Windham County, CT homes for sale & real estate

19 minutes on Rocket

$3,918 Closing Credit¹

$329,900

3 beds • 2.5 baths • 1,388 sqft

5 Chappell St, Chaplin, CT 06235

#24097979, Glenn Stavens, Listing Office: Aspen Realty Group

Coming soon

$4,749 Closing Credit¹

$399,900

5 beds • 1.5 baths • 3,012 sqft

29 Ralph St, Plainfield, CT 06354

#24096964, Christine Johnson, Listing Office: RE/MAX One

Save big

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

3 hours on Rocket

$701 Closing Credit¹

$59,000

2 beds • 1 bath • 1,036 sqft

28 Fairway Dr, Windham, CT 06256

#24095516, Jeanne Crum, Listing Office: Home Selling Team

15 S Pine St, Plainfield, CT 06374 - view of front of property featuring a front yard, driveway, a detached garage, and a shingled roof

Coming soon

$4,631 Closing Credit¹

$389,999

4 beds • 2 baths • 1,387 sqft

15 S Pine St, Plainfield, CT 06374

#24097943, Ashley Walker, Listing Office: Brunet and Company Real Estate

16 hours on Rocket

$10,000 Closing Credit¹

$925,000

3 beds • 2.5 baths • 3,500 sqft

000 Joy Rd, Woodstock, CT 06281

#24097837, Liz Scranton, Listing Office: Kazantzis Real Estate, LLC

Coming soon

$6,886 Closing Credit¹

$579,900

3 beds • 2 baths • 2,056 sqft

11 Pine Knolls Dr, Killingly, CT 06241

#24093327, Christine Johnson, Listing Office: RE/MAX One

Coming soon

$7,124 Closing Credit¹

$599,900

4 beds • 2.5 baths • 2,392 sqft

87 Bunny Ln, Brooklyn, CT 06234

#24097179, Cary Marcoux, Listing Office: RE/MAX Bell Park Realty

Room to negotiate?

Median Sold Price

$347.9K

Avg. Sale Time

16 Days

Based on our April 2025 Market Report.

Coming soon

$4,572 Closing Credit¹

$385,000

4 beds • 1.5 baths • 2,264 sqft

153 Prospect St, Plainfield, CT 06354

#24097673, Skyla Gagnon, Listing Office: RE/MAX Bell Park Realty

1 day on Rocket

$6,828 Closing Credit¹

$575,000

3 beds • 2.5 baths • 2,415 sqft

30 Supina Rd, Ashford, CT 06278

#24094932, Lindsey Niarhakos, Listing Office: RE/MAX One

Coming soon

$6,530 Closing Credit¹

$549,900

3 beds • 1.5 baths • 2,332 sqft

35 Walker Rd, Thompson, CT 06262

#24097414, Jared Meehan, Listing Office: RE/MAX Bell Park Realty

1 day on Rocket

$6,994 Closing Credit¹

$589,000

3 beds • 2 baths • 1,824 sqft

232 Bailey Hill Rd, Killingly, CT 06239

#24097028, Kerri Miller, Listing Office: Taber Realty, LLC

2 days on Rocket

$4,988 Closing Credit¹

$420,000

3 beds • 1.5 baths • 2,408 sqft

16 N Rd, Ashford, CT 06278

#24097054, Kerri Mullen, Listing Office: CR Premier Properties

2 days on Rocket

$6,175 Closing Credit¹

$520,000

3 beds • 2.5 baths • 1,942 sqft

194 Roth Rd, Killingly, CT 06241

#24097353, Patrick Precourt, Listing Office: Dorrance Realty

2 days on Rocket

$4,381 Closing Credit¹

$368,900

3 beds • 1.5 baths • 1,160 sqft

513 Lhomme Street Ext, Killingly, CT 06239

#24094850, Liz Lavallee, Listing Office: Dawn Taylor Real Estate

2 days on Rocket

$5,641 Closing Credit¹

$475,000

3 beds • 2.5 baths • 2,554 sqft

9 Pheasant Ln, Brooklyn, CT 06234

#24096891, Lynn Converse, Listing Office: RE/MAX Bell Park Realty

Coming soon

$5,094 Closing Credit¹

$429,000

3 beds • 2 baths • 1,561 sqft

20 Long Pond Rd, Thompson, CT 06277

#24095636, Rachael Gifford, Listing Office: 1 Worcester Homes

2 days on Rocket

$1,663 Closing Credit¹

$140,000

2 beds • 2 baths • 960 sqft

20 Connecticut Dr, Plainfield, CT 06374

#24092365, Justin Cote, Listing Office: Compass Connecticut, LLC

Coming soon

$4,155 Closing Credit¹

$349,900

3 beds • 2 baths • 1,594 sqft

331 Pond Hill Rd, Plainfield, CT 06354

#24097032, Nicole Perry, Listing Office: RE/MAX Bell Park Realty

Coming soon

$8,906 Closing Credit¹

$750,000

2 beds • 2 baths • 1,338 sqft

72 Lake View Dr, Woodstock, CT 06281

#24097146, Alexcia Merritt, Listing Office: RE/MAX Bell Park Realty

2 days on Rocket

$4,619 Closing Credit¹

$389,000

2 beds • 3 baths • 1,774 sqft

17 Main St, Plainfield, CT 06374

#24094396, Tara Sepe, Listing Office: HERE Realty

2 days on Rocket

$5,580 Closing Credit¹

$469,900

3 beds • 1.5 baths • 2,440 sqft

23 Hell Hollow Rd, Sterling, CT 06384

#24095779, Alexis Devlin, Listing Office: Coldwell Banker Realty

2 days on Rocket

$2,968 Closing Credit¹

$249,900

3 beds • 1 bath • 1,134 sqft

602 Pomfret St, Putnam, CT 06260

#24097070, Jennifer Lehto, Listing Office: Kazantzis Real Estate, LLC

2 days on Rocket

$150,000

Land • 17.30 Acres

Appell Rd, Brooklyn, CT 06234

#24097044, Catherine Duprey, Listing Office: Duprey Real Estate, LLC

Coming soon

$4,986 Closing Credit¹

$419,900

2 beds • 2 baths • 1,582 sqft

266 Buckley Hill Rd, Thompson, CT 06255

#24096913, Ryan Lajoie, Listing Office: Johnston & Associates Real Estate, LLC

3 days on RocketTour

$8,491 Closing Credit¹

$715,000

4 beds • 3.5 baths • 5,408 sqft

105 Mashentuck Rd, Killingly, CT 06239

#24080567, Yvonne Sousa, Listing Office: RISE REC

4 days on Rocket

$10,000 Closing Credit¹

$1,198,600

3 beds • 2.5 baths • 2,797 sqft

40 Shields Rd, Woodstock, CT 06281

#24081089, John Downs, Listing Office: Berkshire Hathaway NE Prop.

Coming soon

$4,452 Closing Credit¹

$374,900

8 beds • 3 baths • 2,092 sqft

14 Palmer St, Killingly, CT 06239

#24095091, Jim Black, Listing Office: Real Broker CT, LLC

Coming soon

$2,374 Closing Credit¹

$199,900

3 beds • 1 bath • 1,920 sqft

1100 Plainfield Pike, Sterling, CT 06373

#24096543, Paul Stone, Listing Office: Kazantzis Real Estate, LLC

6 days on Rocket

$5,522 Closing Credit¹

$465,000

4 beds • 2.5 baths • 2,146 sqft

49 Bennett Pond Rd, Canterbury, CT 06331

#24096497, Skyla Gagnon, Listing Office: RE/MAX Bell Park Realty

Coming soon

$5,938 Closing Credit¹

$500,000

3 beds • 2 baths • 1,989 sqft

255 Killingly Rd, Pomfret, CT 06259

#24095245, Mary Collins, Listing Office: Berkshire Hathaway NE Prop.

6 days on Rocket

$5,343 Closing Credit¹

$449,900

3 beds • 2 baths • 1,642 sqft

34 Bonnette Ave, Thompson, CT 06277

#24096465, Jason Flibbert, Listing Office: O'Rourke Grp RE Professionals

6 days on Rocket

$3,205 Closing Credit¹

$269,900

4 beds • 1.5 baths • 1,184 sqft

32 High St, Killingly, CT 06239

#24096430, Jeremy Bailey, Listing Office: SkyView Realty

6 days on Rocket

$5,641 Closing Credit¹

$475,000

3 beds • 2 baths • 1,728 sqft

1026 Rte 171, Woodstock, CT 06281

#24096272, Daniel Deojay, Listing Office: RE/MAX Bell Park Realty

6 days on Rocket

$2,316 Closing Credit¹

$195,000

2 beds • 1.5 baths • 896 sqft

12 Athol St Unit 12, Killingly, CT 06239

#24096101, Christine Costa, Listing Office: Kazantzis Real Estate, LLC

6 days on RocketBackup offers

$3,443 Closing Credit¹

$289,900

2 beds • 1 bath • 1,383 sqft

13 Alpha St, Putnam, CT 06260

#24096270, Taylor Gildein, Listing Office: Re/Max Results

Coming soon

$1,661 Closing Credit¹

$139,900

2 beds • 1 bath • 720 sqft

1092 Plainfield Pike, Sterling, CT 06373

#24095863, Paul Stone, Listing Office: Kazantzis Real Estate, LLC

7 days on Rocket

$6,769 Closing Credit¹

$570,000

3 beds • 2.5 baths • 2,132 sqft

449 E Thompson Rd, Thompson, CT 06277

#24095074, Rachel Sposato, Listing Office: Berkshire Hathaway NE Prop.

7 days on Rocket

$4,452 Closing Credit¹

$374,900

3 beds • 1.5 baths • 1,184 sqft

25 Logans Way, Sterling, CT 06377

#24095701, Pat Corso, Listing Office: RI Real Estate Services

7 days on Rocket

$1,780 Closing Credit¹

$149,900

1 bed • 1 bath • 475 sqft

23 Mechanics St Unit 101, Putnam, CT 06260

#24096000, Benjamin Carbone, Listing Office: Lamacchia Realty

7 days on Rocket

$1,100,000

Land • 22.09 Acres

36 Plainfield Pike, Plainfield, CT 06374

#24094366, Androula Kazantzis, Listing Office: Kazantzis Real Estate, LLC

Windham County, CT Real Estate Market Overview

There are 279 homes for sale in Windham County, CT. The following market insights reflect all property types in the Windham County, CT real estate market. In April 2025 in Windham County, CT there were 10.6% more homes for sale than in March 2025. The median list price of listings available in April 2025 was $347,904, while the average time on the real estate market was 16 days. In April 2025, from all listings sold in Windham County, CT there were more than 38 sold above asking price, over 31 sold below and more than 15 were sold right at the asked price.

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

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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