Windham County, CT homes for sale & real estate

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ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome home to this expansive 4-bedroom, 3-bathroom split-level style home which offers plenty of space and comfort! The upper level features a bright and airy living room that flows seamlessly into the kitchen and dining area. The kitchen is complete with granite countertops, stainless steel appliances, and a convenient breakfast bar. Down the hall, the expansive primary suite impresses with cathedral ceilings, a walk-in closet, a soaking tub, and private en-suite. A second bedroom and a full bath complete this level. The lower level offers even more living space, including two additional bedrooms, a full bathroom, and a versatile family room-ideal for a media room, home gym, or office! E

$475,000

4 beds3 baths2,860 sq ft

144 Underwood Rd, Putnam, CT 06260

Walk-in closet • Soaking tub • Cathedral ceilings

ABOUT THIS HOME
Windham County, CT Homes for Sale
This beautiful sprawling custom colonial is set on 9 acres of land at the end of a winding long driveway and surrounded by open area. Grand living spaces with cathedral ceilings and a floor to ceiling fireplace, tons of natural light, 4 bedrooms & 3.5 bathrooms, a 1500 sqft in-law suite with additional bedroom, new appliances, spacious 2 car garage, and an out building with electricity and storage loft. Enjoy the "Quiet Corner of Connecticut" today with the most beautiful autumn foliage, nearby hiking, golf, and beautiful country roads.

$659,900

4 beds3.5 baths4,536 sq ft

101 Center Rd, Woodstock, CT 06281

Custom colonial • In-law suite • 9 acres of land

ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome to this 80 acre Connecticut Estate, tucked into the rolling hills of Woodstock Ct. This exceptional 4,655 sq ft contemporary home offers a unique living experience with its own privately owned public FAA approved commercial grade airport. The property is a pilot's paradise, featuring a spacious hangar that not only accommodates multiple small planes and helicopters but also offers ample room for vehicle storage. The hangar is self-sufficient with its own septic, well, electrical, and heating systems, providing convenience and flexibility as well as a finished lounge area to gather and relax. This property is a rare find, offering a blend of luxury, functionality, and the ultimate in

$2,500,000

3 beds4.5 baths4,655 sq ft

80 Bungay Hill Rd, Woodstock, CT 06281

Spacious hangar • Finished lounge area • 80 acre estate

NEW CONSTRUCTION

ABOUT THIS HOME
Windham County, CT Homes for Sale
NEW Construction Raised Ranch in Brooklyn, CT. This move-in ready 3 bed, 2 bath home is nestled on a quiet end lot close to I-395, Route 6, and Route 101. This home offers a bright, open-concept kitchen and living area featuring granite countertops, modern designed light fixtures and plenty of natural light. Enjoy a back deck perfect for coffee in the morning or relaxing, plus a one-car garage and ample storage. Unfinished room in basement ready for your ideas. Convenient location, low maintenance, and great flow throughout-schedule a showing today!

$399,999

3 beds2 baths1,236 sq ft

359 South St, Brooklyn, CT 06234

New construction • Open-concept kitchen • Unfinished room

ABOUT THIS HOME
Windham County, CT Homes for Sale
This nicely appointed one-level ranch offers comfortable living with classic charm and thoughtful updates. Vinyl-sided for easy maintenance, the home welcomes you with gleaming hardwood floors throughout the main level. A brick gas fireplace serves as the centerpiece of the spacious family room, creating a warm and inviting gathering space. Flowing seamlessly from the family room is a generous eat-in kitchen, ideal for everyday dining or entertaining. A side entry from the kitchen leads to a deck-ready for your personal touch. Down the hall, you'll find three ample-sized bedrooms, all with hardwood flooring, and ample closet space, and a full tiled bath that completes the main level. The pa

$349,000

3 beds1.5 baths1,610 sq ft

99 Snake Meadow Rd, Killingly, CT 06239

Vinyl sided • One level ranch • Eat in kitchen

Property at 6 Orleans Ave, Killingly, CT 06239, 3 beds, 1 bath

$299,000

3 beds1 bath1,056 sq ft

6 Orleans Ave, Killingly, CT 06239

Property at 17 Green Is, Thompson, CT 06277, 2 beds, 1 bath

$369,900

2 beds1 bath440 sq ft

17 Green Is, Thompson, CT 06277

Property at 109 Battey St, Putnam, CT 06260, 3 beds, 1 bath

$299,000

3 beds1 bath1,290 sq ft

109 Battey St, Putnam, CT 06260

Property at 4 Perrin Rd, Woodstock, CT 06281, 5 beds, 3.5 baths

$535,000

5 beds3.5 baths4,172 sq ft

4 Perrin Rd, Woodstock, CT 06281

Property at 140 Ragged Hill Rd, Pomfret Center, CT 06259, 3 beds, 2 baths

$529,000

3 beds2 baths1,102 sq ft

140 Ragged Hill Rd, Pomfret Center, CT 06259

Property at 14 Valley View Dr, Dayville, CT 06241, 4 beds, 3 baths

$499,900

4 beds3 baths2,100 sq ft

14 Valley View Dr, Dayville, CT 06241

Property at 26 Perkins St, Plainfield, CT 06374, 3 beds, 1.5 baths

$328,000

3 beds1.5 baths1,760 sq ft

26 Perkins St, Plainfield, CT 06374

Property at 983 Riverside Dr, North Grosvenordale, CT 06255, 6 beds, 2 baths

$299,900

6 beds2 baths2,040 sq ft

983 Riverside Dr, North Grosvenordale, CT 06255

Property at 54 Main St, Plainfield, CT 06374, 3 beds, 2.5 baths

$329,000

3 beds2.5 baths2,004 sq ft

54 Main St, Plainfield, CT 06374

Property at 75 Academy Hill Rd, Plainfield, CT 06374, 3 beds, 2 baths

$349,900

3 beds2 baths1,008 sq ft

75 Academy Hill Rd, Plainfield, CT 06374

Property at 369 Thompson Rd, Thompson, CT 06277, 4 beds, 3.5 baths

$599,900

4 beds3.5 baths2,944 sq ft

369 Thompson Rd, Thompson, CT 06277

Property at 58 Milner Ave, Moosup, CT 06354, 3 beds, 2 baths

$499,000

3 beds2 baths1,440 sq ft

58 Milner Ave, Moosup, CT 06354

Property at 328 County Rd, Woodstock, CT 06281, 3 beds, 2 baths

$375,000

3 beds2 baths1,536 sq ft

328 County Rd, Woodstock, CT 06281

Property at 34 Pine Tree Ter, Brooklyn, CT 06234, 4 beds, 3 baths

$679,900

4 beds3 baths2,944 sq ft

34 Pine Tree Ter, Brooklyn, CT 06234

Property at 5 Nahaco Hill Ln, Eastford, CT 06242, 1 bed, 1.5 baths

$299,900

1 bed1.5 baths1,167 sq ft

5 Nahaco Hill Ln, Eastford, CT 06242

Property at 10 Conrad Park, Dayville, CT 06241, 2 beds, 1 bath

$79,900

2 beds1 bath560 sq ft

10 Conrad Park, Dayville, CT 06241

Property at 43 Parkway Dr, Quinebaug, CT 06262, 1 bed, 1 bath

$137,500

1 bed1 bath864 sq ft

43 Parkway Dr, Quinebaug, CT 06262

Property at 157 S Main St, Brooklyn, CT 06234, 6 beds, 2 baths

$265,000

6 beds2 baths2,170 sq ft

157 S Main St, Brooklyn, CT 06234

Property at 34 Pond Way, North Windham, CT 06256, 3 beds, 2 baths

$129,900

3 beds2 baths1,248 sq ft

34 Pond Way, North Windham, CT 06256

Property at 16 Valley View Dr, Dayville, CT 06241, 4 beds, 3 baths

$499,900

4 beds3 baths2,100 sq ft

16 Valley View Dr, Dayville, CT 06241

Property at 144 Prospect Ave, Killingly, CT 06239, 6 beds, 2 baths

$300,000

6 beds2 baths2,600 sq ft

144 Prospect Ave, Killingly, CT 06239

Property at 297 Main St, Hampton, CT 06247, 3 beds, 2 baths

$160,000

3 beds2 baths1,654 sq ft

297 Main St, Hampton, CT 06247

Property at 14 Buckley Hill Rd, North Grosvenordale, CT 06255, 5 beds, 2.5 baths

$329,900

5 beds2.5 baths2,040 sq ft

14 Buckley Hill Rd, North Grosvenordale, CT 06255

Property at 242 Herrick Rd, Brooklyn, CT 06234, 2 beds, 1 bath

$290,000

2 beds1 bath1,040 sq ft

242 Herrick Rd, Brooklyn, CT 06234

Property at 337 S Windham Rd, Willimantic, CT 06226, 4 beds, 2.5 baths

$420,000

4 beds2.5 baths2,905 sq ft

337 S Windham Rd, Willimantic, CT 06226

Property at 98 Williamsville Rd, Dayville, CT 06241, 3 beds, 2 baths

$425,000

3 beds2 baths1,536 sq ft

98 Williamsville Rd, Dayville, CT 06241

Property at 414 Canterbury Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$565,000

3 beds2 baths1,930 sq ft

414 Canterbury Rd, Brooklyn, CT 06234

Property at 498 Bailey Hill Rd, Killingly, CT 06241, 5 beds, 3 baths

$1,100,000

5 beds3 baths2,771 sq ft

498 Bailey Hill Rd, Killingly, CT 06241

Property at 42 Church St, Moosup, CT 06354, 6 beds, 4 baths

$334,900

6 beds4 baths2,245 sq ft

42 Church St, Moosup, CT 06354

Property at 211 Old Colony Rd, Eastford, CT 06242, 2 beds, 2 baths

$199,999

2 beds2 baths2,713 sq ft

211 Old Colony Rd, Eastford, CT 06242

Property at 30 Mayhew Dr, Dayville, CT 06241, 3 beds, 1 bath

$450,000

3 beds1 bath1,136 sq ft

30 Mayhew Dr, Dayville, CT 06241

Property at 29 Prospect St Unit A, Putnam, CT 06260, 3 beds, 1.5 baths

$294,900

3 beds1.5 baths1,200 sq ft

29 Prospect St Unit A, Putnam, CT 06260

Property at 23 Little Bunggee Hill Rd, Woodstock Valley, CT 06282, 4 beds, 2 baths

$569,000

4 beds2 baths2,160 sq ft

23 Little Bunggee Hill Rd, Woodstock Valley, CT 06282

Property at 564 Hubbard Rd, Killingly, CT 06239, 2 beds, 2 baths

$975,000

2 beds2 baths2,895 sq ft

564 Hubbard Rd, Killingly, CT 06239

Property at 85 Soap St, Dayville, CT 06241, 3 beds, 2.5 baths

$549,900

3 beds2.5 baths2,160 sq ft

85 Soap St, Dayville, CT 06241

Property at 90-94 & 93 Upton Rd, Ashford, CT 06278, 7 beds, 5 baths

$1,700,000

7 beds5 baths4,283 sq ft

90-94 & 93 Upton Rd, Ashford, CT 06278

Viewing page 3 of 7

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$289,000
North Grosvenor Dale homes for sale
$282,450
Lake Bungee homes for sale
$522,000
Willimantic homes for sale
$269,000
Quinebaug homes for sale
$137,500
Brooklyn homes for sale
$407,500
East Brooklyn homes for sale
$369,000
Danielson homes for sale
$312,500
South Woodstock homes for sale
$549,000
Putnam homes for sale
$332,450
Moosup homes for sale
$457,450
Mansfield Center homes for sale
$385,000
Dayville homes for sale
$499,900

Counties

Hartford County homes for sale
$394,000
New Haven County homes for sale
$419,000
New London County homes for sale
$439,950

Windham County, CT real estate trends

All Home Types trends in Windham County, CT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$363,500

+3.9% YoY | Sep 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Sep 2025

Growth

% YoY

Windham County, CT

$363,500

+3.9%

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