Single family homes for sale in Windham County, CT

153 Listings

back of house featuring a gazebo and solar panels

view of front of property with roof mounted solar panels, fence, a front lawn, and a gazebo

kitchen with light countertops, a sink, backsplash, and ceiling fan with notable chandelier

$3,675 Closing Credit¹

$309,500

3 beds • 1 bath • 912 sqft

20 Mason Hill Rd, Brooklyn CT 06234

#24078382, Skyla Gagnon, Listing Office: RE/MAX Bell Park Realty

colonial house with aphalt driveway and brick siding

$6,234 Closing Credit¹

$525,000

4 beds • 2.5 baths • 2,592 sqft

42 Pasay Rd, Thompson CT 06255

#24078300, Carla Zimmerman, Listing Office: Century 21 Limitless

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view of front of house featuring driveway, brick siding, a chimney, and fence

ranch-style house featuring brick siding, a shingled roof, and fence

view of front of property featuring a shingled roof, brick siding, fence, and a chimney

$4,156 Closing Credit¹

$350,000

4 beds • 2 baths • 1,900 sqft

665 N Main St, Killingly CT 06239

#24076833, Amy Brunet, Listing Office: Brunet and Company Real Estate

back of house at dusk featuring fence, a gambrel roof, a yard, roof with shingles, and a chimney

view of home's exterior featuring a gambrel roof

view of outbuilding with fence and an outdoor structure

Backup offers

$3,266 Closing Credit¹

$275,000

2 beds • 2 baths • 1,260 sqft

153 N Rd, Windham CT 06280

#24076298, Stephen Daly, Listing Office: LPT Realty

view of front of home featuring a front yard, a wooden deck, and log siding

drone / aerial view with a view of trees

kitchen with an island with sink, wooden ceiling, log walls, stainless steel appliances, and light brown cabinetry

Coming soonVideo tour

$10,000 Closing Credit¹

$1,250,000

3 beds • 3.5 baths • 4,165 sqft

187 Chaplin Rd, Eastford CT 06242

#24078117, Amy Rio, Listing Office: Executive Real Estate Inc.

$3,438 Closing Credit¹

$289,500

3 beds • 1 bath • 1,868 sqft

188 Willimantic Rd, Chaplin CT 06235

#24077738, Scott Sasinouski, Listing Office: KW Legacy Partners

view of front of house with a shingled roof, an attached garage, driveway, and a front lawn

hall with light wood finished floors and baseboards

living area with ceiling fan, baseboards, vaulted ceiling, and wood finished floors

$4,453 Closing Credit¹

$375,000

2 beds • 2 baths • 1,474 sqft

10 Commonway Dr Unit 10, Brooklyn CT 06234

#24067331, Kyle Wilkinson, Listing Office: Wilkinson Real Estate

Room to negotiate?

Median Sold Price

$340K

Avg. Sale Time

30 Days

Based on our February 2025 Market Report.

stairs featuring a textured ceiling and wood finished floors

kitchen featuring white appliances, light wood-style flooring, brown cabinets, and a sink

kitchen featuring light wood-type flooring, brown cabinets, and a sink

$3,324 Closing Credit¹

$279,900

3 beds • 1.5 baths • 1,327 sqft

399 High St, Windham CT 06226

#24076714, Karan Garewal, Listing Office: Winwin Realty

view of front of home with entry steps, fence, roof with shingles, a chimney, and a front yard

view of front facade with roof with shingles and a chimney

unfurnished living room featuring a wood stove, baseboards, wood finished floors, and recessed lighting

Backup offers

$2,874 Closing Credit¹

$242,000

3 beds • 1.5 baths • 1,306 sqft

33 Roanoak Ave, Windham CT 06226

#24077267, Jenny Dazy, Listing Office: KW Legacy Partners

$7,113 Closing Credit¹

$599,000

4 beds • 3.5 baths • 2,343 sqft

34 Colbridge Rd, Plainfield CT 06374

#24076112, Irene Adams, Listing Office: Signature Properties of NewEng

view of front of property with a sunroom, a chimney, a front lawn, and roof with shingles

view of property exterior with driveway, a deck, an attached garage, and a lawn

$4,091 Closing Credit¹

$344,500

3 beds • 1.5 baths • 1,484 sqft

36 Pratt Rd, Plainfield CT 06374

#24077572, Christine Costa, Listing Office: Kazantzis Real Estate, LLC

dutch colonial with roof with shingles, fence, a chimney, and a gambrel roof

colonial inspired home featuring roof with shingles, fence, a chimney, and a gambrel roof

$4,453 Closing Credit¹

$375,000

3 beds • 2 baths • 1,728 sqft

299 Hampton Rd, Pomfret CT 06259

#24075963, Mary Collins, Listing Office: Berkshire Hathaway NE Prop.

exterior space with roof mounted solar panels and a chimney

kitchen with dark countertops, a sink, wall chimney range hood, and black appliances

kitchen featuring wood finished floors, a kitchen island, stainless steel fridge, and backsplash

$4,037 Closing Credit¹

$339,999

5 beds • 2 baths • 2,600 sqft

670 Wauregan Rd, Brooklyn CT 06234

#24077247, Ann Rochester, Listing Office: RE/MAX One

bi-level home featuring a garage, driveway, and a chimney

back of property with a deck and a chimney

$3,378 Closing Credit¹

$284,500

3 beds • 2 baths • 1,146 sqft

62 Westford Dr, Ashford CT 06278

#24077140, Ryan King, Listing Office: Aspen Realty Group

view of front of property with a garage, driveway, a chimney, and a front lawn

view of front of property featuring driveway, a garage, a chimney, and a front lawn

$5,047 Closing Credit¹

$425,000

4 beds • 2.5 baths • 2,950 sqft

106 Tripp Hollow Rd, Brooklyn CT 06234

#24075795, Anthony Chabot, Listing Office: Chabot & Associates Real Estate

view of front of home with roof mounted solar panels and a chimney

view of front of house featuring a chimney, roof mounted solar panels, and central AC unit

snow covered property featuring a wooden deck

Backup offers

$3,919 Closing Credit¹

$330,000

5 beds • 2.5 baths • 2,660 sqft

114 Highland View Dr, Windham CT 06266

#24077046, Lawrence Ross, Listing Office: Weichert,REALTORS-Four Corners

view of pool featuring fence, a lawn, and a pergola

living area featuring a skylight, wood finished floors, beam ceiling, plenty of natural light, and a glass covered fireplace

$10,000 Closing Credit¹

$1,600,000

6 beds • 6 baths • 4,517 sqft

6 Stone Bridge Rd, Woodstock CT 06281

#24073116, John Downs, Listing Office: Berkshire Hathaway NE Prop.

view of front of property featuring a shingled roof, crawl space, and fence

Backup offers

$4,689 Closing Credit¹

$394,900

4 beds • 3 baths • 1,920 sqft

394 Riverside Dr, Thompson CT 06255

#24076866, Sheena Ruggirello, Listing Office: Real Broker CT, LLC

view of front of property featuring roof with shingles and a chimney

kitchen with appliances with stainless steel finishes, light stone counters, light wood-type flooring, white cabinetry, and a sink

kitchen with white cabinets, light wood-style flooring, stainless steel appliances, and a sink

$4,263 Closing Credit¹

$359,000

4 beds • 1 bath • 1,152 sqft

74 Woodward Rd, Brooklyn CT 06234

#24076668, Androula Kazantzis, Listing Office: Kazantzis Real Estate, LLC

living area featuring a baseboard heating unit, beamed ceiling, and wood finished floors

Backup offers3D tour

$5,332 Closing Credit¹

$449,000

3 beds • 2 baths • 2,086 sqft

47 Tayler Trl, Woodstock CT 06282

#24073145, Tommy Connors, Listing Office: Redfin Corporation

view of front of property featuring a shingled roof, a chimney, a gambrel roof, and a front yard

view of property's community with a water view and a yard

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

$7,719 Closing Credit¹

$650,000

3 beds • 3 baths • 2,720 sqft

49 Huntington Rd, Scotland CT 06264

#24076774, Brian Hammett, Listing Office: Hammett Real Estate

view of front of home featuring a detached garage and a chimney

view of front of property featuring a chimney and fence

view of front facade with a chimney and fence

$3,384 Closing Credit¹

$285,000

3 beds • 1 bath • 1,228 sqft

37 Eden St, Putnam CT 06260

#24076411, Peter Vitale, Listing Office: Century 21 Limitless

kitchen featuring stainless steel appliances, a sink, light countertops, a center island, and a wall mounted air conditioner

kitchen featuring brown cabinetry, glass insert cabinets, appliances with stainless steel finishes, light countertops, and a sink

$4,156 Closing Credit¹

$350,000

3 beds • 2 baths • 1,948 sqft

607 Pettingill Rd, Killingly CT 06241

#24076602, Kyle Seyboth, Listing Office: Century 21 Limitless

single story home featuring a garage and driveway

ranch-style home with an attached garage

$3,741 Closing Credit¹

$315,000

3 beds • 1 bath • 1,080 sqft

45 Cross St, Killingly CT 06239

#24076419, Michael Doherty, Listing Office: KW Legacy Partners

view of front facade featuring roof with shingles

view of snow covered exterior with a chimney

exterior space featuring a garage and a chimney

$6,234 Closing Credit¹

$525,000

2 beds • 2.5 baths • 2,189 sqft

55 Cotton Bridge Rd, Killingly CT 06241

#24076344, Mae Lyons, Listing Office: Stonehouse Real Estate Co., LLC

view of front facade featuring covered porch

exterior space with a storage shed and an outbuilding

Backup offers

$1,496 Closing Credit¹

$126,000

3 beds • 2 baths • 1,512 sqft

19 Carolyn Ln, Windham CT 06256

#24075742, Sue Esposito, Listing Office: Home Selling Team

view of dock featuring a wooded view and a deck with water view

exterior space with a wooden deck and a shingled roof

$5,105 Closing Credit¹

$429,900

2 beds • 1.5 baths • 1,356 sqft

1121 Hartford Pike, Killingly CT 06241

#24076283, Christine Johnson, Listing Office: RE/MAX One

view of side of home featuring stone siding, driveway, and an attached garage

$7,066 Closing Credit¹

$595,000

4 beds • 4 baths • 5,176 sqft

50 High St, Plainfield CT 06354

#24075544, Liz Lavallee, Listing Office: Dawn Taylor Real Estate

view of front of home with stairway, roof with shingles, and a chimney

view of front of home featuring stairway, a chimney, and a shingled roof

$3,978 Closing Credit¹

$335,000

3 beds • 1 bath • 1,510 sqft

6 Lakeview Dr, Ashford CT 06278

#24075776, Alexis Molina, Listing Office: Royal Oak Realty Group

view of front of home with entry steps, a chimney, fence, and a front yard

living room featuring baseboards, crown molding, a ceiling fan, and wood finished floors

living area featuring a ceiling fan, baseboards, ornamental molding, light wood-type flooring, and radiator

Backup offers

$2,672 Closing Credit¹

$225,000

2 beds • 1 bath • 759 sqft

108 Knox Ave, Killingly CT 06239

#24072373, Jessica Boswell, Listing Office: LPT Realty

kitchen featuring a wainscoted wall, a sink, light countertops, gas range oven, and glass insert cabinets

carpeted dining room featuring radiator and baseboards

Backup offers

$2,957 Closing Credit¹

$249,000

3 beds • 1 bath • 1,152 sqft

131 Prospect Ave St, Killingly CT 06239

#24075611, Limmy Evans, Listing Office: Century 21 AllPoints Realty

snow covered back of property featuring a hot tub and a wooden deck

living room featuring a fireplace with flush hearth, a wealth of natural light, a wainscoted wall, and visible vents

Backup offers

$5,759 Closing Credit¹

$485,000

4 beds • 2.5 baths • 1,991 sqft

174 Pond Hill Rd, Plainfield CT 06354

#24075479, Wendy McDonald, Listing Office: Century 21 AllPoints Realty

view of front of property featuring a fenced front yard and a chimney

$8,905 Closing Credit¹

$749,900

6 beds • 5 baths • 4,896 sqft

45 Roseland Park Rd, Woodstock CT 06281

#24075324, Anthony Chabot, Listing Office: Chabot & Associates Real Estate

view of front of property featuring a front lawn

kitchen featuring a kitchen island, stainless steel appliances, white cabinetry, and a baseboard radiator

3D tour

$3,561 Closing Credit¹

$299,900

2 beds • 1 bath • 864 sqft

27 Nichols St, Putnam CT 06260

#24075188, Axel Correia, Listing Office: Century 21 Limitless

doorway to property with ceiling fan and covered porch

view of side of home with a yard and ceiling fan

$10,000 Closing Credit¹

$925,000

4 beds • 5 baths • 3,753 sqft

42 Hyde Rd, Brooklyn CT 06234

#24074327, Androula Kazantzis, Listing Office: Kazantzis Real Estate, LLC

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

foyer featuring light hardwood / wood-style flooring

foyer entrance with light hardwood / wood-style flooring

Backup offers

$7,480 Closing Credit¹

$629,900

3 beds • 2.5 baths • 2,202 sqft

100 Oakwood Cir, Plainville CT 06062

#24074830, Kimberly Burke, Listing Office: Berkshire Hathaway NE Prop.

colonial home with a fenced front yard, a chimney, solar panels, driveway, and an outdoor structure

snow covered property with a garage, a gazebo, a shingled roof, and a hot tub

$9,203 Closing Credit¹

$775,000

5 beds • 4 baths • 3,899 sqft

49 Quinebaug Ave, Putnam CT 06260

#24074411, Mick Marsden, Listing Office: Compass Connecticut, LLC

view of front of house featuring a porch

view of front of property featuring a porch

$4,749 Closing Credit¹

$399,900

3 beds • 2 baths • 2,531 sqft

24 Marie St, Plainfield CT 06374

#24074227, Mae Lyons, Listing Office: Stonehouse Real Estate Co., LLC

$6,828 Closing Credit¹

$575,000

3 beds • 2.5 baths • 2,272 sqft

8 Amberg Dr, Pomfret CT 06259

#24074446, Mary Collins, Listing Office: Berkshire Hathaway NE Prop.

ranch-style home featuring aphalt driveway, a front lawn, a chimney, and an attached garage

view of front of property with driveway, a chimney, and a garage

back of property with a storage unit, an outdoor structure, and a deck

$4,216 Closing Credit¹

$355,000

3 beds • 1 bath • 1,162 sqft

123 Moosup Pond Rd, Plainfield CT 06354

#24073544, Heather Ash Spadola, Listing Office: RE/MAX One

41-80 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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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.

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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, 5:20:49 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.