Windham County, CT homes for sale & real estate

Coming soon

$479,900

3 beds • 2.5 baths • 1,691 sqft

40 Airport Rd, Killingly, CT 06239

#24108714, Mark Tetreault, II, Listing office: RE/MAX Bell Park Realty

3 hours on Rocket

$524,900

3 beds • 2.5 baths • 2,000 sqft

39 Huntington Dr, Plainfield, CT 06374

#24108698, Deb Schusterman, Listing office: Brizo Real Estate Services

Room to negotiate?

Median Sold Price

$350K

Based on our June 2025 Market Report.

Coming soon

$495,000

3 beds • 2 baths • 1,998 sqft

1668 N Rd, Killingly, CT 06241

#24106823, Scott Pempek, Listing office: Berkshire Hathaway NE Prop.

Coming soon

$495,000

5 beds • 2.5 baths • 1,656 sqft

136 Cutler Rd, Killingly, CT 06241

#24106818, Scott Pempek, Listing office: Berkshire Hathaway NE Prop.

Coming soon

$419,000

3 beds • 2 baths • 1,488 sqft

172 Harrisville Rd, Woodstock, CT 06281

#24108438, Lewis Jump III, Listing office: RE/MAX One

split foyer home with an attached garage, dirt driveway, a front lawn, and view of wooded area

15 hours on Rocket

$310,000

3 beds • 2.5 baths • 2,248 sqft

Address Not Disclosed, Windham, CT 06280

#24108641, Valerie Yankus, Listing office: Property Shoppe, LLC

17 hours on Rocket

$200,000

3 beds • 1 bath • 1,068 sqft

117 State Ave, Killingly, CT 06241

#24105265, Ryan Braunagel, Listing office: Keller Williams Realty Prtnrs.

Coming soon

$350,000

4 beds • 2 baths • 1,958 sqft

201 Main St, Hampton, CT 06247

#24108498, Stephen Daly, Listing office: LPT Realty

669 Quaddick Town Farm Rd, Thompson, CT 06277

1 day on Rocket

$149,900

Land • 1.31 Acres

669 Quaddick Town Farm Rd, Thompson, CT 06277

#24088298, Dorothy Fontana, Listing office: Coldwell Banker Realty

1 day on Rocket

$49,900

Land • 0.56 Acres

0 Porter Plain Rd, Thompson, CT 06277

#24108267, Dorothy Fontana, Listing office: Coldwell Banker Realty

1 day on Rocket

$85,000

Land • 1.84 Acres

51 Quinns Hill Rd, Killingly, CT 06241

#24094217, Joanne Lukaskiewicz Wheaton, Listing office: CR Premier Properties

1 day on Rocket

$350,000

2 beds • 1 bath • 1,409 sqft

53 Calvin Burnham Rd, Hampton, CT 06247

#24107885, Lisa Weagle, Listing office: Kazantzis Real Estate, LLC

2 days on Rocket

$125,000

3 beds • 2 baths • 1,296 sqft

49 Haley Ln, Windham, CT 06256

#24108071, Dillon Cass, Listing office: eRealty Advisors, Inc.

2 days on Rocket

$484,999

8 beds • 4 baths • 4,808 sqft

40 Elm St, Windham, CT 06226

#24100884, Robyn Letourneau, Listing office: Berkshire Hathaway NE Prop.

2 days on Rocket

$399,999

7 beds • 3 baths • 2,782 sqft

36 Carter St, Killingly, CT 06239

#24107991, Robbie Santos, Listing office: RE/MAX One

2 days on Rocket

$399,900

3 beds • 1 bath • 1,174 sqft

195 Pompeo Rd, Thompson, CT 06255

#73398277, Patrick Sweeney, Listing office: RE/MAX Prof Associates

668 Quinebaug Rd, Thompson, CT 06255 - view of front of property with an outbuilding

Coming soon

$399,000

3 beds • 2 baths • 1,730 sqft

668 Quinebaug Rd, Thompson, CT 06255

#24107962, Beth Thomas, Listing office: RE/MAX One

2 days on Rocket

$683,500

3 beds • 2.5 baths • 2,140 sqft

115 Center Rd, Woodstock, CT 06281

#24106938, Carol Ryniewicz, Listing office: CR Premier Properties

3 days on Rocket

$318,000

3 beds • 2 baths • 975 sqft

8 Jolley Rd, Plainfield, CT 06239

#24107862, Patrick Papuga, Listing office: CENTURY 21 Shutters & Sails

3 days on Rocket

$489,999

8 beds • 4 baths • 3,828 sqft

389 Pleasant St, Windham, CT 06226

#24101718, Robyn Letourneau, Listing office: Berkshire Hathaway NE Prop.

4 days on Rocket

$300,000

Land • 19.20 Acres

0 Lowell Davis Rd, Thompson, CT 06255

#24107805, Ryan Lajoie, Listing office: Johnston & Associates Real Estate, LLC

4 days on Rocket

$250,000

4 beds • 2 baths • 1,265 sqft

235 High St, Windham, CT 06226

#24107790, Richard Marouski, Listing office: Weichert,REALTORS-Four Corners

4 days on RocketBackup offers

$278,000

6 beds • 3 baths • 2,594 sqft

36 Lebanon Ave, Windham, CT 06226

#24104160, Deb Chabot, Listing office: RE/MAX One

4 days on Rocket

$200,000

2 beds • 1 bath • 1,077 sqft

301 Bricktop Rd, Windham, CT 06280

#24104122, Anne Newmyer, Listing office: Simply Sold Real Estate

Coming soon

$399,900

3 beds • 2 baths • 1,170 sqft

342 County Rd, Woodstock, CT 06281

#24107551, Kimberly Frasier, Listing office: Real Broker CT, LLC

5 days on RocketTour

$439,999

4 beds • 2 baths • 2,754 sqft

168 Miller Rd, Chaplin, CT 06235

#24105286, Crystal Gebhardt Coogan, Listing office: Coldwell Banker Realty

5 days on Rocket

$255,000

3 beds • 1 bath • 1,080 sqft

285 Jackson St, Windham, CT 06226

#24106014, Corrinne Lomazzo S.Windsor, Listing office: Berkshire Hathaway NE Prop.

5 days on Rocket

$325,000

3 beds • 2 baths • 1,862 sqft

64 Bailey St, Brooklyn, CT 06234

#24107523, Carolyn Bassett, Listing office: Remax Host of Homes

226 Harris Rd, Sterling, CT 06377 - split foyer home with a garage and asphalt driveway

5 days on Rocket

$469,000

3 beds • 2 baths • 1,672 sqft

226 Harris Rd, Sterling, CT 06377

#24107284, Coleen Brakenwagen, Listing office: Jason Mitchell Real Estate Connecticut LLC

6 days on Rocket

$325,000

3 beds • 1 bath • 1,008 sqft

15 Denis Dr, Thompson, CT 06255

#24107018, Courtney Ravenelle, Listing office: RE/MAX Bell Park Realty

6 days on Rocket

$315,000

3 beds • 1.5 baths • 1,784 sqft

106 Oxbow Dr, Windham, CT 06226

#24104775, Sondra Reid, Listing office: Home Selling Team

6 days on Rocket

$263,200

3 beds • 1.5 baths • 1,170 sqft

65 Hewitt St, Windham, CT 06226

#24106985, Ellen Mott, Listing office: Berkshire Hathaway NE Prop.

6 days on RocketBackup offers

$450,000

3 beds • 2.5 baths • 2,142 sqft

209 Cemetery Rd, Canterbury, CT 06331

#24102481, Stephanie Howard, Listing office: Berkshire Hathaway NE Prop.

6 days on Rocket

$290,000

3 beds • 2 baths • 1,526 sqft

44 Woodland Dr, Windham, CT 06280

#24100912, Kelley Vanacore, Listing office: Century 21 AllPoints Realty

6 days on Rocket

$359,900

3 beds • 1.5 baths • 1,152 sqft

126 Labby Rd, Thompson, CT 06255

#24104144, Linda Desaulniers, Listing office: 1 Worcester Homes

6 days on Rocket

$489,999

12 beds • 4 baths • 2,750 sqft

251 Jackson St, Windham, CT 06226

#24101711, Robyn Letourneau, Listing office: Berkshire Hathaway NE Prop.

6 days on Rocket

$299,900

4 beds • 2.5 baths • 1,609 sqft

60 Impala Dr, Windham, CT 06226

#24106688, Jacqueline Lovett, Listing office: William Raveis Real Estate

20 Knollwoods Ln Unit 20, Putnam, CT 06260 - traditional home featuring entry steps

6 days on Rocket

$170,000

2 beds • 1.5 baths • 1,174 sqft

20 Knollwoods Ln Unit 20, Putnam, CT 06260

#24106924, Alexa Bush, Listing office: Torch Real Estate Group

7 days on Rocket

$638,000

4 beds • 2.5 baths • 2,880 sqft

18 Jeans Ct, Woodstock, CT 06281

#24106384, Lynn Converse, Listing office: RE/MAX Bell Park Realty

7 days on Rocket

$599,999

12 beds • 5 baths • 4,466 sqft

136 Chapman St, Windham, CT 06226

#24101734, Robyn Letourneau, Listing office: Berkshire Hathaway NE Prop.

Windham County, CT Real Estate Market Overview

There are 300 homes for sale in Windham County, CT. The following market insights reflect all property types in the Windham County, CT real estate market. The number of homes in Windham County, CT increased by 0.2% between May 2025 and June 2025. Listings spent 0 days on the market in June 2025, and had a median list price of $350,000 during the same period. Windham County, CT housing market in June 2025 saw over 55 listings sold above listed price, more than 18 sold at listed price and over 39 sold below.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Windham County, CT

Overview

Windham County is located in Connecticut. There are roughly 118,083 residents, living in 44,600 households. The average temperature for Windham County this time of the year is low of 59F and high of 82F. On average, Windham County gets about 4.1 inches of precipitation in July. Most residents are home owners (69%), have a high school diploma (52%) and are single, no kids (37%).

Data provided by Home Junction

Schools near Windham County, CT

Elementary Schools

North Windham School
112 Jordan Ln
Public District KG-5
Windham Center School
45 North Rd
Public District KG-5
Brooklyn Elementary School
119 Gorman Rd
Public District PK-4

Middle Schools

Ashford School
440 Westford Rd
Public District PK-8
Thompson Middle School
785 Riverside Dr
Public District 5-8
Dr. Helen Baldwin Middle School
45 Westminster Rd
Public District 5-8

High Schools

Tourtellotte Memorial High School
785 Riverside Dr
Public District 9-12
H. H. Ellis Technical High School
613 Upper Maple St
Public District 9-12
Windham Technical High School
210 Birch St
Public District 9-12

Data provided by Great Schools

Homes for sale in Windham County, CT

Windham County, CT Real Estate Market Overview

What is it like to live in Windham County, CT

Overview

Explore popular home types in Windham County, CT

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Schools near Windham County, CT

Housing market reports in Windham County

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