Windham County, CT homes for sale & real estate

45 minutes on Rocket

$509,000

4 beds • 2.5 baths • 1,908 sqft

294 Pine Hill Rd, Sterling, CT 06377

#24113983, Michael Hvizdo, Listing office: Coldwell Banker Realty

1 hour on Rocket

$420,000

4 beds • 1.5 baths • 1,412 sqft

47 Little Bungee Hill Rd, Woodstock, CT 06282

#24114266, Carol Ryniewicz, Listing office: CR Premier Properties

Room to negotiate?

Median Sold Price

$350K

Based on our June 2025 Market Report.

4 hours on Rocket

$210,000

1 bed • 1 bath • 974 sqft

45 Main St Apt 202, Plainfield, CT 06374

#24111942, Deanna Tighe, Listing office: Mott & Chace Sotheby's Intl Rt

Coming soon

$630,000

3 beds • 3 baths • 1,833 sqft

245 Snake Meadow Hill Rd, Sterling, CT 06377

#24114194, Skyla Gagnon, Listing office: RE/MAX Bell Park Realty

247 Green Hollow Rd, Killingly, CT 06239 - photo 1

7 hours on Rocket

$499,900

3 beds • 2 baths • 1,366 sqft

247 Green Hollow Rd, Killingly, CT 06239

#24114196, Mark Tetreault, II, Listing office: RE/MAX Bell Park Realty

Coming soon

$579,900

3 beds • 1 bath • 1,323 sqft

1 Laurel Hill Dr, Woodstock, CT 06282

#24113550, Patricia Malek, Listing office: First Choice Realty

8 hours on Rocket

$725,000

4 beds • 3 baths • 2,944 sqft

34 Pine Tree Ter, Brooklyn, CT 06234

#24114066, Bob Seele, Listing office: Coldwell Banker Realty

17 hours on Rocket

$125,000

Land • 2 Acres

174 Mechanics St, Putnam, CT 06260

#24114044, Scott Pempek, Listing office: Berkshire Hathaway NE Prop.

19 hours on Rocket

$135,000

1 bed • 1 bath • 624 sqft

209 Whetstone Mls Unit 209, Killingly, CT 06241

#24113504, Jamie Meadows, Listing office: William Raveis Real Estate

1 day 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

1 day 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

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

1 day on Rocket

$459,900

5 beds • 2 baths • 2,750 sqft

213 Pomfret, Putnam, CT 06260

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

1 day 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

1 day 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

1 day on Rocket

$459,900

4 beds • 2 baths • 2,750 sqft

213 Pomfret St, Putnam, CT 06260

#24111627, Maribeth Marzeotti, Listing office: Lamacchia Realty

1 day on Rocket

$294,900

3 beds • 1 bath • 960 sqft

64 Moon Rd, Ashford, CT 06278

#24112981, Jessica Boswell, Listing office: LPT Realty

1 day on Rocket

$160,000

Land • 10.30 Acres

Sunnyside Dr, Thompson, CT 06277

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

1 day on RocketBackup offers

$249,999

2 beds • 2 baths • 1,260 sqft

201 Woodstock Ave, Putnam, CT 06260

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

1 day on Rocket

$79,900

2 beds • 1 bath • 924 sqft

10 Terrace Dr, Plainfield, CT 06374

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

2 days 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

2 days 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

2 days 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

85 Mashentuck Rd, Killingly, CT 06239 - photo 1

2 days on Rocket

$115,000

Land • 8.50 Acres

85 Mashentuck Rd, Killingly, CT 06239

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

2 days on Rocket

$149,900

Land • 0.92 Acres

206 Stawicki Rd, Thompson, CT 06255

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

2 days 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

2 days on Rocket

$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

3 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

3 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

3 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

3 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

Windham County, CT Real Estate Market Overview

There are 354 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. In June 2025 median list price was $350,000 and the average listing age was 0 days. 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

Related homes in Windham County, CT

Schools near Windham County, CT

Housing market reports in Windham County

Homes for sale near Windham County, CT

Top real estate cities in Connecticut