Windham County, CT Homes

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  $435,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,832 Sq Ft

  11 Stone House Dr, Plainfield, CT 06374

  In the Highland Court subdivision off of High Street, you'll find this lovely Cape Cod (a one-owner home built in 2017). Gorgeous new homes are currently under construction in this limited cul-de-sac neighborhood. The home offers a flexible floorplan. On the upper level, you'll find 2 generously-sized bedrooms and a full bath. On the main level, you'll find a beautiful dining room adjacent to the

  

  Joan Casey

  RE/MAX Legends

  (860) 850-2035

  11 Stone House Dr, Plainfield, CT 06374
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  /17

  $1,800 total monthly price

  • 2 Beds
  • 1 Bath
  • 2,652 Sq Ft
  • House for Rent

  80 North St, Willimantic, CT 06226

  Available for rent! This renovated 2-Bedroom Apartment in the heart of Willimantic. This updated 2-bedroom, 1-bathroom apartment is located on the first floor of 80 North Street and is approximately 1,020 sq. ft. It features 2 generous bedrooms, 1 full modern bathroom, and a separate dining and living room. On-street parking is available. There is quick access to local shops, dining, ECSU, and a

  

  Sharon Watson Stokland

  List N Show LLC

  (860) 364-6311

  80 North St, Willimantic, CT 06226
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  $627,500 Sold Jul 29, 2025

  407 Starkweather Rd, Plainfield, CT 06374

  • 3 Beds
  • 2 Baths
  • 2,668 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Above List Price
  • $235/SF
  • 7 Days On Market

  Current Estimated Value $565,485

  Last Listing Agent Nathan Cholewa Kazantzis Real Estate, LLC

  407 Starkweather Rd, Plainfield, CT 06374
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  Est $125,622 Not Listed For Sale

  • 3 Beds

  202 Brayman Hollow Rd, Pomfret Center, CT 06259

  202 Brayman Hollow Rd, Pomfret Center, CT 06259
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  $550,000

  • 4 Beds
  • 2.5 Baths
  • 1,656 Sq Ft

  815 Mashamoquet Rd, Pomfret Center, CT 06259

  Motivated seller! Bring an offer! This 4-bedroom, 2.5-bath ranch has been extensively updated inside and out, offering a bright and welcoming layout. The kitchen features new cabinetry, granite countertops, and breakfast bar seating-ideal for cooking and entertaining. The private primary suite includes a walk-in closet and a beautifully finished bath with a double vanity, while three additional

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 345-5906

  815 Mashamoquet Rd, Pomfret Center, CT 06259
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  /13

  $1,800 total monthly price

  • 2 Beds
  • 1 Bath
  • 805 Sq Ft
  • Apartment for Rent

  1153 Main St Unit 3A, Willimantic, CT 06226

  BRAND NEW 2 bedroom, 1 bathroom apartment for rent in the heart of downtown Willimantic. This fully renovated unit features new appliances, modern finishes, and spacious off-street parking. Enjoy the convenience of a laundromat right across the street and all utilities except for electricity included in the rent. Prime location close to everyday essentials: just 0.5 miles to Stop & Shop, under 1

  

  Olivia Crable

  Berkshire Hathaway NE Prop.

  (860) 773-4545

  1153 Main St Unit 3A, Willimantic, CT 06226
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  $271,000 Sold Aug 15, 2025

  30 Mcdermott Ave, Willimantic, CT 06226

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1960

  Last Sold Summary

  • 8% Above List Price
  • $269/SF
  • 4 Days On Market

  Current Estimated Value $265,560

  Last Listing Agent Amber Jones KW Legacy Partners

  30 Mcdermott Ave, Willimantic, CT 06226
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  Est $332,031 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  107 Lambert Rd, Thompson, CT 06277

  107 Lambert Rd, Thompson, CT 06277
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  $739,900 Open Sat 12PM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 2,447 Sq Ft

  349 S Bigelow Rd, Hampton, CT 06247

  Beautiful Post and Beam design home, Tranquil setting nestled on 25+ acres with pond,babbling brook, and hiking trails nature at it best. This home has a unique design spoiling you with Private Hot tub, sauna, and solarium leading to outdoor patio with fireplace overlooking the pond side. Dramatic open layout with Swedish style stucco fireplace. This design offers the ability to have 2 or 3

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 831-4269

  349 S Bigelow Rd, Hampton, CT 06247
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  /19

  $1,850 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,047 Sq Ft
  • Townhouse for Rent

  37 Buckley Hill Rd, North Grosvenordale, CT 06255

  The available unit at 37 Buckley Hill Rd, Thompson offers comfortable living in a freshly updated space. Recent improvements include new appliances, featuring a convenient stackable washer and dryer, adding modern ease to everyday routines. The home provides a clean, functional layout with plenty of natural light. Additional upgrades are scheduled for April, including exterior painting, deck

  

  Patrick Farley

  Statewide Premier Prop. LLC

  (866) 384-4393

  37 Buckley Hill Rd, North Grosvenordale, CT 06255
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  $357,500 Sold Oct 15, 2025

  293 Willimantic Rd, Chaplin, CT 06235

  • 3 Beds
  • 1 Bath
  • 1,052 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Above List Price
  • $340/SF
  • 4 Days On Market

  Current Estimated Value $346,799

  Last Listing Agent Stephen Daly KW Legacy Partners

  293 Willimantic Rd, Chaplin, CT 06235
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  Est $492,965 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  93 Snake Meadow Rd, Moosup, CT 06354

  93 Snake Meadow Rd, Moosup, CT 06354
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  $700,000 Open Sat 12PM - 2PM

  • 5 Beds
  • 4 Baths
  • 3,610 Sq Ft

  310 S Bigelow Rd, Hampton, CT 06247

  Step into the enchanting story of this 1738 Colonial, where historic soul meets a graceful 1987 three-story addition. Lovingly preserved and thoughtfully refined, this home is a beautiful marriage of antique character and contemporary luxury. The main level radiates warmth, centered around a spacious chef's kitchen designed for gathering. Imagine hosting dinners in the formal dining room or

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 979-5631

  310 S Bigelow Rd, Hampton, CT 06247
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  $1,085 - $1,830 total monthly price

  Colonial Townhouse Apartments

  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

  29 Foster Dr, Willimantic, CT 06226
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  $635,000 Sold Sep 15, 2025

  156 Ballamahack Rd, Windham, CT 06280

  • 4 Beds
  • 2 Baths
  • 2,190 Sq Ft
  • Built 1800

  Last Sold Summary

  • 2% Below List Price
  • $290/SF
  • 51 Days On Market

  Current Estimated Value $609,066

  Last Listing Agent Stephen Daly KW Legacy Partners

  156 Ballamahack Rd, Windham, CT 06280
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  Est $258,681 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  193 Brick Top Rd, Windham, CT 06280

  193 Brick Top Rd, Windham, CT 06280
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  $319,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  7 Shelby Cir, Dayville, CT 06241

  Welcome home to this charming 3-bedroom, 1-bath ranch situated on a desirable corner lot. Step inside to find freshly painted interiors and stainless steel appliances that complement the bright, inviting kitchen. The home features public water and sewer, electric baseboard heating, and a new roof installed in 2015, and new water heater 2022. Enjoy outdoor living on the deck overlooking the

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 321-0694

  7 Shelby Cir, Dayville, CT 06241
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  /7

  $1,250 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  Unlisted Address

  This updated, adorable one bedroom is located just steps from the river and to the wonderful shops and restaurants of downtown Danielson.

  Kate Sullivan Compass Connecticut, LLC

  Unlisted Address
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  $471,000 Sold Aug 21, 2025

  53 Windham Rd, Hampton, CT 06247

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • Built 1986

  Last Sold Summary

  • 11% Above List Price
  • $200/SF
  • 45 Days On Market

  Current Estimated Value $459,142

  Last Listing Agent Stephanie Rush RE/MAX Legends

  53 Windham Rd, Hampton, CT 06247
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  Est $219,624 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,146 Sq Ft

  240 Main St, Hampton, CT 06247

  240 Main St, Hampton, CT 06247
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  $324,900

  • 3 Beds
  • 1.5 Baths
  • 1,277 Sq Ft

  11 Woodland Dr, Windham, CT 06280

  New Photos Coming Soon! Welcome to 11 Woodland Drive in Windham, Connecticut. This home has all the charm and character one would find in rural Windham County. The exterior of this property boasts a lovely manicured yard with landscaped bushes, perennial flowers and vegetables, fruit trees, and native plants. The interior of this home has three bedrooms and a large laundry room that can be

  

  Sharon Watson Stokland

  List N Show LLC

  (860) 579-1208

  11 Woodland Dr, Windham, CT 06280
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  $1,825 total monthly price

  Ashford Hills

  3 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.

  95 Varga Rd, Ashford, CT 06278
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  $242,000 Sold Jan 28, 2026

  27 Ash Ave, Willimantic, CT 06226

  • 4 Beds
  • 1 Bath
  • 1,425 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Below List Price
  • $170/SF
  • 9 Days On Market

  Last Listing Agent Amber Jones KW Legacy Partners

  27 Ash Ave, Willimantic, CT 06226
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  Est $439,015 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,436 Sq Ft

  565 Bebbington Rd, Ashford, CT 06278

  565 Bebbington Rd, Ashford, CT 06278
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  /5

  $225,000

  • Land
  • 3.86 Acres
  • $58,290 per Acre

  00 Mashamoquet Rd, Pomfret, CT 06259

  Approved, shovel ready Commercial Building Site. Part of a 15.9 acre 3 Lot approved subdivision. This is Lot #3.02 It has 3.86 acres. Boarders the popular Airline State Park Trail in Back. It is directly on US Route 44. Just after the Commercial Property owned by Centerville Bank. Zoned Village Commercial. Ideal for Retail Centers & Strip Malls. Drive-Thru, Restaurants, Cafe', Chains, Grocery

  

  Mary Collins

  Berkshire Hathaway NE Prop.

  (860) 579-6685

  00 Mashamoquet Rd, Pomfret, CT 06259
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  /5

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 835 Sq Ft
  • Apartment for Rent

  Unlisted Address

  Discover this main level, two bedroom unit just footsteps to the riverfront and to all the shops and restaurants to downtown Danielson.

  Kate Sullivan Compass Connecticut, LLC

  Unlisted Address
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  $260,000 Sold Sep 19, 2025

  8 Chappell St, Chaplin, CT 06235

  • 2 Beds
  • 1 Bath
  • 893 Sq Ft
  • Built 1935

  Last Sold Summary

  • 4% Above List Price
  • $291/SF
  • 25 Days On Market

  Current Estimated Value $244,805

  Last Listing Agent Stephen Daly KW Legacy Partners

  8 Chappell St, Chaplin, CT 06235
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  Est $939,587 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  1227 Thompson Rd, Thompson, CT 06277

  1227 Thompson Rd, Thompson, CT 06277
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  /30

  $199,900

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  235 S Windham Rd, Willimantic, CT 06226

  Bring your vision for this charming 2-bedroom, 1 bath Ranch in South Windham, set on an expansive 6.2-acre lot with plenty of room to enjoy privacy and outdoor space. Built in 1948 and offering 950+ sq ft of comfortable one-level living, this home features vinyl siding, a classic gable roof with asphalt shingles, and a simple, functional layout that is easy to maintain. A full unfinished basement

  

  Anthony D'Amore

  eXp Realty

  (860) 530-6511

  235 S Windham Rd, Willimantic, CT 06226
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  $1,800 - $2,700 per month plus fees

  Woodlawn Apartments

  2 - 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

  80 Bicknell Rd, Ashford, CT 06278
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  $350,000 Sold Jul 02, 2025

  183 Prospect St, Willimantic, CT 06226

  • 6 Beds
  • 3 Baths
  • 3,970 Sq Ft
  • Built 1890

  Last Sold Summary

  • $88/SF
  • 2 Days On Market

  Current Estimated Value $357,928

  Last Listing Agent Stephen Daly KW Legacy Partners

  183 Prospect St, Willimantic, CT 06226
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  Est $455,179 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,022 Sq Ft

  19 Elliott Rd, Brooklyn, CT 06234

  19 Elliott Rd, Brooklyn, CT 06234
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  /30

  $449,000

  • 4 Beds
  • 2 Baths
  • 2,760 Sq Ft

  102 Krapf Rd, Ashford, CT 06278

  Welcome to 102 Krapf Road in Ashford, CT. This custom post-and-beam residence features 250-year-old beams, cathedral ceilings, and skylights. It is located on over three acres of land and includes an above-ground pool, hot tub, gazebo, and a brick grill for outdoor entertaining. This property is conveniently located near I-84, Route 44, and a reasonable drive from the UConn Storrs campus. Some of

  

  Sharon Watson Stokland

  List N Show LLC

  (860) 792-3716

  102 Krapf Rd, Ashford, CT 06278
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  $2,500 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 3,132 Sq Ft
  • Townhouse for Rent

  85 Maple St, Danielson, CT 06239

  Huge 3-bedroom, 2.5-bath duplex, featuring beautiful hardwood floors and new carpeting upstairs. This home offers built-ins with classic charm, that has been thoughtfully, and lovingly remodeled throughout. Enjoy tons of natural light, a well-appointed kitchen with appliances included, washer/dryer hook ups, a full basement and a 1-car garage with two additional parking spaces. Step out back to a

  Danielle Bakanowsky Kazantzis Real Estate, LLC

  85 Maple St, Danielson, CT 06239
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  $275,000 Sold Sep 25, 2025

  28 Cross Creek Rd Unit 28, Plainfield, CT 06374

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft
  • Built 2007

  Last Sold Summary

  • $270/SF
  • 7 Days On Market

  Current Estimated Value $278,712

  Last Listing Agent Melissa DiPiazza RE/MAX One

  28 Cross Creek Rd Unit 28, Plainfield, CT 06374
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  Est $219,722 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 846 Sq Ft

  57 Railroad Ave, Plainfield, CT 06374

  57 Railroad Ave, Plainfield, CT 06374
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  /40

  $575,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 4,538 Sq Ft

  89 John Perry Rd, Eastford, CT 06242

  Welcome to the Benjamin Bosworth House, affectionately known locally as "The Castle." This extraordinary Federal-style home, Circa 1796, blends timeless craftsmanship with historic character. Set on 3 private acres, this 4,538 sq ft estate features 4 bedrooms, 2.5 baths, and 11 fireplaces across a thoughtfully designed layout. Notable architectural details include hand-carved mantels, doors, and

  

  Mary Collins

  Berkshire Hathaway NE Prop.

  (860) 590-4951

  89 John Perry Rd, Eastford, CT 06242
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  /40

  $1,500 - $1,750 per month plus fees

  Birch Hill Apartments

  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!

  149 Ashford Center Rd, Ashford, CT 06278
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  $305,000 Sold Jan 30, 2026

  887 Sterling Rd, Sterling, CT 06377

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $235/SF
  • 59 Days On Market

  Last Listing Agent Miles LaFemina Drawbridge Realty

  887 Sterling Rd, Sterling, CT 06377
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  Est $384,166 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,904 Sq Ft

  85 Robertson Ave, Danielson, CT 06239

  85 Robertson Ave, Danielson, CT 06239

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