Windham County, CT homes for sale & real estate

311 homes

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115 North Rd, Ashford, CT 06278
115 North Rd, Ashford, CT 06278
115 North Rd, Ashford, CT 06278
ABOUT THIS HOME
Windham County, CT Homes for Sale
Two-bedroom trailer featuring a kitchen, living room, and laundry area, situated on a beautiful, sloping one-acre lot offering a private setting and ample off-street parking. Surrounded by nature and abundant wildlife, this property is ideal for those seeking a peaceful, rural atmosphere. Enjoy outdoor living from the deck overlooking the natural landscape. This property is being sold as-is, where-is. The seller has no personal knowledge of the trailer's condition, as they have never occupied it. The roof appears to be in newer condition. The trailer may require some updates and maintenance. Buyers and their agents are responsible for conducting their own research regarding all aspects of t

$84,999

2 beds1 bath780 sq ft

115 North Rd, Ashford, CT 06278

1 acre lot • Car-dependent

NEW CONSTRUCTION

Rr 197 Rd, Woodstock, CT 06281
Rr 197 Rd, Woodstock, CT 06281
Rr 197 Rd, Woodstock, CT 06281
ABOUT THIS HOME
Windham County, CT Homes for Sale
Brand New Construction at an amazingly affordable price! This 4 bedroom 2.5 Colonial will be set on a knoll in the meadows in the picturesque Town of Woodstock. It is private and secluded, yet minutes away from the interstate with easy access to Boston, Worcester and Hartford. The home will have gleaming hardwood oak floors throughout the first floor with an open concept plan. The kitchen will have upgraded stainless steel appliances, Shaker Cabinets and Granite countertops. This home will sit on a 2.7 acre open building lot. The builder holds a Connecticut Real Estate License.

$597,000

4 beds2.5 baths2,212 sq ft

Rr 197 Rd, Woodstock, CT 06281

2.7 acre lot • 2 garage spots • Car-dependent

17 Stanley Dr, Plainfield, CT 06354
17 Stanley Dr, Plainfield, CT 06354
17 Stanley Dr, Plainfield, CT 06354
ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome to Stanley Drive! This impeccably maintained raised ranch is truly move-in ready and packed with features that make it a perfect home. Step inside to an inviting open concept living room, dining area, and kitchen. An ideal layout for entertaining or relaxing. Sliders off the dining area with two-level Procell deck equipped with an automatic awning, offering the perfect spot to enjoy your private backyard in comfort and style. The kitchen is a chef's delight with granite countertops, stainless steel appliances and ample cabinetry. The main floor includes a primary bedroom with a full ensuite bathroom, two additional bedrooms, and a second full bath, offering space and flexibity for g

$390,000

3 beds2 baths1,132 sq ft

17 Stanley Dr, Plainfield, CT 06354

0.53 acre lot • 2 garage spots • Car-dependent

COMING SOON

16 Jolley Rd, Plainfield, CT 06239
16 Jolley Rd, Plainfield, CT 06239
16 Jolley Rd, Plainfield, CT 06239
ABOUT THIS HOME
Windham County, CT Homes for Sale
ADORABLE RANCH w/ 16 x 16 OVERSIZED DECK to enjoy your summer evenings overlooking large back yard or on the 8 x 12 open porch. HARDWOOD floor throughout, REPLACEMENT windows and SLIDER. $18,000 BEAUTIFUL kitchen w/ GRAY cabinets, GRANITE COUNTERS and appliances conveying. LARGE Livingroom w/ BRIGHT bay window (FIREPLACE NOT operational). 3 bedrooms and bathroom in hallway. (NEEDS new TUB see disclosures), roof is a little over 20 years, 1993 SEPTIC, NEWER hot water heater. PAINT your own colors throughout and a few cosmetics needed and gutter downspouts. 1 Car garage too! Close to RTE 6 and RI line.

$250,000

3 beds1 bath1,222 sq ft

16 Jolley Rd, Plainfield, CT 06239

0.39 acre lot • Garage • Car-dependent

COMING SOON

778 Cook Hill Rd, Killingly, CT 06239
778 Cook Hill Rd, Killingly, CT 06239
778 Cook Hill Rd, Killingly, CT 06239
ABOUT THIS HOME
Windham County, CT Homes for Sale
778 Cook Hill offers a delightful blend of convenience and privacy. While nestled discreetly off the road, its accessibility remains excellent, even during winter's snowfall. The property boasts a generous, tree-lined front yard, and a private backyard complete with a deck and fire pit-perfect for enjoying cozy autumn evenings. Inside, this inviting 3-bedroom, 1.5-bathroom home features beautiful hardwood floors and an open-concept layout seamlessly connecting the kitchen, dining area, and living room. The main bathroom showcases attractive tile flooring, adding a nice touch. And for complete peace of mind, the home features a brand new roof! The lower level offers additional living space

$367,000

3 beds1 bath1,084 sq ft

778 Cook Hill Rd, Killingly, CT 06239

0.94 acre lot • 2 garage spots • Car-dependent

Property at 15 Highview Dr, Killingly, CT 06241, 3 beds, 3 baths

$499,900

3 beds3 baths3,024 sq ft

15 Highview Dr, Killingly, CT 06241

Property at 22 Philmar Dr, Plainfield, CT 06374, 5 beds, 3 baths

$399,999

5 beds3 baths2,100 sq ft

22 Philmar Dr, Plainfield, CT 06374

Property at 122 Lovers Ln, Windham, CT 06280, 4 beds, 2 baths

$335,000

4 beds2 baths1,680 sq ft

122 Lovers Ln, Windham, CT 06280

Property at 5 Kies Rd, Killingly, CT 06239, 3 beds, 3.5 baths

$845,000

3 beds3.5 baths2,209 sq ft

5 Kies Rd, Killingly, CT 06239

Property at 393 N Canterbury Rd, Canterbury, CT 06331, 4 beds, 2 baths

$739,000

4 beds2 baths2,443 sq ft

393 N Canterbury Rd, Canterbury, CT 06331

Property at 106 Tripp Hollow Rd, Brooklyn, CT 06234, 4 beds, 2.5 baths

$380,000

4 beds2.5 baths2,220 sq ft

106 Tripp Hollow Rd, Brooklyn, CT 06234

Property at 101 Center Rd, Woodstock, CT 06281, 4 beds, 3.5 baths

$715,000

4 beds3.5 baths4,536 sq ft

101 Center Rd, Woodstock, CT 06281

Property at 367 Pine Hill Rd, Sterling, CT 06377, 2 beds, 1 bath

$425,000

2 beds1 bath900 sq ft

367 Pine Hill Rd, Sterling, CT 06377

Property at 76 Mill Brook Ln, Woodstock, CT 06281, 5 beds, 4 baths

$1,100,000

5 beds4 baths5,079 sq ft

76 Mill Brook Ln, Woodstock, CT 06281

Property at 101 Prospect St, Putnam, CT 06260, 3 beds, 2 baths

$424,999

3 beds2 baths1,320 sq ft

101 Prospect St, Putnam, CT 06260

Property at 118 Ashford Rd #6, Eastford, CT 06278, 2 beds, 2 baths

$295,000

2 beds2 baths1,220 sq ft

118 Ashford Rd #6, Eastford, CT 06278

Property at 571 Squaw Rock Rd, Plainfield, CT 06354, 3 beds, 2 baths

$545,000

3 beds2 baths2,241 sq ft

571 Squaw Rock Rd, Plainfield, CT 06354

Property at Lot 8-5 Old Tatnic Hill Rd, Brooklyn, CT 06234, 3 beds, 2.5 baths

$599,000

3 beds2.5 baths1,800 sq ft

Lot 8-5 Old Tatnic Hill Rd, Brooklyn, CT 06234

Property at 422 Zaicek Rd, Ashford, CT 06278, 3 beds, 2 baths

$449,900

3 beds2 baths1,359 sq ft

422 Zaicek Rd, Ashford, CT 06278

Property at 326 Route 169, Woodstock, CT 06281

$200,000

— beds— baths3,008 sq ft

326 Route 169, Woodstock, CT 06281

Property at Lot 8-1 Old Tatnic Hill Rd, Brooklyn, CT 06234, 2 beds, 2 baths

$424,900

2 beds2 baths1,064 sq ft

Lot 8-1 Old Tatnic Hill Rd, Brooklyn, CT 06234

Property at 366 Sabin St, Putnam, CT 06260, 3 beds, 2 baths

$349,900

3 beds2 baths1,964 sq ft

366 Sabin St, Putnam, CT 06260

Property at 10 Laurel Hill Dr, Woodstock, CT 06282, 2 beds, 1.5 baths

$299,000

2 beds1.5 baths1,196 sq ft

10 Laurel Hill Dr, Woodstock, CT 06282

Property at 3 Brook Front Ln #3, Pomfret, CT 06259, 2 beds, 1 bath

$199,900

2 beds1 bath1,090 sq ft

3 Brook Front Ln #3, Pomfret, CT 06259

Property at 4 Perrin Rd, Woodstock, CT 06281, 5 beds, 3.5 baths

$599,900

5 beds3.5 baths4,172 sq ft

4 Perrin Rd, Woodstock, CT 06281

Property at 271 Snake Meadow Hill Rd, Sterling, CT 06377, 3 beds, 3 baths

$550,000

3 beds3 baths2,814 sq ft

271 Snake Meadow Hill Rd, Sterling, CT 06377

Property at 189 Chaplin Rd, Eastford, CT 06242, 1 bed, 1 bath

$239,900

1 bed1 bath540 sq ft

189 Chaplin Rd, Eastford, CT 06242

Property at 187 Chaplin Rd, Eastford, CT 06242, 3 beds, 3.5 baths

$850,000

3 beds3.5 baths2,502 sq ft

187 Chaplin Rd, Eastford, CT 06242

Property at 240 Walnut St, Windham, CT 06226, 5 beds, 2.5 baths

$349,999

5 beds2.5 baths1,952 sq ft

240 Walnut St, Windham, CT 06226

Property at 14 Finn Ln, Plainfield, CT 06374, 3 beds, 2.5 baths

$799,000

3 beds2.5 baths3,165 sq ft

14 Finn Ln, Plainfield, CT 06374

Property at 32 Mockingbird Dr #32, Killingly, CT 06239, 2 beds, 2 baths

$519,900

2 beds2 baths2,246 sq ft

32 Mockingbird Dr #32, Killingly, CT 06239

Property at 365 Cranberry Bog Rd, Killingly, CT 06239, 4 beds, 3 baths

$799,000

4 beds3 baths3,086 sq ft

365 Cranberry Bog Rd, Killingly, CT 06239

Property at 361 Westminster Rd, Canterbury, CT 06331, 2 beds, 1.5 baths

$439,000

2 beds1.5 baths1,048 sq ft

361 Westminster Rd, Canterbury, CT 06331

Property at 471 Moosup Pond Rd, Plainfield, CT 06354, 3 beds, 2 baths

$439,000

3 beds2 baths1,892 sq ft

471 Moosup Pond Rd, Plainfield, CT 06354

Property at 4 Skylark Ln #4, Killingly, CT 06239, 2 beds, 2 baths

$495,000

2 beds2 baths1,613 sq ft

4 Skylark Ln #4, Killingly, CT 06239

Property at 40 Ference Rd, Ashford, CT 06278, 2 beds, 2 baths

$135,000

2 beds2 baths1,008 sq ft

40 Ference Rd, Ashford, CT 06278

Property at 190 Main St, Plainfield, CT 06354, 4 beds, 4 baths

$399,990

4 beds4 baths2,288 sq ft

190 Main St, Plainfield, CT 06354

Property at 80 Tuckie Rd, Windham, CT 06280, 3 beds, 3.5 baths

$449,900

3 beds3.5 baths2,389 sq ft

80 Tuckie Rd, Windham, CT 06280

Property at 135 Goodwin Rd, Canterbury, CT 06331, 4 beds, 2.5 baths

$539,900

4 beds2.5 baths2,545 sq ft

135 Goodwin Rd, Canterbury, CT 06331

Property at 19 Thompson Pike, Killingly, CT 06241, 3 beds, 1 bath

$350,000

3 beds1 bath1,320 sq ft

19 Thompson Pike, Killingly, CT 06241

Property at 117 Woodside St, Putnam, CT 06260, 4 beds, 2 baths

$429,000

4 beds2 baths2,014 sq ft

117 Woodside St, Putnam, CT 06260

Viewing page 2 of 8

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$469,900
Storrs homes for sale
$407,400
North Grosvenor Dale homes for sale
$399,500
South Windham homes for sale
$325,000
Lake Bungee homes for sale
$499,900
Willimantic homes for sale
$278,000
Brooklyn homes for sale
$484,900
East Brooklyn homes for sale
$380,000
Danielson homes for sale
$385,000
South Woodstock homes for sale
$554,500
Putnam homes for sale
$349,450
Moosup homes for sale
$414,500
Mansfield Center homes for sale

Counties

Hartford County homes for sale
$400,000
New Haven County homes for sale
$429,900
New London County homes for sale
$433,450

Windham County, CT real estate trends

All Home Types trends in Windham County, CT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$399,742

+12.6% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Windham County, CT

$399,742

+12.6%

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