Single family homes for sale in Windham County, CT

153 Listings

living room with hardwood / wood-style flooring, lofted ceiling, ceiling fan with notable chandelier, and baseboard heating

Backup offers

$4,749 Closing Credit¹

$399,900

3 beds • 2.5 baths • 1,190 sqft

20 Brookside Dr, Plainfield CT 06374

#24073794, Denise Moore, Listing Office: Kazantzis Real Estate, LLC

snow covered property with a wooden deck

Backup offers

$5,936 Closing Credit¹

$499,900

2 beds • 2 baths • 1,176 sqft

34 Ashford Lake Dr, Ashford CT 06278

#24073786, Irene Sheehan, Listing Office: Weichert,REALTORS-Four Corners

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$3,432 Closing Credit¹

$289,000

4 beds • 2 baths • 1,229 sqft

73 Cherry Ln, Windham CT 06226

#24070142, Jeanne Crum, Listing Office: Home Selling Team

view of front of home featuring a front lawn and solar panels

view of front of property with a wooden deck and a front yard

Backup offers

$5,046 Closing Credit¹

$424,900

3 beds • 2.5 baths • 2,249 sqft

395 Main St, Sterling CT 06377

#24071485, Rich Jenkins, Listing Office: Real Broker CT, LLC

view of front of house with a front yard

Backup offers

$5,284 Closing Credit¹

$445,000

3 beds • 1.5 baths • 1,820 sqft

835 N Main St, Killingly CT 06239

#24074058, Courtney Miller, Listing Office: Berkshire Hathaway NE Prop.

kitchen featuring sink, stainless steel dishwasher, and white cabinets

Backup offers

$4,155 Closing Credit¹

$349,900

3 beds • 1 bath • 1,932 sqft

54 Westford Rd, Eastford CT 06242

#24073188, Vivian Kozey, Listing Office: CR Premier Properties

Backup offers

$3,324 Closing Credit¹

$279,900

5 beds • 1.5 baths • 1,440 sqft

623 Boston Post Rd, Windham CT 06256

#24072783, Kim Gates, Listing Office: Gateway Real Estate

Room to negotiate?

Median Sold Price

$340K

Avg. Sale Time

30 Days

Based on our February 2025 Market Report.

$1,781 Closing Credit¹

$150,000

3 beds • 2 baths • 1,296 sqft

93 Erin Dr, Plainfield CT 06374

#24072527, Tracie Gagnon, Listing Office: Berkshire Hathaway NE Prop.

kitchen featuring a textured ceiling and white appliances

$3,919 Closing Credit¹

$329,999

2 beds • 1.5 baths • 1,549 sqft

75 Tripp Rd, Woodstock CT 06281

#24072030, Matt Noren, Listing Office: RE/MAX Bell Park Realty

$830 Closing Credit¹

$69,900

2 beds • 1 bath • 938 sqft

17 Pond Way, Windham CT 06256

#24071468, Christopher Grant, Listing Office: Christopher F. Grant Broker

Backup offers

$5,224 Closing Credit¹

$439,900

4 beds • 3 baths • 1,890 sqft

48 Lake St, Plainfield CT 06374

#24071527, John Troland Jr., Listing Office: William Raveis Real Estate

foyer with wooden walls and dark hardwood / wood-style floors

kitchen with tasteful backsplash, white cabinetry, appliances with stainless steel finishes, and sink

$1,009 Closing Credit¹

$85,000

2 beds • 1 bath • 924 sqft

15 James Dr, Windham CT 06256

#24070992, Clarence Russ, Listing Office: Home Selling Team

461 Brayman Hollow Rd, Pomfret CT, 06259, 3 bedrooms, 2 baths house for sale

Listing photo 2 for 461 Brayman Hollow Rd, Pomfret CT 06259

Listing photo 3 for 461 Brayman Hollow Rd, Pomfret CT 06259

Backup offers

$5,926 Closing Credit¹

$499,000

3 beds • 2 baths • 1,861 sqft

461 Brayman Hollow Rd, Pomfret CT 06259

#73330007, Joy Riley, Listing Office: Westcott Properties

view of front facade featuring roof with shingles and a chimney

view of front of home with a front lawn, a chimney, and a shingled roof

kitchen with a wealth of natural light, decorative backsplash, stainless steel appliances, and a sink

$4,453 Closing Credit¹

$375,000

3 beds • 2 baths • 1,065 sqft

300 Kennerson Reservoir Rd, Ashford CT 06278

#24070769, Amy Archambault, Listing Office: CR Premier Properties

manufactured / mobile home featuring a wooden deck and a shed

manufactured / mobile home with a wooden deck

$1,246 Closing Credit¹

$104,900

3 beds • 2 baths • 1,248 sqft

56 Circle Dr, Windham CT 06256

#24070608, Elaine AbouAkar, Listing Office: Century 21 AllPoints Realty

$2,672 Closing Credit¹

$225,000

4 beds • 1.5 baths • 1,883 sqft

50 Mechanics St, Putnam CT 06260

#24071022, Michelle Richardson, Listing Office: Kazantzis Real Estate, LLC

foyer with crown molding and dark hardwood / wood-style floors

Backup offers

$4,334 Closing Credit¹

$365,000

4 beds • 2 baths • 3,180 sqft

371 Prospect St, Windham CT 06226

#24066154, Sadie Saucier, Listing Office: Drawbridge Realty

manufactured / mobile home featuring a gazebo and a deck

$1,661 Closing Credit¹

$139,900

3 beds • 2 baths • 1,620 sqft

78 Lions Way, Windham CT 06256

#24070749, Kristen Merrill, Listing Office: Countryside Realty

cape cod home featuring a porch, roof with shingles, and a chimney

$9,261 Closing Credit¹

$779,900

3 beds • 3.5 baths • 3,024 sqft

263 Tripp Hollow Rd, Brooklyn CT 06234

#24070522, Christine Johnson, Listing Office: RE/MAX One

snow covered back of property with covered porch

modern farmhouse style home with a porch

$7,588 Closing Credit¹

$639,000

3 beds • 2.5 baths • 2,264 sqft

314 Lathrop Rd, Plainfield CT 06374

#24070660, Paige Collelo, Listing Office: Taber Realty, LLC

kitchen featuring tasteful backsplash, sink, light hardwood / wood-style flooring, and appliances with stainless steel finishes

kitchen with appliances with stainless steel finishes, sink, and decorative backsplash

$3,383 Closing Credit¹

$284,900

3 beds • 1 bath • 1,064 sqft

855 Riverside Dr, Thompson CT 06255

#24069837, Michael Mitchell, Listing Office: Carbutti & Co., Realtors

kitchen featuring baseboard heating, white cabinets, stainless steel appliances, sink, and dark hardwood / wood-style floors

Backup offers

$4,501 Closing Credit¹

$379,000

5 beds • 2 baths • 2,117 sqft

50 Ruth St, Killingly CT 06239

#24070515, Derek Greene, Listing Office: The Greene Realty Group

view of property exterior featuring a garage and a yard

view of side of property featuring a garage

Backup offers

$8,905 Closing Credit¹

$749,900

4 beds • 3 baths • 2,372 sqft

207 Hillside Rd, Ashford CT 06278

#24070357, Amber Segetti, Listing Office: RE/MAX RISE

view of front of property with covered porch

view of property exterior featuring a yard and a porch

$2,791 Closing Credit¹

$235,000

3 beds • 1 bath • 1,148 sqft

159 Walnut St, Putnam CT 06260

#24069644, Danielle Bakanowsky, Listing Office: Kazantzis Real Estate, LLC

rear view of house featuring covered porch

room details featuring baseboard heating and wood walls

kitchen with white fridge with ice dispenser, wood ceiling, hanging light fixtures, wood walls, and beam ceiling

Backup offers

$3,978 Closing Credit¹

$335,000

3 beds • 1 bath • 1,200 sqft

114 Lynch Rd, Chaplin CT 06235

#24069339, Nancy Bard, Listing Office: Bard Real Estate, LLC

kitchen featuring sink, white cabinets, light hardwood / wood-style flooring, and white appliances

hallway featuring light hardwood / wood-style floors

Backup offers

$2,957 Closing Credit¹

$249,000

3 beds • 1 bath • 1,088 sqft

497 Pleasant St, Windham CT 06226

#24069362, Jessica Duhaime, Listing Office: Pledge Property Management

view of front of property with a front yard and a garage

kitchen with ceiling fan, kitchen peninsula, sink, appliances with stainless steel finishes, and dark stone counters

kitchen featuring ceiling fan, dishwasher, refrigerator, kitchen peninsula, and sink

$6,530 Closing Credit¹

$549,900

4 beds • 2.5 baths • 2,686 sqft

7 Margaret Cir, Pomfret CT 06259

#24068757, Kerri Mullen, Listing Office: CR Premier Properties

view of front facade featuring stone siding

unfurnished living room featuring arched walkways, dark wood finished floors, a fireplace, baseboard heating, and baseboards

kitchen featuring white cabinets, dishwasher, dark wood-type flooring, light countertops, and a sink

$4,512 Closing Credit¹

$379,999

3 beds • 1.5 baths • 1,456 sqft

77 Charles St, Putnam CT 06260

#24067541, Ashley Walker, Listing Office: Brunet and Company Real Estate

bi-level home with a garage, concrete driveway, and brick siding

$5,213 Closing Credit¹

$439,000

3 beds • 2 baths • 1,400 sqft

1153 Windham Rd, Windham CT 06266

#24059832, Timothy Morse, Listing Office: Home Selling Team

bi-level home featuring a garage, concrete driveway, and brick siding

$5,213 Closing Credit¹

$439,000

3 beds • 2 baths • 1,400 sqft

1157 Windham Rd, Windham CT 06266

#24059900, Timothy Morse, Listing Office: Home Selling Team

view of front facade featuring a front yard

$4,155 Closing Credit¹

$349,900

3 beds • 2 baths • 1,632 sqft

45 Littlefield Rd, Scotland CT 06247

#24053423, Susanna Vermette, Listing Office: RbRE, LLC

view of yard featuring a boat dock and a water view

$2,968 Closing Credit¹

$249,900

2 beds • 1 bath • 604 sqft

86 Island Rd, Killingly CT 06241

#24067753, Patricia Malek, Listing Office: First Choice Realty

$5,937 Closing Credit¹

$499,999

3 beds • 1.5 baths • 2,844 sqft

1260 Hartford Pike, Killingly CT 06241

#24061524, Ashley Walker, Listing Office: Brunet and Company Real Estate

view of front of home with fence and a porch

$4,744 Closing Credit¹

$399,500

3 beds • 1.5 baths • 1,800 sqft

16 Red Bridge Rd, Thompson CT 06255

#24067374, Amy Brunet, Listing Office: Brunet and Company Real Estate

Backup offers

$4,744 Closing Credit¹

$399,500

3 beds • 1.5 baths • 1,800 sqft

3 First St, Thompson CT 06255

#24067250, Amy Brunet, Listing Office: Brunet and Company Real Estate

view of front facade with a front yard and solar panels

view of side of home with a yard and solar panels

view of side of home featuring solar panels

Backup offers

$4,036 Closing Credit¹

$339,900

4 beds • 2 baths • 1,792 sqft

187 Old Colony Rd, Eastford CT 06242

#24067149, Christy Lofstrom, Listing Office: ERA Blanchard & Rossetto

$3,503 Closing Credit¹

$294,999

5 beds • 2.5 baths • 2,250 sqft

38 Lake St, Plainfield CT 06354

#24067134, Marco Epifani, Listing Office: eRealty Advisors, Inc.

ranch-style house featuring solar panels, a patio area, and a front lawn

back of house with a yard and solar panels

$7,113 Closing Credit¹

$599,000

4 beds • 3.5 baths • 4,402 sqft

275 Sand Hill Rd, Hampton CT 06247

#24066864, Irene Adams, Listing Office: Signature Properties of NewEng

front facade with covered porch, a garage, a front lawn, and an outdoor structure

view of front of property with covered porch and a front lawn

view of front of house with covered porch

$3,432 Closing Credit¹

$289,000

3 beds • 2 baths • 1,900 sqft

359 Plains Rd, Windham CT 06226

#24065151, Avi Ron, Listing Office: SSG Real Estate LLC

view of front of home with a garage and a front yard

$3,859 Closing Credit¹

$325,000

3 beds • 2.5 baths • 2,496 sqft

329 Indian Hollow Rd, Windham CT 06280

#24065354, Valerie Yankus, Listing Office: Property Shoppe, LLC

81-120 of 153 Results

Explore popular home types in Windham County, CT

Related homes in Windham County, CT

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

Housing market reports in Windham County

Homes for sale near Windham County, CT

Top real estate cities in Connecticut

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IDX Copyright © 2025 Smart MLS. The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 3/15/2025, 3:20:52 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

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Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 3/15/2025, 12:55:48 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

Disclaimer: The data relating to real estate for sale on this web site comes in part from the IDX Program of the State-Wide Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than this broker are marked with the MLS logo and detailed information about them includes the name of the listing brokers. The purchase price of housing stock as shown on this website may vary depending on factors such as fees, commissions, price negotiations, home inspection results, market conditions, etc. This website in no way warrants or represents that submitting an offer to purchase a property for the list price will result in a sale at that price. Please consult with your REALTOR® to discuss how these variations may affect your real estate transaction. IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information Deemed Reliable, but is neither guaranteed nor independently verified. Interested parties must make their own inquiries. Copyright © 2025 State-Wide MLS, Inc. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 3/15/2025, 3:20:48 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.