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North Windham, CT Homes for Sale

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  • /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
  • /36

    $450,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,071 Sq Ft

    39 Cannon Rd, Hampton, CT 06247

    Welcome to 39 Cannon Road, where peaceful living meets comfort and thoughtful care. Lovingly maintained by its original owner, this beautiful home sits privately on 2.3 acres, bordering Goodwin State Forest and just minutes from Pine Acres Lake. Inside, vaulted ceilings and a stunning floor-to-ceiling stone fireplace create a warm and inviting living room. The first-floor primary suite is a true

    Agent Photo

    Amber Jones

    KW Legacy Partners

    39 Cannon Rd, Hampton, CT 06247
  • /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
  • /27

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    34 Cross Rd, Chaplin, CT 06235

    Welcome to 34 Cross Road, a beautifully maintained home offering the perfect blend of comfort, privacy, and timeless New England appeal. Set on over 2 acres in a serene, wooded setting, this 3-bedroom, 2.5-bath residence offers an inviting layout designed for both everyday living and entertaining. The main level welcomes you with a charming front porch entry and features a spacious living room,

    Ashley Percy Coldwell Banker Realty

    34 Cross 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
  • /34

    $126,900

    $13K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    57 James Dr, North Windham, CT 06256

    Totally remodeled conveniently located in N. Windham in the much desired Stonegate Park. 2 bedroom, one bath with a new Trex Deck with new solar lighting installed in 2026. This deck overlooks a beautifully landscaped yard. The home is located on a dead-end and close to many amenities. You won't be disappointed, inside you will find a freshly painted home, new rugs, new appliances ranging from

    Susan Ouellet RbRE, LLC

    57 James Dr, North Windham, CT 06256
  • /40

    $274,900

    • 4 Beds
    • 2 Baths
    • 1,648 Sq Ft

    27 Gamache Ln, North Windham, CT 06256

    Offered for the first time in 24 years and loaded with high-ticket updates, this spacious 1648 ft.2 Cape Cod offers four bedrooms, two full baths, and is set on a private .61 acre lot in a small neighborhood! Over the past 12 years, the seller performed substantial updates including a new metal roof, installed a new central air system with new ductwork, converted from oil to propane, added a high

    James Burnett Eagle Eye Realty PLLC

    27 Gamache Ln, North Windham, CT 06256
  • /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
  • /40

    $579,000

    Open Sat 12PM - 2PM
    • 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
  • /37

    $74,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    14 Kitty Ln, Windham, CT 06256

    Welcome to Stonegate Manor! This well-maintained 2-bedroom, 2-bath home offers a bright, open floor plan with brand-new neutral carpeting throughout the living areas and bedrooms. The spacious living room features abundant light, a ceiling fan, and flows seamlessly into the eat-in kitchen and dining area. The kitchen offers oak cabinetry with decorative glass-front cabinets, ample counter space,

    Kara Mazzola First Choice Realty

    14 Kitty Ln, 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

    $390,000

    $10K PRICE DROP
    • 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

Frequently Asked Questions

What are the most popular zip codes in North Windham, CT?
The most popular zip codes in North Windham, CT include 06235, 06247, 06256, 06250 and 06280.
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