Windham County, CT homes for sale & real estate

Coming soon

$10,000 Closing Credit¹

$1,400,000

4 beds • 5 baths • 7,136 sqft

562 Taft Pond Rd, Pomfret, CT 06259

#24086121, Jared Meehan, Listing Office: RE/MAX Bell Park Realty

Coming soon

$5,936 Closing Credit¹

$499,900

3 beds • 1 bath • 1,610 sqft

492 Taft Pond Rd, Pomfret, CT 06259

#24086016, Heidi Weed, Listing Office: Lamacchia Realty

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

8 hours on Rocket

$4,750 Closing Credit¹

$400,000

3 beds • 2 baths • 1,418 sqft

17 Lewis Blvd, Killingly, CT 06239

#24087228, Mark Gould, Listing Office: Coldwell Banker Realty

11 hours on Rocket

$2,552 Closing Credit¹

$214,900

2 beds • 2 baths • 1,008 sqft

28 Connecticut Dr, Plainfield, CT 06374

#24087086, Michele Geragotelis, Listing Office: RE/MAX Bell Park Realty

view of front facade featuring roof with shingles, covered porch, and a front lawn

Coming soon

$4,749 Closing Credit¹

$399,900

4 beds • 2 baths • 1,680 sqft

12 Cove St, Killingly, CT 06239

#24084503, David Viveiros, Listing Office: Century 21 Limitless

15 hours on Rocket

$3,563 Closing Credit¹

$300,000

3 beds • 1.5 baths • 1,560 sqft

141 Oak St, Windham, CT 06226

#24086854, Brittany Kimlingen, Listing Office: First Choice Realty

23 hours on Rocket

$3,324 Closing Credit¹

$279,900

4 beds • 2 baths • 1,155 sqft

194 Broad St, Killingly, CT 06239

#24087000, Lori Ciccarelli, Listing Office: RE/MAX One

Room to negotiate?

Median Sold Price

$343.5K

Avg. Sale Time

110 Days

Based on our March 2025 Market Report.

1 day on Rocket

$129,900

Land • 4.04 Acres

130 Cook Hill Rd, Killingly, CT 06239

#24086949, Coleen Brakenwagen, Listing Office: 1 Worcester Homes

1 day on Rocket

$4,275 Closing Credit¹

$360,000

3 beds • 3 baths • 1,384 sqft

268 Buckley Hill Rd, Thompson, CT 06255

#24086824, Lynn Converse, Listing Office: RE/MAX Bell Park Realty

1 day on Rocket

$4,572 Closing Credit¹

$385,000

4 beds • 2 baths • 1,868 sqft

251 Slater Hill Rd, Killingly, CT 06241

#24086724, Skyla Gagnon, Listing Office: RE/MAX Bell Park Realty

1 day on Rocket

$8,301 Closing Credit¹

$699,000

3 beds • 2.5 baths • 2,540 sqft

11 Anderson Rd, Pomfret, CT 06259

#24086247, Cyrille Bosio, Listing Office: CR Premier Properties

Coming soon

$3,859 Closing Credit¹

$325,000

3 beds • 2 baths • 1,344 sqft

18A Proulx St, Brooklyn, CT 06234

#24086478, Cheryl Roireau, Listing Office: William Raveis Real Estate

2 days on Rocket

$4,928 Closing Credit¹

$414,995

5 beds • 2 baths • 2,112 sqft

415 Maple St, Killingly, CT 06239

#24086661, Marco Epifani, Listing Office: eRealty Advisors, Inc.

2 days on Rocket

$3,384 Closing Credit¹

$285,000

1 bed • 1 bath • 802 sqft

3 Maple Dr, Ashford, CT 06278

#24086435, Earl Melendy, Listing Office: RE/MAX One

2 days on Rocket

$3,918 Closing Credit¹

$329,950

3 beds • 1 bath • 1,510 sqft

6 Lakeview Dr, Ashford, CT 06278

#24086301, Alexis Molina, Listing Office: Royal Oak Realty Group

2 days on Rocket

$4,750 Closing Credit¹

$400,000

3 beds • 2 baths • 1,873 sqft

156 Green Hollow Rd, Killingly, CT 06239

#24086603, Catherine Duprey, Listing Office: Duprey Real Estate, LLC

2 days on Rocket

$5,343 Closing Credit¹

$449,900

4 beds • 2 baths • 1,903 sqft

44 Rich Rd, Pomfret, CT 06230

#24086344, Sheena Ruggirello, Listing Office: Real Broker CT, LLC

2 days on Rocket

$2,968 Closing Credit¹

$249,900

4 beds • 2 baths • 1,500 sqft

227 Ash St, Windham, CT 06226

#24086473, Kim Benoit, Listing Office: CENTURY 21 Shutters & Sails

2 days on Rocket

$6,709 Closing Credit¹

$565,000

4 beds • 2.5 baths • 2,266 sqft

519 Rte 169, Woodstock, CT 06281

#24081206, Stephanie Gosselin, Listing Office: CR Premier Properties

Coming soon

$5,936 Closing Credit¹

$499,900

3 beds • 2 baths • 2,096 sqft

1428 Hartford Pike, Killingly, CT 06241

#24085559, Michele Geragotelis, Listing Office: RE/MAX Bell Park Realty

2 days on Rocket

$5,936 Closing Credit¹

$499,900

3 beds • 2 baths • 2,081 sqft

209 Main St, Hampton, CT 06247

#24078025, Elizabeth Zimmer, Listing Office: Berkshire Hathaway NE Prop.

2 days on Rocket

$771 Closing Credit¹

$64,900

3 beds • 2 baths • 924 sqft

337 Tuckie Rd, Windham, CT 06256

#24086168, Jacqueline Kapusta, Listing Office: Navick Properties LLC

Coming soon

$9,499 Closing Credit¹

$799,900

3 beds • 2.5 baths • 3,638 sqft

50 Pheasant Ln, Brooklyn, CT 06234

#24086181, Doug Coby, Listing Office: Property Edge

3 days on Rocket

$1,781 Closing Credit¹

$150,000

2 beds • 1 bath • 854 sqft

Address Not Disclosed, Plainfield, CT 06374

#24086202, Maura Von Deck, Listing Office: Von Deck Realty, LLC

exterior space with a gambrel roof and a chimney

4 days on Rocket

$4,453 Closing Credit¹

$375,000

3 beds • 1.5 baths • 1,300 sqft

27 Meehan Rd, Woodstock, CT 06281

#24085973, Jamie Meadows, Listing Office: William Raveis Real Estate

view of front of house with a front yard

4 days on Rocket

$5,344 Closing Credit¹

$450,000

3 beds • 1 bath • 2,326 sqft

24 Plaza St, Brooklyn, CT 06234

#24085801, Missy Greene-Santos, Listing Office: eXp Realty

5 days on RocketBackup offers

$4,619 Closing Credit¹

$389,000

8 beds • 2 baths • 2,450 sqft

232 Ballouville Rd, Killingly, CT 06241

#24085234, Amy Brunet, Listing Office: Brunet and Company Real Estate

raised ranch featuring a front yard, solar panels, fence, and a chimney

Coming soon

$5,047 Closing Credit¹

$425,000

3 beds • 2 baths • 1,839 sqft

Address Not Disclosed, Plainfield, CT 06354

#24086004, Jennifer Lehto, Listing Office: Kazantzis Real Estate, LLC

5 days on Rocket

$4,155 Closing Credit¹

$349,900

4 beds • 1.5 baths • 1,632 sqft

89 Williamsville Rd, Killingly, CT 06241

#24085773, Joshua Brown, Listing Office: KW Legacy Partners

5 days on Rocket

$4,263 Closing Credit¹

$359,000

4 beds • 2.5 baths • 1,930 sqft

24 Brick Top Ln, Windham, CT 06280

#24085842, Heather Yoreo, Listing Office: Coldwell Banker Realty

5 days on Rocket

$104,900

Land • 2.37 Acres

00 Child Rd, Woodstock, CT 06281

#24085858, Gary Pruitt, Listing Office: Century 21 Classic Homes

5 days on Rocket

$110,000

Land • 1 Acre

50 Wrights Crossing Rd, Pomfret, CT 06259

#24085824, Kerri Mullen, Listing Office: CR Premier Properties

5 days on Rocket

$3,444 Closing Credit¹

$290,000

2 beds • 1 bath • 1,056 sqft

61 Collelo Ave, Plainfield, CT 06354

#24085733, Kristen Tarryk, Listing Office: Duprey Real Estate, LLC

5 days on Rocket

$4,749 Closing Credit¹

$399,900

4 beds • 2 baths • 1,850 sqft

550 Westford Rd, Ashford, CT 06278

#24083102, Linda Goff, Listing Office: Berkshire Hathaway NE Prop.

6 days on Rocket

$4,274 Closing Credit¹

$359,900

6 beds • 2 baths • 2,331 sqft

35-37 N Chestnut St, Plainfield, CT 06374

#24085543, Karly Worth, Listing Office: Call It Closed Realty

6 days on Rocket

$5,569 Closing Credit¹

$469,000

3 beds • 2 baths • 2,046 sqft

350 Pine Hill Rd, Sterling, CT 06377

#1381614, Listing Office: SD Realty Associates

Coming soon

$4,738 Closing Credit¹

$399,000

3 beds • 1.5 baths • 1,622 sqft

15 Marion Ln, Canterbury, CT 06331

#24084687, Diane White, Listing Office: CR Premier Properties

7 days on Rocket

$3,443 Closing Credit¹

$289,900

3 beds • 1 bath • 1,092 sqft

5 Mortimer Rd, Plainfield, CT 06354

#24084437, Christine Johnson, Listing Office: RE/MAX One

7 days on Rocket

$1,306 Closing Credit¹

$110,000

3 beds • 2 baths • 1,296 sqft

46 Lions Way, Windham, CT 06256

#24085071, Ryan Lamb, Listing Office: RE/MAX Coast and Country

7 days on Rocket

$4,156 Closing Credit¹

$350,000

2 beds • 2 baths • 2,064 sqft

364 School St, Putnam, CT 06260

#24078278, Dennis Duga, Listing Office: Northeast Realty

Windham County, CT Real Estate Market Overview

Browse 263 homes for sale in Windham County, CT. View properties, photos, nearby real estate with school and housing market information. Between February 2025 and March 2025, Windham County, CT real estate market has seen increase in the number of listings by 10.7%. In March 2025 median list price was $343,500 and the average listing age was 110 days. In March 2025, from all listings sold in Windham County, CT there were more than 40 sold above asking price, over 27 sold below and more than 12 were sold right at the asked price.

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

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

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