Recently Sold Homes in Windham County, CT

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SOLD SEP 29, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
This must-see property is a rare blend of modern updates, exceptional outdoor living, and endless entertainment options. Situated on 2.1 fully fenced acres with a cedar split-rail fence lined in animal-safe metal, the home boasts a new roof, all-new Andersen windows and doors, and a newer chimney liner for the fireplace. Comfort is ensured year-round with five mini-split heat and A/C units, a five-year-old pellet stove, and beautiful hardwood floors throughout. The updated kitchen and newly tiled walk-in showers add a fresh, modern touch. Outdoors, the amenities are unmatched. The extra-wide driveway is framed by custom pillars and a retaining wall, leading to a backyard designed for gather

$475,000 Last sold price

3 beds2.5 baths1,613 sq ft

262 Moosup Pond Rd, Moosup, CT 06354

SOLD NOV 21, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
Welcome home to this charming 3-bedroom, 1-bath ranch situated on a desirable corner lot in a peaceful neighborhood. Updated in 2018, this home offers modern comforts with granite countertops in the galley-style kitchen and durable vinyl plank flooring throughout. The bright and inviting layout makes it perfect for first-time buyers or anyone looking to downsize and enjoy the convenience of single-level living. An under-house garage provides extra storage and easy parking. With its move-in ready condition and cozy feel, this home is a wonderful opportunity to start your next chapter in comfort and style.

$322,875 Last sold price

3 beds1 bath960 sq ft

14 Northern Dr, Moosup, CT 06354

SOLD OCT 10, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
Cute Ranch style home with nice vaulted ceilings, large double sliders on the front to let in loads of natural light! 2 bedrooms, 2 bathrooms, 2 very nicely sized walk in closets. Property on Lot Lease through Summertime Properties, LLC $450 PER/Month.

$152,000 Last sold price

2 beds2 baths960 sq ft

20 Connecticut Dr, Plainfield, CT 06374

SOLD SEP 12, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
Enjoy breathtaking scenic views from this stunning ranch-style home offering over 2,200 sq ft of beautifully designed living space. The open floor plan features a fireplaced living room with vaulted ceilings and an abundance of natural light. The spacious eat-in kitchen comes fully applianced with granite countertops-perfect for entertaining or quiet evenings at home. The primary suite is a true retreat, showcasing serene views, a walk-in closet, and a luxurious bathroom with a Jacuzzi tub. Additional highlights include 9-foot ceilings, a convenient laundry room, central air, and an attached garage. The full walk-out basement offers endless possibilities for future expansion or storage. Set

$565,000 Last sold price

3 beds2 baths2,241 sq ft

571 Squaw Rock Rd, Moosup, CT 06354

SOLD SEP 12, 2025

ABOUT THIS HOME
Recently Sold Home in Windham County, CT:
Set on nearly 3 acres in a quiet Killingly location, this charming 4-bedroom, 2-bath mini-farm blends country character with modern upgrades. The home features a spacious layout, mini-split AC in the kitchen, a new well pressure tank (2024), wood stove in the bonus building, and added solar panels for energy efficiency. Outside, enjoy an expansive property ideal for equestrian use-including a 6-stall horse barn with water and electric, tack room, outdoor wash area, and space for over 500+ bales of hay. Additional highlights include gutter guards, updated siding and doors, paddocks, a riding arena with drainage, and multiple outbuildings including sheds and a chicken coop. A separate 500+ sq

$435,000 Last sold price

4 beds2 baths1,068 sq ft

686 Cook Hill Rd, Killingly, CT 06239

Property at 103 Gloria Ave, Killingly, CT 06239, 3 beds, 2 baths

$650,000 Last sold price

3 beds2 baths2,065 sq ft

103 Gloria Ave, Killingly, CT 06239

Property at 214 N Shore Rd, Killingly, CT 06241, 4 beds, 3 baths

$727,500 Last sold price

4 beds3 baths1,728 sq ft

214 N Shore Rd, Killingly, CT 06241

Property at 25 Pine Knolls Dr, Dayville, CT 06241, 3 beds, 2.5 baths

$540,000 Last sold price

3 beds2.5 baths2,104 sq ft

25 Pine Knolls Dr, Dayville, CT 06241

Property at 142 Sunset Dr, Killingly, CT 06239, 3 beds, 2.5 baths

$425,000 Last sold price

3 beds2.5 baths2,024 sq ft

142 Sunset Dr, Killingly, CT 06239

Property at 12 John St, Killingly, CT 06239, 3 beds, 1.5 baths

$359,000 Last sold price

3 beds1.5 baths1,248 sq ft

12 John St, Killingly, CT 06239

Property at 67 Mechanic St, Killingly, CT 06239, 6 beds, 2 baths

$339,000 Last sold price

6 beds2 baths2,410 sq ft

67 Mechanic St, Killingly, CT 06239

Property at 24 Mechanic St, Killingly, CT 06239, 6 beds, 2 baths

$280,000 Last sold price

6 beds2 baths2,206 sq ft

24 Mechanic St, Killingly, CT 06239

Property at 12 Saint James Row, Killingly, CT 06239, 6 beds, 2 baths

$320,000 Last sold price

6 beds2 baths2,392 sq ft

12 Saint James Row, Killingly, CT 06239

Property at 27 Hawkins St, Killingly, CT 06239, 4 beds, 3 baths

$412,000 Last sold price

4 beds3 baths3,870 sq ft

27 Hawkins St, Killingly, CT 06239

Property at 280 Cook Hill Rd, Killingly, CT 06239, 3 beds, 1.5 baths

$249,900 Last sold price

3 beds1.5 baths1,344 sq ft

280 Cook Hill Rd, Killingly, CT 06239

Property at 68 Bailey Hill Rd, Killingly, CT 06239, 4 beds, 2 baths

$450,000 Last sold price

4 beds2 baths2,304 sq ft

68 Bailey Hill Rd, Killingly, CT 06239

Property at 45 Carter St, Killingly, CT 06239, 3 beds, 1 bath

$222,000 Last sold price

3 beds1 bath978 sq ft

45 Carter St, Killingly, CT 06239

Property at 36 Carter St, Killingly, CT 06239, 7 beds, 3 baths

$390,000 Last sold price

7 beds3 baths2,782 sq ft

36 Carter St, Killingly, CT 06239

Property at 26 Hillside Vw, Killingly, CT 06239, 4 beds, 1.5 baths

$367,000 Last sold price

4 beds1.5 baths1,348 sq ft

26 Hillside Vw, Killingly, CT 06239

Property at 288 Margaret Henry Rd, Killingly, CT 06239, 3 beds, 1 bath

$192,000 Last sold price

3 beds1 bath1,104 sq ft

288 Margaret Henry Rd, Killingly, CT 06239

Property at 162 Sawmill Hill Rd, Killingly, CT 06239, 4 beds, 2.5 baths

$556,000 Last sold price

4 beds2.5 baths2,376 sq ft

162 Sawmill Hill Rd, Killingly, CT 06239

Property at 193 E Franklin St, Killingly, CT 06239, 4 beds, 1.5 baths

$150,000 Last sold price

4 beds1.5 baths1,332 sq ft

193 E Franklin St, Killingly, CT 06239

Property at 12 Waterman, Killingly, CT 06239, 4 beds, 3 baths

$469,900 Last sold price

4 beds3 baths3,299 sq ft

12 Waterman, Killingly, CT 06239

Property at 33 Soap St, Dayville, CT 06241, 3 beds, 1 bath

$278,000 Last sold price

3 beds1 bath1,104 sq ft

33 Soap St, Dayville, CT 06241

Property at 20 Pineville Rd, Dayville, CT 06241, 3 beds, 2.5 baths

$360,000 Last sold price

3 beds2.5 baths1,985 sq ft

20 Pineville Rd, Dayville, CT 06241

Property at 183 Putnam Pike, Dayville, CT 06241, 7 beds, 3 baths

$480,000 Last sold price

7 beds3 baths3,210 sq ft

183 Putnam Pike, Dayville, CT 06241

Property at 114 Breakneck Hill Rd, Dayville, CT 06241, 3 beds, 1 bath

$430,000 Last sold price

3 beds1 bath1,560 sq ft

114 Breakneck Hill Rd, Dayville, CT 06241

Property at 50 Ware Rd, Dayville, CT 06241, 3 beds, 1.5 baths

$410,000 Last sold price

3 beds1.5 baths1,683 sq ft

50 Ware Rd, Dayville, CT 06241

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Unknown Last sold price

3 beds1 bath1,460 sq ft

282 Bear Hill Rd, Killingly, CT 06241

Property at 11 Conrad Park, Dayville, CT 06241, 2 beds, 1 bath

$50,000 Last sold price

2 beds1 bath752 sq ft

11 Conrad Park, Dayville, CT 06241

Property at 16 Conrads Park, Dayville, CT 06241, 1 bed, 1 bath

$52,000 Last sold price

1 bed1 bath550 sq ft

16 Conrads Park, Dayville, CT 06241

Property at 24 Blumenthal Dr, Dayville, CT 06241, 3 beds, 1.5 baths

$385,000 Last sold price

3 beds1.5 baths1,248 sq ft

24 Blumenthal Dr, Dayville, CT 06241

Property at 20 Pequot Cir, Killingly, CT 06239, 4 beds, 2 baths

$367,000 Last sold price

4 beds2 baths1,084 sq ft

20 Pequot Cir, Killingly, CT 06239

Property at 778 Cook Hill Rd, Killingly, CT 06239, 3 beds, 1 bath

$375,000 Last sold price

3 beds1 bath1,084 sq ft

778 Cook Hill Rd, Killingly, CT 06239

Property at 117 State Ave, Killingly, CT 06241, 3 beds, 1 bath

$126,500 Last sold price

3 beds1 bath1,068 sq ft

117 State Ave, Killingly, CT 06241

Property at 29 Birchwood Dr, Dayville, CT 06241, 3 beds, 2 baths

$415,000 Last sold price

3 beds2 baths1,489 sq ft

29 Birchwood Dr, Dayville, CT 06241

Property at 987 Upper Maple St, Dayville, CT 06241, 3 beds, 1.5 baths

$275,000 Last sold price

3 beds1.5 baths1,258 sq ft

987 Upper Maple St, Dayville, CT 06241

Property at 23 Birchwood Dr, Dayville, CT 06241, 3 beds, 3.5 baths

$440,000 Last sold price

3 beds3.5 baths2,646 sq ft

23 Birchwood Dr, Dayville, CT 06241

Property at 51 Courtney Ln, Dayville, CT 06241, 3 beds, 1 bath

$315,000 Last sold price

3 beds1 bath960 sq ft

51 Courtney Ln, Dayville, CT 06241

Property at 1897 Upper Maple St, Dayville, CT 06241, 4 beds, 2 baths

$360,000 Last sold price

4 beds2 baths1,485 sq ft

1897 Upper Maple St, Dayville, CT 06241

Property at 21 Prince St, Killingly, CT 06239, 4 beds, 2 baths

$322,000 Last sold price

4 beds2 baths1,974 sq ft

21 Prince St, Killingly, CT 06239

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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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