4 bedroom homes for sale in Windham County, CT

view of pool featuring a fenced in pool, fence, a patio area, and a diving board

kitchen featuring open shelves, gray cabinets, appliances with stainless steel finishes, and a sink

living room featuring baseboard heating, a fireplace, and wood finished floors

1 day on Rocket

$7,897 Closing Credit¹

$665,000

4 beds • 2.5 baths • 1,824 sqft

304 Lathrop Rd, Plainfield CT 06374

#24080460, Derek Greene, Listing Office: Derek Greene

colonial-style house with driveway and a chimney

colonial-style house with a front lawn and a chimney

2 days on Rocket3D tour

$4,986 Closing Credit¹

$419,900

4 beds • 2 baths • 1,862 sqft

120 Littlefield Rd, Scotland CT 06247

#24076052, Crystal Gebhardt Coogan, Listing Office: Coldwell Banker Realty

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colonial house with covered porch, a front lawn, a chimney, and a ceiling fan

rear view of house featuring a gazebo, a lawn, and a chimney

back of house featuring a deck, a gazebo, a yard, a shingled roof, and a chimney

Coming soon

$7,124 Closing Credit¹

$599,900

4 beds • 2.5 baths • 2,186 sqft

109 Bailey Hill Rd, Killingly CT 06239

#24079683, Mae Lyons, Listing Office: Stonehouse Real Estate Co., LLC

unfurnished living room featuring beamed ceiling, high vaulted ceiling, hardwood / wood-style floors, a wall unit AC, and a baseboard radiator

3 days on Rocket

$7,125 Closing Credit¹

$600,000

4 beds • 4 baths • 2,712 sqft

124 Elmdale Rd, Canterbury CT 06331

#24079613, Christine Johnson, Listing Office: RE/MAX One

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

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

kitchen featuring a sink, stainless steel appliances, white cabinets, and light wood finished floors

4 days on Rocket

$4,453 Closing Credit¹

$375,000

4 beds • 1 bath • 1,152 sqft

74 Woodward, Brooklyn CT 06234

#73343402, Androula Kazantzis, Listing Office: Kazantzis Real Estate, LLC

view of front facade featuring roof with shingles and covered porch

kitchen featuring a sink, light tile patterned floors, gray cabinets, and crown molding

kitchen with baseboards, light tile patterned flooring, ornamental molding, gray cabinetry, and stainless steel appliances

4 days on Rocket

$4,453 Closing Credit¹

$375,000

4 beds • 2.5 baths • 2,190 sqft

8 Lake St, Plainfield CT 06354

#24079396, Courtney Ravenelle, Listing Office: RE/MAX Bell Park Realty

back of house at dusk with a deck, a patio, and a chimney

colonial-style house with a chimney and a front yard

4 days on RocketVideo tour

$10,000 Closing Credit¹

$939,000

4 beds • 2.5 baths • 3,516 sqft

16 Kings Hwy, Pomfret CT 06259

#24078024, Elizabeth Zimmer, Listing Office: Berkshire Hathaway NE Prop.

Room to negotiate?

Median Sold Price

$340K

Avg. Sale Time

30 Days

Based on our February 2025 Market Report.

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

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

$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 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 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

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

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

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 home with a deck and fence

kitchen with dark wood-style floors, ceiling fan, a textured ceiling, and freestanding refrigerator

dining space with a wealth of natural light, a textured ceiling, and wood finished floors

$3,205 Closing Credit¹

$269,900

4 beds • 2.5 baths • 1,520 sqft

10 Tiffany St, Brooklyn CT 06234

#24074084, Christine Johnson, Listing Office: RE/MAX One

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

$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

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

$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

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 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 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

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

view of yard with a trampoline and a playground

$4,036 Closing Credit¹

$339,900

4 beds • 1.5 baths • 1,480 sqft

28 Lafayette Ave, Plainfield CT 06354

#24065260, Raymond Preece, Listing Office: Signature Properties of NewEng

view of front facade featuring a front lawn

modern inspired farmhouse with a front lawn

$10,000 Closing Credit¹

$849,900

4 beds • 3.5 baths • 2,526 sqft

276 Killingly Rd, Pomfret CT 06259

#1374444, Listing Office: Century 21 Limitless PRG

single story home featuring a front yard and a garage

$5,926 Closing Credit¹

$499,000

4 beds • 2.5 baths • 2,142 sqft

56 Sundale Dr, Windham CT 06280

#24061948, Betsy Diquattro, Listing Office: Johnston & Associates Real Estate, LLC

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

rear view of property featuring a deck and a lawn

$3,563 Closing Credit¹

$300,000

4 beds • 2 baths • 1,416 sqft

11 Lovers Ln, Windham CT 06280

#24061254, Rolando Navarro, Listing Office: KW Legacy Partners

view of front of house featuring a porch and a front yard

exterior space with a lawn and covered porch

view of front of home featuring covered porch

$6,531 Closing Credit¹

$550,000

4 beds • 3 baths • 2,644 sqft

13 Brooklyn Rd, Pomfret CT 06259

#24059909, Margaret Young, Listing Office: CR Premier Properties

view of front of house featuring an outdoor structure and a lawn

$8,301 Closing Credit¹

$699,000

4 beds • 2.5 baths • 2,682 sqft

37 Pulpit Rock Rd, Woodstock CT 06281

#24052708, Kristen Kaskela, Listing Office: Berkshire Hathaway NE Prop.

view of front of property featuring a front lawn

$10,000 Closing Credit¹

$1,150,000

4 beds • 3 baths • 2,542 sqft

227 Pudding Hill Rd, Scotland CT 06247

#24050493, Peter Plourde, Listing Office: Berkshire Hathaway NE Prop.

Windham County, CT Real Estate Market Overview

Browse 32 4 bedroom homes for sale in Windham County, CT. View properties, photos, nearby real estate with school and housing market information. In February 2025 in Windham County, CT there were 6.5% less homes for sale than in January 2025. The median list price of listings available in February 2025 was $340,000, while the average time on the real estate market was 30 days. While more than 36 listings in Windham County, CT in February 2025 were sold above asking price, there were more than 14 listings sold at asking price, and more than 25 were sold below.

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

4 bedroom 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

Schools near Windham County, CT

Housing market reports in Windham County

Homes for sale near Windham County, CT

Top real estate cities in Connecticut