Windham County, CT homes for sale & real estate

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72 Lake View Dr, Woodstock, CT 06281
72 Lake View Dr, Woodstock, CT 06281
72 Lake View Dr, Woodstock, CT 06281
ABOUT THIS HOME
Windham County, CT Homes for Sale
* * * MOTIVATED SELLER * * * Welcome to your summer getaway or year-round oasis. This 2-bedroom 2- bathroom updated lake front retreat will have you feeling right at home no matter what season. Enjoy sunset cruises on your pontoon boat, the stunning views and colors in the fall and let's not forget ice fishing in the winter. This home has been completely renovated inside and out. Entering on the main level you have open concept of living room, dining room, kitchen, a full bathroom and the secondary bedroom. Continue up the stairs to your primary bedroom oasis. Sip your coffee in bed and enjoy the view from your large window overlooking the lake. Every detail of this home has been meticu

$674,000

2 beds2 baths1,338 sq ft

72 Lake View Dr, Woodstock, CT 06281

0.4 acre lot • Garage • Car-dependent

87 North St, Windham, CT 06226
87 North St, Windham, CT 06226
87 North St, Windham, CT 06226
ABOUT THIS HOME
Windham County, CT Homes for Sale
TWO HOUSES ON ONE PROPERTY! This unique investment opportunity at 87-89 North Street in Willimantic, CT, presents a compelling proposition for investors. The property comprises TWO single-family homes situated on a single lot, each with its own driveway and access to a large garage located conveniently on the front house's driveway. The rear house, a charming 1,224 square-foot dwelling, currently offers two bedrooms, a spacious kitchen, dining room, a laundry area, and a full bathroom. Its existing condition presents a stable rental income stream, mitigating risk during the renovation of the front house. The front house, approximately 1,757 square feet, has been completely stripped to the s

$320,000

6 beds2 baths2,981 sq ft

87 North St, Windham, CT 06226

9,147 sq ft lot • Very walkable

NEW CONSTRUCTION

1 Johns Cir, Sterling, CT 06377
1 Johns Cir, Sterling, CT 06377
1 Johns Cir, Sterling, CT 06377
ABOUT THIS HOME
Windham County, CT Homes for Sale
* NEW CONSTRUCTION * LAST REMINAING LOT * Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Colonial offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous Granite Kitchen, complete with a view of the valley while you do dishes! Enjoy the ease of a maintenance-free lifestyle, including lawn, road maintenance, and snow removal for just $140 a month. This one-of-a-kind home sits at the end of a cul-de-sac amidst fine homes, offering privacy and prestige. With a lower level ready for your personal touch, plus a 2-car ga

$419,900

3 beds2.5 baths1,776 sq ft

1 Johns Cir, Sterling, CT 06377

$140 HOA • 2 garage spots • Car-dependent

34 Pleasant St #8, Plainfield, CT 06374
34 Pleasant St #8, Plainfield, CT 06374
34 Pleasant St #8, Plainfield, CT 06374
ABOUT THIS HOME
Windham County, CT Homes for Sale
NOTE: Units are priced to sell! These newly renovated units will not last! Looking for low-maintenance living without sacrificing space or style? Look no further than The Junction House, a beautifully updated 8-unit condo community offering a peaceful lifestyle in a convenient Plainfield location. Choose from spacious 2-bedroom or 3-bedroom units, all fully renovated with modern kitchens, updated baths, new flooring, and in-unit laundry. Whether you're downsizing, buying your first home, or looking for easy living, these move-in-ready condos check all the boxes. Enjoy days by the in-ground pool or relax in the cabana-perfect for entertaining or unwinding. Best of all, the HOA takes care of

$279,900

3 beds1.5 baths1,429 sq ft

34 Pleasant St #8, Plainfield, CT 06374

$466 HOA • Pool • Car-dependent

34 Pleasant St #7, Plainfield, CT 06374
34 Pleasant St #7, Plainfield, CT 06374
34 Pleasant St #7, Plainfield, CT 06374
ABOUT THIS HOME
Windham County, CT Homes for Sale
NOTE: Units are priced to sell! These newly renovated units will not last! Looking for low-maintenance living without sacrificing space or style? Look no further than The Junction House, a beautifully updated 8-unit condo community offering a peaceful lifestyle in a convenient Plainfield location. Choose from spacious 2-bedroom or 3-bedroom units, all fully renovated with modern kitchens, updated baths, new flooring, and in-unit laundry. Whether you're downsizing, buying your first home, or looking for easy living, these move-in-ready condos check all the boxes. Enjoy days by the in-ground pool or relax in the cabana-perfect for entertaining or unwinding. Best of all, the HOA takes care of

$249,900

3 beds1.5 baths1,259 sq ft

34 Pleasant St #7, Plainfield, CT 06374

$410 HOA • Pool • Car-dependent

Property at 34 Pleasant St #6, Plainfield, CT 06374, 2 beds, 1 bath

$229,900

2 beds1 bath1,215 sq ft

34 Pleasant St #6, Plainfield, CT 06374

Property at 34 Pleasant St #5, Plainfield, CT 06374, 2 beds, 1 bath

$254,900

2 beds1 bath1,343 sq ft

34 Pleasant St #5, Plainfield, CT 06374

Property at 34 Pleasant St #4, Plainfield, CT 06374, 3 beds, 1 bath

$284,900

3 beds1 bath1,314 sq ft

34 Pleasant St #4, Plainfield, CT 06374

Property at 34 Pleasant St #3, Plainfield, CT 06374, 2 beds, 1 bath

$239,900

2 beds1 bath1,188 sq ft

34 Pleasant St #3, Plainfield, CT 06374

Property at 31 Cherry Hill Rd, Brooklyn, CT 06234, 3 beds, 3 baths

$494,900

3 beds3 baths2,464 sq ft

31 Cherry Hill Rd, Brooklyn, CT 06234

Property at 369 Thompson Rd, Thompson, CT 06277, 4 beds, 3.5 baths

$624,900

4 beds3.5 baths2,944 sq ft

369 Thompson Rd, Thompson, CT 06277

Property at 5 Nahaco Hill Ln, Eastford, CT 06242, 1 bed, 2 baths

$328,900

1 bed2 baths1,167 sq ft

5 Nahaco Hill Ln, Eastford, CT 06242

Property at 1026 Route 171, Woodstock, CT 06281, 3 beds, 2 baths

$449,999

3 beds2 baths1,728 sq ft

1026 Route 171, Woodstock, CT 06281

Property at 37 Pulpit Rock Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$649,900

4 beds2.5 baths2,682 sq ft

37 Pulpit Rock Rd, Woodstock, CT 06281

Property at 000 Joy Rd, Woodstock, CT 06281, 3 beds, 2.5 baths

$925,000

3 beds2.5 baths3,500 sq ft

000 Joy Rd, Woodstock, CT 06281

Property at 20 Connecticut Dr, Plainfield, CT 06374, 2 beds, 2 baths

$140,000

2 beds2 baths960 sq ft

20 Connecticut Dr, Plainfield, CT 06374

Property at 23 Hell Hollow Rd, Sterling, CT 06384, 3 beds, 1.5 baths

$449,900

3 beds1.5 baths2,440 sq ft

23 Hell Hollow Rd, Sterling, CT 06384

Property at 9 Ann St, Windham, CT 06226, 5 beds, 2 baths

$330,000

5 beds2 baths2,200 sq ft

9 Ann St, Windham, CT 06226

Property at 104 Pulpit Rock Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$575,000

4 beds2.5 baths2,016 sq ft

104 Pulpit Rock Rd, Woodstock, CT 06281

Property at 11 Stone House Dr, Plainfield, CT 06354, 3 beds, 2 baths

$475,000

3 beds2 baths1,832 sq ft

11 Stone House Dr, Plainfield, CT 06354

Property at 101 Child Hill Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$559,000

4 beds2.5 baths2,150 sq ft

101 Child Hill Rd, Woodstock, CT 06281

Property at 25 Route 197 Rte Lot 40, Woodstock, CT 06281, 1 bed, 1 bath

$29,900

1 bed1 bath300 sq ft

25 Route 197 Rte Lot 40, Woodstock, CT 06281

Property at 30 Huntley Rd, Killingly, CT 06241, 3 beds, 1 bath

$248,500

3 beds1 bath1,008 sq ft

30 Huntley Rd, Killingly, CT 06241

Property at 91 Pomfret Landing Rd, Brooklyn, CT 06234, 3 beds, 2.5 baths

$549,900

3 beds2.5 baths2,119 sq ft

91 Pomfret Landing Rd, Brooklyn, CT 06234

Property at 180 Tripp Hollow Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$459,900

3 beds2 baths1,428 sq ft

180 Tripp Hollow Rd, Brooklyn, CT 06234

Property at 178 Tripp Hollow Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$454,900

3 beds2 baths1,428 sq ft

178 Tripp Hollow Rd, Brooklyn, CT 06234

Property at 270 S Windham Rd Apt 63, Windham, CT 06226, 2 beds, 1 bath

$127,500

2 beds1 bath790 sq ft

270 S Windham Rd Apt 63, Windham, CT 06226

Property at 56 Laurel Hill Dr, Woodstock, CT 06282, 3 beds, 1.5 baths

$499,000

3 beds1.5 baths1,008 sq ft

56 Laurel Hill Dr, Woodstock, CT 06282

Property at 57 Circle Dr, Windham, CT 06256, 3 beds, 2 baths

$65,000

3 beds2 baths1,152 sq ft

57 Circle Dr, Windham, CT 06256

Property at 267 Chase Rd, Thompson, CT 06277, 3 beds, 4 baths

$850,000

3 beds4 baths3,431 sq ft

267 Chase Rd, Thompson, CT 06277

Property at 1 First St, Thompson, CT 06255, 3 beds, 1.5 baths

$399,500

3 beds1.5 baths1,800 sq ft

1 First St, Thompson, CT 06255

Property at 297 Main St, Hampton, CT 06247, 3 beds, 2 baths

$280,000

3 beds2 baths1,654 sq ft

297 Main St, Hampton, CT 06247

Property at 48 Wrights Crossing Rd, Pomfret, CT 06259, 3 beds, 3 baths

$695,000

3 beds3 baths2,546 sq ft

48 Wrights Crossing Rd, Pomfret, CT 06259

Property at 29 Tiffany St, Brooklyn, CT 06234, 19 beds, 12 baths

$1,495,000

19 beds12 baths11,775 sq ft

29 Tiffany St, Brooklyn, CT 06234

Property at 3 Woodstock Ave W, Putnam, CT 06260, 3 beds, 1.5 baths

$399,999

3 beds1.5 baths1,922 sq ft

3 Woodstock Ave W, Putnam, CT 06260

Property at 206 Stawicki Rd, Thompson, CT 06255, 3 beds, 2.5 baths

$529,000

3 beds2.5 baths1,900 sq ft

206 Stawicki Rd, Thompson, CT 06255

Property at 18 Ware Rd, Killingly, CT 06241, 6 beds, 3 baths

$1,100,000

6 beds3 baths1,800 sq ft

18 Ware Rd, Killingly, CT 06241

Property at Undisclosed address, Canterbury, CT 06331, 4 beds, 4.5 baths

$1,199,000

4 beds4.5 baths3,705 sq ft

Undisclosed address, Canterbury, CT 06331

Property at 227 Ash St, Windham, CT 06226, 4 beds, 2 baths

$225,000

4 beds2 baths1,500 sq ft

227 Ash St, Windham, CT 06226

Property at 109 Hnath Rd, Ashford, CT 06278, 3 beds, 2.5 baths

$579,900

3 beds2.5 baths3,260 sq ft

109 Hnath Rd, Ashford, CT 06278

Property at 36 Olde Meadow Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$895,000

4 beds2.5 baths3,356 sq ft

36 Olde Meadow Rd, Woodstock, CT 06281

Viewing page 5 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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