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.
Under contract
$449,900
39 Winslow Road, Cheshire, CT 06410
3beds
1,758sqft
Single Family Residence
Built in 1956
0.58 Acres Lot
$473,800 Zestimate®
$256/sqft
$-- HOA
What's special
- 45 days |
- 142 |
- 8 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Joe R. Snell (860)839-8331,
Luxe Realty LLC 860-839-5035
Source: Smart MLS,MLS#: 24168914
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Laundry, Sitting Room, Workshop
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 & HOA
Community
- Features: Golf, Health Club, Library, Medical Facilities, Park, Private School(s)
HOA
- Has HOA: No
Location
- Region: Cheshire
Financial & listing details
- Price per square foot: $256/sqft
- Tax assessed value: $212,590
- Annual tax amount: $6,322
- Date on market: 5/6/2026
Estimated market value
$473,800
$450,000 - $497,000
$3,018/mo
Price history
| Date | Event | Price |
|---|---|---|
| 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 | $109,200 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
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.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- New Haven County
- Cheshire
- 06410
- 39 Winslow Road
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