46,235

Windham County, CT Homes

Section Image
    • 125 Main St, Sterling, CT 06377

      Est $288,726

      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

  • 4 Johns Cir Unit Lot 31, Sterling, CT 06377
    4 Johns Cir Unit Lot 31, Sterling, CT 06377
    4 Johns Cir Unit Lot 31, Sterling, CT 06377
    /35

    $369,000

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    4 Johns Cir Unit Lot 31, Sterling, CT 06377

    *To Be Built* Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Raised Ranch offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous Granite Kitchen, complete with a view of the valley while you do dishes! Enjoy the ease of a

    Patrick Farrell Compass Connecticut, LLC

    4 Johns Cir Unit Lot 31, Sterling, CT 06377
  • 121 Highland View Dr, Windham, CT 06266

    $50,000

    Sold Sep 26, 2025

    121 Highland View Dr, Windham, CT 06266

    • Land
    • 40,075 Sq Ft
    • $54,348 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 8 Days On Market

    Last Listing Agent Jeanne Crum Home Selling Team

    121 Highland View Dr, Windham, CT 06266
  • 34 Prince St, Danielson, CT 06239
    34 Prince St, Danielson, CT 06239
    34 Prince St, Danielson, CT 06239
    /13

    $299,900

    Pending
    • 1 Bed
    • 1 Bath
    • 832 Sq Ft

    34 Prince St, Danielson, CT 06239

    Welcome to this charming bungalow-style home located in the heart of Danielson! This well-maintained 3-bedroom, 1-bath single-family residence offers approximately 1,165 square feet of comfortable living space, perfect for first-time buyers or those looking to downsize. Situated on a generous 0.42-acre level lot, the property provides ample outdoor space for entertaining and gardening. Solar

    Claritza Fong Torres Coldwell Banker Realty

    34 Prince St, Danielson, CT 06239
  • 256 Pine Hill Rd, Sterling, CT 06377

    $135,000

    Sold Aug 18, 2025

    256 Pine Hill Rd, Sterling, CT 06377

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft
    • Built 1955

    Last Sold Summary

    • 4% Above List Price
    • $188/SF
    • 5 Days On Market

    Current Estimated Value $144,424

    Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

    256 Pine Hill Rd, Sterling, CT 06377
  • 35 S Main St, Brooklyn, CT 06234
    35 S Main St, Brooklyn, CT 06234
    /2

    $200,000

    $50K PRICE DROP
    • Land
    • 34,848 Sq Ft
    • $250,000 per Acre

    35 S Main St, Brooklyn, CT 06234

    Bring your ideas for this commercial lot, centrally located in a high traffic area located right off route 6. Was previously approved for a 4800 sq.ft. retail/office building with two cutouts as an entrance/exit. Several options for commercial use such as retail shopping, office space, farmers market, restaurant, and more in the zoning regulations.

    Andrew Kausch Kazantzis Real Estate, LLC

    35 S Main St, Brooklyn, CT 06234
  • 245 Brooklyn Rd, Canterbury, CT 06331

    $725,000

    Sold Jan 23, 2026

    245 Brooklyn Rd, Canterbury, CT 06331

    • 4 Beds
    • 2.5 Baths
    • 3,285 Sq Ft
    • Built 1787

    Last Sold Summary

    • 8% Below List Price
    • $221/SF
    • 64 Days On Market

    Current Estimated Value $718,899

    Last Listing Agent Cary Marcoux RE/MAX Bell Park Realty

    245 Brooklyn Rd, Canterbury, CT 06331
  • 0 Pond St Unit 24037041, Plainfield, CT 06374
    0 Pond St Unit 24037041, Plainfield, CT 06374
    0 Pond St Unit 24037041, Plainfield, CT 06374
    /8

    $28,900

    $2K PRICE INCREASE Pending
    • Land
    • 5,227 Sq Ft
    • $240,833 per Acre

    0 Pond St Unit 24037041, Plainfield, CT 06374

    APPROVED BUILDING LOT! Perfect lot to place a modular home or a conventional build. Level lot with public sewer in street. Minutes from I-395, and Rhode Island. Close to all amenities. Priced to SELL!!!

    Dale Bunn Riverview Realty, LLC

    0 Pond St Unit 24037041, Plainfield, CT 06374
  • 43 Hiawatha Heights, Woodstock Valley, CT 06282

    $789,000

    Sold Aug 15, 2025

    43 Hiawatha Heights, Woodstock Valley, CT 06282

    • 2 Beds
    • 2 Baths
    • 1,918 Sq Ft
    • Built 1988

    Last Sold Summary

    • $411/SF
    • 42 Days On Market

    Current Estimated Value $795,011

    Last Listing Agent Jennie Kesselman Berkshire Hathaway NE Prop.

    43 Hiawatha Heights, Woodstock Valley, CT 06282
  • 13 Henry Dr, Moosup, CT 06354
    13 Henry Dr, Moosup, CT 06354
    13 Henry Dr, Moosup, CT 06354
    /39

    $415,000

    $10K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,304 Sq Ft

    13 Henry Dr, Moosup, CT 06354

    Welcome to 13 Henry Drive, a beautifully maintained ranch-style home designed for comfort, convenience, and easy living. Step inside to an inviting open floor plan highlighted by an upgraded kitchen featuring granite countertops and stainless-steel appliances. Perfect for both everyday living and entertaining. The spacious primary bedroom offers a private ensuite bath with a walk-in shower,

    Michael Houser, Jr. Capital Property Group, LLC

    13 Henry Dr, Moosup, CT 06354
  • 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
  • 651 Cook Hill Rd, Danielson, CT 06239
    651 Cook Hill Rd, Danielson, CT 06239
    651 Cook Hill Rd, Danielson, CT 06239
    /8

    $849,900

    Open Sat 12PM - 2PM Coming Soon
    • 5 Beds
    • 3 Baths
    • 2,246 Sq Ft

    651 Cook Hill Rd, Danielson, CT 06239

    Rare opportunity to own 32 breathtaking acres ideal for multi-generational living, farming, horses, recreation, a private compound/family homestead or even potential income-producing ventures. The beautifully updated circa-1920 farmhouse offers 5 bedrooms, 3 full baths, and a flexible office/bonus room with closet. Recent renovations blend modern convenience with timeless farmhouse charm and

    Joseph Bonneau eXp Realty

    651 Cook Hill Rd, Danielson, CT 06239
  • 1350 Thompson Rd, Thompson, CT 06277

    $620,000

    Sold May 11, 2026

    1350 Thompson Rd, Thompson, CT 06277

    • 3 Beds
    • 2.5 Baths
    • 2,610 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Above List Price
    • $238/SF
    • 3 Days On Market

    Current Estimated Value $605,354

    Last Listing Agent Christine Johnson RE/MAX One

    1350 Thompson Rd, Thompson, CT 06277
  • 278 N Bigelow Rd, Hampton, CT 06247
    278 N Bigelow Rd, Hampton, CT 06247
    278 N Bigelow Rd, Hampton, CT 06247
    /40

    $339,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,085 Sq Ft

    278 N Bigelow Rd, Hampton, CT 06247

    Set on 13.75 acres of beautiful wooded land in Hampton, CT, this unique colonial single family with in-law property offers space, character, and endless potential. Featuring 4 bedrooms and 3.5 bathrooms, the home showcases warm wooden floors, a cozy wood stoves, multiple closets for abundant storage, and an unfinished basement for additional storage. Enjoy peaceful outdoor living with a charming

    Thomas Mele Social & Co Realty

    278 N Bigelow Rd, Hampton, CT 06247
  • 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 $405,371

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    16 Porter Plain Rd, Thompson, CT 06277
    • 61 Laiho Rd, Sterling, CT 06377

      Est $315,927

      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

  • 74 Perry St Unit 183, Putnam, CT 06260
    74 Perry St Unit 183, Putnam, CT 06260
    74 Perry St Unit 183, Putnam, CT 06260
    /30

    $329,900

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    74 Perry St Unit 183, Putnam, CT 06260

    Welcome to easy, low-maintenance condo living in the heart of Putnam! This well-appointed 2-bedroom, 1.5-bath home offers a bright and inviting main level featuring a sun-filled living room with beautiful hardwood floors and direct access to a private wood deck-perfect for seamless indoor/outdoor living. The kitchen is designed for both function and comfort, complete with a dining area, pantry

    Genevieve Botelho Lamacchia Realty

    74 Perry St Unit 183, Putnam, CT 06260
  • 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 $343,710

    Last Listing Agent Gregory Hanner Garden Realty

    5 Chappell St, Chaplin, CT 06235
  • 221 Eastford Rd, Eastford, CT 06242
    221 Eastford Rd, Eastford, CT 06242
    221 Eastford Rd, Eastford, CT 06242
    /37

    $350,000

    Pending
    • 2 Beds
    • 1 Bath
    • 888 Sq Ft

    221 Eastford Rd, Eastford, CT 06242

    ** Highest & Best Deadline for Monday 5/11 at 10 AM** .Step into this thoughtfully crafted post-and-beam home set on over 3 peaceful acres, with the Still River gently running through the property. Built in 1985, it offers warmth, character, and a serene setting with frequent wildlife sightings. The spacious eat-in kitchen features a walk-in pantry, custom island, and sliding barn door, along

    Skyla Gagnon RE/MAX Bell Park Realty

    221 Eastford Rd, Eastford, CT 06242
  • 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 $427,257

    Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

    50 Crooked Trail, Woodstock, CT 06281
  • 177 Slater Hill Rd, Dayville, CT 06241
    177 Slater Hill Rd, Dayville, CT 06241
    177 Slater Hill Rd, Dayville, CT 06241
    /36

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,062 Sq Ft

    177 Slater Hill Rd, Dayville, CT 06241

    Circa 1870 Colonial farmhouse blending vintage character with thoughtful updates, offering 2,062 sqft, 4 bedrooms & 2 full baths on 3.53 picturesque acres of rolling farmland. Inside, rustic charm meets everyday comfort with vinyl & wood plank flooring, an eat-in kitchen & formal dining room. An humongous 3-season room w/electric fireplace creates the perfect gathering space, while replacement

    Sharon Pelletier Hope Real Estate Group, Inc.

    177 Slater Hill Rd, Dayville, CT 06241
  • 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
  • 13 Bates Rd, Chaplin, CT 06235
    13 Bates Rd, Chaplin, CT 06235
    13 Bates Rd, Chaplin, CT 06235
    /36

    $449,900

    • 5 Beds
    • 2.5 Baths
    • 2,887 Sq Ft

    13 Bates Rd, Chaplin, CT 06235

    Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra

    Kristen Merrill Countryside Realty

    13 Bates Rd, Chaplin, CT 06235
  • 0 Lustig Rd, Ashford, CT 06278

    $80,000

    Sold Aug 29, 2025

    0 Lustig Rd, Ashford, CT 06278

    • Land
    • 13.18 Acres
    • $6,070 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 10 Days On Market

    Last Listing Agent Amy Rio Better Homes and Gardens Real Estate Executive Real Estate

    0 Lustig Rd, Ashford, CT 06278
  • 45 Breaults Landing Rd, Thompson, CT 06277
    45 Breaults Landing Rd, Thompson, CT 06277
    45 Breaults Landing Rd, Thompson, CT 06277
    /36

    $349,900

    $10K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,643 Sq Ft

    45 Breaults Landing Rd, Thompson, CT 06277

    Enjoy the serenity of lake living with water views and sunset skies. Elevated home has 1,643 sqft, 2-bed, 2-bath home overlooking Quaddick Lake with panoramic water views and deeded water privileges. The primary suite features vaulted ceilings, a skylight, and beautiful lake views, creating a bright, airy space. A flexible loft area adds versatility for a variety of uses. The open concept main

    Christine Johnson RE/MAX One

    45 Breaults Landing Rd, Thompson, CT 06277
  • 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 $396,724

    Last Listing Agent Derek Greene Derek Greene

    1370 Plainfield Pike, Sterling, CT 06377
    • 78 Smith Rd, Moosup, CT 06354

      Est $483,516

      Not Listed For Sale

      78 Smith Rd, Moosup, CT 06354

      • 3 Beds
      • 1 Bath
      • 2,493 Sq Ft
      • Built 1962
      78 Smith Rd, Moosup, CT 06354

      Last Sold Summary

      • 8 Days On Market

  • 85 Wauregan Rd, Danielson, CT 06239
    85 Wauregan Rd, Danielson, CT 06239
    85 Wauregan Rd, Danielson, CT 06239
    /12

    $215,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,446 Sq Ft

    85 Wauregan Rd, Danielson, CT 06239

    Check out this antique Cape just minutes from downtown Danielson! This home has 3 bedrooms located on the upper floor, with plenty of flexible space. The primary floor has many wonderful features including a large kitchen that opens up to the back deck, a full bath, and a dining space. Enjoy overlooking the yard from the enclosed deck! Plumbing did not hold positive air pressure at the time of

    Ryan King Aspen Realty Group

    85 Wauregan Rd, Danielson, CT 06239
  • 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 $332,341

    Last Listing Agent Kyle West eXp Realty

    164 Tower Hill Rd, Chaplin, CT 06235
    • 78 Cranska Rd, Moosup, CT 06354

      Est $369,521

      Not Listed For Sale

      78 Cranska Rd, Moosup, CT 06354

      • 3 Beds
      • 2 Baths
      • 2,582 Sq Ft
      • Built 1963
      78 Cranska Rd, Moosup, CT 06354

      Last Sold Summary

      • 42 Days On Market

Showing Results 281 - 320, Page 8 of 18

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