Windham County, CT homes for sale & real estate

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ABOUT THIS HOME
Windham County, CT Homes for Sale
Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-fl

$549,000

4 beds3 baths2,150 sq ft

101 Child Hill Rd, Woodstock, CT 06281

0.9 acre lot • Garage • Built 1830

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
Adorable Ranch style home with nice backyard and deck for enjoyment. Offered here is living room, kitchen, eat in area, 3 bedrooms and full bathroom. New kitchen cabinets and stainless steel appliances.

$349,900

3 beds2 baths1,008 sq ft

75 Academy Hill Rd, Plainfield, CT 06374

Eat in area • Kitchen • Living room

SHORT SALE

ABOUT THIS HOME
Windham County, CT Homes for Sale
No entry into this property will be available to the public due to the inhabitable condition and all offers will be submitted sight unseen. This property is being sold as is, in an Estate, and will require Probate Court approval. The sale of this property is a short sale.

$198,500

4 beds2 baths1,152 sq ft

50 South St, Willimantic, CT 06226

9,583 sq ft lot • Built 1991 • Listed 33 days

ABOUT THIS HOME
Windham County, CT Homes for Sale
New Price Improvement. Motivated Seller! Come visit and fall in love with the possibilities. This property must be seen to be fully appreciated. Prepare to be enchanted & immersed in nature. Here is your opportunity to own property on Blackwell Brook. This sprawling ranch sits on 6.18 acres. Built to last & adorned with shelves & built in's. The main bedroom has it's own full bathroom, built in shelves and a generous double closet. On the main level there are two other bedrooms and a main full bathroom. Updated custom drawer & cabinet doors & granite countertops. The attached living room has a spacious dining area with built in shelves, a living space fireplace

$565,000

3 beds2 baths1,930 sq ft

414 Canterbury Rd, Brooklyn, CT 06234

Attached deck • Custom cabinets • Built in shelves

Property at 37 Buckley Hill Rd, North Grosvenordale, CT 06255, 6 beds, 2 baths

$225,000

6 beds2 baths2,094 sq ft

37 Buckley Hill Rd, North Grosvenordale, CT 06255

Property at 29 Pleasant St, Plainfield, CT 06374, 3 beds, 2 baths

$380,000

3 beds2 baths1,650 sq ft

29 Pleasant St, Plainfield, CT 06374

Property at 462 Wauregan Rd, Brooklyn, CT 06234, 4 beds, 2.5 baths

$475,000

4 beds2.5 baths2,256 sq ft

462 Wauregan Rd, Brooklyn, CT 06234

Property at 513 Lhomme Street Ext, Killingly, CT 06239, 3 beds, 1.5 baths

$365,000

3 beds1.5 baths1,160 sq ft

513 Lhomme Street Ext, 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 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 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 16 Pilfershire Rd, Eastford, CT 06242, 3 beds, 3 baths

$699,000

3 beds3 baths2,854 sq ft

16 Pilfershire Rd, Eastford, CT 06242

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 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 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 72 South St, Brooklyn, CT 06234, 3 beds, 3 baths

$474,900

3 beds3 baths1,795 sq ft

72 South St, Brooklyn, CT 06234

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

$424,000

4 beds1.5 baths1,904 sq ft

381 Bungay Hill Rd, Woodstock, CT 06281

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 6 Meadowside Rd, Woodstock, CT 06281, 2 beds, 1 bath

$65,000

2 beds1 bath775 sq ft

6 Meadowside Rd, Woodstock, CT 06281

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 98 Breakneck Hill Rd, Dayville, CT 06241, 4 beds, 2.5 baths

$659,000

4 beds2.5 baths2,954 sq ft

98 Breakneck Hill Rd, Dayville, CT 06241

Property at 26 Maple Ave, Willimantic, CT 06226, 7 beds, 3 baths

$309,000

7 beds3 baths3,419 sq ft

26 Maple Ave, Willimantic, CT 06226

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

$349,000

3 beds1.5 baths1,610 sq ft

99 Snake Meadow Rd, Killingly, CT 06239

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 60 Chaplin St, Chaplin, CT 06235, 3 beds, 2 baths

$425,000

3 beds2 baths2,438 sq ft

60 Chaplin St, Chaplin, CT 06235

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 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 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 14 R And R Park, Dayville, CT 06241, 2 beds, 1 bath

$69,000

2 beds1 bath672 sq ft

14 R And R Park, 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 287 S Bear Hill Rd, Chaplin, CT 06235, 4 beds, 2.5 baths

$789,000

4 beds2.5 baths2,900 sq ft

287 S Bear Hill Rd, Chaplin, CT 06235

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 71 Rawson Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$534,900

4 beds2.5 baths1,887 sq ft

71 Rawson Rd, Woodstock, CT 06281

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 402 Whetstone Mls #402, Dayville, CT 06241, 2 beds, 1.5 baths

$279,000

2 beds1.5 baths1,318 sq ft

402 Whetstone Mls #402, Dayville, CT 06241

Property at 115 Babbitt Hill Rd, Pomfret Center, CT 06259, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths3,222 sq ft

115 Babbitt Hill Rd, Pomfret Center, CT 06259

Property at 36 Olde Meadow Rd, Woodstock, CT 06281, 4 beds, 3.5 baths

$895,000

4 beds3.5 baths3,300 sq ft

36 Olde Meadow Rd, Woodstock, CT 06281

Property at 8 John's Cir Lot 33, Sterling, CT 06377, 3 beds, 2 baths

$449,900

3 beds2 baths1,400 sq ft

8 John's Cir Lot 33, Sterling, CT 06377

Property at 285 E Quasset Rd, Woodstock, CT 06281, 4 beds, 1 bath

$425,000

4 beds1 bath1,144 sq ft

285 E Quasset Rd, Woodstock, CT 06281

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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