Welcome to 39 Winslow Rd in Cheshire-a beautifully updated Cape set in one of the town's most desirable locations. This 3-bedroom, 2 full bath home blends charm, functionality, and modern updates in all the right ways. Step inside to a spacious foyer that doubles as a cozy sitting area, complete with a built-in coffee bar-perfect for starting or ending your day. The fully renovated kitchen features stainless steel appliances, ample cabinetry, and generous counter space, flowing seamlessly into a formal dining room with refinished hardwood floors. Across the way, the sun-filled living room showcases a stunning bay window that floods the space with natural light. The main level also offers a versatile bedroom and a beautifully remodeled full bath-ideal for guests or a private home office. Upstairs, you'll find two additional bedrooms along with a large family room anchored by a wood stove, creating the perfect setting for cozy winter nights. An additional office space in the rear adds even more flexibility. Outside, enjoy a professionally landscaped front yard bursting with seasonal color, while the backyard offers a peaceful natural setting overlooking a stream. Additional highlights include a partially finished basement, updated roof, vinyl siding, thermopane windows, and ceiling fans in every bedroom. Truly move-in ready-just unpack and enjoy.
Sold for $450,000
$450,000
39 Winslow Road, Cheshire, CT 06410
3beds
1,758sqft
Single Family Residence
Built in 1956
0.58 Acres Lot
$450,100 Zestimate®
$256/sqft
$3,128 Estimated rent
Home value
$450,100
$410,000 - $495,000
$3,128/mo
Zestimate® history
Owner options
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$3,209/mo
Est. payment
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$3,209/mo
Est. payment
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Zillow last checked:
Listing updated:
Listed by:
Joe R. Snell (860)839-8331,
Luxe Realty LLC 860-839-5035
Bought with:
Simonne E. Corriveau, RES.0767192
KW Legacy Partners
Source: Smart MLS,MLS#: 24168914
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: Main
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bathroom
- Level: Main
Bathroom
- Level: Upper
Dining room
- Features: Hardwood Floor
- Level: Main
Family room
- Features: Ceiling Fan(s)
- Level: Upper
Kitchen
- Features: Remodeled, Tile Floor
- Level: Main
Living room
- Features: Bay/Bow Window
- Level: Main
Office
- Features: Balcony/Deck
- Level: Upper
Heating
- Hot Water, Oil
Cooling
- Window Unit(s)
Appliances
- Included: Oven/Range, Refrigerator, Dishwasher, Water Heater
- Laundry: Lower Level
Features
- Entrance Foyer
- Windows: Thermopane Windows
- Basement: Full,Partially Finished
- Attic: None
- Has fireplace: No
Interior area
- Total structure area: 1,758
- Total interior livable area: 1,758 sqft
- Finished area above ground: 1,758
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Patio & porch: Deck
- Exterior features: Balcony
Lot
- Size: 0.58 Acres
- Features: Few Trees
Details
- Parcel number: 1079181
- Zoning: R-20
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Vinyl Siding, Wood Siding
- Foundation: Block, Concrete Perimeter
- Roof: Fiberglass
Condition
- New construction: No
- Year built: 1956
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Green energy
- Energy efficient items: Windows
Community & neighborhood
Community
- Community features: Golf, Health Club, Library, Medical Facilities, Park, Private School(s)
Location
- Region: Cheshire
Price history
| Date | Event | Price |
|---|---|---|
| 6/25/2026 | Sold | $450,000+0%$256/sqft |
Source:  Smart MLS #24168914 Report a problem | ||
| 5/13/2026 | Pending sale | $449,900$256/sqft |
Source: Smart MLS #24168914 Report a problem | ||
| 5/7/2026 | Listed for sale | $449,900+15.4%$256/sqft |
Source: Smart MLS #24168914 Report a problem | ||
| 6/28/2022 | Listing removed | -- |
Source: Smart MLS #170499663 Report a problem | ||
| 6/14/2022 | Listed for sale | $389,900+18.2%$222/sqft |
Source: Smart MLS #170499663 Report a problem | ||
| 6/25/2021 | Sold | $330,000+10%$188/sqft |
Source: Smart MLS #170397871 Report a problem | ||
| 5/11/2021 | Contingent | $299,900$171/sqft |
Source: Smart MLS #170397871 Report a problem | ||
| 5/8/2021 | Listed for sale | $299,900$171/sqft |
Source: Smart MLS #170397871 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,322 +8.3% | $212,590 |
| 2024 | $5,838 +7.3% | $212,590 +37.1% |
| 2023 | $5,442 +2.2% | $155,100 |
| 2022 | $5,323 +1.8% | $155,100 |
| 2021 | $5,230 +1% | $155,100 |
| 2020 | $5,179 +0.5% | $155,100 |
| 2019 | $5,152 +2.6% | $155,100 +0.7% |
| 2018 | $5,022 +2.1% | $153,950 |
| 2017 | $4,917 +3.4% | $153,950 |
| 2016 | $4,755 +0.6% | $153,950 |
| 2015 | $4,725 +1.5% | $153,950 |
| 2014 | $4,657 -2.3% | $153,950 -10.9% |
| 2013 | $4,768 +1.4% | $172,760 |
| 2012 | $4,704 +1.4% | $172,760 |
| 2011 | $4,639 +1.3% | $172,760 |
| 2010 | $4,578 +1.7% | $172,760 |
| 2009 | $4,500 +12.6% | $172,760 +21.2% |
| 2008 | $3,997 +1.6% | $142,510 |
| 2007 | $3,933 +1.7% | $142,510 |
| 2006 | $3,869 +1.9% | $142,510 |
| 2005 | $3,798 +15.8% | $142,510 +40.1% |
| 2002 | $3,280 +8% | $101,720 -6.8% |
| 1997 | $3,036 | $109,200 |
Find assessor info on the county website
Neighborhood: 06410
Nearby schools
GreatSchools rating
- 9/10Doolittle SchoolGrades: K-6Distance: 2.9 mi
- 8/10Dodd Middle SchoolGrades: 7-8Distance: 2.7 mi
- 9/10Cheshire High SchoolGrades: 9-12Distance: 3.8 mi
Schools provided by the listing agent
- Elementary: Doolittle
- Middle: Dodd
- High: Cheshire
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- New Haven County
- Cheshire
- 06410
- 39 Winslow Road
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