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Windham County is a beautiful region located in northeastern Connecticut, with a population of over 116,000 people. The area is known for its charming small towns, rolling hills, and abundant natural beauty.

The region’s economy is diverse, with a mix of industries including healthcare, education, manufacturing, and tourism. The area is also home to a growing arts and culture scene, with many galleries, museums, and performing arts venues located throughout the county.

Real estate in Windham County is affordable, with the median home value around $200,000. Housing options range from historic homes in quaint villages to modern apartments in vibrant downtown areas.

With its natural beauty, rich cultural offerings, and strong sense of community, Windham County is a wonderful place to call home. Whether you’re looking for a place to live, work, or play, this region offers something for everyone. Towns that make up the county:

Towns that make up the county:

Min. Price
Max. Price
Beds
Baths
433 Wrights Crossing Road Pomfret, CT 06259
$6,950,000
12 Beds 7 | 2 Baths 10,517 SqFt Listing No. 24101484 Property Type: House camera (40)
Details
282 & 260 Searles Road Pomfret, CT 06259
$2,950,000
4 Beds 3 | 2 Baths 4,442 SqFt Listing No. 24115278 Property Type: House camera (40)
Details
158 West Quasset Road Woodstock, CT 06281
$2,495,000
4 Beds 4 Baths 3,723 SqFt Listing No. 24180508 Property Type: House camera (40)
Details
357 Wrights Crossing Road Pomfret, CT 06259
$2,100,000
5 Beds 5 | 1 Baths 7,772 SqFt Listing No. 24115029 Property Type: House camera (40)
Details
1374 Route 171 Woodstock, CT 06282
$1,450,000
3 Beds 5 | 1 Baths 6,394 SqFt Listing No. 24177811 Property Type: House camera (40)
Details
354 Pomfret Street Pomfret, CT 06259
$1,295,000
6 Beds 4 | 1 Baths 5,459 SqFt Listing No. 24172480 Property Type: House camera (38) Open House: Jun 26, 2026, 4:00 PM - 6:00 PM
Details
95 Pole Bridge Road Woodstock, CT 06281
$1,275,000
4 Beds 3 | 1 Baths 3,868 SqFt Listing No. 24185273 Property Type: House camera Virtual Tour camera (40)
Details
46 Cemetery Road Canterbury, CT 06331
$1,200,000
3 Beds 2 Baths 2,393 SqFt Listing No. 24179809 Property Type: House camera (40)
Details
82 Kennerson Reservoir Road Eastford, CT 06242
$995,000
4 Beds 3 Baths 5,176 SqFt Listing No. 24178434 Property Type: House camera (40)
Details
9 Becola Road Thompson, CT 06277
$899,000
3 Beds 2 | 1 Baths 1,437 SqFt Listing No. 24169232 Property Type: House camera (26)
Details
48 Grey Fox Landing Woodstock, CT 06281
$880,000
4 Beds 5 Baths 5,087 SqFt Listing No. 24180671 Property Type: House camera (39)
Details
254 Beaver Hill Road Windham, CT 06256
$874,000
3 Beds 2 Baths 1,808 SqFt Listing No. 24174325 Property Type: House camera (39)
Details
 433 Wrights Crossing Road, Pomfret, CT 06259
camera (40)
price

$6,950,000

beds

12 12 Beds

baths

7 | 2 7 | 2 Baths

lot size

10,517 SqFt 10,517 SqFt

listing no.

24101484 Listing No. 24101484

property type

House Property Type: House

gallery photos

camera (40)

 282 & 260 Searles Road, Pomfret, CT 06259
camera (40)
price

$2,950,000

beds

4 4 Beds

baths

3 | 2 3 | 2 Baths

lot size

4,442 SqFt 4,442 SqFt

listing no.

24115278 Listing No. 24115278

property type

House Property Type: House

gallery photos

camera (40)

 158 West Quasset Road, Woodstock, CT 06281
camera (40)
price

$2,495,000

beds

4 4 Beds

baths

4 4 Baths

lot size

3,723 SqFt 3,723 SqFt

listing no.

24180508 Listing No. 24180508

property type

House Property Type: House

gallery photos

camera (40)

 357 Wrights Crossing Road, Pomfret, CT 06259
camera (40)
price

$2,100,000

beds

5 5 Beds

baths

5 | 1 5 | 1 Baths

lot size

7,772 SqFt 7,772 SqFt

listing no.

24115029 Listing No. 24115029

property type

House Property Type: House

gallery photos

camera (40)

 1374 Route 171, Woodstock, CT 06282
camera (40)
price

$1,450,000

beds

3 3 Beds

baths

5 | 1 5 | 1 Baths

lot size

6,394 SqFt 6,394 SqFt

listing no.

24177811 Listing No. 24177811

property type

House Property Type: House

gallery photos

camera (40)

 354 Pomfret Street, Pomfret, CT 06259
camera (38)
price

$1,295,000

beds

6 6 Beds

baths

4 | 1 4 | 1 Baths

lot size

5,459 SqFt 5,459 SqFt

listing no.

24172480 Listing No. 24172480

property type

House Property Type: House

gallery photos

camera (38)

Open House: Jun 26, 2026, 4:00 PM - 6:00 PM

 95 Pole Bridge Road, Woodstock, CT 06281
camera VIRTUAL TOUR camera (40)
price

$1,275,000

beds

4 4 Beds

baths

3 | 1 3 | 1 Baths

lot size

3,868 SqFt 3,868 SqFt

listing no.

24185273 Listing No. 24185273

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (40)

 46 Cemetery Road, Canterbury, CT 06331
camera (40)
price

$1,200,000

beds

3 3 Beds

baths

2 2 Baths

lot size

2,393 SqFt 2,393 SqFt

listing no.

24179809 Listing No. 24179809

property type

House Property Type: House

gallery photos

camera (40)

 82 Kennerson Reservoir Road, Eastford, CT 06242
camera (40)
price

$995,000

beds

4 4 Beds

baths

3 3 Baths

lot size

5,176 SqFt 5,176 SqFt

listing no.

24178434 Listing No. 24178434

property type

House Property Type: House

gallery photos

camera (40)

 9 Becola Road, Thompson, CT 06277
camera (26)
price

$899,000

beds

3 3 Beds

baths

2 | 1 2 | 1 Baths

lot size

1,437 SqFt 1,437 SqFt

listing no.

24169232 Listing No. 24169232

property type

House Property Type: House

gallery photos

camera (26)

 48 Grey Fox Landing, Woodstock, CT 06281
camera (39)
price

$880,000

beds

4 4 Beds

baths

5 5 Baths

lot size

5,087 SqFt 5,087 SqFt

listing no.

24180671 Listing No. 24180671

property type

House Property Type: House

gallery photos

camera (39)

 254 Beaver Hill Road, Windham, CT 06256
camera (39)
price

$874,000

beds

3 3 Beds

baths

2 2 Baths

lot size

1,808 SqFt 1,808 SqFt

listing no.

24174325 Listing No. 24174325

property type

House Property Type: House

gallery photos

camera (39)

IDX information is provided by SmartMLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 the SmartMLS All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
SmartMLS (CTMLS-GFC) data last updated at June 26, 2026, 10:43 AM ET
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