46,234

Windham County, CT Homes

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  • /40

    $349,900

    Pending
    • 7 Beds
    • 3.5 Baths
    • 2,150 Sq Ft

    25-27 Farrows St, Putnam, CT 06260

    OFFER DEADLINE: 5/18/26 @ 4pm. Turnkey investment opportunity in the heart of Putnam! This well-maintained two-family property at 25-27 Farrows Street is ideal for both owner-occupants and savvy investors looking to build long-term equity. Each unit offers comfortable layouts with spacious living areas, generous bedrooms, and plenty of natural light throughout. Recent updates and solid

    Mark Tetreault, II RE/MAX Bell Park Realty

    25-27 Farrows St, Putnam, CT 06260
  • 91 Insalaco Dr, Windham, CT 06280

    $362,900

    Sold Mar 27, 2026

    91 Insalaco Dr, Windham, CT 06280

    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $171/SF
    • 98 Days On Market

    Current Estimated Value $370,215

    Last Listing Agent Mike Thompson Countryside Realty

    91 Insalaco Dr, Windham, CT 06280
  • /40

    $887,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    158 Allen Hill Rd, Brooklyn, CT 06234

    One-of-a-kind luxury home designed straight out of a Pottery Barn magazine, set on 2.44 private acres and built for a true million-dollar lifestyle - just 15 minutes to top-performing private schools Pomfret School and Rectory School. This versatile estate fits all needs - a growing family, private resort-style retreat, first-floor living, or in-law setup. The heart of the home is a chef's dream

    Lisa Raiche Town & Shore Realty

    158 Allen Hill Rd, Brooklyn, CT 06234
  • /33

    $710,000

    Sold Jun 30, 2025

    291 Moosup Pond Rd, Plainfield, CT 06354

    • 4 Beds
    • 2.5 Baths
    • 2,479 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $286/SF
    • 62 Days On Market

    Last Listing Agent Doug Taber Taber Realty, Inc.

    291 Moosup Pond Rd, Plainfield, CT 06354
  • /2

    $65,000

    • Land
    • 12,196 Sq Ft
    • $232,143 per Acre

    64 Westcott Rd, Killingly, CT 06239

    Vacant land, undeveloped. Buyers to do due diligence.

    Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    64 Westcott Rd, Killingly, CT 06239
  • 4 Skylark Ln Unit 4, Killingly, CT 06239

    $495,000

    Sold Sep 12, 2025

    4 Skylark Ln Unit 4, Killingly, CT 06239

    • 2 Beds
    • 2 Baths
    • 1,613 Sq Ft
    • Built 2017

    Last Sold Summary

    • $307/SF
    • 17 Days On Market

    Current Estimated Value $490,112

    Last Listing Agent Cary Marcoux RE/MAX Bell Park Realty

    4 Skylark Ln Unit 4, Killingly, CT 06239
  • /36

    $499,900

    $40K PRICE DROP Under Contract
    • 9 Beds
    • 3.5 Baths
    • 5,046 Sq Ft

    115 Grove St, Putnam, CT 06260

    INSTANT EQUITY in this beautiful and incredibly spacious two-family home. Sellers just had the home independently appraised for more than their asking price! With 10 foot ceilings throughout this turn of the century manse, the first floor unit features over 2,100 sq ft of living space with 3 large bedrooms, formal dining room, 2 full baths (1 roll-in handicap accessible, fully tiled with shower

    Gerard Hartmann Rockoff Realty

    115 Grove St, Putnam, CT 06260
  • 34 Taft St, Danielson, CT 06239

    $435,000

    Sold Aug 15, 2025

    34 Taft St, Danielson, CT 06239

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • Built 1978

    Last Sold Summary

    • 10% Above List Price
    • $322/SF
    • 2 Days On Market

    Current Estimated Value $427,050

    Last Listing Agent Elizabeth Scranton Kazantzis Real Estate, LLC

    34 Taft St, Danielson, CT 06239
  • /16

    $299,900

    Pending
    • 2 Beds
    • 1 Bath
    • 480 Sq Ft

    339 Ference Rd, Ashford, CT 06278

    Best and final offer deadline Thursday May 21tst 6:00 p.m.____Nestled in the sought-after Lake Chaffee community, this charming 2-bedroom year-round cottage offers the perfect blend of cozy comfort and lakeside living. Whether you're searching for a peaceful full-time residence or a weekend retreat, this inviting home delivers the quintessential Connecticut lake lifestyle._____ Inside, you'll

    Lynsie M. White KW Legacy Partners

    339 Ference Rd, Ashford, CT 06278
  • 12 Ann St, Plainfield, CT 06374

    $467,500

    Sold Dec 08, 2025

    12 Ann St, Plainfield, CT 06374

    • 6 Beds
    • 3.5 Baths
    • 2,547 Sq Ft
    • Built 1967

    Last Sold Summary

    • 5% Below List Price
    • $184/SF
    • 41 Days On Market

    Current Estimated Value $470,813

    Last Listing Agent Benjamin Carbone Lamacchia Realty

    12 Ann St, Plainfield, CT 06374
    • 11 Bigelow Rd, Hampton, CT 06247

      Est $309,598

      Not Listed For Sale

      11 Bigelow Rd, Hampton, CT 06247

      • 2 Beds
      • 1.5 Baths
      • 1,092 Sq Ft
      • Built 1968
      11 Bigelow Rd, Hampton, CT 06247

      Last Sold Summary

      • 27 Days On Market

  • /5

    $49,900

    Pending
    • Land
    • 21,780 Sq Ft
    • $99,800 per Acre

    0 Bebbington Rd, Ashford, CT 06278

    Half-Acre Parcel - Opportunity Awaits Discover the potential of this .50-acre parcel offering a peaceful setting with room to bring your vision to life. Whether you're exploring future development possibilities or seeking land as a long-term investment, this property presents a valuable opportunity in today's market. The lot is being sold as-is. Buildability and permitted uses are unknown. Buyers

    Lisa Burns KW Legacy Partners

    0 Bebbington Rd, Ashford, CT 06278
  • 19 Church St, Plainfield, CT 06374

    $300,000

    Sold May 29, 2026

    19 Church St, Plainfield, CT 06374

    • 4 Beds
    • 1 Bath
    • 1,533 Sq Ft
    • Built 1921

    Last Sold Summary

    • $196/SF
    • 5 Days On Market

    Current Estimated Value $299,267

    Last Listing Agent William Johnston Coldwell Banker Realty

    19 Church St, Plainfield, CT 06374
  • /8

    $99,900

    • Land
    • 2.17 Acres
    • $46,037 per Acre

    26 Bass Ln, Brooklyn, CT 06234

    Welcome to 26 Bass Lane. Total package consist of 8 lots consisting of 1.83 acres combined. Roughly 250 feet road frontage on Happy Lane while 26 Bass lane is the interior property sharing the road with just one other house. Property has been used for gardening and raising sheep. Mostly cleared dry, high and level land. Two sheds will remain. If you're looking for a quiet, spacious lot with lots

    Catherine Howard Berkshire Hathaway NE Prop.

    26 Bass Ln, Brooklyn, CT 06234
  • 738 Squaw Rock Rd, Moosup, CT 06354

    $350,000

    Sold Jul 18, 2025

    738 Squaw Rock Rd, Moosup, CT 06354

    • 3 Beds
    • 2 Baths
    • 2,712 Sq Ft
    • Built 1969

    Last Sold Summary

    • 11% Below List Price
    • $129/SF
    • 48 Days On Market

    Current Estimated Value $355,971

    Last Listing Agent Mark Benard Brunet and Company Real Estate

    738 Squaw Rock Rd, Moosup, CT 06354
  • /31

    $335,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,050 Sq Ft

    7 Old Cranston Rd, Sterling, CT 06377

    Nicely maintained home nicely tucked away on 1.87 acre lot on non thru street just minutes from the Rhode Island line. Large eat i n kitchen with slider to large deck for all your summer picnics. Gleaming floors in your living room and hall to bedrooms. Primary bedroom has convenient half bath. Roof is 2003, windows 2 years old, newer efficient hot water heater. Fully finished lower level with

    Cathy Duprey Duprey Real Estate, LLC

    7 Old Cranston Rd, Sterling, CT 06377
  • 28 Crooked Trail, Woodstock, CT 06281

    $420,000

    Sold Jul 18, 2025

    28 Crooked Trail, Woodstock, CT 06281

    • 3 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Built 1984

    Last Sold Summary

    • 5% Below List Price
    • $261/SF
    • 80 Days On Market

    Current Estimated Value $440,336

    Last Listing Agent Rich Jenkins Real Broker CT, LLC

    28 Crooked Trail, Woodstock, CT 06281
  • /32

    $285,000

    Pending
    • 3 Beds
    • 1 Bath
    • 912 Sq Ft

    252 Roanoak Ave, Willimantic, CT 06226

    This charming, move in ready, three bedroom, two bathroom home offers comfort, convenience, and flexibility in a great location close to Windham Middle School and Eastern Connecticut State University. Featuring 912 sq ft of living space on the upper level, plus a partially finished walk-out basement, the lower level includes a full bath and mini kitchenette, offering great potential for an in-law

    Franchesca Pescatello Prue Realty LLC

    252 Roanoak Ave, Willimantic, CT 06226
  • 291 Bingham Rd Unit 8, Canterbury, CT 06331

    $140,000

    Sold Jun 10, 2025

    291 Bingham Rd Unit 8, Canterbury, CT 06331

    • 2 Beds
    • 2 Baths
    • 938 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $149/SF
    • 57 Days On Market

    Last Listing Agent Jennifer Holt Coldwell Banker Realty

    291 Bingham Rd Unit 8, Canterbury, CT 06331
  • /28

    $679,900

    • 4 Beds
    • 2.5 Baths
    • 3,038 Sq Ft

    12 Red Oak Dr, Danielson, CT 06239

    Set back from the road, this spacious 4 bedroom, 2.5 bath Colonial offers the perfect blend of privacy, comfort, and summer fun with a beautiful 2.5 year old heated inground pool. A welcoming covered wraparound porch, paved drive, oversized 2 car garage, and dramatic two story foyer create a stunning first impression the moment you walk inside. The main level features an inviting eat in kitchen

    Kara Mazzola First Choice Realty

    12 Red Oak Dr, Danielson, CT 06239
  • 24 Plaza St, Brooklyn, CT 06234

    $400,000

    Sold Jun 27, 2025

    24 Plaza St, Brooklyn, CT 06234

    • 3 Beds
    • 1 Bath
    • 2,326 Sq Ft
    • Built 1962

    Last Sold Summary

    • 11% Below List Price
    • $172/SF
    • 30 Days On Market

    Current Estimated Value $403,384

    Last Listing Agent Missy Greene eXp Realty

    24 Plaza St, Brooklyn, CT 06234
  • /15

    $389,900

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    633 Wauregan Rd, Brooklyn, CT 06234

    2 full nice bathrooms and 3 bedrooms with one having access to fully finished and heated attic. Dining room could be used as a first floor bedroom with closet. New 4 bedroom septic installed.

    Ray Preece Signature Properties of N.E.

    633 Wauregan Rd, Brooklyn, CT 06234
  • 19 High St, Moosup, CT 06354

    $230,000

    Sold Jul 31, 2025

    19 High St, Moosup, CT 06354

    • 3 Beds
    • 2 Baths
    • 1,652 Sq Ft
    • Built 1876

    Last Sold Summary

    • 23% Below List Price
    • $139/SF
    • 233 Days On Market

    Current Estimated Value $254,465

    Last Listing Agent Lexie Brunet Brunet and Company Real Estate

    19 High St, Moosup, CT 06354
    • 132 Geer Rd, Danielson, CT 06239

      Est $577,015

      Not Listed For Sale

      132 Geer Rd, Danielson, CT 06239

      • 3 Beds
      • 2.5 Baths
      • 2,583 Sq Ft
      • Built 2001
      132 Geer Rd, Danielson, CT 06239

      Last Sold Summary

      • 60 Days On Market

  • /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
  • 146 Lathrop Rd, Plainfield, CT 06374

    $572,900

    Sold Dec 12, 2025

    146 Lathrop Rd, Plainfield, CT 06374

    • 5 Beds
    • 3.5 Baths
    • 2,750 Sq Ft
    • Built 1995

    Last Sold Summary

    • 9% Below List Price
    • $208/SF
    • 14 Days On Market

    Last Listing Agent Irene Adams Signature Properties of N.E.

    146 Lathrop Rd, Plainfield, CT 06374
  • /38

    $630,000

    • 5 Beds
    • 2.5 Baths
    • 3,215 Sq Ft

    1645 Route 169, Woodstock, CT 06281

    Perched on a hilltop in Woodstock, admired for decades for those who drove past on scenic Route 169, this single owner home is being offered for the first time. Thoughtfully built, and cared for, inside and out. The house looks modest from the road, however there is a surprising 3215sqft of living space. The original home has a few additions, including a generous sized family room with a

    Lynn Converse RE/MAX Bell Park Realty

    1645 Route 169, Woodstock, CT 06281
  • 409 Pomfret Rd, Brooklyn, CT 06234

    $551,000

    Sold Sep 26, 2025

    409 Pomfret Rd, Brooklyn, CT 06234

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $216/SF
    • 8 Days On Market

    Current Estimated Value $553,383

    Last Listing Agent Ambre Theroux Berkshire Hathaway NE Prop.

    409 Pomfret Rd, Brooklyn, CT 06234
  • /40

    $1,695,000

    • 7 Beds
    • 5 Baths
    • 4,283 Sq Ft

    93 & 90-94 Upton Rd, Ashford, CT 06278

    GRAND LEGACY ESTATE ON 291.6 ACRES w/REMODELED HISTORIC PRIMARY RESIDENCE & 2 ACCESSORY DWELLINGS! Gracefully spanning 2 contiguous parcels, this exceptional Eastern CT sanctuary embodies a rare convergence of early American heritage, refined country living, & remarkable land stewardship. Discreetly set along a quiet, town-maintained road, 93 & 90-94 Upton Road unfolds as a singular offering of

    Kiara Rusconi William Raveis Real Estate

    93 & 90-94 Upton Rd, Ashford, CT 06278

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