Windham County, CT homes for sale & real estate

7 hours on Rocket

$4,452 Closing Credit¹

$374,900

3 beds • 1 bath • 1,304 sqft

41 Elaine St, Thompson, CT 06277

#24089940, Lori Berry, Listing Office: 1 Worcester Homes

10 hours on Rocket

$8,311 Closing Credit¹

$699,900

3 beds • 2.5 baths • 2,952 sqft

26 Center Rd, Woodstock, CT 06281

#73367584, Conrad Allen, Listing Office: RE/MAX Prof Associates

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13 hours on Rocket

$95,000

Land • 3.36 Acres

S Brook Rd Lot 4, Hampton, CT 06247

#24090331, Lisa Labadia, Listing Office: Houlihan Lawrence WD

Coming soon

$2,077 Closing Credit¹

$174,900

2 beds • 2 baths • 960 sqft

91 Colonial Rd, Plainfield, CT 06374

#24092305, Brittany Lewis, Listing Office: RE/MAX on the Bay

Coming soon

$4,026 Closing Credit¹

$339,000

3 beds • 1.5 baths • 1,470 sqft

34 Seagrave St, Killingly, CT 06239

#24092307, Patrick Papuga, Listing Office: CENTURY 21 Shutters & Sails

17 hours on Rocket

$5,344 Closing Credit¹

$449,990

1 bed • 2 baths • 752 sqft

377 Brandy Hill Rd, Thompson, CT 06277

#24092064, Jared Meehan, Listing Office: RE/MAX Bell Park Realty

18 hours on Rocket

$149,900

Land • 3.53 Acres

190 Covell Rd, Pomfret, CT 06259

#24092190, Daniel Nixon, Listing Office: Coldwell Banker Realty

Room to negotiate?

Median Sold Price

$343.5K

Avg. Sale Time

110 Days

Based on our March 2025 Market Report.

18 hours on Rocket

$3,563 Closing Credit¹

$300,000

3 beds • 1 bath • 1,480 sqft

12 Chena Dr, Windham, CT 06280

#24091654, Ted Jarrett, Listing Office: Berkshire Hathaway NE Prop.

Coming soon

$5,569 Closing Credit¹

$469,000

4 beds • 3 baths • 2,238 sqft

549 Bailey Hill Rd, Killingly, CT 06241

#24086795, Kristen Kaskela, Listing Office: Berkshire Hathaway NE Prop.

23 hours on Rocket

$10,000 Closing Credit¹

$879,000

3 beds • 4 baths • 3,431 sqft

267 Chase Rd, Thompson, CT 06277

#24091801, Lynn Converse, Listing Office: RE/MAX Bell Park Realty

1 day on Rocket

$7,113 Closing Credit¹

$599,000

2 beds • 2.5 baths • 2,092 sqft

41 Senexet Village Rd, Woodstock, CT 06281

#24089015, Androula Kazantzis, Listing Office: Kazantzis Real Estate, LLC

Coming soon

$4,738 Closing Credit¹

$399,000

3 beds • 1 bath • 1,664 sqft

468 Liberty Hwy, Putnam, CT 06260

#24083412, Lauren Heidelberger, Listing Office: Berkshire Hathaway NE Prop.

1 day on Rocket

$8,253 Closing Credit¹

$695,000

4 beds • 2.5 baths • 2,204 sqft

279 Moosup Pond Rd, Plainfield, CT 06354

#24091882, Paige Collelo, Listing Office: Taber Realty, LLC

1 day on Rocket

$4,988 Closing Credit¹

$420,000

4 beds • 3 baths • 2,726 sqft

5 Chaplin St, Chaplin, CT 06235

#24091493, Oz Pariser, Listing Office: Premier Re Group LLC

1 day on Rocket

$4,511 Closing Credit¹

$379,900

3 beds • 2.5 baths • 1,568 sqft

58 High Meadow Dr, Plainfield, CT 06374

#24091593, Jonathan Bolano, Listing Office: eXp Realty

Coming soon

$2,968 Closing Credit¹

$249,900

2 beds • 1.5 baths • 1,543 sqft

63 Robbins Rd, Thompson, CT 06277

#24090874, Christine Johnson, Listing Office: RE/MAX One

2 days on RocketTour

$3,978 Closing Credit¹

$335,000

3 beds • 2 baths • 2,427 sqft

9 Golden Dr, Plainfield, CT 06374

#24091462, Lee Barr, Listing Office: William Raveis Real Estate

2 days on Rocket

$4,768 Closing Credit¹

$401,500

3 beds • 1.5 baths • 1,800 sqft

14 Red Bridge Rd, Thompson, CT 06255

#24090590, Amy Brunet, Listing Office: Brunet and Company Real Estate

2 days on Rocket

$4,744 Closing Credit¹

$399,500

3 beds • 1.5 baths • 1,800 sqft

1 First St, Thompson, CT 06255

#24090567, Amy Brunet, Listing Office: Brunet and Company Real Estate

2 days on Rocket

$2,553 Closing Credit¹

$215,000

4 beds • 1.5 baths • 1,332 sqft

193 E Franklin St, Killingly, CT 06239

#24091327, Nicole Garbutt, Listing Office: RE/MAX Bell Park Realty

2 days on Rocket

$4,156 Closing Credit¹

$350,000

3 beds • 1 bath • 1,260 sqft

64 Parish Hill Rd, Windham, CT 06256

#24091150, Melinda Walencewicz, Listing Office: eXp Realty

2 days on Rocket

$2,672 Closing Credit¹

$225,000

2 beds • 1 bath • 1,148 sqft

44 Old Plains Rd, Windham, CT 06226

#24091166, Melinda Walencewicz, Listing Office: eXp Realty

2 days on Rocket

$350,000

Land • 3.01 Acres

199 Shippee School House Rd, Killingly, CT 06241

#24091192, Jennifer Morton-Dumais, Listing Office: LPT Realty - IConn Team

Coming soon

$7,124 Closing Credit¹

$599,900

3 beds • 2 baths • 2,440 sqft

50 Pine Knolls Dr, Killingly, CT 06241

#24088720, Lauren Kennerson, Listing Office: RE/MAX Bell Park Realty

3 days on Rocket

$1,021 Closing Credit¹

$86,000

3 beds • 1.5 baths • 924 sqft

11 Elizabeth Ln, Windham, CT 06256

#24083532, Rebecca Zager, Listing Office: The Agency

3 days on Rocket

$5,284 Closing Credit¹

$445,000

3 beds • 2.5 baths • 2,145 sqft

79 Pierce Rd, Putnam, CT 06260

#24091300, Jennifer Lehto, Listing Office: Kazantzis Real Estate, LLC

3 days on Rocket

$3,444 Closing Credit¹

$290,000

3 beds • 3 baths • 2,382 sqft

269 Jackson St, Windham, CT 06226

#24086628, Michael Tarallo, Listing Office: Giner Real Estate

4 days on Rocket

$1,781 Closing Credit¹

$150,000

2 beds • 1 bath • 1,035 sqft

29 Kathleen Dr Apt 9D, Windham, CT 06226

#24090557, Bud Bowes, Listing Office: RE/MAX on the Bay

single story home featuring a chimney, roof with shingles, a front yard, fence, and brick siding

5 days on Rocket

$3,859 Closing Credit¹

$325,000

4 beds • 1 bath • 1,878 sqft

241 Ballamahack Rd, Windham, CT 06280

#24090798, Sonja Perpignan, Listing Office: ERA Key Realty Services

6 days on Rocket

$10,000 Closing Credit¹

$999,900

3 beds • 4 baths • 3,600 sqft

72 Indian Spring Rd, Woodstock, CT 06281

#24086693, Carol Ryniewicz, Listing Office: CR Premier Properties

6 days on Rocket

$7,124 Closing Credit¹

$599,900

7 beds • 4.5 baths • 4,421 sqft

100 Windham Rd, Windham, CT 06226

#24090616, Richard Marouski, Listing Office: Weichert,REALTORS-Four Corners

6 days on RocketTour

$10,000 Closing Credit¹

$995,000

3 beds • 2 baths • 3,261 sqft

187 Chaplin Rd, Eastford, CT 06242

#24090628, Amy Rio, Listing Office: Executive Real Estate Inc.

6 days on RocketBackup offers

$5,164 Closing Credit¹

$434,900

3 beds • 2.5 baths • 2,024 sqft

142 Sunset Dr, Killingly, CT 06239

#1383313, Listing Office: Real Broker, LLC

6 days on Rocket

$8,016 Closing Credit¹

$675,000

4 beds • 2.5 baths • 3,211 sqft

6 Amanda Cir, Pomfret, CT 06259

#24090117, Mary Collins, Listing Office: Berkshire Hathaway NE Prop.

7 days on Rocket

$5,166 Closing Credit¹

$435,000

3 beds • 3 baths • 1,728 sqft

23-25 Waterfall Rd, Ashford, CT 06278

#24085412, Franchesca Pescatello, Listing Office: Prue Realty LLC

7 days on Rocket

$3,503 Closing Credit¹

$295,000

3 beds • 2 baths • 1,519 sqft

1212 Norwich Rd, Plainfield, CT 06374

#24090421, Tanya McDermott, Listing Office: Berkshire Hathaway NE Prop.

Coming soon

$4,750 Closing Credit¹

$400,000

3 beds • 2 baths • 2,389 sqft

337 Wauregan Rd, Killingly, CT 06239

#24089180, Mary Collins, Listing Office: Berkshire Hathaway NE Prop.

$3,799 Closing Credit¹

$319,900

2 beds • 1 bath • 1,440 sqft

174 N Sterling Rd, Plainfield, CT 06354

#24085490, Christine Johnson, Listing Office: RE/MAX One

$3,859 Closing Credit¹

$325,000

3 beds • 2 baths • 1,654 sqft

297 Main St, Hampton, CT 06247

#24090160, Missy Greene-Santos, Listing Office: eXp Realty

$3,889 Closing Credit¹

$327,500

3 beds • 1.5 baths • 2,462 sqft

17 Eastford Rd, Eastford, CT 06242

#1383177, Listing Office: eXp Realty

Windham County, CT Real Estate Market Overview

Browse 268 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, listings were on the market for 110 days. During the same period, the median list price in this real estate market was $343,500. Windham County, CT housing market in March 2025 saw over 40 listings sold above listed price, more than 12 sold at listed price and over 27 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 45F and high of 69F. On average, Windham County gets about 3.92 inches of precipitation in May. 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

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Schools near Windham County, CT

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