45,761

Windham County, CT Homes

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  • 123 Ashford Rd Unit 4, Eastford, CT 06242
    123 Ashford Rd Unit 4, Eastford, CT 06242
    123 Ashford Rd Unit 4, Eastford, CT 06242
    /37

    $359,900

    Open Sat 1PM - 2:30PM $9K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,513 Sq Ft

    123 Ashford Rd Unit 4, Eastford, CT 06242

    Modern, low-maintenance living meets the tranquility of Eastford in this beautifully appointed 2-bedroom, 2-bath stand-alone condo offering approximately 1,513 square feet of thoughtfully designed living space. Built in 2019, this home offers the feel of a newer property with the convenience of condo living and no exterior maintenance to worry about. The bright, open-concept layout features

    Joshua Somers P&H Property Consulting, Inc.

    123 Ashford Rd Unit 4, Eastford, CT 06242
  • 16 Pond Way, North Windham, CT 06256

    $72,000

    Sold Apr 30, 2026

    16 Pond Way, North Windham, CT 06256

    • 2 Beds
    • 2 Baths
    • 1,218 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Above List Price
    • $59/SF
    • 5 Days On Market

    Last Listing Agent Stephen Daly KW Legacy Partners

    16 Pond Way, North Windham, CT 06256
    • 244 Snake Meadow Hill Rd, Sterling, CT 06377

      Est $476,002

      Not Listed For Sale

      244 Snake Meadow Hill Rd, Sterling, CT 06377

      • 3 Beds
      • 2.5 Baths
      • 1,764 Sq Ft
      • Built 2007
      244 Snake Meadow Hill Rd, Sterling, CT 06377

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Christine Johnson RE/MAX One

  • 943 N Main St, Danielson, CT 06239
    943 N Main St, Danielson, CT 06239
    943 N Main St, Danielson, CT 06239
    /9

    $349,900

    Coming Soon
    • 6 Beds
    • 2 Baths
    • 1,976 Sq Ft

    943 N Main St, Danielson, CT 06239

    2024 Siding redone and painted $20,000, 2021 Chimney Repointed, chimney cap and new liner installed $2000. 2021 Gas Furnace in Unit B $7000. 2019 New ROOF. CITY WATER, SEWER, GAS! HUGE Side Yard .82 acres (playground does not convey) One Unit will be ready to occupy or rent and make your own lease. Each side has their own DECK, pay their own utilities/heat.

    Christine Johnson RE/MAX One

    943 N Main St, Danielson, CT 06239
  • 16 Porter Plain Rd, Thompson, CT 06277

    $400,000

    Sold Oct 03, 2025

    16 Porter Plain Rd, Thompson, CT 06277

    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft
    • Built 1974

    Last Sold Summary

    • 5% Above List Price
    • $204/SF
    • 3 Days On Market

    Current Estimated Value $431,899

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    16 Porter Plain Rd, Thompson, CT 06277
    • 125 Main St, Sterling, CT 06377

      Est $297,382

      Not Listed For Sale

      125 Main St, Sterling, CT 06377

      • 3 Beds
      • 1 Bath
      • 2,016 Sq Ft
      • Built 1900
      125 Main St, Sterling, CT 06377

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Skyla Gagnon RE/MAX Bell Park Realty

  • 117 Pineville Rd, Dayville, CT 06241
    117 Pineville Rd, Dayville, CT 06241
    117 Pineville Rd, Dayville, CT 06241
    /9

    $299,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 1 Bath
    • 1,386 Sq Ft

    117 Pineville Rd, Dayville, CT 06241

    A classic New England ranch, tucked away in a setting that feels like your own little escape. Built in 1949 and set well back from the road, this 3-bedroom, 1-bath, 1,386-square-foot home sits on .71 acres beneath a canopy of mature trees, with a sprawling lawn, plenty of privacy, and the kind of peaceful setting that immediately makes you want to stay awhile. Inside, you'll find the charm and

    Bridget Voght Compass Connecticut, LLC

    117 Pineville Rd, Dayville, CT 06241
  • 11 Munyan Rd, Putnam, CT 06260

    $475,000

    Sold Aug 10, 2026

    11 Munyan Rd, Putnam, CT 06260

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $265/SF
    • 2 Days On Market

    Current Estimated Value $461,393

    Last Listing Agent Donna Navarro Signature Properties of N.E.

    11 Munyan Rd, Putnam, CT 06260
    • 33 Railroad Ave, Sterling, CT 06377

      Est $515,865

      Not Listed For Sale

      33 Railroad Ave, Sterling, CT 06377

      • 3 Beds
      • 3 Baths
      • 2,586 Sq Ft
      • Built 2004
      33 Railroad Ave, Sterling, CT 06377

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Christine Johnson RE/MAX One

  • 874 Brook Rd, Hampton, CT 06427
    874 Brook Rd, Hampton, CT 06427
    874 Brook Rd, Hampton, CT 06427
    /38

    $565,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    874 Brook Rd, Hampton, CT 06427

    STUNNING 2026 new construction home on almost 2 ACRES. Showcasing open concept living with functional bright kitchen QUARTZ counters and island, stainless appliances, modern lighting and vaulted ceiling. CUSTOM craftsmanship throughout. 16 x 16 trex DECK ($15,000) overlooking back yard. Primary bedroom has a VAULTED ceiling, primary bathroom TILED shower, tiled flooring and GRANITE vanity.

    Christine Johnson RE/MAX One

    874 Brook Rd, Hampton, CT 06427
  • 5 Chappell St, Chaplin, CT 06235

    $355,000

    Sold Jan 14, 2026

    5 Chappell St, Chaplin, CT 06235

    • 3 Beds
    • 2.5 Baths
    • 1,748 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Above List Price
    • $203/SF
    • 53 Days On Market

    Current Estimated Value $355,819

    Last Listing Agent Gregory Hanner Garden Realty

    5 Chappell St, Chaplin, CT 06235
    • 629 Margaret Henry Rd, Sterling, CT 06377

      Est $514,739

      Not Listed For Sale

      629 Margaret Henry Rd, Sterling, CT 06377

      • 3 Beds
      • 3 Baths
      • 2,156 Sq Ft
      • Built 2003
      629 Margaret Henry Rd, Sterling, CT 06377

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Christine Johnson RE/MAX One

  • 272 Horse Hill Rd, Ashford, CT 06278
    272 Horse Hill Rd, Ashford, CT 06278
    272 Horse Hill Rd, Ashford, CT 06278
    /40

    $599,000

    $100K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,634 Sq Ft

    272 Horse Hill Rd, Ashford, CT 06278

    Nestled at the end of a long, winding driveway, this exquisite Colonial home offers timeless New England elegance on over three private, picturesque acres. Surrounded by classic stone walls, sprawling lawns, mature gardens, and inviting outdoor dining spaces, this exceptional property is a secluded retreat rich in historic details and charm. Inside, you'll find four spacious bedrooms with one on

    Jay Kelly William Raveis Real Estate

    272 Horse Hill Rd, Ashford, CT 06278
  • 16 Walnut Rd, Woodstock, CT 06281

    $409,900

    Sold Jul 31, 2026

    16 Walnut Rd, Woodstock, CT 06281

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Above List Price
    • $330/SF
    • 5 Days On Market

    Current Estimated Value $411,376

    Last Listing Agent Conrad Allen RE/MAX Professional Associates

    16 Walnut Rd, Woodstock, CT 06281
    • 910 Plainfield Pike, Sterling, CT 06377

      Est $516,861

      Not Listed For Sale

      910 Plainfield Pike, Sterling, CT 06377

      • 3 Beds
      • 2.5 Baths
      • 2,820 Sq Ft
      • Built 2008
      910 Plainfield Pike, Sterling, CT 06377

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Paula Decubellis Brian Buonaiuto

  • 61 Red Cedar Rd, Woodstock Valley, CT 06282
    61 Red Cedar Rd, Woodstock Valley, CT 06282
    61 Red Cedar Rd, Woodstock Valley, CT 06282
    /37

    $549,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft

    61 Red Cedar Rd, Woodstock Valley, CT 06282

    There's something special about being the first to call a brand-new home your own! Set within a desirable Bunggee lake community in Woodstock Valley, this new construction Cape offers approximately 2,230 sq. ft. of finished living space across three levels with 3 bedrooms and 2.5 baths. The main level features an expansive wraparound kitchen, sliders leading to the back deck, and two separate

    Sheena Ruggirello Real Broker CT, LLC

    61 Red Cedar Rd, Woodstock Valley, CT 06282
  • 50 Crooked Trail, Woodstock, CT 06281

    $395,000

    Sold Nov 03, 2025

    50 Crooked Trail, Woodstock, CT 06281

    • 3 Beds
    • 3 Baths
    • 2,339 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Below List Price
    • $169/SF
    • 16 Days On Market

    Current Estimated Value $461,268

    Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

    50 Crooked Trail, Woodstock, CT 06281
    • 13 Sterling Ridge Ln, Sterling, CT 06377

      Est $386,161

      Not Listed For Sale

      13 Sterling Ridge Ln, Sterling, CT 06377

      • 3 Beds
      • 2.5 Baths
      • 1,669 Sq Ft
      • Built 2007
      13 Sterling Ridge Ln, Sterling, CT 06377

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Anthony Chabot Chabot & Associates Real Estate

  • 80 Aldrich Rd, Putnam, CT 06260
    80 Aldrich Rd, Putnam, CT 06260
    80 Aldrich Rd, Putnam, CT 06260
    /27

    $789,900

    New Construction $20K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 2,032 Sq Ft

    80 Aldrich Rd, Putnam, CT 06260

    *Pictures are similar to built* Discover the convenience of one-level living in this beautifully crafted new to-be-built construction ranch offering 2,032 square feet of thoughtfully designed space. Featuring 3 bedrooms and 2 full baths, this home blends comfort and style with an open-concept kitchen, dining, and living area - perfect for entertaining or everyday living. A stunning four-season

    Georgi Morin S.C.E. Real Estate

    80 Aldrich Rd, Putnam, CT 06260
  • 10 School Street Extension, Plainfield, CT 06374

    $399,000

    Sold Feb 20, 2026

    10 School Street Extension, Plainfield, CT 06374

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft
    • Built 2025

    Last Sold Summary

    • 13% Below List Price
    • $219/SF
    • 63 Days On Market

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

    10 School Street Extension, Plainfield, CT 06374
    • 562 Sterling Rd, Sterling, CT 06377

      Est $553,981

      Not Listed For Sale

      562 Sterling Rd, Sterling, CT 06377

      • 3 Beds
      • 2 Baths
      • 2,096 Sq Ft
      • Built 2002
      562 Sterling Rd, Sterling, CT 06377

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Michele Geragotelis RE/MAX Bell Park Realty

  • 73 Lakeview Dr, Ashford, CT 06278
    73 Lakeview Dr, Ashford, CT 06278
    73 Lakeview Dr, Ashford, CT 06278
    /40

    $384,900

    • 2 Beds
    • 1 Bath
    • 848 Sq Ft

    73 Lakeview Dr, Ashford, CT 06278

    Lakefront living at its best on beautiful Lake Chaffee! This considerately renovated two bedroom, one full-bath cottage offers the perfect blend of charm, comfort, and modern updates. Features include a versatile loft, propane heating stove, generator hookup, new roof, and new electrical and plumbing throughout. Enjoy relaxing or entertaining on the spacious deck overlooking the lake, with a

    Franchesca Pescatello Prue Realty LLC

    73 Lakeview Dr, Ashford, CT 06278
  • 1370 Plainfield Pike, Sterling, CT 06377

    $402,000

    Sold Apr 24, 2026

    1370 Plainfield Pike, Sterling, CT 06377

    • 5 Beds
    • 2 Baths
    • 1,498 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Above List Price
    • $268/SF
    • 14 Days On Market

    Current Estimated Value $416,277

    Last Listing Agent Derek Greene Derek Greene

    1370 Plainfield Pike, Sterling, CT 06377
    • 1100 Plainfield Pike, Sterling, CT 06377

      Est $228,007

      Not Listed For Sale

      1100 Plainfield Pike, Sterling, CT 06377

      • 3 Beds
      • 1 Bath
      • 1,920 Sq Ft
      • Built 1750
      1100 Plainfield Pike, Sterling, CT 06377

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Paul Stone Kazantzis Real Estate, LLC

  • 19 North Rd, Ashford, CT 06278
    19 North Rd, Ashford, CT 06278
    19 North Rd, Ashford, CT 06278
    /29

    $389,900

    • 4 Beds
    • 1 Bath
    • 2,332 Sq Ft

    19 North Rd, Ashford, CT 06278

    Welcome to the Benjamin Clarke House - a grand 1700s center entrance colonial located on a 2-acre country lot - complete with rolling lawn, gardens, restored shed and a pond. Spacious house with much restoration complete - 2 upstairs rooms and a bathroom still to be completed by the new owners. Charm and warmth prevail in this beautiful home, including wide board floors, fabulous stone fireplaces

    Tom Ferguson ERA Blanchard & Rossetto

    19 North Rd, Ashford, CT 06278
  • 164 Tower Hill Rd, Chaplin, CT 06235

    $352,500

    Sold May 22, 2026

    164 Tower Hill Rd, Chaplin, CT 06235

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Above List Price
    • $350/SF
    • 4 Days On Market

    Current Estimated Value $358,987

    Last Listing Agent Kyle West eXp Realty

    164 Tower Hill Rd, Chaplin, CT 06235
    • 637 Margaret Henry Rd, Sterling, CT 06377

      Est $498,769

      Not Listed For Sale

      637 Margaret Henry Rd, Sterling, CT 06377

      • 4 Beds
      • 2.5 Baths
      • 2,254 Sq Ft
      • Built 2005
      637 Margaret Henry Rd, Sterling, CT 06377

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Christine Johnson RE/MAX One

  • 0 West Pkwy, Plainfield, CT 06374
    0 West Pkwy, Plainfield, CT 06374
    0 West Pkwy, Plainfield, CT 06374
    /5

    $399,900

    • Land
    • 8.29 Acres
    • $48,239 per Acre

    0 West Pkwy, Plainfield, CT 06374

    Positioned within a well-established industrial park, this 8+ acre parcel offers a prime opportunity for industrial development just 1/2 mile from Interstate 395, providing excellent regional access for transportation, logistics, and distribution operations. The property's location allows for efficient connectivity to major Northeast markets, making it ideal for manufacturing, warehousing,

    Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    0 West Pkwy, Plainfield, CT 06374
  • 25 Snake Meadow Rd, Moosup, CT 06354

    $349,900

    Sold Apr 03, 2026

    25 Snake Meadow Rd, Moosup, CT 06354

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1982

    Last Sold Summary

    • $350/SF
    • 34 Days On Market

    Current Estimated Value $356,954

    Last Listing Agent Rachael Gifford The Neighborhood Realty Group

    25 Snake Meadow Rd, Moosup, CT 06354
    • 53 Brookstone Dr, Sterling, CT 06377

      Est $1,060,208

      Not Listed For Sale

      53 Brookstone Dr, Sterling, CT 06377

      • 5 Beds
      • 3.5 Baths
      • 5,462 Sq Ft
      • Built 2006
      53 Brookstone Dr, Sterling, CT 06377

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Kyle Seyboth Century 21 Limitless

  • 33 MacHine Shop Hill Rd, South Windham, CT 06266
    33 MacHine Shop Hill Rd, South Windham, CT 06266
    33 MacHine Shop Hill Rd, South Windham, CT 06266
    /30

    $549,900

    • 4 Beds
    • 3.5 Baths
    • 2,548 Sq Ft

    33 MacHine Shop Hill Rd, South Windham, CT 06266

    Historic 1850 Charm with Modern Updates & In-Law Living! Step inside this beautifully remodeled 1850 home, thoughtfully updated for today's lifestyle while maintaining the character and charm that makes an older home so special. The main living portion of the home offers 3 spacious bedrooms, 2.5 baths, and a dedicated office space. The heart of the home features a bright and inviting open-concept

    Michele Geragotelis RE/MAX Bell Park Realty

    33 MacHine Shop Hill Rd, South Windham, CT 06266
  • 11 Breaults Landing Rd, Thompson, CT 06277

    $385,000

    Sold Jun 23, 2026

    11 Breaults Landing Rd, Thompson, CT 06277

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1974

    Last Sold Summary

    • $401/SF
    • 6 Days On Market

    Current Estimated Value $393,148

    Last Listing Agent Lauren Heidelberger Berkshire Hathaway NE Prop.

    11 Breaults Landing Rd, Thompson, CT 06277
    • 61 Laiho Rd, Sterling, CT 06377

      Est $322,851

      Not Listed For Sale

      61 Laiho Rd, Sterling, CT 06377

      • 4 Beds
      • 1.5 Baths
      • 1,566 Sq Ft
      • Built 1933
      61 Laiho Rd, Sterling, CT 06377

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Derek Greene Derek Greene

  • 0 Baxter Rd Unit 24177023, Woodstock, CT 06281
    0 Baxter Rd Unit 24177023, Woodstock, CT 06281
    0 Baxter Rd Unit 24177023, Woodstock, CT 06281
    /4

    $74,900

    $10K PRICE DROP Pending
    • Land
    • 21,780 Sq Ft
    • $149,800 per Acre

    0 Baxter Rd Unit 24177023, Woodstock, CT 06281

    Build your dream home near the lake! This unique offering includes two adjoining parcels being sold together for a combined total of approximately 0.7 acres. The primary 0.5-acre parcel features a beautiful cleared and level homesite with open grassy space, ideal for new construction. Previous perc testing and a site development plan in 2008 outlines proposed home placement, septic system, and

    Donna Bertram Signature Properties of N.E.

    0 Baxter Rd Unit 24177023, Woodstock, CT 06281
  • 470 Fabyan Rd, North Grosvenordale, CT 06255

    $445,000

    Sold May 08, 2026

    470 Fabyan Rd, North Grosvenordale, CT 06255

    • 3 Beds
    • 2 Baths
    • 1,910 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Above List Price
    • $233/SF
    • 9 Days On Market

    Current Estimated Value $472,098

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

    470 Fabyan Rd, North Grosvenordale, CT 06255
    • 242 Harris Rd, Sterling, CT 06377

      Est $658,025

      Not Listed For Sale

      242 Harris Rd, Sterling, CT 06377

      • 4 Beds
      • 3.5 Baths
      • 4,184 Sq Ft
      • Built 1977
      242 Harris Rd, Sterling, CT 06377

      Last Sold Summary

      • 322 Days On Market

      Last Listing Agent Jennifer Lehto Real Broker CT, LLC

  • 577 Fabyan Rd, North Grosvenordale, CT 06255
    577 Fabyan Rd, North Grosvenordale, CT 06255
    577 Fabyan Rd, North Grosvenordale, CT 06255
    /29

    $554,900

    New Construction $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,700 Sq Ft

    577 Fabyan Rd, North Grosvenordale, CT 06255

    Brand New Construction! Raised Ranch style home sitting on just over 1 AC abutting Army Corp of Engineers/protected land from the West Thompson Dam property. Home features 3 bedrooms 2.5 Bathrooms. A vaulted Kitchen/Dining/Living Room with gleaming true hardwood floors. A rear slider to the oversized back deck for entertaining & enjoying nature. All three bedrooms are located on the main level

    Ryan LaJoie Johnston & Associates Real Estate, LLC

    577 Fabyan Rd, North Grosvenordale, CT 06255
  • 1 First St, North Grosvenordale, CT 06255

    $365,000

    Sold Dec 22, 2025

    1 First St, North Grosvenordale, CT 06255

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • Built 2025

    Last Sold Summary

    • 9% Below List Price
    • $203/SF
    • 233 Days On Market

    Current Estimated Value $367,396

    Last Listing Agent Amy Brunet Brunet and Company Real Estate

    1 First St, North Grosvenordale, CT 06255
    • 297 Sabin St Unit 34, Putnam, CT 06260

      Est $469,262

      Not Listed For Sale

      297 Sabin St Unit 34, Putnam, CT 06260

      • 4 Beds
      • 3 Baths
      • 3,171 Sq Ft
      • Built 2018
      297 Sabin St Unit 34, Putnam, CT 06260

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Pat Malek First Choice Realty

  • 167 Old Tatnic Hill Rd Unit Lot 8-6, Brooklyn, CT 06234
    167 Old Tatnic Hill Rd Unit Lot 8-6, Brooklyn, CT 06234
    /2

    $475,000

    New Construction $25K PRICE INCREASE Pending
    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft

    167 Old Tatnic Hill Rd Unit Lot 8-6, Brooklyn, CT 06234

    Welcome to Brooklyn's newest subdivision! Six beautiful lots in a peaceful, quiet country setting. This lovely ranch style home is on a front lot, with a spacious yard, and a private driveway. Bright, open floorplan features a custom kitchen with granite counters, an island, and a door to the back deck, a large dining area and living room, and first floor laundry. Also on the main level is the

    Barbara Diaz RE/MAX Bell Park Realty

    167 Old Tatnic Hill Rd Unit Lot 8-6, Brooklyn, CT 06234

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