46,345

Windham County, CT Homes

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  • 593 Pomfret St, Putnam, CT 06260
    593 Pomfret St, Putnam, CT 06260
    593 Pomfret St, Putnam, CT 06260
    /19

    $599,999

    Pending
    • 3 Beds
    • 1.5 Baths
    • 2,308 Sq Ft

    593 Pomfret St, Putnam, CT 06260

    Welcome to a truly special country estate offering the perfect blend of historic character, functional farm amenities, and natural beauty. The property features approximately 5-6 acres of fenced pastureland and an additional 5 acres of wooded trails, ideal for horseback riding, hiking, or simply enjoying the outdoors. Multiple divided pastures are enclosed with reinforced, goat-proof fencing

    Ashley Walker Kazantzis Real Estate, LLC

    593 Pomfret St, Putnam, CT 06260
  • 90 Broad St, Danielson, CT 06239

    $380,000

    Sold Aug 14, 2025

    90 Broad St, Danielson, CT 06239

    • 3 Beds
    • 2 Baths
    • 1,869 Sq Ft
    • Built 1925

    Last Sold Summary

    • $203/SF
    • 15 Days On Market

    Current Estimated Value $378,538

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

    90 Broad St, Danielson, CT 06239
  • 25 Bebbington Rd, Ashford, CT 06278
    25 Bebbington Rd, Ashford, CT 06278
    25 Bebbington Rd, Ashford, CT 06278
    /10

    $499,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,604 Sq Ft

    25 Bebbington Rd, Ashford, CT 06278

    ANOTHER REFINED LIVING EXCLUSIVE! To Be Built! A very rare NEW CONSTRUCTION home opportunity that offers 1,604 SF, attached 1 car garage, 3 large bedrooms, primary bedroom with it's own full bath and his & hers closets, 2 & 1/2 baths total, eat-in kitchen, dining room & main level laundry room. Large full basement. Well sought community. A new buyer can BE IN BY SEPTEMBER! (School season)!!

    Robert Letskus Platinum Associates

    25 Bebbington Rd, Ashford, CT 06278
  • 45 Main St Unit 409, Plainfield, CT 06374

    $221,000

    Sold Jul 25, 2025

    45 Main St Unit 409, Plainfield, CT 06374

    • 2 Beds
    • 2 Baths
    • 1,807 Sq Ft
    • Built 1987

    Last Sold Summary

    • 8% Above List Price
    • $122/SF
    • 85 Days On Market

    Current Estimated Value $226,983

    Last Listing Agent Ryan Smith Tier 1 Real Estate

    45 Main St Unit 409, Plainfield, CT 06374
  • 0 Drain St, Hampton, CT 06247
    0 Drain St, Hampton, CT 06247
    0 Drain St, Hampton, CT 06247
    /4

    $89,900

    • Land
    • 6.27 Acres
    • $14,338 per Acre

    0 Drain St, Hampton, CT 06247

    This lot was created in 2005. Perc tests are 20 years old and might change based on where the home is desired to be located on the property.

    Mae Lyons Stonehouse Real Estate Co., LLC

    0 Drain St, Hampton, CT 06247
  • 96 Mcdermott Ave, Willimantic, CT 06226

    $335,000

    Sold Apr 13, 2026

    96 Mcdermott Ave, Willimantic, CT 06226

    • 4 Beds
    • 2 Baths
    • 1,708 Sq Ft
    • Built 1970

    Last Sold Summary

    • 12% Above List Price
    • $196/SF
    • 38 Days On Market

    Current Estimated Value $323,946

    Last Listing Agent Sue Esposito Home Selling Team

    96 Mcdermott Ave, Willimantic, CT 06226
  • 19 Henry Dr Unit 19, Plainfield, CT 06354
    19 Henry Dr Unit 19, Plainfield, CT 06354
    19 Henry Dr Unit 19, Plainfield, CT 06354
    /28

    $419,000

    • 2 Beds
    • 2 Baths
    • 1,471 Sq Ft

    19 Henry Dr Unit 19, Plainfield, CT 06354

    Moosup River Estates is a 55 and over community of stand alone condos along the Moosup River. This unit was thoughtfully completed, and is now ready for it next owner to enjoy low maintenance living. 1471sqft of indoor finished living space, plus a pretty front porch, and a 12x15 patio. The main living area is open concept. In the kitchen area, find a comfortable breakfast bar, walk in pantry

    Lynn Converse RE/MAX Bell Park Realty

    19 Henry Dr Unit 19, Plainfield, CT 06354
  • 52 Singleton Rd, Chaplin, CT 06235

    $365,000

    Sold Oct 08, 2025

    52 Singleton Rd, Chaplin, CT 06235

    • 3 Beds
    • 2.5 Baths
    • 2,440 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Above List Price
    • $150/SF
    • 67 Days On Market

    Current Estimated Value $352,172

    Last Listing Agent Alexis John RE/MAX One

    52 Singleton Rd, Chaplin, CT 06235
  • 21 Duffy Rd, Pomfret Center, CT 06259
    21 Duffy Rd, Pomfret Center, CT 06259
    21 Duffy Rd, Pomfret Center, CT 06259
    /40

    $429,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft

    21 Duffy Rd, Pomfret Center, CT 06259

    Welcome to 21 Duffy Road in Pomfret, where comfort, space, and convenience come together in a desirable setting. This 4-bedroom, 2.5-bath home offers a flexible floor plan with a main-level bedroom and full bath, ideal for guests, multi-generational living, or a home office. The remodeled kitchen serves as the heart of the home and flows into the dining area, where sliding glass doors lead to a

    Lauren Heidelberger Berkshire Hathaway NE Prop.

    21 Duffy Rd, Pomfret Center, CT 06259
  • 64 May Brook, Woodstock, CT 06281

    $715,000

    Sold Oct 21, 2025

    64 May Brook, Woodstock, CT 06281

    • 4 Beds
    • 5 Baths
    • 3,795 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Below List Price
    • $188/SF
    • 35 Days On Market

    Current Estimated Value $746,409

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    64 May Brook, Woodstock, CT 06281
  • 61 Beecher Rd, Brooklyn, CT 06234
    61 Beecher Rd, Brooklyn, CT 06234
    61 Beecher Rd, Brooklyn, CT 06234
    /40

    $789,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 2.5 Baths
    • 2,226 Sq Ft

    61 Beecher Rd, Brooklyn, CT 06234

    Welcome to 61 Beecher Road, a beautifully upgradedhome that seamlessly blends luxurious comfort with modern living. This meticulously maintained property boasts a range of impressive improvements that elevate both style and functionality. Step into a culinary haven featuring a full suite of GE Cafe appliances in a sleek matte white finish. Enjoy the convenience of a built-in microwave drawer,

    Jennifer Lehto Real Broker CT, LLC

    61 Beecher Rd, Brooklyn, CT 06234
  • 19 Bolles St, Putnam, CT 06260

    $297,500

    Sold May 08, 2026

    19 Bolles St, Putnam, CT 06260

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Below List Price
    • $163/SF
    • 19 Days On Market

    Current Estimated Value $296,799

    Last Listing Agent Casey Hardell CR Premier Properties

    19 Bolles St, Putnam, CT 06260
  • 12 Loyola Rd, Woodstock, CT 06281
    12 Loyola Rd, Woodstock, CT 06281
    12 Loyola Rd, Woodstock, CT 06281
    /27

    $439,000

    Pending
    • 1 Bed
    • 1 Bath
    • 711 Sq Ft

    12 Loyola Rd, Woodstock, CT 06281

    This cottage in Woodstock is a quintessential charming retreat located on Quasset Lake. It offers the perfect blend of comfort relaxation and simplicity. Making it the ideal year round home or weekend getaway. Filled with natural light, the warm interior creates a welcoming atmosphere, while the peaceful setting provides the tranquility you have been searching for. Enjoy lake recreation private

    Amy Vinal Pine Knoll Real Estate

    12 Loyola Rd, Woodstock, CT 06281
  • 173 Bennett Pond Rd, Canterbury, CT 06331

    $455,000

    Sold Jun 01, 2026

    173 Bennett Pond Rd, Canterbury, CT 06331

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Above List Price
    • $298/SF
    • 4 Days On Market

    Current Estimated Value $434,864

    Last Listing Agent Jennifer Mahr RE/MAX Bell Park Realty

    173 Bennett Pond Rd, Canterbury, CT 06331
    • 33 Cady St, Danielson, CT 06239

      Est $305,004

      Not Listed For Sale

      33 Cady St, Danielson, CT 06239

      • 2 Beds
      • 1 Bath
      • 1,240 Sq Ft
      • Built 1957
      33 Cady St, Danielson, CT 06239

      Last Sold Summary

      • 245 Days On Market

  • 514 Mashamoquet Rd, Pomfret Center, CT 06259
    514 Mashamoquet Rd, Pomfret Center, CT 06259
    514 Mashamoquet Rd, Pomfret Center, CT 06259
    /37

    $309,999

    Pending
    • 2 Beds
    • 1 Bath
    • 1,135 Sq Ft

    514 Mashamoquet Rd, Pomfret Center, CT 06259

    Welcome to this classic 1910 Cape with flexible living, set on a gorgeous, sprawling 1.8-acre lot with peach and pear trees, raspberries and plenty of gardens in highly desirable Pomfret, CT! Offering peaceful rural privacy at an incredible entry-level value, this home is a fantastic opportunity for conventional buyers, hobbyists, or smart investors. brand-new, fully permitted 200-Amp electrical

    Dianne Barrett Johnston & Associates Real Estate, LLC

    514 Mashamoquet Rd, Pomfret Center, CT 06259
  • 33 Meehan Rd, Woodstock, CT 06281

    $1,000,000

    Sold Jun 10, 2026

    33 Meehan Rd, Woodstock, CT 06281

    • 3 Beds
    • 4 Baths
    • 4,190 Sq Ft
    • Built 1993

    Last Sold Summary

    • $239/SF
    • 9 Days On Market

    Last Listing Agent John Downs Berkshire Hathaway NE Prop.

    33 Meehan Rd, Woodstock, CT 06281
  • 21-23 George St, Putnam, CT 06260
    21-23 George St, Putnam, CT 06260
    21-23 George St, Putnam, CT 06260
    /27

    $264,900

    $55K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 1,993 Sq Ft

    21-23 George St, Putnam, CT 06260

    Exceptional opportunity for investors and owner-occupants alike! This fully rented two-family home generates $3,025 per month in gross rental income ($36,300 annually) while being offered at just $265,000. Opportunities to acquire a property with this level of income at this price point are becoming increasingly difficult to find. This Putnam two-family is located on a quiet dead-end street just

    Carl Guild Carl Guild & Associates

    21-23 George St, Putnam, CT 06260
  • 215 Walnut St, Putnam, CT 06260

    $347,000

    Sold Jul 15, 2026

    215 Walnut St, Putnam, CT 06260

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1867

    Last Sold Summary

    • 2% Above List Price
    • $217/SF
    • 6 Days On Market

    Current Estimated Value $343,159

    Last Listing Agent Danielle Kiser LPT Realty

    215 Walnut St, Putnam, CT 06260
  • 45 Main St Unit 206, Plainfield, CT 06374
    45 Main St Unit 206, Plainfield, CT 06374
    45 Main St Unit 206, Plainfield, CT 06374
    /26

    $195,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    45 Main St Unit 206, Plainfield, CT 06374

    Step into the timeless character of this beautifully maintained 2-bedroom, 1.5-bath mill-style condominium, where historic architectural details blend seamlessly with modern living. Featuring soaring ceilings, oversized windows that fill the home with natural light, and the distinctive character these sought-after mill conversions are known for, this inviting residence offers a warm and unique

    Lisa Gervais Team Bassett Realty LLC

    45 Main St Unit 206, Plainfield, CT 06374
  • 31 Deer Meadow Ln, Woodstock, CT 06281

    $500,000

    Sold Oct 31, 2025

    31 Deer Meadow Ln, Woodstock, CT 06281

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Below List Price
    • $213/SF
    • 11 Days On Market

    Current Estimated Value $514,532

    Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

    31 Deer Meadow Ln, Woodstock, CT 06281
  • 24 Black Hill Rd, Plainfield, CT 06374
    24 Black Hill Rd, Plainfield, CT 06374
    24 Black Hill Rd, Plainfield, CT 06374
    /31

    $325,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft

    24 Black Hill Rd, Plainfield, CT 06374

    Charming 3 bedroom home with loads of potential. Some updates including 2 year old roof. Includes 1 car detached garage, and small sauna building. The AG pool sitting in the park like setting. Seller not sure of condition. Being sold in as is condition, subject to probate court approval.

    Cathy Duprey Duprey Real Estate, LLC

    24 Black Hill Rd, Plainfield, CT 06374
  • 360 N Society Rd, Canterbury, CT 06331

    $280,000

    Sold Jun 23, 2026

    360 N Society Rd, Canterbury, CT 06331

    • 3 Beds
    • 1.5 Baths
    • 2,236 Sq Ft
    • Built 1984

    Last Sold Summary

    • $125/SF
    • 6 Days On Market

    Current Estimated Value $305,602

    Last Listing Agent Dale Bunn Riverview Realty, LLC

    360 N Society Rd, Canterbury, CT 06331
  • 37 Pond Way, North Windham, CT 06256
    37 Pond Way, North Windham, CT 06256
    37 Pond Way, North Windham, CT 06256
    /28

    $115,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    37 Pond Way, North Windham, CT 06256

    Welcome to this well-maintained 2008 mobile home located in the desirable Stonegate Manor community. This inviting home offers a bright, open floor plan filled with natural light, creating a warm and welcoming atmosphere throughout. The spacious kitchen flows seamlessly into the living room, making it perfect for everyday living and entertaining. Offering three bedrooms and two full baths, this

    Jeanne Crum Home Selling Team

    37 Pond Way, North Windham, CT 06256
  • 420 Moosup Pond Rd, Moosup, CT 06354

    $520,000

    Sold Jun 15, 2026

    420 Moosup Pond Rd, Moosup, CT 06354

    • 3 Beds
    • 2.5 Baths
    • 1,751 Sq Ft
    • Built 2019

    Last Sold Summary

    • 6% Above List Price
    • $297/SF
    • 39 Days On Market

    Current Estimated Value $496,963

    Last Listing Agent Kelsie Griffin Wolfburg Kazantzis Real Estate, LLC

    420 Moosup Pond Rd, Moosup, CT 06354
  • 26 Plains Rd, Windham, CT 06280
    26 Plains Rd, Windham, CT 06280
    26 Plains Rd, Windham, CT 06280
    /32

    $239,900

    $20K PRICE DROP Under Contract
    • 4 Beds
    • 1.5 Baths
    • 2,758 Sq Ft

    26 Plains Rd, Windham, CT 06280

    *** Dutch Colonial Style Home Brimming with History and Potential *** This home is the former parsonage for St. Paul's Episcopal Church, with many antique features reminiscent of its time - gambrel style roof, colonial American style woodwork, wide plank floors, field stone foundation and walk ways, and accretive architecture. The home is sprawling with over 2700 Sqft, 4 bedrooms, 1 1/2 baths,

    Christy Lofstrom Driscoll ERA Blanchard & Rossetto

    26 Plains Rd, Windham, CT 06280
  • 106 Riley Chase Rd, Killingly, CT 06241

    $85,000

    Sold Jun 01, 2026

    106 Riley Chase Rd, Killingly, CT 06241

    • Land
    • 10.9 Acres
    • $7,798 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 29 Days On Market

    Current Estimated Value $98,000

    Last Listing Agent Anthony Chabot Chabot & Associates Real Estate

    106 Riley Chase Rd, Killingly, CT 06241
  • 10 Cemetery Rd Unit 10, Plainfield, CT 06374
    10 Cemetery Rd Unit 10, Plainfield, CT 06374
    10 Cemetery Rd Unit 10, Plainfield, CT 06374
    /27

    $369,000

    New Construction Open Wed 9AM - 11AM
    • 2 Beds
    • 1.5 Baths
    • 1,022 Sq Ft

    10 Cemetery Rd Unit 10, Plainfield, CT 06374

    Welcome to these newly built, detached townhouse-style condominiums offering low-maintenance living with a low HOA. The main level features an open-concept living room with an electric fireplace and mantel, a dining area, and a beautiful kitchen with a farmers sink, quartz countertops, stainless steel appliances, and a half bath. Also, offering a pantry closet. Step through the dining area to

    Paige Collelo Taber Realty, LLC

    10 Cemetery Rd Unit 10, Plainfield, CT 06374

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