • /39

    $874,000

    $125K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,808 Sq Ft

    254 Beaver Hill Rd, North Windham, CT 06256

    Hidden Acres is a rare opportunity to own 70+ secluded acres where rustic charm, craftsmanship, and modern functionality come together. Tucked away in a private setting, this extraordinary farm features a 14,400-square-foot equestrian facility with a 12-stall barn and indoor riding arena, ideal for horse enthusiasts, trainers, or those seeking a premier recreational property. A heated

    Lori Vogel William Raveis Real Estate

    254 Beaver Hill Rd, North Windham, CT 06256
  • /27

    $344,900

    • 3 Beds
    • 1 Bath
    • 1,710 Sq Ft

    288 Bedlam Rd, Chaplin, CT 06235

    Step into a beautifully restored piece of history with this enchanting 1830s home, nestled on a serene, private acre. This property perfectly captures the balance of historic character and modern ease, offering a warm, welcoming retreat from the everyday. The main level features a flexible, sun-drenched layout highlighted by a convenient primary bedroom and a fully renovated bathroom with new

    Georgia LaBonne William Pitt Sotheby's Int'l

    288 Bedlam Rd, Chaplin, CT 06235
  • /23

    $389,000

    • 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
  • /28

    $399,999

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 2,158 Sq Ft

    187 Tuckie Rd, North Windham, CT 06256

    Welcome to your own retreat! Perfectly positioned on a gorgeous, level 1 acre lot surrounded by mature trees, this beautifully maintained Cape offers the peaceful lifestyle you've been dreaming of. From the moment you arrive, you'll picture slow mornings spent on the charming front porch w/a cup of coffee and your favorite book, soaking in the quiet beauty that surrounds you. Out back, you'll

    Meghan Wininger Real Broker CT, LLC

    187 Tuckie Rd, North Windham, CT 06256
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