Windham County, CT Homes

• 

  $268,000

  Sold Dec 10, 2025

  17 Woodstock Meadows, Woodstock, CT 06281

  • 1 Bed
  • 1 Bath
  • 768 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Above List Price
  • $349/SF
  • 36 Days On Market

  Current Estimated Value $260,136

  Last Listing Agent Tracie Gagnon Berkshire Hathaway NE Prop.

  17 Woodstock Meadows, Woodstock, CT 06281
• 

  Est $388,037

  Not Listed For Sale

  475 Putnam Pike, Dayville, CT 06241

  • 4 Beds
  • 2 Baths
  • 2,120 Sq Ft
  • Built 1930

  475 Putnam Pike, Dayville, CT 06241

  Last Sold Summary

  • 63 Days On Market
• 

  

  /2

  $124,900

  • Land
  • 2.06 Acres
  • $60,631 per Acre

  161 Lisbon Rd, Canterbury, CT 06331

  EMILY'S VALLEY IN CANTERBURY, CT. SUPERIOR PARCELS IN A REPRODUCTION STYLE NEIGHBORHOOD OF HIGH VALUE HOMES. IT'S WORTH THE EFFORT TO BUILD A NEW QUALITY HOUSE TO YOUR OWN SPECIFICATIONS. QUALITY COUNTRY LIFESTYLE, PLENTY OF NEARBY GOODS AND SERVICES, REASONABLE TAXES AND IN TOWN SCHOOLS WITH A CHOICE OF GREAT AREA HIGH SCHOOLS (FULLY PAID BY THE TOWN).

  Derek Greene Derek Greene

  161 Lisbon Rd, Canterbury, CT 06331
• 

  $485,000

  Sold Oct 17, 2025

  31 Cherry Hill Rd, Brooklyn, CT 06234

  • 3 Beds
  • 3 Baths
  • 2,464 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $197/SF
  • 141 Days On Market

  Current Estimated Value $481,802

  Last Listing Agent Nathan Cholewa Kazantzis Real Estate, LLC

  31 Cherry Hill Rd, Brooklyn, CT 06234
• 

  Est $376,089

  Not Listed For Sale

  93 Babula Rd, Thompson, CT 06277

  • 3 Beds
  • 1.5 Baths
  • 1,061 Sq Ft
  • Built 1918

  93 Babula Rd, Thompson, CT 06277

  Last Sold Summary

  • 7 Days On Market
• 

  

  /14

  $399,000

  • 11 Beds
  • 2.5 Baths
  • 3,748 Sq Ft

  30 Main St, Plainfield, CT 06374

  Nestled in the heart of history, this extraordinary three-level estate exudes timeless elegance and vintage charm. With soaring ceilings, sprawling rooms, and intricate architectural details, this home captures the essence of a bygone era while offering the space and amenities for today's lifestyle. Every corner of this impressive residence tells a story-from the grand entryway with original

  Adam Gonzalez Century 21 Limitless

  30 Main St, Plainfield, CT 06374
• 

  $486,000

  Sold Apr 22, 2026

  344 Sabin St, Putnam, CT 06260

  • 3 Beds
  • 2.5 Baths
  • 2,142 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $227/SF
  • 8 Days On Market

  Current Estimated Value $481,200

  Last Listing Agent Ashley Walker Kazantzis Real Estate, LLC

  344 Sabin St, Putnam, CT 06260
• 

  Est $399,208

  Not Listed For Sale

  486 Fabyan Rd, North Grosvenordale, CT 06255

  • 3 Beds
  • 2.5 Baths
  • 2,290 Sq Ft
  • Built 1990

  486 Fabyan Rd, North Grosvenordale, CT 06255

  Last Sold Summary

  • 5 Days On Market
• 

  

  /14

  $250,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,075 Sq Ft

  222 Parish Hill Rd, Scotland, CT 06247

  Nestled on 2 private acres, this Cape Cod offers a peaceful country lifestyle with an open-concept floor plan and abundant potential. With some cosmetic updates, this home can truly shine. The expansive property features established gardens, chicken coop, duck pen, pond and a charming greenhouse. Ideal for those seeking space, privacy and a connection to the outdoors. The back yard has a 1 acre

  Carol Thornhill Campbell-Keune Realty Inc

  222 Parish Hill Rd, Scotland, CT 06247
• 

  $262,000

  Sold May 19, 2026

  63 Prospect Ave, Danielson, CT 06239

  • 6 Beds
  • 2 Baths
  • 2,004 Sq Ft
  • Built 1915

  Last Sold Summary

  • 1% Above List Price
  • $131/SF
  • 2 Days On Market

  Current Estimated Value $258,989

  Last Listing Agent Christine Johnson RE/MAX One

  63 Prospect Ave, Danielson, CT 06239
• 

  Est $417,359

  Not Listed For Sale

  327 Church St, Brooklyn, CT 06234

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1966

  327 Church St, Brooklyn, CT 06234

  Last Sold Summary

  • 9 Days On Market
• 

  

  /35

  $450,000

  Pending

  • 6 Beds
  • 3 Baths
  • 3,214 Sq Ft

  9 Ellen Ln, Woodstock, CT 06281

  Discover a fantastic investment or owner-occupied opportunity in the heart of Woodstock, CT! This well-maintained two-family property offers spacious and versatile living across both units. Unit 1 features 4 generously sized bedrooms and 2 full bathrooms, complemented by a bright open floor plan that seamlessly connects the living, kitchen, and dining areas. The kitchen boasts a large island

  Jessica Deojay RE/MAX Bell Park Realty

  9 Ellen Ln, Woodstock, CT 06281
• 

  $150,000

  Sold Nov 18, 2025

  9 Sherman Rd, Woodstock, CT 06281

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft
  • Built 1951

  Last Sold Summary

  • 21% Below List Price
  • $169/SF
  • 23 Days On Market

  Last Listing Agent Ryan Braunagel Keller Williams Realty Prtnrs.

  9 Sherman Rd, Woodstock, CT 06281
• 

  Est $306,083

  Not Listed For Sale

  33 Jennings Ln, Windham, CT 06280

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1967

  33 Jennings Ln, Windham, CT 06280

  Last Sold Summary

  • 31 Days On Market
• 

  

  /34

  $599,000

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,700 Sq Ft

  41 Millbridge Rd, Eastford, CT 06242

  Welcome to 41 Millbridge Rd, Eastford, CT, a spacious country property set on 8.7 acres of peaceful rural land offering privacy, space, and endless potential. This home features 5 bedrooms and 3.5 bathrooms, providing a flexible layout ideal for multi-generational living, entertaining, or creating your own private retreat. Enjoy the charm of quiet country living with plenty of outdoor space for

  Amaurys Valdera Brokerbe Inc.

  41 Millbridge Rd, Eastford, CT 06242
• 

  

  /32

  $475,000

  Sold Feb 13, 2026

  394 Killingly Ave, Putnam, CT 06260

  • 3 Beds
  • 3 Baths
  • 2,148 Sq Ft
  • Built 1999

  Last Sold Summary

  • $221/SF
  • 3 Days On Market

  Current Estimated Value $480,341

  Last Listing Agent Audrey Martinez LAER Realty Partners

  394 Killingly Ave, Putnam, CT 06260
• 

  Est $281,381

  Not Listed For Sale

  260 Jackson St, Willimantic, CT 06226

  • 5 Beds
  • 2 Baths
  • 2,464 Sq Ft
  • Built 1900

  260 Jackson St, Willimantic, CT 06226

  Last Sold Summary

  • 8 Days On Market
• 

  

  /33

  $274,900

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 984 Sq Ft

  519 Brooklyn Rd, Canterbury, CT 06331

  Charming antique cottage nestled along a bucolic country road in Canterbury, Connecticut. Set on a generous 2.14-acre partially wooded lot, this inviting 3-bedroom, 1 full bath home offers 984 square feet of comfortable living space filled with character and warmth. A sweet front porch welcomes you home and provides the perfect spot to relax and take in the peaceful country surroundings. Freshly

  Cyrille Bosio Berkshire Hathaway NE Prop.

  519 Brooklyn Rd, Canterbury, CT 06331
• 

  $72,000

  Sold Aug 25, 2025

  115 North Rd, Ashford, CT 06278

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • Built 1965

  Last Sold Summary

  • 15% Below List Price
  • $92/SF
  • 35 Days On Market

  Last Listing Agent Adrian Cote William Raveis Real Estate

  115 North Rd, Ashford, CT 06278
• 

  Est $521,595

  Not Listed For Sale

  122 Brandy Hill Rd, Thompson, CT 06277

  • 3 Beds
  • 2.5 Baths
  • 2,180 Sq Ft
  • Built 2006

  122 Brandy Hill Rd, Thompson, CT 06277

  Last Sold Summary

  • 4 Days On Market

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