Windham County, CT Homes

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  /40

  $350,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,438 Sq Ft

  60 Chaplin St, Chaplin, CT 06235

  Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places.

  

  Stephen Daly

  KW Legacy Partners

  60 Chaplin St, Chaplin, CT 06235
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  /7

  $1,350 Per Month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Property for Rent

  291 Westford Rd, Eastford, CT 06242

  Updated 1-bedroom, 1-bath mobile home available for rent in a peaceful rural setting in Eastford Ct. This well-maintained home offers an updated kitchen, bright living area, spacious bedroom, and full bath. Enjoy the privacy and tranquility of country living while remaining close to major routes. Monthly rent is $1,350 with a one-year lease. Tenant is responsible for utilities. Pets considered on

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  291 Westford Rd, Eastford, CT 06242
• 

  $550,000

  Sold Jun 26, 2026

  37 Manners Ave, Willimantic, CT 06226

  • 8 Beds
  • 5 Baths
  • 4,824 Sq Ft
  • Built 1972

  Last Sold Summary

  • 16% Above List Price
  • $114/SF
  • 6 Days On Market

  Current Estimated Value $464,387

  Last Listing Agent Stephen Daly KW Legacy Partners

  37 Manners Ave, Willimantic, CT 06226
• 

  Est $369,061

  Not Listed For Sale

  523 Wauregan Rd, Danielson, CT 06239

  • 3 Beds
  • 2 Baths
  • 2,149 Sq Ft
  • Built 1991

  523 Wauregan Rd, Danielson, CT 06239

  Last Sold Summary

  • 10 Days On Market
• 

  

  

  /38

  $645,500

  • 3 Beds
  • 2.5 Baths
  • 2,478 Sq Ft

  429 New Sweden Rd, Woodstock, CT 06281

  Step back in time and discover the charm of this beautifully preserved 2,400 sq. ft. farmhouse, originally built in 1805. Rich in character and timeless appeal, this property offers the perfect blend of country living and modern convenience. Whether you dream of cultivating extensive gardens, raising animals, creating a self-sustaining homestead, or simply enjoying wide-open spaces, this property

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  429 New Sweden Rd, Woodstock, CT 06281
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  /14

  Starting at $1,825 Plus Fees

  • 3 Beds

  80 Bicknell Rd, Ashford, CT 06278

  Can you hear the "birds chirping and woodpeckers pecking" in your current home? Woodlawn Apartments consists of 12 charming buildings on 11 beautiful acres. Our residents enjoy the peace and quiet of nature in a convenient location, along with a caring management and maintenance staff. Only five miles from UConn. Also, call us about our nearby Wood Edge Apartments in Mansfield Center 4 miles from

  Woodlawn Apartments

  80 Bicknell Rd, Ashford, CT 06278
• 

  $430,000

  Sold Jul 07, 2026

  116 Tatnic Hill Rd, Brooklyn, CT 06234

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft
  • Built 2012

  Last Sold Summary

  • $351/SF
  • 42 Days On Market

  Current Estimated Value $437,284

  Last Listing Agent Nathan Cholewa Kazantzis Real Estate, LLC

  116 Tatnic Hill Rd, Brooklyn, CT 06234
• 

  Est $575,780

  Not Listed For Sale

  222 Route 197, Woodstock, CT 06281

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1991

  222 Route 197, Woodstock, CT 06281

  Last Sold Summary

  • 8 Days On Market
• 

  

  /38

  $789,000

  • 4 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  287 S Bear Hill Rd, Chaplin, CT 06235

  Set on 3.39 picturesque acres, this beautifully renovated property offers the perfect blend of luxury, function, and country charm-ideal for a mini farm, homestead, or private retreat. The heated and insulated 36x48 Morton barn features front and rear sliding barn doors, 2 horse stalls with potential for 6, 5 doggy doors, water, electric, skylights, and year-round water access-perfect for horses,

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  287 S Bear Hill Rd, Chaplin, CT 06235
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  /12

  $2,150 Per Month

  • 2 Beds
  • 1 Bath
  • 3,168 Sq Ft
  • House for Rent

  191 Providence St, Putnam, CT 06260

  Enjoy comfortable living in the beautifully renovated 2 bedroom apartment. Featuring a spacious kitchen and large rooms throughout. For your convenience, a washer and dryer are included, along with dishwasher. Heat and electricity are included in the rent, making budgeting simple. Ideally located just minutes from downtown, you'll have easy access to shopping, dining, and everyday conveniences.

  

  Mandy Gruslin

  Kazantzis Real Estate, LLC

  191 Providence St, Putnam, CT 06260
• 

  $22,000

  Sold Aug 07, 2025

  40 S Prospect St, Putnam, CT 06260

  • Land
  • 1.05 Acres
  • $20,952 per Acre

  Last Sold Summary

  • 72 Days On Market

  Current Estimated Value $136,085

  Last Listing Agent Derek Greene Derek Greene

  40 S Prospect St, Putnam, CT 06260
• 

  Est $480,205

  Not Listed For Sale

  25 Charlton Ave, Dayville, CT 06241

  • 4 Beds
  • 2.5 Baths
  • 3,163 Sq Ft
  • Built 1984

  25 Charlton Ave, Dayville, CT 06241

  Last Sold Summary

  • 40 Days On Market
• 

  

  /39

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 2,655 Sq Ft

  53 Colleen St, Danielson, CT 06239

  Welcome to this spacious Colonial, ideally situated on a corner lot in a quiet neighborhood in Killingly. Offering over 2,600 square feet of living space, this home features generously sized rooms, a flexible layout, and plenty of space to fit a variety of needs. The updated kitchen and bathrooms provide modern convenience, while the dining room fireplace adds warmth and character. An oversized

  

  Monique Frigon

  Toro Real Estate LLC

  53 Colleen St, Danielson, CT 06239
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  /41

  Starting at $1,085

  Total Monthly Price

  • Studio - 2 Beds

  29 Foster Dr, Willimantic, CT 06226

  Come experience life at Colonial Townhouse Apartments! Lots of improvements have been made to the property to make us energy efficient with a modern appearance. This includes new windows, new siding, new EV chargers, fresh signage, and upgraded apartments. You'll get the most value for your money around! Located on the WRTD bus line for easy access to all the area has to offer. **Screening Fee is

  Colonial Townhouse Apartments

  

  29 Foster Dr, Willimantic, CT 06226
• 

  $325,000

  Sold Jul 01, 2026

  124 S Main St, Brooklyn, CT 06234

  • 4 Beds
  • 1.5 Baths
  • 1,644 Sq Ft
  • Built 1930

  Last Sold Summary

  • 10% Above List Price
  • $198/SF
  • 17 Days On Market

  Current Estimated Value $292,674

  Last Listing Agent Heather Ash Spadola RE/MAX One

  124 S Main St, Brooklyn, CT 06234
• 

  Est $440,766

  Not Listed For Sale

  28 Crooked Trail, Woodstock, CT 06281

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

  28 Crooked Trail, Woodstock, CT 06281

  Last Sold Summary

  • 80 Days On Market
• 

  

  /39

  $579,900

  $10K PRICE DROP Under Contract

  • 3 Beds
  • 3 Baths
  • 3,096 Sq Ft

  2 Legacy Dr, Sterling, CT 06354

  Beautifully maintained one-owner Colonial built in 2020 and set on a spacious 1.36-acre lot in Sterling's desirable Legacy subdivision. Offering over 2,000 sq ft above grade plus a fully finished lower level, this home combines comfort, functionality, and energy efficiency with fully owned solar panels and underground utilities. The main level features hardwood flooring, an open-concept layout,

  

  Gia Parmentier

  J. Christopher Real Estate Group

  2 Legacy Dr, Sterling, CT 06354
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  /23

  $2,900 Per Month

  • 4 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • House for Rent

  223 High St, Willimantic, CT 06226

  Cozy, well maintained 4 bedroom 2 bath home situated in hill section of Willimantic. This house offers central air, ample storage as well as a washer and dryer, central air, oil heat and has room for 5 tenants. This property sits across the street from ECSU, is on the bus route to UConn and is just 8 miles from campus with convenient access to grocery stores, gyms and night life. Close to

  

  Rick Nassiff

  KW Legacy Partners

  223 High St, Willimantic, CT 06226
• 

  $570,000

  Sold Jun 17, 2026

  153 Mansfield Rd, Ashford, CT 06278

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Above List Price
  • $271/SF
  • 69 Days On Market

  Current Estimated Value $546,972

  Last Listing Agent Noah King Home Selling Team

  153 Mansfield Rd, Ashford, CT 06278
• 

  Est $526,586

  Not Listed For Sale

  6 Margaret Cir, Pomfret Center, CT 06259

  • 4 Beds
  • 2.5 Baths
  • 2,138 Sq Ft
  • Built 1999

  6 Margaret Cir, Pomfret Center, CT 06259

  Last Sold Summary

  • 35 Days On Market
• 

  

  /40

  $549,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  341 Main St, Hampton, CT 06247

  Welcome home to this charming country property where timeless character meets exceptional functionality. Set on a beautifully landscaped lot filled with mature gardens and an abundance of perennials including peonies, lilies, and seasonal blooms, this property offers the perfect blend of comfort, charm, and versatility. Inside, you'll appreciate the warmth of beautiful hardwood floors throughout

  

  Cindy Forlenzo

  Coldwell Banker Realty

  341 Main St, Hampton, CT 06247
• 

  

  /19

  Starting at $1,495

  Total Monthly Price

  • 1 - 2 Beds

  95 Varga Rd, Ashford, CT 06278

  Conveniently located, but full of quiet country charm, Ashford Hills offers one, two, and three-bedroom apartments, perfect to match any lifestyle! Located just six miles from the University of Connecticut right off route 44.Ashford Hills is an apartment community located in Windham County and the 06278 ZIP Code. This area is served by the Mansfield attendance zone.

  Ashford Hills

  95 Varga Rd, Ashford, CT 06278
• 

  $70,000

  Sold Aug 18, 2025

  26 Jacqueline Ln, North Windham, CT 06256

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1987

  Last Sold Summary

  • $76/SF
  • 34 Days On Market

  Last Listing Agent Derek Greene Derek Greene

  26 Jacqueline Ln, North Windham, CT 06256
• 

  Est $317,863

  Not Listed For Sale

  3 Maple Dr, Ashford, CT 06278

  • 1 Bed
  • 1 Bath
  • 802 Sq Ft
  • Built 1952

  3 Maple Dr, Ashford, CT 06278

  Last Sold Summary

  • 8 Days On Market
• 

  

  /26

  $289,900

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,820 Sq Ft

  43 Hilltop Dr Unit 43, North Windham, CT 06256

  This charming 3bedroom home blends fresh updates with future possibilities. The remodeled kitchen and new flooring (main level) create a bright, modern feel from the moment you walk in. Enjoy morning coffee on the deck, easy parking with the attached garage, and the freedom to design the lower level into whatever space you've been dreaming of. A home that fits your life today-and tomorrow. There

  

  Joan Casey

  RE/MAX Legends

  43 Hilltop Dr Unit 43, North Windham, CT 06256
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  /40

  Starting at $1,550 Plus Fees

  • 2 Beds

  52 Perry Hill Rd, Ashford, CT 06278

  Perry Hill Apartments offers two bedroom townhouse apartment homes for rent in Ashford, CT. Our pet friendly community features amenities such as on-site laundry, dishwashers and private patios. We are located close to University of Connecticut and major highways.

  Perry Hill Apartments

  52 Perry Hill Rd, Ashford, CT 06278
• 

  $380,000

  Sold May 15, 2026

  3 Oriole Dr, Danielson, CT 06239

  • 2 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Above List Price
  • $265/SF
  • 2 Days On Market

  Current Estimated Value $362,043

  Last Listing Agent Jennifer Mahr RE/MAX Bell Park Realty

  3 Oriole Dr, Danielson, CT 06239
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  Est $232,693

  Not Listed For Sale

  87 Hayden St, Willimantic, CT 06226

  • 6 Beds
  • 2 Baths
  • 1,546 Sq Ft
  • Built 1920

  87 Hayden St, Willimantic, CT 06226

  Last Sold Summary

  • 8 Days On Market
• 

  

  /26

  $359,900

  Pending

  • 2 Beds
  • 1 Bath
  • 1,168 Sq Ft

  366 Fabyan Rd, North Grosvenordale, CT 06255

  Discover the opportunity waiting at 366 Fabyan Rd! Set on a scenic stretch in North Grosvenordale, this property offers space, setting, and potential. With a little sweat equity, this home could truly shine and offers a fantastic opportunity to build value while making it your own. Enjoy a peaceful location with easy access to shopping, dining, and commuter routes while still embracing the quiet

  

  John Croteau

  The Neighborhood Realty Group

  366 Fabyan Rd, North Grosvenordale, CT 06255
• 

  

  /40

  Starting at $1,500 Plus Fees

  • 2 Beds

  149 Ashford Center Rd, Ashford, CT 06278

  Stunning remodeled units available now! Call/text manager for details! Don't miss out on this opportunity!

  Birch Hill Apartments

  149 Ashford Center Rd, Ashford, CT 06278
• 

  $225,000

  Sold Oct 30, 2025

  214 Park Rd, Putnam, CT 06260

  • Land
  • 5.41 Acres
  • $41,590 per Acre

  Last Sold Summary

  • 36% Below List Price
  • 790 Days On Market

  Current Estimated Value $276,793

  Last Listing Agent Michael Collins Berkshire Hathaway NE Prop.

  214 Park Rd, Putnam, CT 06260
• 

  Est $285,956

  Not Listed For Sale

  80 North St, Willimantic, CT 06226

  • 6 Beds
  • 2 Baths
  • 2,652 Sq Ft
  • Built 1910

  80 North St, Willimantic, CT 06226

  Last Sold Summary

  • 50 Days On Market
• 

  

  /40

  $499,900

  Open Sun 12PM - 2PM

  • 2 Beds
  • 1.5 Baths
  • 2,428 Sq Ft

  6 Autumn Ridge, Windham, CT 06280

  Experience exceptional craftsmanship in this magnificent timber frame home, thoughtfully designed with quality, comfort, and energy efficiency in mind. The stunning great room features soaring ceilings and an open-concept layout that flows seamlessly into the dining area and custom kitchen, creating an ideal space for everyday living and entertaining. A cozy propane stove adds warmth and ambiance

  

  Rick Nassiff

  KW Legacy Partners

  6 Autumn Ridge, Windham, CT 06280
• 

  

  /17

  $1,750

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Townhouse for Rent

  105 Cushman Rd, Ashford, CT 06278

  Beautiful setting. Nice lawn and wooded areas. Recently renovated townhome with bonus room in the basement. Heat and hot water included.

  105 Cushman Rd, Ashford, CT 06278
• 

  $52,000

  Sold Nov 05, 2025

  16 Conrad's Park, Killingly, CT 06241

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • Built 1961

  Last Sold Summary

  • 26% Below List Price
  • $95/SF
  • 23 Days On Market

  Last Listing Agent Tina Luft Kazantzis Real Estate, LLC

  16 Conrad's Park, Killingly, CT 06241
• 

  Est $436,866

  Not Listed For Sale

  34 Bonnette Ave, Thompson, CT 06277

  • 3 Beds
  • 2 Baths
  • 1,642 Sq Ft
  • Built 1970

  34 Bonnette Ave, Thompson, CT 06277

  Last Sold Summary

  • 34 Days On Market
• 

  

  /40

  $699,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,702 Sq Ft

  29 Braaten Hill Rd, Woodstock, CT 06281

  Welcome to the Top of Connecticut's Last Green Valley. Views sweep across the east and soak up the sunrise every day from the peak of 12 acres that are exclusively yours. Peaceful adventure and native wildflowers beckon you to embrace it all. Step inside your renovated New England Farmhouse and let the home guide you: hand-hewn beams, wide-plank floors, leaded-glass windows, and a cozy working

  

  Stephen Daly

  KW Legacy Partners

  29 Braaten Hill Rd, Woodstock, CT 06281
• 

  

  /13

  Starting at $1,050 Plus Fees

  • Studio - 2 Beds

  560 Main St, Willimantic, CT 06226

  Overlooking scenic Willimantic Falls and adjacent to the famous Frog Bridge, 560 On Main features spacious apartments complete with an artistic, warehouse, loft feel and unique floor plans thoughtfully designed within the walls of the historic Willimantic thread mill. 560 on Main provides each resident with the ultimate in comfort and enjoyment by offering state of the art amenities, outstanding

  560 On Main

  560 Main St, Willimantic, CT 06226
• 

  $295,000

  Sold Sep 02, 2025

  118 Ashford Rd Unit 6, Eastford, CT 06242

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $242/SF
  • 9 Days On Market

  Current Estimated Value $296,610

  Last Listing Agent Brittany Kimlingen First Choice Realty

  118 Ashford Rd Unit 6, Eastford, CT 06242
• 

  Est $351,779

  Not Listed For Sale

  636 Thompson Rd, Thompson, CT 06277

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1960

  636 Thompson Rd, Thompson, CT 06277

  Last Sold Summary

  • 35 Days On Market

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