Windham County, CT homes for sale & real estate

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ABOUT THIS HOME
Windham County, CT Homes for Sale
Pristine High Vista Land: As you drive through the gated entrance up the winding drive, take in the flora and fauna. This magnificent building lot lends itself to an abundance of opportunities such as solar and wind power to comfortably live off grid. Located in the corner of CT-RI-MA (the Quiet Corner) of Northeast CT. Perfect location for the kings castle. This Mashentuck mountain top is 600ft above sea level offering spectacular east and west views(sunrise & sunset) in every season. Perfect for a private estate and paradise with wildlife galore. 23 acres, there is ample room for a heliport and livestock. Paved drive (with installed utilities) leads up to roughed in graveled drivewa

$399,000

— beds— baths— sq ft

612 Cook Hill Rd, Killingly, CT 06239

Solar and wind power • Gated entrance • Winding drive

ABOUT THIS HOME
Windham County, CT Homes for Sale
Beautiful wooded lot off a paved country back road in Canterbury. Get ready to build your dream home! A2 survey already done. Engineered plan for the septic system already done. Proposed driveway approved to be put in passing over the wetlands. There is a seasonal snowmelt stream that runs through that could be an amazing landscape opportunity. If you want to build a house in the backwoods, country setting you've always imagined set up an appointment to see lot ASAP!

$83,000

— beds— baths— sq ft

Bennett Pond Rd, Canterbury, CT 06331

Wooded lot • A2 survey • 3.2 acre lot

ABOUT THIS HOME
Windham County, CT Homes for Sale
Located in a peaceful rural setting near I-395 and Rhode Island, this spacious plot of land offers abundant potential for subdivision or development. Its strategic location provides easy access to major transportation routes, making it an ideal opportunity for creating residential lots. Surrounded by natural beauty and tranquil surroundings, this property presents endless possibilities for building.

$115,000

— beds— baths— sq ft

85 Mashentuck Rd, Killingly, CT 06239

8.5 acre lot • Listed 93 days

ABOUT THIS HOME
Windham County, CT Homes for Sale
216+/- acre tract of absolutely gorgeous woodland with some fields, small stream, some wetlands, pine & hardwood forests, apple and chestnut trees, hiking and vehicle and Quad trails, Whole tract currently consists of 8 separate contiguous parcels of land with 650+/- feet of road frontage, this property is very sub-dividable, first parcel had a 9 lot sub-division, entitled: "Fawn Ridge" completely approved by the Killingly P & Z Commission approximately 17 years ago. This large tract of land is teeming with wildlife. Ideal for family compound, equestrian estate or for large upper bracket homes for the persons that wants a lot of elbow room, a rare find and must see prop

$2,195,000

— beds— baths— sq ft

333 Breakneck Hill Rd, Dayville, CT 06241

Vehicle trails • Apple trees • Chestnut trees

ABOUT THIS HOME
Windham County, CT Homes for Sale
Expansive 37.5-acre parcel offering excellent potential for development or subdivision, per town zoning regulations. With a mix of open space and woodlands, this versatile property lends itself to a variety of uses-from building a private estate or homestead to exploring subdivision options for future development. Enjoy the peace and privacy of a rural setting with convenient access to nearby amenities and major routes. A rare opportunity for investors, builders, or anyone seeking space and flexibility in the quiet countryside. Property is being sold as is. Buyer to perform their own due diligence.

$300,000

— beds— baths— sq ft

35 River Rd, Sterling, CT 06377

Mature woodlands • Open space • Convenient access

Property at 00 pilfershire Rd, Eastford, CT 06242

$102,000

— beds— baths— sq ft

00 pilfershire Rd, Eastford, CT 06242

Property at 350 Breakneck Hill Rd, Killingly, CT 06241

$179,900

— beds— baths— sq ft

350 Breakneck Hill Rd, Killingly, CT 06241

Property at 597 East Thompson Rd Lot 10C, Thompson, CT 06277

$144,000

— beds— baths— sq ft

597 East Thompson Rd Lot 10C, Thompson, CT 06277

Property at Brooklyn Rd, Canterbury, CT 06331

$899,000

— beds— baths— sq ft

Brooklyn Rd, Canterbury, CT 06331

Property at Aplin Hill Ln, Woodstock, CT 06281

$85,000

— beds— baths— sq ft

Aplin Hill Ln, Woodstock, CT 06281

Property at 241 Killingly Ave, Putnam, CT 06260

$350,000

— beds— baths— sq ft

241 Killingly Ave, Putnam, CT 06260

Property at Dow Rd, Plainfield, CT 06374

$199,900

— beds— baths— sq ft

Dow Rd, Plainfield, CT 06374

Property at 38 Elm St, Willimantic, CT 06226

$84,900

— beds— baths— sq ft

38 Elm St, Willimantic, CT 06226

Property at 43 fallbrook Rd, Killingly, CT 06243

$75,000

— beds— baths— sq ft

43 fallbrook Rd, Killingly, CT 06243

Property at 97 Blossom Dr, Pomfret Center, CT 06259

$125,000

— beds— baths— sq ft

97 Blossom Dr, Pomfret Center, CT 06259

Property at Lot 12-1 Tripp Hollow Rd, Brooklyn, CT 06234

$179,900

— beds— baths— sq ft

Lot 12-1 Tripp Hollow Rd, Brooklyn, CT 06234

Property at 18 Ledge Hill Rd, Sterling, CT 06377

$85,000

— beds— baths— sq ft

18 Ledge Hill Rd, Sterling, CT 06377

Property at 70 cutler Rd, Killingly, CT 06243

$100,000

— beds— baths— sq ft

70 cutler Rd, Killingly, CT 06243

Property at 1450 North Rd, Killingly, CT 06241

$349,000

— beds— baths— sq ft

1450 North Rd, Killingly, CT 06241

Property at Plainfield Pike, Plainfield, CT 06374

$85,000

— beds— baths— sq ft

Plainfield Pike, Plainfield, CT 06374

Property at 1248 hartford Pike, Killingly, CT 06243

$75,000

— beds— baths2,274 sq ft

1248 hartford Pike, Killingly, CT 06243

Property at 00 No Brook St, Hampton, CT 06427

$49,900

— beds— baths— sq ft

00 No Brook St, Hampton, CT 06427

Property at 70 Brayman Hollow Rd, Pomfret Center, CT 06259

$89,000

— beds— baths— sq ft

70 Brayman Hollow Rd, Pomfret Center, CT 06259

Property at 64 Westcott Rd, Danielson, CT 06239

$65,000

— beds— baths— sq ft

64 Westcott Rd, Danielson, CT 06239

Property at Brook Rd Lot 4, Hampton, CT 06247

$85,000

— beds— baths— sq ft

Brook Rd Lot 4, Hampton, CT 06247

Property at Wauregan Rd, Plainfield, CT 06374

$750,000

— beds— baths— sq ft

Wauregan Rd, Plainfield, CT 06374

Property at 53 S Main St, Brooklyn, CT 06234

$39,000

— beds— baths— sq ft

53 S Main St, Brooklyn, CT 06234

Property at Lot 0 Kozey Rd, Eastford, CT 06242

$800,000

— beds— baths— sq ft

Lot 0 Kozey Rd, Eastford, CT 06242

Property at 834 Hampton Rd, Pomfret, CT 06230

$100,000

— beds— baths— sq ft

834 Hampton Rd, Pomfret, CT 06230

Property at 130 Cook Hill Rd, Killingly, CT 06239

$115,000

— beds— baths— sq ft

130 Cook Hill Rd, Killingly, CT 06239

Property at Wolf Den Rd, Brooklyn, CT 06234

$363,000

— beds— baths— sq ft

Wolf Den Rd, Brooklyn, CT 06234

Property at 308 Orchard Hill Rd, Pomfret Center, CT 06259

$210,000

— beds— baths— sq ft

308 Orchard Hill Rd, Pomfret Center, CT 06259

Property at 36 Plainfield Pike, Plainfield, CT 06374

$1,100,000

— beds— baths1,545 sq ft

36 Plainfield Pike, Plainfield, CT 06374

Property at 842 Hartford Pike, Killingly, CT 06241

$2,816,000

— beds— baths— sq ft

842 Hartford Pike, Killingly, CT 06241

Property at 121 Walker Rd, Canterbury, CT 06331

$550,000

— beds— baths1,275 sq ft

121 Walker Rd, Canterbury, CT 06331

Property at Putnam Rd, Plainfield, CT 06374

$450,000

— beds— baths— sq ft

Putnam Rd, Plainfield, CT 06374

$159,500

— beds— baths— sq ft

Brooklyn Rd, Canterbury, CT 06331

Property at 405 Providence Rd, Brooklyn, CT 06234

$799,500

— beds— baths1,764 sq ft

405 Providence Rd, Brooklyn, CT 06234

Property at 80 Averill Rd, Pomfret Center, CT 06259

$225,000

— beds— baths— sq ft

80 Averill Rd, Pomfret Center, CT 06259

Property at 00 Mashamoquet Rd, Pomfret Center, CT 06259

$225,000

— beds— baths— sq ft

00 Mashamoquet Rd, Pomfret Center, CT 06259

Property at 0 Hampton Rd, Chaplin, CT 06235

$139,000

— beds— baths— sq ft

0 Hampton Rd, Chaplin, CT 06235

Viewing page 6 of 7

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$289,000
North Grosvenor Dale homes for sale
$282,450
Lake Bungee homes for sale
$522,000
Willimantic homes for sale
$269,000
Quinebaug homes for sale
$137,500
Brooklyn homes for sale
$407,500
East Brooklyn homes for sale
$369,000
Danielson homes for sale
$312,500
South Woodstock homes for sale
$549,000
Putnam homes for sale
$332,450
Moosup homes for sale
$457,450
Mansfield Center homes for sale
$385,000
Dayville homes for sale
$499,900

Counties

Hartford County homes for sale
$394,000
New Haven County homes for sale
$419,000
New London County homes for sale
$439,950

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)

$363,500

+3.9% YoY | Sep 2025

1 year
3 year
5 year

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

Location

Data

Sep 2025

Growth

% YoY

Windham County, CT

$363,500

+3.9%

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