Recently Sold Homes in Winchester, CT

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SOLD OCT 22, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, CT:
Discover the potential in this raised ranch located in beautiful Winsted, CT! Featuring 3 bedrooms and 1.5 bathrooms, this home offers a functional layout and a great opportunity to bring your vision to life. An attached two-car garage adds everyday convenience and plenty of storage. Set on a nice lot, the property is close to town amenities, schools, and outdoor recreation that make Winsted such a great place to call home. With the right updates, it's an excellent option for buyers looking to personalize their space or investors seeking a solid opportunity. Bring your ideas and make this house your own! BEST AND FINAL OFFERS DUE THURSDAY 9/11/25 BY 8 PM - DECISION WILL BE MADE ON FRIDAY 9/

$240,000 Last sold price

3 beds1.5 baths1,056 sq ft

210 Walnut St, Winsted, CT 06098

SOLD AUG 13, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, CT:
Located just a short stroll from Holland Beach and only a 3-minute drive to the public boat launch, this charming Colonial offers the perfect blend of comfort, convenience, and year-round recreation. Nestled on a level corner lot in a well-established neighborhood, this home invites you to enjoy all the amenities of Connecticut's second-largest lake - from kayaking and boating to lakeside walks and summer swims. Step inside and you'll find a classic 4-bedroom, 2.5-bath layout that suits both everyday living and entertaining. The main floor features a spacious living room, a cozy family room with a wood-burning fireplace, and a sunny eat-in kitchen ready for your personal touch. Upstairs, yo

$425,000 Last sold price

4 beds2.5 baths2,086 sq ft

50 Lakeview Rd, Winsted, CT 06098

SOLD SEP 30, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, CT:
First-time homebuyers and downsizers take notice!. Some improvements have been done in this cozy Ranch boasting a metal roof and well-maintained mechanics. What an incredible opportunity to pick your colors and let the cosmetic upgrades take shape. A 1-car detached garage and space for a garden or outbuilding are possible on this 2.5-acre country parcel. An As-Is sale is preferred.

$320,000 Last sold price

3 beds1 bath960 sq ft

128 Danbury Quarter Rd, Winsted, CT 06098

SOLD OCT 17, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, CT:
Welcome to 115 Laurel Way! Tucked away in a peaceful neighborhood surrounded by nature, this charming well maintained 1-bedroom, 1-bathroom home offers the perfect blend of comfort and serenity. Set on just over half an acre, the property provides ample space for outdoor living. Imagine relaxing by a cozy fire pit, enjoying warm evenings under the stars, or simply soaking in the natural beauty all around. Inside, you'll find beautiful hardwood floors throughout, complementing the cozy layout. With central air and natural gas for heating, comfort is guaranteed year-round. The shed is a standout feature, offering electricity and a mini-split unit for cooling. This versatile space can serve as

$261,000 Last sold price

1 bed1 bath604 sq ft

115 Laurel Way, Winsted, CT 06098

SOLD SEP 3, 2025

ABOUT THIS HOME
Recently Sold Home in Winchester, CT:
Completely Updated Raised Ranch on a Peaceful, Secluded Lot in Winsted! Escape the noise and discover this beautifully updated Raised Ranch, set on a private 0.78-acre lot in the quiet town of Winsted. Surrounded by nature and tucked away in a serene setting, this home offers the perfect balance of indoor comfort and outdoor living. Inside, you'll love the bright, open layout and thoughtful updates throughout - including a fully remodeled kitchen and bathrooms, all new flooring, new plumbing, new windows, and more. The sunny living room flows seamlessly into the eat-in kitchen, which features modern finishes and ample space to gather. Just off the kitchen, a bonus room with sliders is perfe

$320,000 Last sold price

3 beds2 baths1,616 sq ft

107 Old North Rd, Winsted, CT 06098

Property at 141 Maloney Ct, Winsted, CT 06098, 4 beds, 2.5 baths

$320,000 Last sold price

4 beds2.5 baths1,752 sq ft

141 Maloney Ct, Winsted, CT 06098

Property at 226 E Wakefield Blvd, Winsted, CT 06098, 3 beds, 1.5 baths

$380,000 Last sold price

3 beds1.5 baths1,196 sq ft

226 E Wakefield Blvd, Winsted, CT 06098

Property at 415 N Main St, Winsted, CT 06098, 3 beds, 1 bath

$172,500 Last sold price

3 beds1 bath1,446 sq ft

415 N Main St, Winsted, CT 06098

Property at 144 Marshall St, Winsted, CT 06098, 3 beds, 2 baths

$540,000 Last sold price

3 beds2 baths1,744 sq ft

144 Marshall St, Winsted, CT 06098

Property at 39 Colony Dr, Winsted, CT 06098, 3 beds, 1 bath

$279,900 Last sold price

3 beds1 bath1,183 sq ft

39 Colony Dr, Winsted, CT 06098

Property at 538 Wheelers Pt, Winsted, CT 06098, 4 beds, 3 baths

$1,500,000 Last sold price

4 beds3 baths2,496 sq ft

538 Wheelers Pt, Winsted, CT 06098

Property at 111 Torringford St Apt 25, Winsted, CT 06098, 2 beds, 2 baths

$190,000 Last sold price

2 beds2 baths1,156 sq ft

111 Torringford St Apt 25, Winsted, CT 06098

Property at 22 Stanton Ave, Winsted, CT 06098, 3 beds, 1 bath

$270,000 Last sold price

3 beds1 bath1,058 sq ft

22 Stanton Ave, Winsted, CT 06098

Property at 174 Wallens St Apt D3, Winsted, CT 06098, 2 beds, 2 baths

$260,000 Last sold price

2 beds2 baths1,352 sq ft

174 Wallens St Apt D3, Winsted, CT 06098

Property at 1 Hamill Dr, Winsted, CT 06098, 3 beds, 1.5 baths

$180,000 Last sold price

3 beds1.5 baths976 sq ft

1 Hamill Dr, Winsted, CT 06098

Property at 29 Walnut St, Winsted, CT 06098, 3 beds, 4 baths

$321,000 Last sold price

3 beds4 baths2,623 sq ft

29 Walnut St, Winsted, CT 06098

Property at 409 N Main St, Winsted, CT 06098, 5 beds, 2 baths

$388,000 Last sold price

5 beds2 baths2,403 sq ft

409 N Main St, Winsted, CT 06098

Property at 50 Manchester Hts, Winsted, CT 06098, 3 beds, 1 bath

$330,000 Last sold price

3 beds1 bath1,287 sq ft

50 Manchester Hts, Winsted, CT 06098

Property at 279 Pratt St, Winsted, CT 06098, 4 beds, 1 bath

$290,000 Last sold price

4 beds1 bath1,978 sq ft

279 Pratt St, Winsted, CT 06098

Property at 12 Cherry St, Winsted, CT 06098, 4 beds, 1 bath

$277,000 Last sold price

4 beds1 bath1,492 sq ft

12 Cherry St, Winsted, CT 06098

Property at 30 Mountain Ave, Winsted, CT 06098, 5 beds, 1.5 baths

$178,500 Last sold price

5 beds1.5 baths2,310 sq ft

30 Mountain Ave, Winsted, CT 06098

Property at 435/434 W Wakefield Blvd, Winsted, CT 06098, 8 beds, 4.5 baths

$1,215,000 Last sold price

8 beds4.5 baths5,231 sq ft

435/434 W Wakefield Blvd, Winsted, CT 06098

Property at 42 Maloney Ct, Winsted, CT 06098, 3 beds, 1 bath

$240,000 Last sold price

3 beds1 bath1,008 sq ft

42 Maloney Ct, Winsted, CT 06098

Property at 17 Woodland Ave, Winsted, CT 06098, 3 beds, 2 baths

$410,000 Last sold price

3 beds2 baths2,105 sq ft

17 Woodland Ave, Winsted, CT 06098

Property at 17 Adams St, Winsted, CT 06098, 3 beds, 1.5 baths

$315,000 Last sold price

3 beds1.5 baths1,747 sq ft

17 Adams St, Winsted, CT 06098

Property at 233 Grantville Rd, Winsted, CT 06098, 1 bed, 1 bath

$250,000 Last sold price

1 bed1 bath1,168 sq ft

233 Grantville Rd, Winsted, CT 06098

Property at 160 Walnut St, Winsted, CT 06098, 3 beds, 1.5 baths

$320,000 Last sold price

3 beds1.5 baths1,674 sq ft

160 Walnut St, Winsted, CT 06098

Property at 343 W Wakefield Blvd, Winsted, CT 06098, 2 beds, 1 bath

$236,434 Last sold price

2 beds1 bath674 sq ft

343 W Wakefield Blvd, Winsted, CT 06098

Property at 102 Hollow Hill Rd, Winsted, CT 06098, 3 beds, 2.5 baths

$639,000 Last sold price

3 beds2.5 baths2,692 sq ft

102 Hollow Hill Rd, Winsted, CT 06098

Property at 267 Rockwell St, Winsted, CT 06098, 4 beds, 3 baths

$302,500 Last sold price

4 beds3 baths2,861 sq ft

267 Rockwell St, Winsted, CT 06098

Property at 41 Lovely St, Winsted, CT 06098, 5 beds, 2 baths

$383,000 Last sold price

5 beds2 baths2,531 sq ft

41 Lovely St, Winsted, CT 06098

Property at 36 Whiting St, Winsted, CT 06098, 3 beds, 2.5 baths

$310,000 Last sold price

3 beds2.5 baths1,608 sq ft

36 Whiting St, Winsted, CT 06098

Property at 179 Gilbert Ave, Winsted, CT 06098, 3 beds, 2 baths

$275,000 Last sold price

3 beds2 baths1,744 sq ft

179 Gilbert Ave, Winsted, CT 06098

Property at 266 Perch Rock Trl, Winsted, CT 06098, 3 beds, 2 baths

$800,000 Last sold price

3 beds2 baths1,488 sq ft

266 Perch Rock Trl, Winsted, CT 06098

Property at 920 Main St, Winsted, CT 06098, 6 beds, 4 baths

$275,000 Last sold price

6 beds4 baths4,635 sq ft

920 Main St, Winsted, CT 06098

Property at 711 W Wakefield Blvd, Winsted, CT 06098

$281,000 Last sold price

— beds— baths1,015 sq ft

711 W Wakefield Blvd, Winsted, CT 06098

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Recently Sold Homes in Winchester

There are currently 36 recently sold homes for sale in Winchester at a median listing price of $315K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 54 days and receive 1 offers. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 15 homes have been sold in Winchester. In addition to houses in Winchester, there were also 4 condos, 0 townhouses, and 7 multi-family units for sale in Winchester last month. Find your dream home in Winchester 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 Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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