45,761

Windham County, CT Homes

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  • 81 Chestnut St, Willimantic, CT 06226

    $320,000

    Sold Aug 20, 2026

    81 Chestnut St, Willimantic, CT 06226

    • 3 Beds
    • 2 Baths
    • 2,412 Sq Ft
    • Built 1918

    Last Sold Summary

    • 4% Above List Price
    • $133/SF
    • 69 Days On Market

    Current Estimated Value $309,472

    Last Listing Agent Jeanne Crum Home Selling Team

    81 Chestnut St, Willimantic, CT 06226
    • 46 Union Dr, Ashford, CT 06278

      Est $304,851

      Not Listed For Sale

      46 Union Dr, Ashford, CT 06278

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft
      • Built 1976
      46 Union Dr, Ashford, CT 06278

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kim Ricard Priority Real Estate Group,LLC

  • 126 E Putnam Rd, Putnam, CT 06260
    126 E Putnam Rd, Putnam, CT 06260
    126 E Putnam Rd, Putnam, CT 06260
    /40

    $1,200,000

    • 3 Beds
    • 4 Baths
    • 3,430 Sq Ft

    126 E Putnam Rd, Putnam, CT 06260

    Enter this property with a long winding driveway to the home nestled and surrounding by woods. 10.25 Acres zoned AG-2.Three bay Garage attached with an above Covered Deck for large family gatherings! Plus a separate Garage with front and back doors. Outdoor Wood Boiler to heat your home, Patio and Heated Inground Pool, Irrigation system and underground Utilities. Primary Bedroom with his and her

    Rachel Sposato Berkshire Hathaway NE Prop.

    126 E Putnam Rd, Putnam, CT 06260
  • 17 Wayne Dr, North Windham, CT 06256

    $45,000

    Sold Sep 03, 2026

    17 Wayne Dr, North Windham, CT 06256

    • 2 Beds
    • 1.5 Baths
    • 672 Sq Ft
    • Built 1972

    Last Sold Summary

    • 25% Below List Price
    • $67/SF
    • 48 Days On Market

    Last Listing Agent Clarence Russ Home Selling Team

    17 Wayne Dr, North Windham, CT 06256
    • 530 Wauregan Rd, Danielson, CT 06239

      Est $348,744

      Not Listed For Sale

      530 Wauregan Rd, Danielson, CT 06239

      • 2 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1946
      530 Wauregan Rd, Danielson, CT 06239

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Christine Costa Kazantzis Real Estate, LLC

  • 18 Philmar Dr, Plainfield, CT 06374
    18 Philmar Dr, Plainfield, CT 06374
    18 Philmar Dr, Plainfield, CT 06374
    /40

    $349,900

    Pending
    • 3 Beds
    • 1 Bath
    • 1,156 Sq Ft

    18 Philmar Dr, Plainfield, CT 06374

    Welcome home to this beautifully maintained ranch-style property, perfectly situated on a quiet dead-end road. Offering 3 bedrooms, 1 full bathroom, and hardwood floors throughout, this home combines comfort, convenience, and charm. The updated kitchen serves as the heart of the home, while major mechanical updates provide peace of mind for years to come. A finished sunroom at the rear of the

    Sheena Ruggirello Real Broker CT, LLC

    18 Philmar Dr, Plainfield, CT 06374
  • 96 Mcdermott Ave, Willimantic, CT 06226

    $335,000

    Sold Apr 13, 2026

    96 Mcdermott Ave, Willimantic, CT 06226

    • 4 Beds
    • 2 Baths
    • 1,708 Sq Ft
    • Built 1970

    Last Sold Summary

    • 12% Above List Price
    • $196/SF
    • 38 Days On Market

    Current Estimated Value $347,268

    Last Listing Agent Sue Esposito Home Selling Team

    96 Mcdermott Ave, Willimantic, CT 06226
    • 101 Quinebaug Rd, North Grosvenordale, CT 06255

      Est $339,776

      Not Listed For Sale

      101 Quinebaug Rd, North Grosvenordale, CT 06255

      • 3 Beds
      • 1.5 Baths
      • 1,331 Sq Ft
      • Built 1939
      101 Quinebaug Rd, North Grosvenordale, CT 06255

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Jennifer Pagan RE/MAX One

  • 188 Laurel Point Rd, Dayville, CT 06241
    188 Laurel Point Rd, Dayville, CT 06241
    188 Laurel Point Rd, Dayville, CT 06241
    /23

    $690,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,268 Sq Ft

    188 Laurel Point Rd, Dayville, CT 06241

    Lakefront Living at Its Finest! Experience the beauty of waterfront living in this charming 3-bedroom, 2 full-bath home nestled on the shores of a Alexanders Lake. Wake up to breathtaking water views and enjoy peaceful mornings from the inviting three-season room, the perfect place to relax, entertain, or take in the beauty of every season. Inside, you'll find a welcoming layout designed for

    Colleen Rybacki Brunet and Company Real Estate

    188 Laurel Point Rd, Dayville, CT 06241
  • 52 Singleton Rd, Chaplin, CT 06235

    $365,000

    Sold Oct 08, 2025

    52 Singleton Rd, Chaplin, CT 06235

    • 3 Beds
    • 2.5 Baths
    • 2,440 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Above List Price
    • $150/SF
    • 67 Days On Market

    Current Estimated Value $378,824

    Last Listing Agent Alexis John RE/MAX One

    52 Singleton Rd, Chaplin, CT 06235
    • 739 Route 171, Woodstock, CT 06281

      Est $658,344

      Not Listed For Sale

      739 Route 171, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 2,277 Sq Ft
      • Built 1977
      739 Route 171, Woodstock, CT 06281

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

  • 81-83 Community Ave, Plainfield, CT 06374
    81-83 Community Ave, Plainfield, CT 06374
    81-83 Community Ave, Plainfield, CT 06374
    /23

    $389,900

    $10K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,673 Sq Ft

    81-83 Community Ave, Plainfield, CT 06374

    This well-maintained duplex offers an excellent opportunity for investors or owner-occupants looking to build equity while generating rental income. Each unit features 3 bedrooms, 1 full bathroom, and nearly 1,300 square feet of living space, providing spacious layouts and strong rental potential. One unit will be vacant at the time of purchase and has been recently renovated, allowing a new

    Benjamin Carbone Lamacchia Realty

    81-83 Community Ave, Plainfield, CT 06374
  • 64 May Brook, Woodstock, CT 06281

    $715,000

    Sold Oct 21, 2025

    64 May Brook, Woodstock, CT 06281

    • 4 Beds
    • 5 Baths
    • 3,795 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Below List Price
    • $188/SF
    • 35 Days On Market

    Current Estimated Value $785,517

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    64 May Brook, Woodstock, CT 06281
    • 135 Franklin St, Danielson, CT 06239

      Est $280,397

      Not Listed For Sale

      135 Franklin St, Danielson, CT 06239

      • 3 Beds
      • 2 Baths
      • 1,758 Sq Ft
      • Built 1935
      135 Franklin St, Danielson, CT 06239

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Coleen Brakenwagen Real Broker CT, LLC

  • 189 Black Hill Rd, Plainfield, CT 06374
    189 Black Hill Rd, Plainfield, CT 06374
    189 Black Hill Rd, Plainfield, CT 06374
    /39

    $495,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,688 Sq Ft

    189 Black Hill Rd, Plainfield, CT 06374

    Set on nearly eight acres of rolling land on Black Hill in Plainfield, this versatile property offers a flexible 4-bedroom home, substantial barn infrastructure and plenty of usable outdoor space. Built in 2003, this home centers around an open great-room layout where the kitchen, dining and living areas connect naturally. A pellet stove provides supplemental heat, while mini-split heat pumps

    Darius Baturo Berkshire Hathaway NE Prop.

    189 Black Hill Rd, Plainfield, CT 06374
  • 19 Bolles St, Putnam, CT 06260

    $297,500

    Sold May 08, 2026

    19 Bolles St, Putnam, CT 06260

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Below List Price
    • $163/SF
    • 19 Days On Market

    Current Estimated Value $304,573

    Last Listing Agent Casey Hardell CR Premier Properties

    19 Bolles St, Putnam, CT 06260
    • 15 Rachel Dr, North Grosvenordale, CT 06255

      Est $354,597

      Not Listed For Sale

      15 Rachel Dr, North Grosvenordale, CT 06255

      • 3 Beds
      • 1 Bath
      • 1,040 Sq Ft
      • Built 1963
      15 Rachel Dr, North Grosvenordale, CT 06255

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Skyla Gagnon RE/MAX Bell Park Realty

  • 21 River Walk Dr, Brooklyn, CT 06234
    21 River Walk Dr, Brooklyn, CT 06234
    21 River Walk Dr, Brooklyn, CT 06234
    /40

    $285,000

    Pending
    • 1 Bed
    • 1 Bath
    • 1,098 Sq Ft

    21 River Walk Dr, Brooklyn, CT 06234

    Enjoy carefree one level living in the Beautiful River Walk over 55 Condo Complex. You'll love the open floor plan where the kitchen and dining area flows into the large living room with cathedral ceilings and big windows for great natural light. There's a spacious primary bedroom with double closets for plenty of storage, and an additional room that's perfect for an office or study. In the bath

    Loni Wright Signature Properties of N.E.

    21 River Walk Dr, Brooklyn, CT 06234
  • 173 Bennett Pond Rd, Canterbury, CT 06331

    $455,000

    Sold Jun 01, 2026

    173 Bennett Pond Rd, Canterbury, CT 06331

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Above List Price
    • $298/SF
    • 4 Days On Market

    Current Estimated Value $460,006

    Last Listing Agent Jennifer Mahr RE/MAX Bell Park Realty

    173 Bennett Pond Rd, Canterbury, CT 06331
    • 210 Mechanic St, Danielson, CT 06239

      Est $393,643

      Not Listed For Sale

      210 Mechanic St, Danielson, CT 06239

      • 4 Beds
      • 2 Baths
      • 2,584 Sq Ft
      • Built 1900
      210 Mechanic St, Danielson, CT 06239

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Brecken Ellsworth Kazantzis Real Estate, LLC

  • 56 River Rd, Dayville, CT 06241
    56 River Rd, Dayville, CT 06241
    56 River Rd, Dayville, CT 06241
    /40

    $850,000

    Pending
    • 5 Beds
    • 3 Baths
    • 3,982 Sq Ft

    56 River Rd, Dayville, CT 06241

    OPEN HOUSE CANCELED! BACK ON MARKET - NO FAULT OF THE PROPERTY OR SELLER. Previous buyer was unable to complete the sale of their existing home. Property is now available and ready for a new buyer! Welcome to your own retreat on more than 5 acres along 5 Mile River. Offering more than 5,000 square feet of beautifully designed living space, this custom Colonial combines timeless craftsmanship with

    Ashley Singh mygoodagent

    56 River Rd, Dayville, CT 06241
  • 33 Meehan Rd, Woodstock, CT 06281

    $1,000,000

    Sold Jun 10, 2026

    33 Meehan Rd, Woodstock, CT 06281

    • 3 Beds
    • 4 Baths
    • 4,190 Sq Ft
    • Built 1993

    Last Sold Summary

    • $239/SF
    • 9 Days On Market

    Last Listing Agent John Downs Berkshire Hathaway NE Prop.

    33 Meehan Rd, Woodstock, CT 06281
    • 329 South St, Willimantic, CT 06226

      Est $427,086

      Not Listed For Sale

      329 South St, Willimantic, CT 06226

      • 3 Beds
      • 2 Baths
      • 1,840 Sq Ft
      • Built 1900
      329 South St, Willimantic, CT 06226

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Amber Alcazar Coldwell Banker Realty

  • 39 Sterling Hill Rd, Moosup, CT 06354
    39 Sterling Hill Rd, Moosup, CT 06354
    39 Sterling Hill Rd, Moosup, CT 06354
    /7

    $265,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    39 Sterling Hill Rd, Moosup, CT 06354

    Check out this home with great potential! With a little vision and sweat equity this house could be transformed into the home of your dreams. The backyard is spacious, private, and ready for you to relax in. Subject to probate court approval.

    Erin Gardner RE/MAX Realty Group

    39 Sterling Hill Rd, Moosup, CT 06354
  • 215 Walnut St, Putnam, CT 06260

    $347,000

    Sold Jul 15, 2026

    215 Walnut St, Putnam, CT 06260

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1867

    Last Sold Summary

    • 2% Above List Price
    • $217/SF
    • 6 Days On Market

    Current Estimated Value $350,848

    Last Listing Agent Danielle Kiser LPT Realty

    215 Walnut St, Putnam, CT 06260
    • 1115 Route 169, Woodstock, CT 06281
      1115 Route 169, Woodstock, CT 06281
      1115 Route 169, Woodstock, CT 06281
      /39

      Est $562,114

      Not Listed For Sale

      1115 Route 169, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 2,644 Sq Ft
      • Built 1986
      1115 Route 169, Woodstock, CT 06281

      Last Sold Summary

      • 214 Days On Market

      Last Listing Agent VIvian Kozey CR Premier Properties

  • 57 Brooklyn Rd, Canterbury, CT 06331
    57 Brooklyn Rd, Canterbury, CT 06331
    /2

    $90,000

    Pending
    • Land
    • 2.26 Acres
    • $39,823 per Acre

    57 Brooklyn Rd, Canterbury, CT 06331

    Approved building lot located on country Rd, slightly wooded. Don't wait come build your dream home.

    Maura Von Deck Von Deck Realty, LLC

    57 Brooklyn Rd, Canterbury, CT 06331
  • 31 Deer Meadow Ln, Woodstock, CT 06281

    $500,000

    Sold Oct 31, 2025

    31 Deer Meadow Ln, Woodstock, CT 06281

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Below List Price
    • $213/SF
    • 11 Days On Market

    Current Estimated Value $550,083

    Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

    31 Deer Meadow Ln, Woodstock, CT 06281
    • 35 King St, Putnam, CT 06260

      Est $327,688

      Not Listed For Sale

      35 King St, Putnam, CT 06260

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1978
      35 King St, Putnam, CT 06260

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kendra Bonette Coldwell Banker Realty

  • 39 Selden St, Willimantic, CT 06226
    39 Selden St, Willimantic, CT 06226
    39 Selden St, Willimantic, CT 06226
    /21

    $299,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,263 Sq Ft

    39 Selden St, Willimantic, CT 06226

    Welcome home to this inviting ranch, offering the ease and convenience of one-level living just outside the city. Inside, you'll find hardwood floors, a freshly painted interior, a beautiful stone fireplace, and a bright sunroom with skylights the perfect place to relax year-round. Recent improvements include new flooring in the foyer, kitchen, and hallway, an updated bathroom, and a new water

    Cassie Ryniewicz CR Premier Properties

    39 Selden St, Willimantic, CT 06226
  • 360 N Society Rd, Canterbury, CT 06331

    $280,000

    Sold Jun 23, 2026

    360 N Society Rd, Canterbury, CT 06331

    • 3 Beds
    • 1.5 Baths
    • 2,236 Sq Ft
    • Built 1984

    Last Sold Summary

    • $125/SF
    • 6 Days On Market

    Current Estimated Value $291,260

    Last Listing Agent Dale Bunn Riverview Realty, LLC

    360 N Society Rd, Canterbury, CT 06331
    • 55 Colonial Rd, Plainfield, CT 06374

      Est $254,152

      Not Listed For Sale

      55 Colonial Rd, Plainfield, CT 06374

      • 2 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 1987
      55 Colonial Rd, Plainfield, CT 06374

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Loni Wright Signature Properties of N.E.

  • 48 Athol St Unit 48, Danielson, CT 06239
    48 Athol St Unit 48, Danielson, CT 06239
    48 Athol St Unit 48, Danielson, CT 06239
    /23

    $187,000

    $8K PRICE DROP Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,076 Sq Ft

    48 Athol St Unit 48, Danielson, CT 06239

    Welcome home to this beautiful townhouse-style condo featuring 2 bedrooms and 1.5 baths. The open-concept first floor offers a bright and inviting layout, where a modern eat-in kitchen flows seamlessly into the dining area. Step through the sliders to your private back deck and take in the expansive backyard view, perfect for morning coffee or evening relaxation. A convenient half bath for guests

    Kara Mazzola First Choice Realty

    48 Athol St Unit 48, Danielson, CT 06239
  • 420 Moosup Pond Rd, Moosup, CT 06354

    $520,000

    Sold Jun 15, 2026

    420 Moosup Pond Rd, Moosup, CT 06354

    • 3 Beds
    • 2.5 Baths
    • 1,751 Sq Ft
    • Built 2019

    Last Sold Summary

    • 6% Above List Price
    • $297/SF
    • 39 Days On Market

    Current Estimated Value $536,438

    Last Listing Agent Kelsie Griffin Wolfburg Kazantzis Real Estate, LLC

    420 Moosup Pond Rd, Moosup, CT 06354
    • 140 Katherine Ave, Danielson, CT 06239

      Est $353,759

      Not Listed For Sale

      140 Katherine Ave, Danielson, CT 06239

      • 3 Beds
      • 1 Bath
      • 1,132 Sq Ft
      • Built 2004
      140 Katherine Ave, Danielson, CT 06239

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Kara Mazzola First Choice Realty

  • Lot 03-2 New Sweden Rd, Woodstock, CT 06281
    Lot 03-2 New Sweden Rd, Woodstock, CT 06281
    Lot 03-2 New Sweden Rd, Woodstock, CT 06281
    /5

    $99,000

    • Land
    • 3.5 Acres
    • $28,286 per Acre

    Lot 03-2 New Sweden Rd, Woodstock, CT 06281

    This site is well off the road, and ready to go. The driveway is owned, and the neighbor has a right of way over it. Once past the neighbors property, rise up to the building site. The site is level and open, and the lot then slopes down to the south and west. This portion of the land is wooded. Conduit for power is in place. Agent related to seller.

    Lynn Converse RE/MAX Bell Park Realty

    Lot 03-2 New Sweden Rd, Woodstock, CT 06281
  • 106 Riley Chase Rd, Killingly, CT 06241

    $85,000

    Sold Jun 01, 2026

    106 Riley Chase Rd, Killingly, CT 06241

    • Land
    • 10.9 Acres
    • $7,798 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 29 Days On Market

    Current Estimated Value $85,365

    Last Listing Agent Anthony Chabot Chabot & Associates Real Estate

    106 Riley Chase Rd, Killingly, CT 06241
    • 26 Hungry Hill Rd, Sterling, CT 06377

      Est $319,293

      Not Listed For Sale

      26 Hungry Hill Rd, Sterling, CT 06377

      • 2 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1903
      26 Hungry Hill Rd, Sterling, CT 06377

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Brooke Gelhaus Compass Connecticut, LLC

  • 133 Route 198, Woodstock Valley, CT 06282
    133 Route 198, Woodstock Valley, CT 06282
    133 Route 198, Woodstock Valley, CT 06282
    /19

    $329,000

    $21K PRICE DROP Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,894 Sq Ft

    133 Route 198, Woodstock Valley, CT 06282

    This sprawling country style ranch home has plenty of space! Over 1800 sq.ft of living space all on one level. Street card states 2 bedrooms but the house is arranged and used as a 3-4 bedroom. Cozy eat in kitchen with built in dining area. Formal living room has a stone fireplace and hardwood flooring. Formal dining room. Family room is huge but currently used as the seller's primary bedroom,

    Robin Smith RE/MAX Bell Park Realty

    133 Route 198, Woodstock Valley, CT 06282
  • 63 Glebas Rd, Plainfield, CT 06374

    $400,000

    Sold May 01, 2026

    63 Glebas Rd, Plainfield, CT 06374

    • 4 Beds
    • 2 Baths
    • 2,104 Sq Ft
    • Built 1968

    Last Sold Summary

    • $190/SF
    • 149 Days On Market

    Current Estimated Value $407,938

    Last Listing Agent Lorraine Bandoni CrossRoads Real Estate Group

    63 Glebas Rd, Plainfield, CT 06374

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