Recently Sold Homes in Windham County, CT

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SOLD SEP 19, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
Stunning 3-bedroom, 2-bath Colonial in picturesque Woodstock, CT, situated on 2 serene acres. This home has undergone a complete renovation with approximately $150,000 in high-end upgrades, blending modern luxury with classic New England charm. Step inside to discover a brand-new kitchen featuring top-of-the-line appliances, sleek cabinetry, and elegant countertops. Gleaming new floors flow throughout, complemented by all-new windows that bathe the home in natural light. The spacious layout includes an office, as well as a versatile family room or playroom, perfect for relaxation or entertainment. The exterior is equally impressive, boasting a $30,000 stone paver patio with a custom firepla

$450,000 Last sold price

3 beds2 baths1,728 sq ft

1026 Route 171, Woodstock, CT 06281

SOLD OCT 8, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
Welcome to 179 Hill Road, a stunning 4,000+ sq ft Colonial set on a private, pastoral lot in a high-end Thompson, CT neighborhood. This beautifully maintained home features 4 bedrooms, 3.5 baths, and a flexible layout (private 1st floor in-law apartment) ideal for multi-generational living. The first-floor primary suite offers hardwood floors, a walk-in closet, and a luxurious private bath. The bright kitchen with granite counters flows into a formal dining room with a bay window, and a spacious living room with French doors leading to an enclosed porch and deck. A private in-law apartment includes its own kitchen, full bath, living room, and dedicated deck-offering comfort and independence

$650,000 Last sold price

4 beds3.5 baths4,016 sq ft

179 Hill Rd, Thompson, CT 06277

SOLD OCT 15, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
RUSTIC COUNTRY RANCH ON 1.15 ACRES right on the RI LINE. 10 x 16 and 16 x 26 HUGE DECK off the back of the home for entertaining overlooking FENCED area for your animals. 20 x 20 GARAGE for your vehicle and STORAGE. LARGE FIREPLACE living room, STAINLESS APPLIANCE kitchen w/ BEAUTIFUL GRANITE COUNTERS, NEW flooring leads to SPACIOUS dining area w/ SLIDER to DECK. 1 full bathroom and 3 bedrooms w/ NEW FLOORING and hallway too. FRESHLY PAINTED and ready for new owners who enjoy COUNTRY living w/ no sidewalks or street lights. CLOSE to 395 and RTE 6 for convenience. OUT in the COUNTRY but close to all shopping.

$319,900 Last sold price

3 beds1 bath1,290 sq ft

534 Margaret Henry Rd, Sterling, CT 06377

3D WALKTHROUGH

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Unknown Last sold price

2 beds1 bath1,152 sq ft

26 Hungry Hill Rd, Sterling, CT 06377

SOLD OCT 29, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
Investor alert! This professionally managed, fully occupied 5-family property is a rare turn-key opportunity delivering strong and consistent cash flow. All five units are currently leased, making this a seamless addition to your portfolio with income from day one. The building features a new roof. Tenants pay for their own electric heat and hot water, keeping operating costs low for the owner. This property will require commercial lending and is ideal for both new and seasoned investors looking for stable, hands-off income in a well-run asset.

$485,000 Last sold price

8 beds5 baths4,400 sq ft

47 Commerce Ave, Killingly, CT 06239

Property at 5 Kies Rd, Killingly, CT 06239, 3 beds, 3.5 baths

$799,000 Last sold price

3 beds3.5 baths2,209 sq ft

5 Kies Rd, Killingly, CT 06239

Property at 69 Lyon Hill Rd, Woodstock, CT 06281, 3 beds, 2 baths

$435,000 Last sold price

3 beds2 baths1,210 sq ft

69 Lyon Hill Rd, Woodstock, CT 06281

Property at 16 Porter Plain Rd, Thompson, CT 06277, 3 beds, 2 baths

$400,000 Last sold price

3 beds2 baths1,960 sq ft

16 Porter Plain Rd, Thompson, CT 06277

Property at 166 Fabyan Rd, North Grosvenordale, CT 06255, 3 beds, 2 baths

$550,000 Last sold price

3 beds2 baths2,167 sq ft

166 Fabyan Rd, North Grosvenordale, CT 06255

Property at 67 Perry St #120, Putnam, CT 06260, 2 beds, 2 baths

$255,000 Last sold price

2 beds2 baths1,600 sq ft

67 Perry St #120, Putnam, CT 06260

Property at 13 Westside Dr Apt 89, North Grosvenordale, CT 06255, 2 beds, 1.5 baths

$280,000 Last sold price

2 beds1.5 baths1,704 sq ft

13 Westside Dr Apt 89, North Grosvenordale, CT 06255

Property at 987 Riverside Dr, North Grosvenordale, CT 06255, 4 beds, 2 baths

$275,000 Last sold price

4 beds2 baths2,040 sq ft

987 Riverside Dr, North Grosvenordale, CT 06255

Property at 78 Peake Brook Rd, Woodstock, CT 06281, 3 beds, 2 baths

$301,000 Last sold price

3 beds2 baths1,340 sq ft

78 Peake Brook Rd, Woodstock, CT 06281

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

$370,000 Last sold price

3 beds2 baths1,536 sq ft

328 County Rd, Woodstock, CT 06281

Property at 86 Lebanon Hill Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$415,000 Last sold price

4 beds2.5 baths1,602 sq ft

86 Lebanon Hill Rd, Woodstock, CT 06281

Property at 72 Lake View Dr, Woodstock, CT 06281, 2 beds, 2 baths

$570,000 Last sold price

2 beds2 baths1,338 sq ft

72 Lake View Dr, Woodstock, CT 06281

Property at 9 Sherman Rd, Woodstock, CT 06281, 2 beds, 1 bath

$150,000 Last sold price

2 beds1 bath888 sq ft

9 Sherman Rd, Woodstock, CT 06281

Property at 62 Crooked Trl, Woodstock, CT 06281, 2 beds, 1.5 baths

$475,000 Last sold price

2 beds1.5 baths1,734 sq ft

62 Crooked Trl, Woodstock, CT 06281

Property at 21 Old Sawmill Rd, Woodstock, CT 06281, 3 beds, 2 baths

$460,000 Last sold price

3 beds2 baths1,564 sq ft

21 Old Sawmill Rd, Woodstock, CT 06281

Property at 36 Dunleavy Dr, Woodstock, CT 06281, 3 beds, 2 baths

$524,000 Last sold price

3 beds2 baths2,036 sq ft

36 Dunleavy Dr, Woodstock, CT 06281

Property at 115 Crooked Trail Ext, Woodstock, CT 06281, 3 beds, 2 baths

$653,950 Last sold price

3 beds2 baths1,922 sq ft

115 Crooked Trail Ext, Woodstock, CT 06281

Property at 37 Pulpit Rock Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$625,000 Last sold price

4 beds2.5 baths2,682 sq ft

37 Pulpit Rock Rd, Woodstock, CT 06281

Property at 42 Roseland Park Rd, Woodstock, CT 06281, 3 beds, 2.5 baths

$285,000 Last sold price

3 beds2.5 baths1,914 sq ft

42 Roseland Park Rd, Woodstock, CT 06281

Property at 170 Lyon Hill Rd, Woodstock, CT 06281, 3 beds, 2.5 baths

$700,000 Last sold price

3 beds2.5 baths2,960 sq ft

170 Lyon Hill Rd, Woodstock, CT 06281

Property at 1 Laurel Hill Dr, Woodstock Valley, CT 06282, 3 beds, 1 bath

$480,000 Last sold price

3 beds1 bath1,323 sq ft

1 Laurel Hill Dr, Woodstock Valley, CT 06282

Property at 359 Barlow Cemetery Rd, Woodstock, CT 06281, 3 beds, 2.5 baths

$525,000 Last sold price

3 beds2.5 baths2,362 sq ft

359 Barlow Cemetery Rd, Woodstock, CT 06281

Property at 55 Lebanon Hill Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$875,000 Last sold price

4 beds2.5 baths3,114 sq ft

55 Lebanon Hill Rd, Woodstock, CT 06281

Property at 15 Windswept Dr, Woodstock, CT 06281, 3 beds, 2.5 baths

$430,000 Last sold price

3 beds2.5 baths1,560 sq ft

15 Windswept Dr, Woodstock, CT 06281

Property at 31 Deer Meadow Ln, Woodstock, CT 06281, 3 beds, 2.5 baths

$500,000 Last sold price

3 beds2.5 baths2,344 sq ft

31 Deer Meadow Ln, Woodstock, CT 06281

Property at 64 May Brk, Woodstock, CT 06281, 4 beds, 4 baths

$715,000 Last sold price

4 beds4 baths3,795 sq ft

64 May Brk, Woodstock, CT 06281

Property at 50 Crooked Trl, Woodstock, CT 06281, 3 beds, 3 baths

$395,000 Last sold price

3 beds3 baths2,339 sq ft

50 Crooked Trl, Woodstock, CT 06281

Property at 185 Child Hill Rd, Woodstock, CT 06281, 4 beds, 2.5 baths

$571,185 Last sold price

4 beds2.5 baths4,096 sq ft

185 Child Hill Rd, Woodstock, CT 06281

Property at 115 Center Rd, Woodstock, CT 06281, 3 beds, 2.5 baths

$690,500 Last sold price

3 beds2.5 baths2,140 sq ft

115 Center Rd, Woodstock, CT 06281

Property at 78 Laurel Hill Dr, Woodstock Valley, CT 06282, 1 bed, 1 bath

$325,000 Last sold price

1 bed1 bath852 sq ft

78 Laurel Hill Dr, Woodstock Valley, CT 06282

Property at 13 Rapids Trl, Canterbury, CT 06331, 3 beds, 2 baths

$375,000 Last sold price

3 beds2 baths1,674 sq ft

13 Rapids Trl, Canterbury, CT 06331

Property at 16 Gooseneck Hill Rd, Canterbury, CT 06331, 4 beds, 3 baths

$430,900 Last sold price

4 beds3 baths2,441 sq ft

16 Gooseneck Hill Rd, Canterbury, CT 06331

Property at 162 Wright Pond Rd, Canterbury, CT 06331, 2 beds, 1 bath

$300,000 Last sold price

2 beds1 bath1,040 sq ft

162 Wright Pond Rd, Canterbury, CT 06331

Property at 69 Elmdale Rd, Canterbury, CT 06331, 4 beds, 3 baths

$475,000 Last sold price

4 beds3 baths4,300 sq ft

69 Elmdale Rd, Canterbury, CT 06331

Property at 59 Ulasik Rd, Canterbury, CT 06331, 4 beds, 2 baths

$375,000 Last sold price

4 beds2 baths1,524 sq ft

59 Ulasik Rd, Canterbury, CT 06331

Property at 316 Westminster Rd, Canterbury, CT 06331, 3 beds, 1 bath

$365,000 Last sold price

3 beds1 bath1,392 sq ft

316 Westminster Rd, Canterbury, CT 06331

Property at 208 Water St, Canterbury, CT 06331, 3 beds, 2.5 baths

$435,000 Last sold price

3 beds2.5 baths2,210 sq ft

208 Water St, Canterbury, CT 06331

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Recently Sold Homes in Windham County

There are currently 378 recently sold homes for sale in Windham County at a median listing price of $389K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windham County stay on the market for 44 days and receive 1 offers. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 143 homes have been sold in Windham County. In addition to houses in Windham County, there were also 31 condos, 1 townhouse, and 30 multi-family units for sale in Windham County last month. Find your dream home in Windham County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windham County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windham County. If you're looking to sell your home in the Windham County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windham County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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