Windham County, CT homes for sale & real estate

1 hour on Rocket

$329,900

6 beds • 2 baths • 2,392 sqft

12 Saint James Row, Killingly, CT 06239

#24113972, Benjamin Carbone, Listing office: Lamacchia Realty

2 hours on Rocket

$279,000

4 beds • 2 baths • 2,673 sqft

98 Windham St, Windham, CT 06226

#24113958, Sue Esposito, Listing office: Home Selling Team

Room to negotiate?

Median Sold Price

$350K

Based on our June 2025 Market Report.

Coming soon

$335,000

2 beds • 2.5 baths • 1,904 sqft

433 Norwich Rd, Plainfield, CT 06374

#24113863, Cheryl Roireau, Listing office: William Raveis Real Estate

Coming soon

$439,000

3 beds • 2.5 baths • 1,189 sqft

35 Tripp Hollow Rd, Brooklyn, CT 06234

#24113993, Joseph Bonneau, Listing office: eXp Realty

4 hours on Rocket

$459,900

5 beds • 2 baths • 2,750 sqft

213 Pomfret, Putnam, CT 06260

#73408449, Maribeth Marzeotti, Listing office: Lamacchia Realty, Inc.

5 hours on Rocket

$400,000

1 bed • 1 bath • 517 sqft

31 Green Is, Thompson, CT 06277

#24113935, Dick Loomis, Listing office: RE/MAX Bell Park Realty

Coming soon

$349,900

2 beds • 1 bath • 1,664 sqft

126 Pine Hill Rd, Sterling, CT 06377

#24113795, Christine Johnson, Listing office: RE/MAX One

7 hours on Rocket

$599,000

4 beds • 3.5 baths • 4,476 sqft

104 Windham Center Rd, Windham, CT 06280

#24113837, Lawrence Ross, Listing office: Weichert,REALTORS-Four Corners

8 hours on Rocket

$459,900

4 beds • 2 baths • 2,750 sqft

213 Pomfret St, Putnam, CT 06260

#24111627, Maribeth Marzeotti, Listing office: Lamacchia Realty

9 hours on Rocket

$294,900

3 beds • 1 bath • 960 sqft

64 Moon Rd, Ashford, CT 06278

#24112981, Jessica Boswell, Listing office: LPT Realty

9 hours on Rocket

$160,000

Land • 10.30 Acres

Sunnyside Dr, Thompson, CT 06277

#24113563, Cary Marcoux, Listing office: RE/MAX Bell Park Realty

9 hours on Rocket

$249,999

2 beds • 2 baths • 1,260 sqft

201 Woodstock Ave, Putnam, CT 06260

#24113048, Anthony Florenzano, Listing office: Signature Properties of NewEng

12 hours on Rocket

$79,900

2 beds • 1 bath • 924 sqft

10 Terrace Dr, Plainfield, CT 06374

#24113668, Ilya Whittemore, Listing office: First Choice Realty

1 day on Rocket

$465,000

4 beds • 2 baths • 1,524 sqft

59 Ulasik Rd, Canterbury, CT 06331

#24113322, Sue Esposito, Listing office: Home Selling Team

1 day on Rocket

$139,900

3 beds • 2 baths • 924 sqft

30 R And R Park, Killingly, CT 06241

#24113718, Matthew Riley, Listing office: Freehold Real Estate

1 day on Rocket

$239,500

4 beds • 1 bath • 1,078 sqft

129 Walnut St, Windham, CT 06226

#24113710, Lisa Therecka, Listing office: Therecka & Associates LLC

19 Florence St, Putnam, CT 06260 - photo 1

Coming soon

$300,000

4 beds • 2 baths • 1,496 sqft

19 Florence St, Putnam, CT 06260

#24112744, Kimberly Synott, Listing office: Castinetti Realty Group

Coming soon

$425,000

3 beds • 1.5 baths • 1,528 sqft

68 Allen Hill Rd, Brooklyn, CT 06234

#24102535, Androula Kazantzis, Listing office: Kazantzis Real Estate, LLC

85 Mashentuck Rd, Killingly, CT 06239 - photo 1

1 day on Rocket

$115,000

Land • 8.50 Acres

85 Mashentuck Rd, Killingly, CT 06239

#24113359, Androula Kazantzis, Listing office: Kazantzis Real Estate, LLC

1 day on Rocket

$149,900

Land • 0.92 Acres

206 Stawicki Rd, Thompson, CT 06255

#24113574, Rich Jenkins, Listing office: Real Broker CT, LLC

1 day on Rocket

$299,999

3 beds • 1.5 baths • 1,440 sqft

566 Rte 197, Woodstock, CT 06281

#24113568, Skyla Gagnon, Listing office: RE/MAX Bell Park Realty

Coming soon

$489,000

8 beds • 5 baths • 4,400 sqft

47 Commerce Ave, Killingly, CT 06239

#24112207, Jason Pollard, Listing office: Compass Connecticut, LLC

114 Breakneck Hill Rd, Killingly, CT 06241 - photo 1

Coming soon

$459,000

3 beds • 1 bath • 1,560 sqft

114 Breakneck Hill Rd, Killingly, CT 06241

#24113507, Lisa Therecka, Listing office: Therecka & Associates LLC

Coming soon

$250,000

3 beds • 1 bath • 1,008 sqft

30 Mcdermott Ave, Windham, CT 06226

#24031110, Amber Jones, Listing office: KW Legacy Partners

Coming soon

$399,000

8 beds • 3 baths • 3,913 sqft

85 Lewiston Ave, Windham, CT 06226

#24113198, Anne Newmyer, Listing office: Simply Sold Real Estate

2 days on Rocket

$449,900

3 beds • 1.5 baths • 1,632 sqft

31 Pond Factory Rd, Woodstock, CT 06281

#24113389, Jared Meehan, Listing office: RE/MAX Bell Park Realty

Coming soon

$464,900

3 beds • 2 baths • 1,836 sqft

156 Quaddick Rd, Thompson, CT 06277

#24113451, Ryan Lajoie, Listing office: Johnston & Associates Real Estate, LLC

2 days on Rocket

$350,000

3 beds • 2 baths • 2,158 sqft

187 Tuckie Rd, Windham, CT 06256

#24111089, Lauren Iraeta, Listing office: KW Legacy Partners

2 days on Rocket

$224,900

2 beds • 1.5 baths • 1,200 sqft

61 Perry St Unit 101, Putnam, CT 06260

#24113431, Ryan Lajoie, Listing office: Johnston & Associates Real Estate, LLC

2 days on Rocket

$84,999

2 beds • 1 bath • 780 sqft

115 N Rd, Ashford, CT 06278

#24112733, Adrian Cote, Listing office: William Raveis Real Estate

2 days on Rocket

$225,000

3 beds • 1.5 baths • 1,557 sqft

4 Linnell St, Plainfield, CT 06354

#24094260, Beth Fournier, Listing office: Compass Connecticut, LLC

Coming soon

$250,000

3 beds • 1 bath • 1,222 sqft

16 Jolley Rd, Plainfield, CT 06239

#24113117, Christine Johnson, Listing office: RE/MAX One

Coming soon

$367,000

3 beds • 1 bath • 1,084 sqft

778 Cook Hill Rd, Killingly, CT 06239

#24113079, Rachael Gifford, Listing office: The Neighborhood Realty Group

Coming soon

$499,900

3 beds • 3 baths • 3,024 sqft

15 Highview Dr, Killingly, CT 06241

#24113053, Christine Costa, Listing office: Kazantzis Real Estate, LLC

4 days on Rocket

$399,999

5 beds • 3 baths • 2,100 sqft

22 Philmar Dr, Plainfield, CT 06374

#24112874, Vito Uva, Listing office: Scalzo Real Estate

4 days on Rocket

$335,000

4 beds • 2 baths • 1,680 sqft

122 Lovers Ln, Windham, CT 06280

#24112908, Michael Hernandez, Listing office: Signature Realty LLC

4 days on Rocket

$380,000

4 beds • 2.5 baths • 2,220 sqft

106 Tripp Hollow Rd, Brooklyn, CT 06234

#24112702, Donna Copeland, Listing office: William Raveis Real Estate

4 days on Rocket

$715,000

4 beds • 3.5 baths • 4,536 sqft

101 Center Rd, Woodstock, CT 06281

#24112390, Jeff Valentine, Listing office: William Pitt Sotheby's Int'l

5 days on Rocket

$425,000

2 beds • 1 bath • 900 sqft

367 Pine Hill Rd, Sterling, CT 06377

#1390386, Listing office: BHHS Commonwealth Real Estate

141 Groveland Ave, Putnam, CT 06260 - photo 1

5 days on Rocket

$49,900

Land • 1.38 Acres

141 Groveland Ave, Putnam, CT 06260

#73406654, Conrad Allen, Listing office: RE/MAX Prof Associates

Windham County, CT Real Estate Market Overview

There are 352 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. While more than 55 listings in Windham County, CT in June 2025 were sold above asking price, there were more than 18 listings sold at asking price, and more than 39 were 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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