46,115

Windham County, CT Homes

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  • 156 Quaddick Rd, Thompson, CT 06277

    $470,000 Sold Sep 12, 2025

    156 Quaddick Rd, Thompson, CT 06277

    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Above List Price
    • $256/SF
    • 10 Days On Market

    Current Estimated Value $464,974

    Last Listing Agent Ryan LaJoie Johnston & Associates Real Estate, LLC

    156 Quaddick Rd, Thompson, CT 06277
    • 34 Cardinal Dr, Dayville, CT 06241

      Est $433,260 Not Listed For Sale

      34 Cardinal Dr, Dayville, CT 06241

      • 3 Beds
      • 2 Baths
      • 1,646 Sq Ft
      • Built 2007
      34 Cardinal Dr, Dayville, CT 06241

      Last Sold Summary

      • 3% Above List Price
      • $255/SF
      • 20 Days On Market

      Last Sold Price $419,900

      Last Listing Agent Mark Tetreault, II RE/MAX

  • 18 Bob White Way, Moosup, CT 06354
    18 Bob White Way, Moosup, CT 06354
    18 Bob White Way, Moosup, CT 06354
    /39

    $515,000

    • 5 Beds
    • 2.5 Baths
    • 3,249 Sq Ft

    18 Bob White Way, Moosup, CT 06354

    NEW TO THE MARKET! Spacious & private 5 Bedroom, 2 1/2 bath Colonial sitting on close to 1 1/2 acres and located off of a quiet country road is ready and quietly waiting for you! Set back on a long and private driveway, this home offers you the peace and serenity you are looking for. From the inviting farmers porch to the large primary suite, there is just so much to love about this home! The

    Lorraine Bandoni CrossRoads Real Estate Group

    18 Bob White Way, Moosup, CT 06354
  • 449 E Thompson Rd, Thompson, CT 06277

    $560,000 Sold Jul 01, 2025

    449 E Thompson Rd, Thompson, CT 06277

    • 3 Beds
    • 2.5 Baths
    • 2,132 Sq Ft
    • Built 1989

    Last Sold Summary

    • 2% Below List Price
    • $263/SF
    • 12 Days On Market

    Current Estimated Value $548,605

    Last Listing Agent Rachel Sposato Berkshire Hathaway NE Prop.

    449 E Thompson Rd, Thompson, CT 06277
    • 32 Ladds Ln, Dayville, CT 06241

      Est $452,099 Not Listed For Sale

      32 Ladds Ln, Dayville, CT 06241

      • 3 Beds
      • 2.5 Baths
      • 1,888 Sq Ft
      • Built 2008
      32 Ladds Ln, Dayville, CT 06241

      Last Sold Summary

      • 13% Above List Price
      • $212/SF
      • 34 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Kara Mazzola First Choice Realty

  • 323 Snake Meadow Rd, Moosup, CT 06354
    323 Snake Meadow Rd, Moosup, CT 06354
    /2

    $59,900

    • Land
    • 7.6 Acres
    • $7,882 per Acre

    323 Snake Meadow Rd, Moosup, CT 06354

    Rare opportunity to own 7.6 acres of land in a peaceful rural setting. This lot of record offers approximately 600 feet of road frontage. The property is unimproved with no approvals currently in place, offering a blank canvas for your vision. Whether you are looking to build your dream home, create a private retreat, or invest in land, this parcel offers endless possibilities while still being

    Cary Marcoux RE/MAX Bell Park Realty

    323 Snake Meadow Rd, Moosup, CT 06354
  • 80 Ventura Dr, Brooklyn, CT 06234

    $350,000 Sold Dec 17, 2025

    80 Ventura Dr, Brooklyn, CT 06234

    • 2 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1982

    Last Sold Summary

    • 8% Below List Price
    • $183/SF
    • 155 Days On Market

    Current Estimated Value $350,843

    Last Listing Agent Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    80 Ventura Dr, Brooklyn, CT 06234
    • 81 Pine Knolls Dr, Dayville, CT 06241

      Est $562,515 Not Listed For Sale

      81 Pine Knolls Dr, Dayville, CT 06241

      • 3 Beds
      • 2.5 Baths
      • 2,074 Sq Ft
      • Built 2007
      81 Pine Knolls Dr, Dayville, CT 06241

      Last Sold Summary

      • 7% Above List Price
      • $254/SF
      • 13 Days On Market

      Last Sold Price $526,000

      Last Listing Agent Glenn Stavens Aspen Realty Group

  • 365-367 Putnam Rd, Plainfield, CT 06239
    365-367 Putnam Rd, Plainfield, CT 06239
    365-367 Putnam Rd, Plainfield, CT 06239
    /40

    $465,000 Under Contract

    • 8 Beds
    • 3 Baths
    • 4,272 Sq Ft

    365-367 Putnam Rd, Plainfield, CT 06239

    Looking for easy, low maintenance and low overhead - this fully remastered, High-Yield Two-Family Investment located on the Danielson boarder...Renovated from roof down with only $4k in annual taxes; This investment offers exceptional scale, condition, and income potential. With a gross expected rent of $79k/year, our expected cap rate comes in at 13%. Each unit is configured as a massive

    Kyle Neumann Houlihan Lawrence

    365-367 Putnam Rd, Plainfield, CT 06239
  • 23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

    $559,000 Sold Feb 02, 2026

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1960

    Last Sold Summary

    • 11% Below List Price
    • $259/SF
    • 198 Days On Market

    Current Estimated Value $544,197

    Last Listing Agent Alan Berman Signature Properties of N.E.

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
    • 41 Fieldstone Rd, Dayville, CT 06241

      Est $476,458 Not Listed For Sale

      41 Fieldstone Rd, Dayville, CT 06241

      • 3 Beds
      • 2 Baths
      • 1,576 Sq Ft
      • Built 2011
      41 Fieldstone Rd, Dayville, CT 06241

      Last Sold Summary

      • 2% Above List Price
      • $298/SF
      • 2 Days On Market

      Last Sold Price $469,000

      Last Listing Agent Tracy O'Donnell Berkshire Hathaway Home Services

  • 43 Woodward St, Danielson, CT 06239
    43 Woodward St, Danielson, CT 06239
    43 Woodward St, Danielson, CT 06239
    /6

    $319,900 Open Fri 5PM - 6:30PM

    • 3 Beds
    • 1 Bath
    • 1,309 Sq Ft

    43 Woodward St, Danielson, CT 06239

    Welcome to this charming new listing in Killingly! This well-maintained 3-bedroom, 1-bath ranch offers the perfect blend of comfort, convenience, and easy one-level living. Nestled in a great location, you'll love how close you are to local amenities while still enjoying a peaceful neighborhood feel. Inside, you'll find newer flooring that adds a fresh, updated touch throughout the home. You will

    Jessica Fowler RE/MAX Bell Park Realty

    43 Woodward St, Danielson, CT 06239
  • 11 Stone House Dr, Plainfield, CT 06374

    $425,000 Sold Feb 27, 2026

    11 Stone House Dr, Plainfield, CT 06374

    • 3 Beds
    • 2 Baths
    • 1,832 Sq Ft
    • Built 2017

    Last Sold Summary

    • 2% Below List Price
    • $232/SF
    • 80 Days On Market

    Last Listing Agent Joan Casey RE/MAX Legends

    11 Stone House Dr, Plainfield, CT 06374
    • 162 Cedar Swamp Rd, Hampton, CT 06247

      Est $414,330 Not Listed For Sale

      162 Cedar Swamp Rd, Hampton, CT 06247

      • 3 Beds
      • 2 Baths
      • 1,919 Sq Ft
      • Built 2008
      162 Cedar Swamp Rd, Hampton, CT 06247

      Last Sold Summary

      • 4% Above List Price
      • $208/SF
      • 82 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Stephanie Baker Baker Realty Group

  • 454 Providence Rd, Brooklyn, CT 06234
    454 Providence Rd, Brooklyn, CT 06234
    454 Providence Rd, Brooklyn, CT 06234
    /13

    $497,500 Under Contract

    • Land
    • 2.32 Acres
    • $214,440 per Acre

    454 Providence Rd, Brooklyn, CT 06234

    2.32 Acres vacant land zoned (PC) Planned Commercial located directly at the 4-way traffic light to the entrance of the Brooklyn Walmart Supercenter. Easement agreement in the public record would allow for access to the parcel from the Walmart driveway entrance. Less than 2.5 miles from I-395 (NB Exit 37/SB Exit 37B). Situated in the heart of the Route 6 retail corridor. National tenants in the

    Ron Lyman Lyman Real Estate

    454 Providence Rd, Brooklyn, CT 06234
  • 625 Riverside Dr, North Grosvenordale, CT 06255

    $430,000 Sold Jun 30, 2025

    625 Riverside Dr, North Grosvenordale, CT 06255

    • 4 Beds
    • 2 Baths
    • 2,271 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Above List Price
    • $189/SF
    • 8 Days On Market

    Current Estimated Value $437,620

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    625 Riverside Dr, North Grosvenordale, CT 06255
    • 257 Willimantic Rd, Chaplin, CT 06235

      Est $194,223 Not Listed For Sale

      257 Willimantic Rd, Chaplin, CT 06235

      • 2 Beds
      • 1 Bath
      • 1,050 Sq Ft
      • Built 1952
      257 Willimantic Rd, Chaplin, CT 06235

      Last Sold Summary

      • 16% Above List Price
      • $160/SF
      • 60 Days On Market

      Last Sold Price $168,000

      Last Listing Agent Robert Ferrigno Ferrigno-Willimantic REALTORS

  • 119 Quercus Ave, Willimantic, CT 06226
    119 Quercus Ave, Willimantic, CT 06226
    119 Quercus Ave, Willimantic, CT 06226
    /29

    $285,000

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    119 Quercus Ave, Willimantic, CT 06226

    Tucked into The Oaks, one of Willimantic's most beloved neighborhoods, this 1890s Cape Cod is a home that feels instantly welcoming. Built by the Willimantic Linen Company, it reflects a simpler time, beginning with a covered front porch and a thoughtfully scaled interior that feels comfortable and inviting. The 1,160 square foot home offers three bedrooms and a cozy living room featuring the

    Kristen Kaskela Berkshire Hathaway NE Prop.

    119 Quercus Ave, Willimantic, CT 06226
  • 72 Old Canterbury Rd, Hampton, CT 06247

    $430,000 Sold Aug 21, 2025

    72 Old Canterbury Rd, Hampton, CT 06247

    • 3 Beds
    • 2 Baths
    • 2,508 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Below List Price
    • $171/SF
    • 82 Days On Market

    Current Estimated Value $440,376

    Last Listing Agent Jennifer Lehto Kazantzis Real Estate, LLC

    72 Old Canterbury Rd, Hampton, CT 06247
    • 202 South St, Brooklyn, CT 06234

      Est $365,403 Not Listed For Sale

      202 South St, Brooklyn, CT 06234

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1953
      202 South St, Brooklyn, CT 06234

      Last Sold Summary

      • 4% Below List Price
      • $211/SF
      • 7 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Rachael Zagurski RE/MAX

  • 23 Pine Crest Ridge, Woodstock, CT 06281
    23 Pine Crest Ridge, Woodstock, CT 06281
    23 Pine Crest Ridge, Woodstock, CT 06281
    /29

    $4,320,000 Under Contract

    • 9 Beds
    • 8 Baths
    • 14,103 Sq Ft

    23 Pine Crest Ridge, Woodstock, CT 06281

    Pinecrest Apartments is a meticulously maintained 14-unit residential community situated on 5.5 acres in Woodstock, CT, reflecting clear pride of ownership, durable construction, and sustained tenant demand. Built in 1989, the property is 100% occupied and offers a highly desirable mix of 13 townhome-style units and one ranch-style residence. The unit mix includes: (2) 1BR/1BA, (9) 2BR/1.5BA, (1)

    Lisa Cozzi Century 21 AllPoints Realty

    23 Pine Crest Ridge, Woodstock, CT 06281
  • 10 Ralph St, Moosup, CT 06354

    $335,000 Sold Nov 21, 2025

    10 Ralph St, Moosup, CT 06354

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1962

    Last Sold Summary

    • 7% Below List Price
    • $317/SF
    • 17 Days On Market

    Current Estimated Value $336,553

    Last Listing Agent Ashley Walker Kazantzis Real Estate, LLC

    10 Ralph St, Moosup, CT 06354
    • 239 Turnpike Rd, Ashford, CT 06278

      Est $634,051 Not Listed For Sale

      239 Turnpike Rd, Ashford, CT 06278

      • 3 Beds
      • 2.5 Baths
      • 2,704 Sq Ft
      • Built 2007
      239 Turnpike Rd, Ashford, CT 06278

      Last Sold Summary

      • 6% Above List Price
      • $222/SF
      • 30 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Lauren Iraeta KW Legacy Partners

  • 251 Wauregan Rd, Brooklyn, CT 06234
    251 Wauregan Rd, Brooklyn, CT 06234
    251 Wauregan Rd, Brooklyn, CT 06234
    /35

    $599,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,720 Sq Ft

    251 Wauregan Rd, Brooklyn, CT 06234

    Classic Colonial charm meets modern comfort in this beautifully maintained home in Brooklyn, CT, offering three levels of sun filled living! The main level features a warm and inviting layout, including a spacious kitchen with rich cherry cabinets, stainless steel appliances, stylish backsplash, a large island, and a dining area with sliders leading out to the deck-perfect for indoor-outdoor

    Heather Armbruster Lamacchia Realty

    251 Wauregan Rd, Brooklyn, CT 06234
  • 7 Lockwood St, Brooklyn, CT 06234

    $338,000 Sold Mar 06, 2026

    7 Lockwood St, Brooklyn, CT 06234

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $241/SF
    • 49 Days On Market

    Current Estimated Value $326,967

    Last Listing Agent Shawn Mercer Coldwell Banker Realty

    7 Lockwood St, Brooklyn, CT 06234
    • 208 Baxter Rd, Woodstock, CT 06281

      Not Listed For Sale

      208 Baxter Rd, Woodstock, CT 06281

      • 2 Beds
      • 0.5 Baths
      • 480 Sq Ft
      • Built 1947
      208 Baxter Rd, Woodstock, CT 06281

      Last Sold Summary

      • 145% Above List Price
      • $254/SF
      • 5 Days On Market

      Last Sold Price $122,000

      Last Listing Agent Kathleen Holland KW Legacy Partners

  • 6 Grace Ln, Moosup, CT 06354
    6 Grace Ln, Moosup, CT 06354
    6 Grace Ln, Moosup, CT 06354
    /38

    $475,000

    • 2 Beds
    • 2 Baths
    • 1,780 Sq Ft

    6 Grace Ln, Moosup, CT 06354

    Moosup River Estates - 55+ Luxury Living Discover an unparalleled lifestyle at Moosup River Estates, a premier 55 and over community offering elegant homes designed for comfort and sophistication. This home features 2 bedrooms and 2 full bathrooms with a nice open floor plan. The applianced custom kitchen design has a center island and granite countertops, perfect for entertaining or casual

    Cary Marcoux RE/MAX Bell Park Realty

    6 Grace Ln, Moosup, CT 06354
  • 35-37 N Chestnut St, Plainfield, CT 06374

    $367,000 Sold Jun 02, 2025

    35-37 N Chestnut St, Plainfield, CT 06374

    • 6 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • Built 1860

    Last Sold Summary

    • 2% Above List Price
    • $157/SF
    • 27 Days On Market

    Current Estimated Value $372,031

    Last Listing Agent Karly Worth Call It Closed Realty

    35-37 N Chestnut St, Plainfield, CT 06374
    • 264 Brooklyn Turnpike, Hampton, CT 06247

      Est $270,705 Not Listed For Sale

      264 Brooklyn Turnpike, Hampton, CT 06247

      • 3 Beds
      • 1 Bath
      • 1,014 Sq Ft
      • Built 1981
      264 Brooklyn Turnpike, Hampton, CT 06247

      Last Sold Summary

      • 18% Above List Price
      • $227/SF
      • 77 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Glenn Stavens Aspen Realty Group

  • 99 Squaw Rock Rd, Moosup, CT 06354
    99 Squaw Rock Rd, Moosup, CT 06354
    99 Squaw Rock Rd, Moosup, CT 06354
    /30

    $279,900

    • 3 Beds
    • 1 Bath
    • 1,240 Sq Ft

    99 Squaw Rock Rd, Moosup, CT 06354

    Adorable Ranch w/ ENCLOSED SUNROOM off of the 1 car garage for entertaining in the SUMMER/ Fall evenings and a huge back yard to enjoy. 3 bedrooms (one does not have a closet) Large bright Livingroom off of eat in galley kitchen (appliances convey) and 1 full bathroom. PAVED driveway and plenty of parking, UPDATED roof and furnace, 200 amps and some 2 prong outlets throughout, generator hookup

    Christine Johnson RE/MAX One

    99 Squaw Rock Rd, Moosup, CT 06354
  • 47 Insalaco Dr, Windham, CT 06280

    $379,900 Sold Dec 09, 2025

    47 Insalaco Dr, Windham, CT 06280

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • Built 1970

    Last Sold Summary

    • $180/SF
    • 30 Days On Market

    Current Estimated Value $380,325

    Last Listing Agent Karan Garewal Winwin Realty

    47 Insalaco Dr, Windham, CT 06280
    • 190 Underwood Rd, Putnam, CT 06260

      Est $354,913 Not Listed For Sale

      190 Underwood Rd, Putnam, CT 06260

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1888
      190 Underwood Rd, Putnam, CT 06260

      Last Sold Summary

      • 10% Above List Price
      • $207/SF
      • 7 Days On Market

      Last Sold Price $323,000

      Last Listing Agent Michael Deyorio CR Premier Properties

  • 170 Windham Center Rd, Windham, CT 06280
    170 Windham Center Rd, Windham, CT 06280
    170 Windham Center Rd, Windham, CT 06280
    /37

    $299,900 Pending

    • 3 Beds
    • 1 Bath
    • 1,423 Sq Ft

    170 Windham Center Rd, Windham, CT 06280

    OFFER DEADLINE MON 5:00PM. Tucked into the countryside of South Windham, this move-in-ready 1,423-square-foot home offers a wonderful blend of country living and modern practical updates. Completely refreshed from top to bottom-including the peace of mind of all new plumbing-the house sits on a beautiful, level lot featuring quiet water views, giving you a sense of rural escape while staying just

    Brenda Chubbuck Berkshire Hathaway NE Prop.

    170 Windham Center Rd, Windham, CT 06280
  • Unlisted Address

    $160,000 Sold May 20, 2025

    Unlisted Address

    • Land
    • 16.75 Acres
    • $9,552 per Acre

    Last Sold Summary

    • 54% Below List Price
    • 241 Days On Market

    Last Listing Agent Clarence Russ Home Selling Team

    Unlisted Address
    • 8 Beechwood Blvd, Plainfield, CT 06374

      Est $330,897 Not Listed For Sale

      8 Beechwood Blvd, Plainfield, CT 06374

      • 3 Beds
      • 2 Baths
      • 1,988 Sq Ft
      • Built 1979
      8 Beechwood Blvd, Plainfield, CT 06374

      Last Sold Summary

      • 5% Below List Price
      • $176/SF
      • 6 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Brenda Cuoco Cuoco & Co. Real Estate

  • 18 Ledge Hill Rd, Sterling, CT 06377
    18 Ledge Hill Rd, Sterling, CT 06377
    18 Ledge Hill Rd, Sterling, CT 06377
    /3

    $79,900

    • Land
    • 1.87 Acres
    • $42,727 per Acre

    18 Ledge Hill Rd, Sterling, CT 06377

    Land was approved for a 3 bedroom home in 2004 - please do your due diligence with the town. Beautiful country lot that is high and dry to build your dream home. 4.5 Miles to 395 and close to RI line. 617Ft of road frontage.

    Christine Johnson RE/MAX One

    18 Ledge Hill Rd, Sterling, CT 06377
  • 10 Tiffany St, Brooklyn, CT 06234

    $279,900 Sold Aug 25, 2025

    10 Tiffany St, Brooklyn, CT 06234

    • 4 Beds
    • 2.5 Baths
    • 1,520 Sq Ft
    • Built 1920

    Last Sold Summary

    • $184/SF
    • 10 Days On Market

    Current Estimated Value $276,116

    Last Listing Agent Christine Johnson RE/MAX One

    10 Tiffany St, Brooklyn, CT 06234
    • 189 Main St, Sterling, CT 06377

      Est $331,921 Not Listed For Sale

      189 Main St, Sterling, CT 06377

      • 3 Beds
      • 1.5 Baths
      • 1,229 Sq Ft
      • Built 1983
      189 Main St, Sterling, CT 06377

      Last Sold Summary

      • 2% Below List Price
      • $276/SF
      • 44 Days On Market

      Last Sold Price $339,000

      Last Listing Agent Catherine Howard Berkshire Hathaway Home Services

  • 9 Highland View Dr, South Windham, CT 06266
    9 Highland View Dr, South Windham, CT 06266
    9 Highland View Dr, South Windham, CT 06266
    /22

    $315,000 Pending

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    9 Highland View Dr, South Windham, CT 06266

    Perfect first home, or downsize, with the big updates already done. This move-in ready property offers peace of mind for first-time buyers looking to avoid costly repairs and enjoy homeownership from day one. Three Bedrooms, open layout, pellet stove, garage with attic storage, an open breezeway, and Hard Wood Floors! Off street parking, Paved driveway. Recent improvements include a brand-new

    Brian Connolly Real Broker CT, LLC

    9 Highland View Dr, South Windham, CT 06266
  • 44 Woodland Dr, Windham, CT 06280

    $310,000 Sold Oct 08, 2025

    44 Woodland Dr, Windham, CT 06280

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft
    • Built 1956

    Last Sold Summary

    • 7% Above List Price
    • $203/SF
    • 104 Days On Market

    Current Estimated Value $302,949

    Last Listing Agent Kelley Vanacore Century 21 AllPoints Realty

    44 Woodland Dr, Windham, CT 06280

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