Windham County, CT homes for sale & real estate

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ABOUT THIS HOME
Windham County, CT Homes for Sale
Discover the potential of this 1.07 acre lot. The property currently features a barn structure, but the true value lies in the land itself, being located on a private - no outlet road! With ample space to develop to dream property. Explore the possibilities this well-situated property has to offer. Trailer on property does not convey.

$299,900

— beds— baths— sq ft

71 Deerfield Dr, Sterling, CT 06373

Barn structure • 1.07 acre lot • Ample space

ABOUT THIS HOME
Windham County, CT Homes for Sale
Discover this beautiful 0.61-acre lot-ready and waiting for your dream build. Tucked away on a private road in Sterling, CT, this property offers the perfect opportunity to create your own peaceful retreat. Whether you're envisioning a custom home or a quiet getaway, this slice of heaven provides the privacy and space you've been looking for.

$60,000

— beds— baths— sq ft

81 Deerfield Dr, Sterling, CT 06373

Private road • Custom home • 0.61-acre lot

ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome to Pinedale Farms, a rare large-scale development opportunity in the heart of Brooklyn. This offering includes 136.38 acres of industrial-zoned land along with the additional 2.8-acre parcel at 22 Allen Hill Rd, creating a substantial combined footprint of 139.18 acres for future projects. The property provides three access points which are 22 Allen Hill, south of 68 Allen Hill Rd and between 63 and 69 Fortin Dr. Public water is stubbed near this portion of the site. The acreage features mostly manageable terrain with natural buffers, allowing flexible design options. Approximately 15 acres near the Allen Hill entrance are zoned RA, with the remainder zoned Industrial. This is one o

$6,000,000

— beds— baths— sq ft

Allen Hill Rd, Brooklyn, CT 06234

136.38 acre lot • Listed 13 days

ABOUT THIS HOME
Windham County, CT Homes for Sale
Fully approved and shovel ready for 60 Multi Family Units! Affordable project can be developed in phases. Public sewer available, private well and 3 Phase Power. Close to the airline trail for hiking and cycling. Conveniently located restaurants and shopping. Close proximity to the casinos, Worcester, Providence, Boston and the Rhode Island and Ct Shoreline.

$1,295,000

— beds— baths— sq ft

99 Azud Rd, Thompson, CT 06277

Public sewer • 3 phase power • Private well

ABOUT THIS HOME
Windham County, CT Homes for Sale
Great opportunity awaits on this 11 acre multi use property that runs along the airline trail. Some of the many potential uses would be townhouses, duplex's, multi families and single family homes. Gravel is on site. City sewer and 3 phase power. This property is located near 395 which is great for easy commuting into Massachusetts. .

$499,900

— beds— baths— sq ft

117 Riverside Dr, Thompson, CT 06255

3 phase power • City sewer • 11.15 acre lot

Property at Hanover Rd, Canterbury, CT 06331

$54,000

— beds— baths— sq ft

Hanover Rd, Canterbury, CT 06331

Property at 253 Brick Top Rd, Windham, CT 06280

$799,900

— beds— baths— sq ft

253 Brick Top Rd, Windham, CT 06280

Property at Boston Tpke, Eastford, CT 06242

$180,000

— beds— baths— sq ft

Boston Tpke, Eastford, CT 06242

Property at Wilsonville Rd, Thompson, CT 06277

$125,000

— beds— baths— sq ft

Wilsonville Rd, Thompson, CT 06277

Property at 147 South St, Brooklyn, CT 06234

$179,900

— beds— baths— sq ft

147 South St, Brooklyn, CT 06234

Property at Lot 89 Paradise Dr, Brooklyn, CT 06234

$14,900

— beds— baths— sq ft

Lot 89 Paradise Dr, Brooklyn, CT 06234

Property at 4 Short St, Brooklyn, CT 06234

$7,900

— beds— baths— sq ft

4 Short St, Brooklyn, CT 06234

Property at 232 Paradise Dr, Brooklyn, CT 06234

$24,900

— beds— baths— sq ft

232 Paradise Dr, Brooklyn, CT 06234

Property at Lot 172 Paradise Dr, Brooklyn, CT 06234

$14,900

— beds— baths— sq ft

Lot 172 Paradise Dr, Brooklyn, CT 06234

Property at 37 Katherine Ave, Killingly, CT 06239

$62,500

— beds— baths— sq ft

37 Katherine Ave, Killingly, CT 06239

Property at Undisclosed address, Killingly, CT 06239

$409,000

— beds— baths— sq ft

Undisclosed address, Killingly, CT 06239

Property at 00 Norwich Rd, Plainfield, CT 06374

$30,000

— beds— baths— sq ft

00 Norwich Rd, Plainfield, CT 06374

Property at 468 Fabyan Rd, North Grosvenordale, CT 06255

$119,900

— beds— baths— sq ft

468 Fabyan Rd, North Grosvenordale, CT 06255

Property at 3 Pomfret Rd, Brooklyn, CT 06234

$450,000

— beds— baths— sq ft

3 Pomfret Rd, Brooklyn, CT 06234

Property at 00 Ide Perrin Rd, Woodstock, CT 06281

$349,900

— beds— baths— sq ft

00 Ide Perrin Rd, Woodstock, CT 06281

Property at 66 Bates Ave, Putnam, CT 06260

$149,000

— beds— baths— sq ft

66 Bates Ave, Putnam, CT 06260

Property at 106 Riley Chase Rd, Killingly, CT 06241

$100,000

— beds— baths— sq ft

106 Riley Chase Rd, Killingly, CT 06241

Property at 0 Rt 171, Woodstock, CT 06281

$335,000

— beds— baths— sq ft

0 Rt 171, Woodstock, CT 06281

Property at 0 Church St, Thompson, CT 06277

$225,000

— beds— baths— sq ft

0 Church St, Thompson, CT 06277

Property at Dow Rd, Plainfield, CT 06374

$199,900

— beds— baths— sq ft

Dow Rd, Plainfield, CT 06374

Property at 333 Breakneck Hill Rd, Dayville, CT 06241

$2,195,000

— beds— baths— sq ft

333 Breakneck Hill Rd, Dayville, CT 06241

Property at 165 Lisbon Rd, Canterbury, CT 06331

$129,900

— beds— baths— sq ft

165 Lisbon Rd, Canterbury, CT 06331

Property at 80 Aldrich Rd, Putnam, CT 06260

$150,000

— beds— baths— sq ft

80 Aldrich Rd, Putnam, CT 06260

Property at 49 Stone Rd, Killingly, CT 06241

$164,900

— beds— baths— sq ft

49 Stone Rd, Killingly, CT 06241

Property at 338 Brooklyn Rd, Pomfret Center, CT 06259

$500,000

— beds— baths— sq ft

338 Brooklyn Rd, Pomfret Center, CT 06259

Property at Brooklyn Rd, Canterbury, CT 06331

$899,000

— beds— baths— sq ft

Brooklyn Rd, Canterbury, CT 06331

Property at Bennett Pond Rd, Canterbury, CT 06331

$83,000

— beds— baths— sq ft

Bennett Pond Rd, Canterbury, CT 06331

Property at 1450 North Rd, Killingly, CT 06241

$349,000

— beds— baths— sq ft

1450 North Rd, Killingly, CT 06241

Property at 241 Killingly Ave, Putnam, CT 06260

$350,000

— beds— baths— sq ft

241 Killingly Ave, Putnam, CT 06260

Property at Aplin Hill Ln, Woodstock, CT 06281

$85,000

— beds— baths— sq ft

Aplin Hill Ln, Woodstock, CT 06281

Property at Putnam Rd, Plainfield, CT 06374

$450,000

— beds— baths— sq ft

Putnam Rd, Plainfield, CT 06374

Property at Wauregan Rd, Plainfield, CT 06374

$750,000

— beds— baths— sq ft

Wauregan Rd, Plainfield, CT 06374

Property at 128 Lathrop Rd, Plainfield, CT 06374

$1,200,000

— beds— baths— sq ft

128 Lathrop Rd, Plainfield, CT 06374

Property at 85 Mashentuck Rd, Killingly, CT 06239

$115,000

— beds— baths— sq ft

85 Mashentuck Rd, Killingly, CT 06239

$159,500

— beds— baths— sq ft

Brooklyn Rd, Canterbury, CT 06331

Property at 00 Prospect St, Woodstock, CT 06281

$99,900

— beds— baths— sq ft

00 Prospect St, Woodstock, CT 06281

Viewing page 5 of 6

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$329,000
East Brooklyn homes for sale
$389,450
North Grosvenor Dale homes for sale
$365,000
Danielson homes for sale
$287,500
South Woodstock homes for sale
$479,000
Willimantic homes for sale
$264,900
Putnam homes for sale
$379,450
Moosup homes for sale
$420,000
Quinebaug homes for sale
$347,500
Mansfield Center homes for sale
Brooklyn homes for sale
$365,000
Dayville homes for sale
$499,900

Counties

Hartford County homes for sale
$379,900
New Haven County homes for sale
$399,900
New London County homes for sale
$415,000

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)

$360,000

+5.9% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Windham County, CT

$360,000

+5.9%

See more Windham County, CT market insights

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