46,234

Windham County, CT Homes

Section Image
  • 33 Bassett Hill Rd, Woodstock, CT 06281

    $460,000

    Sold Dec 11, 2025

    33 Bassett Hill Rd, Woodstock, CT 06281

    • 3 Beds
    • 1.5 Baths
    • 2,258 Sq Ft
    • Built 1941

    Last Sold Summary

    • 10% Above List Price
    • $204/SF
    • 14 Days On Market

    Current Estimated Value $454,774

    Last Listing Agent Jonathan Bolano eXp Realty

    33 Bassett Hill Rd, Woodstock, CT 06281
  • 94 Little Pond Rd, Woodstock, CT 06281
    94 Little Pond Rd, Woodstock, CT 06281
    94 Little Pond Rd, Woodstock, CT 06281
    /20

    $369,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,118 Sq Ft

    94 Little Pond Rd, Woodstock, CT 06281

    Welcome home to this beautifully maintained 3-bedroom, 1-bath residence nestled on a generous half-acre lot. Perfectly situated for privacy and room to roam, the expansive yard offers endless possibilities-whether you dream of a lush garden, a fire-pit or gathering spot. Step inside and be greeted by warm hardwood floors that flow seamlessly throughout the entire home, creating a bright, cohesive

    Jessica Deojay RE/MAX Bell Park Realty

    94 Little Pond Rd, Woodstock, CT 06281
  • 25 Barlow Cemetery Rd, Woodstock Valley, CT 06282

    $490,000

    Sold Oct 03, 2025

    25 Barlow Cemetery Rd, Woodstock Valley, CT 06282

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Above List Price
    • $284/SF
    • 4 Days On Market

    Current Estimated Value $483,537

    Last Listing Agent Carol Ryniewicz CR Premier Properties

    25 Barlow Cemetery Rd, Woodstock Valley, CT 06282
  • 241 N Sterling Rd, Sterling, CT 06377
    241 N Sterling Rd, Sterling, CT 06377
    241 N Sterling Rd, Sterling, CT 06377
    /40

    $549,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    241 N Sterling Rd, Sterling, CT 06377

    Spacious, well-maintained 3-bedroom, 2-full-bath ranch set on two lots totaling 9.78 private acres. The open floor plan features cathedral ceilings in the living room and kitchen, creating a bright and airy feel. Recent updates include brand-new hardwood floors, windows, exterior doors, and an updated primary bath. The lower level offers a two-bay garage under the home with access to a paved

    Noah Houle RE/MAX Bell Park Realty

    241 N Sterling Rd, Sterling, CT 06377
  • 184 Phoenixville Rd, Chaplin, CT 06235

    $375,000

    Sold Oct 15, 2025

    184 Phoenixville Rd, Chaplin, CT 06235

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1790

    Last Sold Summary

    • 3% Below List Price
    • $203/SF
    • 20 Days On Market

    Current Estimated Value $372,756

    Last Listing Agent Derek Greene Derek Greene

    184 Phoenixville Rd, Chaplin, CT 06235
  • 45 Brooklyn Rd, Canterbury, CT 06331
    45 Brooklyn Rd, Canterbury, CT 06331
    /2

    $90,000

    • Land
    • 4.25 Acres
    • $21,176 per Acre

    45 Brooklyn Rd, Canterbury, CT 06331

    Located on country Rd. Lightly treed lot. Perc tested and septic plans available.

    Maura Von Deck Von Deck Realty, LLC

    45 Brooklyn Rd, Canterbury, CT 06331
  • 0 Rt 198, Woodstock, CT 06281

    $75,000

    Sold Oct 06, 2025

    0 Rt 198, Woodstock, CT 06281

    • Land
    • 9.64 Acres
    • $7,780 per Acre

    Last Sold Summary

    • 24% Below List Price
    • 198 Days On Market

    Last Listing Agent Nicole Gleason CR Premier Properties

    0 Rt 198, Woodstock, CT 06281
    • 15 Circle Dr, Ashford, CT 06278

      Est $278,310

      Not Listed For Sale

      15 Circle Dr, Ashford, CT 06278

      • 2 Beds
      • 1 Bath
      • 1,064 Sq Ft
      • Built 1964
      15 Circle Dr, Ashford, CT 06278

      Last Sold Summary

      • 4 Days On Market

  • 34 Courtney Ln, Sterling, CT 06377
    34 Courtney Ln, Sterling, CT 06377
    34 Courtney Ln, Sterling, CT 06377
    /39

    $599,900

    • 3 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    34 Courtney Ln, Sterling, CT 06377

    Set at the end of a quiet cul-de-sac in Sterling, this 3-bedroom, 2.5-bath colonial offers over 2,000 square feet of comfortable living space with the added bonus of a finished walkout basement. The main level features an expansive living room with a cozy propane fireplace, flowing seamlessly into the dining area and kitchen-creating an open, connected layout that's perfect for everyday living

    Sheena Ruggirello Real Broker CT, LLC

    34 Courtney Ln, Sterling, CT 06377
  • 132 Grove St, Putnam, CT 06260

    $335,000

    Sold Apr 17, 2026

    132 Grove St, Putnam, CT 06260

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1929

    Last Sold Summary

    • 4% Below List Price
    • $249/SF
    • 163 Days On Market

    Current Estimated Value $331,180

    Last Listing Agent Mat Chojnicki CR Premier Properties

    132 Grove St, Putnam, CT 06260
  • 0 Route 171, Woodstock, CT 06281
    0 Route 171, Woodstock, CT 06281
    /2

    $335,000

    • Land
    • 34.6 Acres
    • $9,682 per Acre

    0 Route 171, Woodstock, CT 06281

    Spanning just over 37 acres this raw land parcel offers a picturesque pond and a wooded landscape, creating a versatile setting with a variety of potential uses. A rare opportunity to own a large tract of land in a lovely location.

    Nicole Gleason CR Premier Properties

    0 Route 171, Woodstock, CT 06281
  • 686 Cook Hill Rd, Danielson, CT 06239

    $435,000

    Sold Sep 12, 2025

    686 Cook Hill Rd, Danielson, CT 06239

    • 4 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Built 1870

    Last Sold Summary

    • 6% Above List Price
    • $407/SF
    • 17 Days On Market

    Current Estimated Value $418,307

    Last Listing Agent Jonathan Bolano eXp Realty

    686 Cook Hill Rd, Danielson, CT 06239
  • 4 Short St, Brooklyn, CT 06234
    4 Short St, Brooklyn, CT 06234
    /2

    $7,900

    Pending
    • Land
    • 6,098 Sq Ft
    • $56,429 per Acre

    4 Short St, Brooklyn, CT 06234

    Affordable opportunity for builders and investors! Bring your plans and creativity to this 0.14-acre lot located off of the peaceful Paradise Drive. This property offers an excellent entry point for a new build or small development project, with nearby amenities and continued neighborhood growth adding to its value. Easy access, manageable lot size, and placement within the Paradise Drive Overlay

    Catherine Howard Berkshire Hathaway NE Prop.

    4 Short St, Brooklyn, CT 06234
  • 609 Water St, Canterbury, CT 06331

    $275,000

    Sold Jan 20, 2026

    609 Water St, Canterbury, CT 06331

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Built 1955

    Last Sold Summary

    • 4% Above List Price
    • $183/SF
    • 1 Day On Market

    Current Estimated Value $278,101

    Last Listing Agent Denise Robillard Continental Realty Associates

    609 Water St, Canterbury, CT 06331
  • 61 Philip Ln, Dayville, CT 06241
    61 Philip Ln, Dayville, CT 06241
    /2

    $399,900

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,947 Sq Ft

    61 Philip Ln, Dayville, CT 06241

    Available for the first time, this charming 4-bedroom, 2-bath Cape offers the perfect blend of warmth, character, and functionality. From the moment you arrive, you'll fall in love with the inviting feel and beautifully maintained lot, offering plenty of room to relax, entertain, or simply enjoy the outdoors. Inside, the home features an ideal layout with spacious living areas and flexible space

    Lexie Brunet Brunet and Company Real Estate

    61 Philip Ln, Dayville, CT 06241
  • 10 Elizabeth Ln, North Windham, CT 06256

    $135,000

    Sold May 15, 2026

    10 Elizabeth Ln, North Windham, CT 06256

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1997

    Last Sold Summary

    • 4% Above List Price
    • $117/SF
    • 39 Days On Market

    Last Listing Agent Clarence Russ Home Selling Team

    10 Elizabeth Ln, North Windham, CT 06256
  • 99 Reilly Rd, Hampton, CT 06247
    99 Reilly Rd, Hampton, CT 06247
    99 Reilly Rd, Hampton, CT 06247
    /29

    $500,000

    New Construction Open Sat 11AM - 2PM
    • 4 Beds
    • 3 Baths
    • 1,795 Sq Ft

    99 Reilly Rd, Hampton, CT 06247

    Set back on 1.40 ACRES this 2026 Raised ranch is COMPLETED and can CLOSE ANYTIME! Last one available in a 3 lot subdivision. Brand new Stainless appliances in kitchen w/ white shaker cabinets, GRANITE and island. Vaulted ceiling open floor plan great for entertaining. BRIGHT Living room and dining area has slider to deck to enjoy your Fall evenings. Primary bedroom with its own bathroom, walkin

    Christine Johnson RE/MAX One

    99 Reilly Rd, Hampton, CT 06247
  • 95 Lauter Ave, Willimantic, CT 06226

    $321,130

    Sold Jul 25, 2025

    95 Lauter Ave, Willimantic, CT 06226

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft
    • Built 1956

    Last Sold Summary

    • 11% Above List Price
    • $176/SF
    • 44 Days On Market

    Current Estimated Value $316,311

    Last Listing Agent Jerome Zolobkowski Real Broker CT, LLC

    95 Lauter Ave, Willimantic, CT 06226
  • 125 Mountain St, Willimantic, CT 06226
    125 Mountain St, Willimantic, CT 06226
    125 Mountain St, Willimantic, CT 06226
    /40

    $310,000

    $15K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,781 Sq Ft

    125 Mountain St, Willimantic, CT 06226

    Investors take notice! This home is a money maker. Whether you decide to owner-occupy this spacious home while rental income helps with the mortgage, or rent out both units, you can't go wrong. The living areas provide warm spaces perfect for relaxing or gathering with friends and family. The kitchens offer ample cabinet and counter space, making everyday cooking convenient and enjoyable. The

    Lisa Antrum KW Legacy Partners

    125 Mountain St, Willimantic, CT 06226
  • 17 Woodstock Meadows, Woodstock, CT 06281

    $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
  • 47 Texas Heights Rd, Plainfield, CT 06374
    47 Texas Heights Rd, Plainfield, CT 06374
    47 Texas Heights Rd, Plainfield, CT 06374
    /20

    $289,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    47 Texas Heights Rd, Plainfield, CT 06374

    RANCH HOME! Bring your vision and make this 3-bedroom, 1-bath ranch your own! Situated on a corner lot, this 960 sq ft home offers great potential with a full basement for added space or storage. Enclosed porch. With some repairs and updates, this property could shine again-ideal for investors, DIY enthusiasts, or first-time buyers looking for a project. Features a dirt driveway and solid bones

    Doug Taber Taber Realty, LLC

    47 Texas Heights Rd, Plainfield, CT 06374
  • 31 Cherry Hill Rd, Brooklyn, CT 06234

    $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
  • 100 Hubbard Hill Rd, Killingly, CT 06239
    100 Hubbard Hill Rd, Killingly, CT 06239
    /2

    $300,000

    • Land
    • 8.8 Acres
    • $34,091 per Acre

    100 Hubbard Hill Rd, Killingly, CT 06239

    Experience the quintessential beauty of this New England countryside on this breathtaking 8.8 acres. This property offers a rare sense of pastoral peace without sacrificing convenience. Located less than a quarter-mile from I-395, you can enjoy a quiet, rural lifestyle with seamless transit to Boston, Providence, and NYC right at your doorstep. This is also listed as part of 4 properties which

    Jill Pilgrim William Pitt Sotheby's Int'l

    100 Hubbard Hill Rd, Killingly, CT 06239
  • 344 Sabin St, Putnam, CT 06260

    $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
  • 369 Thompson Rd, Thompson, CT 06277
    369 Thompson Rd, Thompson, CT 06277
    369 Thompson Rd, Thompson, CT 06277
    /39

    $594,900

    • 4 Beds
    • 2.5 Baths
    • 2,944 Sq Ft

    369 Thompson Rd, Thompson, CT 06277

    In the heart of Thompson Hill, step into history with the Jeremiah Olney House owned by the famous banker Jeremiah Olney in 1860, with its significant Greek Revival and Italianate features. This stunning 4-bed, 3.5-bath colonial farmhouse sits on nearly an acre of picturesque land and has been completely renovated. Overflowing with character, this home blends classic charm with modern

    Sheena Ruggirello Real Broker CT, LLC

    369 Thompson Rd, Thompson, CT 06277
  • 63 Prospect Ave, Danielson, CT 06239

    $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
    • 71 Lovers Ln, Windham, CT 06280

      Est $404,386

      Not Listed For Sale

      71 Lovers Ln, Windham, CT 06280

      • 3 Beds
      • 2 Baths
      • 1,938 Sq Ft
      • Built 2002
      71 Lovers Ln, Windham, CT 06280

      Last Sold Summary

      • 4 Days On Market

  • 161 Lisbon Rd, Canterbury, CT 06331
    161 Lisbon Rd, Canterbury, CT 06331
    /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
  • 9 Sherman Rd, 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

Showing Results 641 - 680, Page 17 of 18

Connecticut Windham County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group