Windham County, CT homes for sale & real estate

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ABOUT THIS HOME
Windham County, CT Homes for Sale
3 acres. 3 buildings. 3 bedrooms. The lot is surrounded by Wyndham Land Trust protected land with many trails for horse, bike, walking, and bird watching. The 3 buildings include the 3 bedroom, 2 bath ranch, a barn, and an 84x48 metal building with a separate electric service. The house was renovated in 2009, and offers an open kitchen/living room, and a primary bedroom with it's own bath. The carpet is brand new, and the bedrooms have nice hardwood floors. The basement is walk out, with an oversized door to bring in large items, if needed. The 3 acres includes a barn, small spring fed pond, stonewalls, is lightly wooded. The building was erected in 1997, with it's own electric service, hea

$499,900

3 beds2 baths1,102 sq ft

140 Ragged Hill Rd, Pomfret Center, CT 06259

Barn • Small pond • Walk out basement

ABOUT THIS HOME
Windham County, CT Homes for Sale
This Large 3 Family has great income potential. With 9 total bedrooms and over 4,000 square feet of living space. Located in the heart of Willimantic on over a half acre with tons of Victorian Charm. Walking distance to ECSU, downtown Willimantic and The Willimantic Food Co-op.

$375,000

9 beds3.5 baths4,057 sq ft

41 Spring St, Willimantic, CT 06226

Victorian charm • 0.62 acre lot • 10 parking spots

NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
Windham County, CT Homes for Sale
Construction has begun on this New Contemporary Raised Ranch on a Beautiful Wooded Lot. Check out those Pics & Virtual Reality Tour. There is still time to make some choices!! Estimated Completion Date is Late December 2025! Four Bedrooms & 3 Full Bathrooms. Central AC. Two Car Garage. Vaulted Ceilings. Luxury Plank Flooring, Custom Kitchen w/ Granite Counters & Center Island. Spacious Vaulted Ceilings. High Efficiency Gas Heat. Finished Lower Level that is perfect for that aging teenager or the visiting In-Laws! Terrific lot in a residential area. Welcome VA & FHA Buyers. We are always here to help.

$459,900

4 beds3 baths1,800 sq ft

14 South St, Brooklyn, CT 06234

Custom kitchen • Beautiful wooded lot • Granite counters

ABOUT THIS HOME
Windham County, CT Homes for Sale
Located at 1032 N Main St U:9, Killingly, CT, this mobile home offers a unique opportunity to embrace simplified living within a recently renovated dwelling. The residence contains a bathroom, which provides a private and practical space for daily routines. This personal area allows for both efficiency and comfort. Within the home, you will find a single bedroom, offering a dedicated space for rest and rejuvenation. With 600 square feet of living area situated on a 1000 square foot lot, this property provides a compact and manageable environment. Constructed in 2023, this home offers a modern and efficient design. Lot rent is $675 and includes water/sewer, trash and street snowplowing Home

$47,900

1 bed1 bath600 sq ft

1032 N Main St #9, Dayville, CT 06241

1,000 sq ft lot • Garage • Built 2023

ABOUT THIS HOME
Windham County, CT Homes for Sale
Set on a private 25-acre lot, this spacious Colonial-style home offers the perfect blend of flexibility, comfort, and convenience. The main level features a bright living room with a fireplace, hardwood floors, a large kitchen, 3 bedrooms, and 2 full bathrooms, including a primary suite with its own bath. The attached in-law unit provides an ideal setup for extended family or guests, offering its own kitchen, living room, dining area, 2 bedrooms, and a full bath - creating five total bedrooms and three full bathrooms throughout the home. Each unit enjoys its own deck overlooking the peaceful, wooded surroundings, as well as separate laundry areas for added convenience. Additional features i

$364,900

5 beds3.5 baths2,496 sq ft

385 Hampton Rd, Chaplin, CT 06235

Private 25 acre lot • Attached in law unit • Close to highways

Property at 153 Bluebird Ln, Brooklyn, CT 06234, 3 beds, 2 baths

$549,900

3 beds2 baths1,582 sq ft

153 Bluebird Ln, Brooklyn, CT 06234

Property at 99 Snake Meadow Rd, Killingly, CT 06239, 3 beds, 1.5 baths

$339,000

3 beds1.5 baths1,610 sq ft

99 Snake Meadow Rd, Killingly, CT 06239

Property at 106 Tripp Hollow Rd, Brooklyn, CT 06234, 4 beds, 2.5 baths

$365,000

4 beds2.5 baths2,220 sq ft

106 Tripp Hollow Rd, Brooklyn, CT 06234

Property at 23 Pond Way, North Windham, CT 06256, 2 beds, 1 bath

$74,900

2 beds1 bath938 sq ft

23 Pond Way, North Windham, CT 06256

Property at 34 Pleasant St #7, Plainfield, CT 06374, 3 beds, 1.5 baths

$249,900

3 beds1.5 baths1,259 sq ft

34 Pleasant St #7, Plainfield, CT 06374

Property at 224 Pomfret St, Putnam, CT 06260, 3 beds, 2 baths

$399,000

3 beds2 baths1,944 sq ft

224 Pomfret St, Putnam, CT 06260

Property at 381 Bungay Hill Rd, Woodstock, CT 06281, 4 beds, 1.5 baths

$423,000

4 beds1.5 baths1,904 sq ft

381 Bungay Hill Rd, Woodstock, CT 06281

Property at 173 Westford Hill Rd, Ashford, CT 06278, 3 beds, 1.5 baths

$350,000

3 beds1.5 baths1,394 sq ft

173 Westford Hill Rd, Ashford, CT 06278

Property at 393 N Canterbury Rd, Canterbury, CT 06331, 5 beds, 2 baths

$595,000

5 beds2 baths2,443 sq ft

393 N Canterbury Rd, Canterbury, CT 06331

Property at 81 Parkway Dr, Thompson, CT 06277, 1 bed, 1 bath

$99,000

1 bed1 bath720 sq ft

81 Parkway Dr, Thompson, CT 06277

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

$323,000

3 beds1.5 baths1,760 sq ft

26 Perkins St, Plainfield, CT 06374

Property at 383 Lathrop Rd, Plainfield, CT 06374, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths2,258 sq ft

383 Lathrop Rd, Plainfield, CT 06374

Property at 101 Center Rd, Woodstock, CT 06281, 4 beds, 3.5 baths

$659,900

4 beds3.5 baths4,536 sq ft

101 Center Rd, Woodstock, CT 06281

Property at 70 Laurel Hill Dr, Woodstock, CT 06281, 3 beds, 2.5 baths

$420,000

3 beds2.5 baths1,682 sq ft

70 Laurel Hill Dr, Woodstock, CT 06281

Property at 395 Bailey Hill Rd, Killingly, CT 06239, 3 beds, 2 baths

$485,000

3 beds2 baths2,170 sq ft

395 Bailey Hill Rd, Killingly, CT 06239

Property at 132 Grove St, Putnam, CT 06260, 3 beds, 1 bath

$340,900

3 beds1 bath1,344 sq ft

132 Grove St, Putnam, CT 06260

Property at 7 Devotion Rd, Scotland, CT 06264, 4 beds, 2 baths

$415,000

4 beds2 baths1,787 sq ft

7 Devotion Rd, Scotland, CT 06264

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

$315,000

3 beds2 baths1,008 sq ft

75 Academy Hill Rd, Plainfield, CT 06374

Property at 48 Wrights Crossing Rd, Pomfret Center, CT 06259, 3 beds, 3 baths

$647,000

3 beds3 baths2,546 sq ft

48 Wrights Crossing Rd, Pomfret Center, CT 06259

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 679 Bailey Hill Rd, Dayville, CT 06241, 3 beds, 3 baths

$674,900

3 beds3 baths3,150 sq ft

679 Bailey Hill Rd, Dayville, CT 06241

Property at 1415 North Rd, Dayville, CT 06241, 3 beds, 3 baths

$559,000

3 beds3 baths1,515 sq ft

1415 North Rd, Dayville, CT 06241

Property at 127 Plains Rd, Windham, CT 06280, 4 beds, 2 baths

$395,000

4 beds2 baths1,700 sq ft

127 Plains Rd, Windham, CT 06280

Property at 102 Krapf Rd, Ashford, CT 06278, 4 beds, 2 baths

$449,000

4 beds2 baths2,760 sq ft

102 Krapf Rd, Ashford, CT 06278

Property at 80 Bungay Hill Rd, Woodstock, CT 06281, 3 beds, 4.5 baths

$2,500,000

3 beds4.5 baths4,655 sq ft

80 Bungay Hill Rd, Woodstock, CT 06281

Property at 29 Crooked Trail Ext, Woodstock, CT 06281, 4 beds, 2 baths

$689,000

4 beds2 baths2,630 sq ft

29 Crooked Trail Ext, Woodstock, CT 06281

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 47 Texas Heights Rd, Plainfield, CT 06374, 3 beds, 1 bath

$289,000

3 beds1 bath960 sq ft

47 Texas Heights Rd, Plainfield, CT 06374

Property at 34 Pleasant St #3, Plainfield, CT 06374, 2 beds, 1 bath

$219,500

2 beds1 bath1,188 sq ft

34 Pleasant St #3, Plainfield, CT 06374

Property at 101 Child Hill Rd, Woodstock, CT 06281, 4 beds, 3 baths

$549,000

4 beds3 baths2,150 sq ft

101 Child Hill Rd, Woodstock, CT 06281

Property at 815 Mashamoquet Rd, Pomfret Center, CT 06259, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths1,656 sq ft

815 Mashamoquet Rd, Pomfret Center, CT 06259

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

$289,999

6 beds2 baths2,600 sq ft

144 Prospect Ave, Killingly, CT 06239

Property at 69 N Bedlam Rd, Chaplin, CT 06235, 3 beds, 2 baths

$599,000

3 beds2 baths1,979 sq ft

69 N Bedlam Rd, Chaplin, CT 06235

Property at 189 Center Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$774,900

4 beds2.5 baths3,662 sq ft

189 Center Rd, Woodstock, CT 06281

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 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

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Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$319,000
North Grosvenor Dale homes for sale
$365,000
Lake Bungee homes for sale
$447,500
Willimantic homes for sale
$264,900
Quinebaug homes for sale
$347,500
Brooklyn homes for sale
$415,000
East Brooklyn homes for sale
$389,450
Danielson homes for sale
$287,500
South Woodstock homes for sale
$423,000
Putnam homes for sale
$359,900
Moosup homes for sale
$434,950
Mansfield Center homes for sale
Dayville homes for sale
$499,900

Counties

Hartford County homes for sale
$379,900
New Haven County homes for sale
$399,900
New London County homes for sale
$405,000

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)

$360,000

+5.9% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Windham County, CT

$360,000

+5.9%

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