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North Windham, CT Homes for Sale

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  • /38

    $789,000

    • 4 Beds
    • 2.5 Baths
    • 2,900 Sq Ft

    287 S Bear Hill Rd, Chaplin, CT 06235

    Set on 3.39 picturesque acres, this beautifully renovated property offers the perfect blend of luxury, function, and country charm-ideal for a mini farm, homestead, or private retreat. The heated and insulated 36x48 Morton barn features front and rear sliding barn doors, 2 horse stalls with potential for 6, 5 doggy doors, water, electric, skylights, and year-round water access-perfect for horses,

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    287 S Bear Hill Rd, 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
  • /33

    $64,900

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    26 Long Dr, North Windham, CT 06256

    Welcome to Country Club Estates! This beautifully maintained 2-bedroom, 1-bath mobile home is truly move-in ready and showcases pride of ownership throughout. The home offers a bright and inviting interior, comfortable living spaces, and has been meticulously cared for inside and out. Enjoy the well-manicured yard featuring attractive landscaping, established gardens, and a covered deck-perfect

    Agent Photo

    Alexis John

    RE/MAX One

    26 Long Dr, North Windham, CT 06256
  • /19

    $54,000

    $6K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 672 Sq Ft

    17 Wayne Dr, North Windham, CT 06256

    This is a well maintained, 1972, 2 Bedroom Bath and a half unit that has numerous updates that include updated kitchen and full bath, and replacement windows. There is enclosed porch, central air and large storage shed. There are some furnishings that can be included. Close to shopping, medical facilities and outdoor attractions. Park residence approval is required. the lot is $835 a month. This

    Clarence Russ Home Selling Team

    17 Wayne Dr, North Windham, CT 06256
  • /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
  • /35

    $599,000

    • 5 Beds
    • 4 Baths
    • 2,760 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
  • /18

    $165,500

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    28 Circle Dr, Windham, CT 06256

    Completely remodeled 3-bedroom, 2-bath mobile home in North Windham! This move-in-ready home has been thoughtfully updated throughout and features a brand-new roof, new appliances, and modern finishes from top to bottom. The interior offers a bright and functional layout with updated flooring, refreshed kitchen and bathrooms, and comfortable living space. With recent upgrades throughout, this

    Arielle Ruffin Choice Realty

    28 Circle Dr, Windham, CT 06256
  • /15

    $149,999

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft

    137 Boulevard Rd, North Windham, CT 06256

    Tucked away on .63 private acres, this unique property offers endless possibilities for those seeking peace, privacy, and room to roam. The two-bedroom mobile home sits on its own land surrounded by nature. Enjoy open space conveniently located while still offering a secluded feel, this property is ideal for outdoor enthusiasts, investors, or anyone looking to escape the hustle and bustle.

    Antonio Incontro Countryside Realty

    137 Boulevard Rd, North Windham, CT 06256
  • /40

    $434,000

    $10K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,522 Sq Ft

    7 Bates Rd, Chaplin, CT 06235

    Step back in time while enjoying modern comforts in this charming 1800s Colonial offering 10 spacious rooms filled with character and natural light. The eat-in kitchen features an original butler's pantry, while the formal dining room and inviting living room each showcase stunning stone fireplaces-both complete with rare beehive ovens. French doors lead from the living room to a beautiful

    Emily Turker Berkshire Hathaway NE Prop.

    7 Bates Rd, Chaplin, CT 06235
  • /34

    $474,900

    New Construction
    • 4 Beds
    • 3 Baths
    • 1,890 Sq Ft

    19 Zoldak Dr, North Windham, CT 06256

    A Wonderful opportunity to own a BRAND NEW and quality constructed home in Windham, located on a newer cul-de-sac street on 2.77 acres of land. The home will soon ready for a new owner to move right in and enjoy. This is a spacious FOUR bedroom and THREE FULL bath, Contemporary Raised Ranch, consisting of 1890 square feet of living space. The home has an open concept with vaulted ceilings and

    John Troland William Raveis Real Estate

    19 Zoldak Dr, North Windham, CT 06256
  • /39

    $495,000

    $100K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,504 Sq Ft

    203 Willimantic Rd, Chaplin, CT 06235

    Well-maintained 3-bedroom, 1.5-bath Cape that offers unique flexibility. For more than 75 years, this property was home to a family-run monument business, seamlessly blending residential living with a working space-an ideal setup for today's live/work lifestyle or those simply seeking extra room to fit their needs. Inside, you'll find a functional and inviting layout filled with character. The

    Sherry Borgeson Berkshire Hathaway NE Prop.

    203 Willimantic Rd, Chaplin, CT 06235
  • /27

    $344,900

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

    288 Bedlam Rd, Chaplin, CT 06235

    *multiple offers received, highest and best due by Saturday 7/4, 5:00pm* Step into timeless charm and peaceful country living with this beautifully restored 1830 home, set on a serene 1 acre lot. Blending historic character with a warm, welcoming feel, this 3 bedroom, 1 bath home offers a flexible layout, including a convenient first-floor primary bedroom and full bath. Inside, you'll find a

    Natascia Klimas William Pitt Sotheby's Int'l

    288 Bedlam Rd, Chaplin, CT 06235
  • /23

    $389,900

    • 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
  • /25

    $90,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    5 Jessie Ln, North Windham, CT 06256

    This clean and bright unit has a nice open floor plan The kitchen comes fully applianced and has lots of cabinets and counter space. Plenty of room for your table. Open concept to living room, all with nice flooring. The primary bedroom and full bath with soaking tub and shower are on one side, with the second bedroom and full bath on the other side. Laundry is conveniently placed. There is a

    Cathy Duprey Duprey Real Estate, LLC

    5 Jessie Ln, North Windham, CT 06256
  • /29

    $139,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    38 Long Dr, North Windham, CT 06256

    Beautifully maintained 2007 Mobile Home located in desirable Country Club Estates! This inviting home offers a bright, open floor plan featuring a spacious kitchen with abundant cabinetry and counter space, a dining area, and a large living room filled with natural light. The private primary bedroom includes its own full bath, while two additional bedrooms and another full bathroom provide plenty

    Jeanne Crum Home Selling Team

    38 Long Dr, North Windham, CT 06256
  • /23

    $330,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    156 Brick Top Rd, Windham, CT 06280

    Welcome home to this charming 3-bedroom, 2 full bath colonial set on a picturesque 1.68-acre lot offering privacy, space, and tranquility. The bright and inviting kitchen feature a new dishwasher and beautiful french doors that open to an expansive private deck - Perfect for outdoor entertaining or relaxing while enjoying the wooded views. A sun filled dining room with a bay window flows

    Patricia Scarpa Marino Realty LLC

    156 Brick Top Rd, Windham, CT 06280

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, 06256, 06250, 06247 and 06268.
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