39 Winslow Road Cheshire, CT $ 449,900
39 Winslow Road
$ 449,900
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39 Winslow Road

Cheshire, CT, 06410
$ 449,900
Bedrooms3 Baths2.0 Sq 1,758

Monthly Estimate*

$ 2,770

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Single Family Home for sale in Cheshire, CT

for $449,900 with 3 bedrooms and 2 full baths. This 1,758 square foot home was built in 1956 on a lot size of 0.58.

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.

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Single Family Contingent

Price

$ 449,900

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 6,322

Style

Lot Size

0.58

Year Built

1956

Town/City

Cheshire

MLS | Web ID

24168914

Features
General
Zoning R-20
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract
Acres 0.58
Directions GPS Friendly
High School Cheshire
City Cheshire
Elementary School Doolittle
Sq Ft Total 1758
DOM 5
Year Built 1956
Style Cape Cod
Year Built Source Public Records
Energy Features Thermopane Windows
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Interior
Cooling System Window Unit
Total Rooms 9
Basement Description Full Partially Finished
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Exterior
Water Source Private Well
Lot Description Lightly Wooded
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* Excluded Features
List By
Joe Snell

Listing Agent

Luxe Realty Llc

Broker

joesnellrealestate@gmail.com

Email

Affordability Calculator

$3,297
Per Month
84%
16%
0%
Monthly Principal & Interest
$2,770
Monthly Property Taxes
$527
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
900809 Elementary School
1232875 Middle School
Cheshire High School High School
Pricing History
DatePricePrice ChangeDescription
5/6/2026$449,900 Listed Price

Map


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39 Winslow Road, Cheshire, CT, 06410 is a Single Family Home for sale at $449,900 with 1,758 sqft and a lot size of 0.58. 39 Winslow Road has 3 bedrooms, 2.0 baths, and was built in 1956. The property's zip code is 06410 which is in Cheshire, CT