Windham County, CT homes for sale & real estate

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ABOUT THIS HOME
Windham County, CT Homes for Sale
COUNTRY SPRAWLING RANCH set back on 2.30 ACRES close to the RI LINE! ENORMOUS 8 x 60 COVERED open porch to enjoy your FALL evenings. BEAUTIFUL HARDWOOD flooring throughout with BRIGHT windows letting the natural light shine in. REMODELED kitchen w/ STAINLESS appliances open to FIREPLACE living room or use as a FORMAL dining room for the holidays! Dining area and open floor plan with more space for a sitting area and HUGE SLIDER leading outside. 1 st floor laundry and all 3 bedrooms have plenty of closet space w/ built ins. REMODELED bathroom w/ TILED GLASS shower and another REMODELED bathroom w/ double vanity and tub. UPDATED electrical panel, , boiler, oil tank and holding tank! CLOSE to

$449,900

3 beds2 baths1,856 sq ft

540 Squaw Rock Rd, Moosup, CT 06354

Formal dining room • Covered open porch • Remodeled kitchen

ABOUT THIS HOME
Windham County, CT Homes for Sale
What started as just a summer cottage has been transformed over the 50 years of ownership into a great lake view & access home. This home features over 1,700 sq. ft. on two floors, 4 total bedrooms along with 2 full bathrooms. The first floor has a large living room with pellet stove heating that satisfies the major of the heating needs. There is a good working space kitchen along with a rear sunroom/plant room/dining area. There are two bedrooms, a full bathroom with tub/shower along with the laundry on the main level. The second floor was a full addition years ago. There are two very good-sized bedrooms, a sitting area/den, along with an additional full bathroom. You will even find

$339,900

4 beds2 baths1,712 sq ft

101 Beaver Dam Rd, Woodstock Valley, CT 06282

Rear sunroom • Open deck • Deeded access

OPEN SUN, 9AM TO 12PM

ABOUT THIS HOME
Windham County, CT Homes for Sale
Welcome to 62 Bates Pond Road in Canterbury-a three-bedroom, one-bath home on just over two acres, offering privacy and a peaceful country setting. The newly finished basement provides flexible space for relaxing, entertaining, a home office, or hobbies. Canterbury offers town-funded high school options, including Woodstock Academy and other area schools, with tuition supported through local taxes. The home will be sold with a full oil tank and a brand-new generator included with the purchase

$375,000

3 beds1 bath1,356 sq ft

62 Bates Pond Rd, Canterbury, CT 06331

Privacy • Over 2 acres of land • Peaceful setting

ABOUT THIS HOME
Windham County, CT Homes for Sale
HISTORIC CHARM MEETS VALUE ADD POTENTIAL in Connecticut's Quiet Corner! This distinctive multi family property offers 3 residential units plus a fourth space with commercial potential, and a fascinating history as Kenney's Store, a post office and train depot. Units 1, 2 and 3 feature spacious layouts, beautiful hardwood floors and timeless character. Two units offer 3 bedrooms, while the third offers 2 bedrooms. Unit 1 is currently configured as a 1-bedroom but can be converted back to a 2 or 3 bedroom layout. The property is ready to be repositioned, with one or two residential units requiring significant renovation and the former commercial space offering a true blank canvas for its next

$349,999

9 beds3.5 baths4,336 sq ft

6 Old Route 12, Thompson, CT 06277

Spacious layouts • Commercial potential • Large rooms

FLOOR PLAN

ABOUT THIS HOME
Windham County, CT Homes for Sale
A unique opportunity in the heart of Eastford! Offering approximately 3,324 sq ft of space and residential/commercial zoning, this character-filled 1821 built property offers possibilities that go well beyond the typical single-family home. Whether you're looking for a spacious residence, a property with potential for a home-based business or office, or simply an antique home you can restore and make your own, 5 Eastford Road offers tremendous flexibility. The large kitchen features granite countertops, stainless steel appliances, a commercial-grade range with hood, and a spacious pantry. A generously sized living room with pellet stove provides an inviting gathering space, while the flexib

$329,900

4 beds1.5 baths3,324 sq ft

5 Eastford Rd, Eastford, CT 06242

Spacious pantry • Large kitchen • Granite countertops

Property at 19 North Rd, Ashford, CT 06278, 4 beds, 1 bath

$379,900

4 beds1 bath2,332 sq ft

19 North Rd, Ashford, CT 06278

Property at 78 Hammond Hill Rd, Hampton, CT 06247, 4 beds, 2 baths

$449,900

4 beds2 baths2,002 sq ft

78 Hammond Hill Rd, Hampton, CT 06247

Property at 332 Ravenelle Rd, North Grosvenordale, CT 06255, 3 beds, 2.5 baths

$789,000

3 beds2.5 baths3,913 sq ft

332 Ravenelle Rd, North Grosvenordale, CT 06255

Property at 178 Farrows St, Putnam, CT 06260, 3 beds, 2 baths

$345,000

3 beds2 baths1,344 sq ft

178 Farrows St, Putnam, CT 06260

Property at 33 King St, Putnam, CT 06260, 3 beds, 2 baths

$379,900

3 beds2 baths1,302 sq ft

33 King St, Putnam, CT 06260

Property at 157 Paradise Dr, Brooklyn, CT 06234, 1 bed, 1 bath

$299,900

1 bed1 bath918 sq ft

157 Paradise Dr, Brooklyn, CT 06234

Property at 66 High Meadow Dr, Plainfield, CT 06374, 4 beds, 2 baths

$389,900

4 beds2 baths1,736 sq ft

66 High Meadow Dr, Plainfield, CT 06374

Property at 49 Fox Rd, Putnam, CT 06260, 4 beds, 2.5 baths

$599,999

4 beds2.5 baths3,212 sq ft

49 Fox Rd, Putnam, CT 06260

Property at 45 Fairview St, Killingly, CT 06239, 2 beds, 1 bath

$315,000

2 beds1 bath832 sq ft

45 Fairview St, Killingly, CT 06239

Property at 45 Wolf Den Dr, Pomfret Center, CT 06259, 3 beds, 2.5 baths

$449,900

3 beds2.5 baths1,775 sq ft

45 Wolf Den Dr, Pomfret Center, CT 06259

Property at 10 Centennial St, Putnam, CT 06260, 3 beds, 1 bath

$289,000

3 beds1 bath956 sq ft

10 Centennial St, Putnam, CT 06260

Property at 91 Church St, Thompson, CT 06277, 5 beds, 3.5 baths

$799,000

5 beds3.5 baths2,990 sq ft

91 Church St, Thompson, CT 06277

Property at 972 Quaddick Town Farm Rd, Thompson, CT 06277, 3 beds, 1 bath

$329,900

3 beds1 bath1,360 sq ft

972 Quaddick Town Farm Rd, Thompson, CT 06277

Property at 85 Robertson Ave, Killingly, CT 06239, 4 beds, 2 baths

$393,000

4 beds2 baths1,904 sq ft

85 Robertson Ave, Killingly, CT 06239

Property at 500 Route 169, Woodstock, CT 06281, 5 beds, 3.5 baths

$779,000

5 beds3.5 baths2,467 sq ft

500 Route 169, Woodstock, CT 06281

Property at 29 Vandall St, North Grosvenordale, CT 06255, 3 beds, 2 baths

$499,000

3 beds2 baths4,907 sq ft

29 Vandall St, North Grosvenordale, CT 06255

Property at 108 Krapf Rd, Ashford, CT 06278, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths1,564 sq ft

108 Krapf Rd, Ashford, CT 06278

Property at 549 Squaw Rock Rd Ext, Killingly, CT 06239, 3 beds, 2 baths

$410,000

3 beds2 baths1,144 sq ft

549 Squaw Rock Rd Ext, Killingly, CT 06239

Property at 354 Pomfret St, Pomfret Center, CT 06259, 6 beds, 4.5 baths

$975,000

6 beds4.5 baths4,601 sq ft

354 Pomfret St, Pomfret Center, CT 06259

Property at 154 Manners Ave, Willimantic, CT 06226, 3 beds, 1 bath

$288,000

3 beds1 bath1,032 sq ft

154 Manners Ave, Willimantic, CT 06226

Property at 28 Lovers Ln, Windham, CT 06280, 2 beds, 1 bath

$189,000

2 beds1 bath1,000 sq ft

28 Lovers Ln, Windham, CT 06280

Property at 357 Wrights Crossing Rd, Pomfret Center, CT 06259, 5 beds, 5.5 baths

$2,500,000

5 beds5.5 baths7,772 sq ft

357 Wrights Crossing Rd, Pomfret Center, CT 06259

Property at 110 Church St, Putnam, CT 06260, 7 beds, 2.5 baths

$475,000

7 beds2.5 baths3,071 sq ft

110 Church St, Putnam, CT 06260

Property at 47 Sherman Rd, Woodstock, CT 06281, 4 beds, 3 baths

$595,000

4 beds3 baths2,072 sq ft

47 Sherman Rd, Woodstock, CT 06281

Property at 31 Canterbury Rd, Brooklyn, CT 06234, 4 beds, 3.5 baths

$485,000

4 beds3.5 baths2,879 sq ft

31 Canterbury Rd, Brooklyn, CT 06234

Property at 122 Child Hill Rd, Woodstock, CT 06281, 4 beds, 3 baths

$679,000

4 beds3 baths3,865 sq ft

122 Child Hill Rd, Woodstock, CT 06281

Property at 160 Halls Hill Rd, Danielson, CT 06239, 3 beds, 1.5 baths

$699,900

3 beds1.5 baths3,119 sq ft

160 Halls Hill Rd, Danielson, CT 06239

Property at 345 Cook Hill Rd, Killingly, CT 06239, 3 beds, 2.5 baths

$544,900

3 beds2.5 baths1,848 sq ft

345 Cook Hill Rd, Killingly, CT 06239

Property at 1619 Route 171, Woodstock Valley, CT 06281, 3 beds, 1.5 baths

$379,000

3 beds1.5 baths1,824 sq ft

1619 Route 171, Woodstock Valley, CT 06281

Property at 85 Mansfield Rd, Ashford, CT 06278, 3 beds, 2 baths

$349,900

3 beds2 baths1,134 sq ft

85 Mansfield Rd, Ashford, CT 06278

Property at 31 Chetelat Dr, Ashford, CT 06278, 2 beds, 2 baths

$310,000

2 beds2 baths1,776 sq ft

31 Chetelat Dr, Ashford, CT 06278

Property at 40 Fitts Rd, Ashford, CT 06278, 3 beds, 1 bath

$345,000

3 beds1 bath1,239 sq ft

40 Fitts Rd, Ashford, CT 06278

Property at 9 Ellen Ln, Woodstock, CT 06281, 6 beds, 3 baths

$499,900

6 beds3 baths3,214 sq ft

9 Ellen Ln, Woodstock, CT 06281

Property at 813 Westford Rd, Ashford, CT 06278, 3 beds, 2 baths

$533,000

3 beds2 baths2,010 sq ft

813 Westford Rd, Ashford, CT 06278

Property at 183 Hillside Rd, Ashford, CT 06278, 4 beds, 2 baths

$790,000

4 beds2 baths2,323 sq ft

183 Hillside Rd, Ashford, CT 06278

Property at 166 PARADISE Dr, Brooklyn, CT 06234, 3 beds, 3 baths

$519,900

3 beds3 baths1,700 sq ft

166 PARADISE Dr, Brooklyn, CT 06234

Viewing page 2 of 8

Average home prices near Windham County, CT

Cities

Plainfield Village homes for sale
$369,450
Storrs homes for sale
$291,450
North Grosvenor Dale homes for sale
$469,450
Wauregan homes for sale
$365,000
Willimantic homes for sale
$290,000
Quinebaug homes for sale
$512,400
Brooklyn homes for sale
$387,450
East Brooklyn homes for sale
$394,950
Danielson homes for sale
$332,500
South Woodstock homes for sale
$595,000
Putnam homes for sale
$347,450
Moosup homes for sale
$372,450
Mansfield Center homes for sale
$395,000
Dayville homes for sale
$529,900

Counties

Hartford County homes for sale
$398,000
New Haven County homes for sale
$419,900
New London County homes for sale
$440,000

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)

$381,147

+5.9% YoY | Sep 2026

1 year
3 year
5 year

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

Location

Data

Sep 2026

Growth

% YoY

Windham County, CT

$381,147

+5.9%

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Deals*

4.4

Satisfaction

369

Homes closed*

* Data from the last year

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