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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
80 Bungay Hill Road Woodstock, CT 06281
$2,500,000
3 Beds 4 | 1 Baths 4,655 SqFt Listing No. 24105709 Property Type: House camera (39)
Details
357 Wrights Crossing Road Pomfret, CT 06259
$2,500,000
5 Beds 5 | 1 Baths 7,772 SqFt Listing No. 24115029 Property Type: House camera (40)
Details
155 Paine Road Woodstock, CT 06281
$1,650,000
4 Beds 5 | 1 Baths 4,873 SqFt Listing No. 24174159 Property Type: House camera (40)
Details
354 Pomfret Street Pomfret, CT 06259
$1,350,000
6 Beds 4 | 1 Baths 5,459 SqFt Listing No. 24172480 Property Type: House camera (40)
Details
33 Meehan Road Woodstock, CT 06281
$1,000,000
3 Beds 2 | 2 Baths 4,190 SqFt Listing No. 24155151 Property Type: House camera (39)
Details
254 Beaver Hill Road Windham, CT 06256
$999,000
3 Beds 2 Baths 1,808 SqFt Listing No. 24174325 Property Type: House camera (39)
Details
564 Hubbard Road Killingly, CT 06241
$975,000
2 Beds 2 Baths 2,895 SqFt Listing No. 24159319 Property Type: House camera Virtual Tour camera (30)
Details
17 Quaddick Road Thompson, CT 06277
$950,000
4 Beds 3 | 1 Baths 3,667 SqFt Listing No. 24159991 Property Type: House camera (40) Open House: Jun 6, 2026, 11:00 AM - 1:00 PM
Details
9 Becola Road Thompson, CT 06277
$950,000
3 Beds 2 | 1 Baths 1,437 SqFt Listing No. 24169232 Property Type: House camera (20)
Details
524 Wauregan Road Brooklyn, CT 06234
$950,000
3 Beds 2 | 2 Baths 3,004 SqFt Listing No. 24173131 Property Type: House camera (33)
Details
316 Allen Hill Road Brooklyn, CT 06234
$850,000
4 Beds 3 | 2 Baths 5,479 SqFt Listing No. 24165938 Property Type: House camera (40)
Details
36 Olde Meadow Road Woodstock, CT 06281
$799,900
4 Beds 2 | 1 Baths 2,900 SqFt Listing No. 24165439 Property Type: House camera (14)
Details
 80 Bungay Hill Road, Woodstock, CT 06281
camera (39)
price

$2,500,000

beds

3 3 Beds

baths

4 | 1 4 | 1 Baths

lot size

4,655 SqFt 4,655 SqFt

listing no.

24105709 Listing No. 24105709

property type

House Property Type: House

gallery photos

camera (39)

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

$2,500,000

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)

 155 Paine Road, Woodstock, CT 06281
camera (40)
price

$1,650,000

beds

4 4 Beds

baths

5 | 1 5 | 1 Baths

lot size

4,873 SqFt 4,873 SqFt

listing no.

24174159 Listing No. 24174159

property type

House Property Type: House

gallery photos

camera (40)

 354 Pomfret Street, Pomfret, CT 06259
camera (40)
price

$1,350,000

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 (40)

 33 Meehan Road, Woodstock, CT 06281
camera (39)
price

$1,000,000

beds

3 3 Beds

baths

2 | 2 2 | 2 Baths

lot size

4,190 SqFt 4,190 SqFt

listing no.

24155151 Listing No. 24155151

property type

House Property Type: House

gallery photos

camera (39)

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

$999,000

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)

 564 Hubbard Road, Killingly, CT 06241
camera VIRTUAL TOUR camera (30)
price

$975,000

beds

2 2 Beds

baths

2 2 Baths

lot size

2,895 SqFt 2,895 SqFt

listing no.

24159319 Listing No. 24159319

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (30)

 17 Quaddick Road, Thompson, CT 06277
Coming Soon
camera (40)
price

$950,000

beds

4 4 Beds

baths

3 | 1 3 | 1 Baths

lot size

3,667 SqFt 3,667 SqFt

listing no.

24159991 Listing No. 24159991

property type

House Property Type: House

gallery photos

camera (40)

Open House: Jun 6, 2026, 11:00 AM - 1:00 PM

 9 Becola Road, Thompson, CT 06277
camera (20)
price

$950,000

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 (20)

 524 Wauregan Road, Brooklyn, CT 06234
camera (33)
price

$950,000

beds

3 3 Beds

baths

2 | 2 2 | 2 Baths

lot size

3,004 SqFt 3,004 SqFt

listing no.

24173131 Listing No. 24173131

property type

House Property Type: House

gallery photos

camera (33)

 316 Allen Hill Road, Brooklyn, CT 06234
camera (40)
price

$850,000

beds

4 4 Beds

baths

3 | 2 3 | 2 Baths

lot size

5,479 SqFt 5,479 SqFt

listing no.

24165938 Listing No. 24165938

property type

House Property Type: House

gallery photos

camera (40)

 36 Olde Meadow Road, Woodstock, CT 06281
camera (14)
price

$799,900

beds

4 4 Beds

baths

2 | 1 2 | 1 Baths

lot size

2,900 SqFt 2,900 SqFt

listing no.

24165439 Listing No. 24165439

property type

House Property Type: House

gallery photos

camera (14)

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 May 11, 2026, 11:16 PM ET
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