Home Homes for Sale Cheshire, CT 39 Winslow Road

39 Winslow Road, Cheshire, CT 06410

Single Family For Sale

$449,900
$256/sqft
39 Winslow Road, Cheshire, CT
Coming Soon Open House 5/9 · 11am–1pm
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3
Bedrooms
2
Bathrooms
1,758
Sq Ft
0.58
Acres
1956
Year Built

About This Home

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.

Listed by Joe Snell (860) 839-8331 with Luxe Realty LLC (860) 839-5035

Listing Snapshot

Price $449,900 Days on Our Site 0 days
Property Tax $7,169/yr Style Cape Cod
Year Built 1956 Total Sq Ft 1,758
Lot Size 0.58 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 2
Total Rooms 9 Half Baths 0

Key Features

Appliances
  • Oven/Range
  • Refrigerator
  • Dishwasher
Outdoor
  • Balcony
  • Deck
Nearby
  • Golf Course
  • Health Club
  • Library
  • Medical Facilities
  • Park
  • Private School(s)

Structure & Parking

Construction Frame
Roof Fiberglass Shingle
Garage Spaces 2
Garage Type Attached Garage

Systems & Utilities

Heat Hot Water
Fuel Oil
Cooling Window Unit
Hot Water Domestic
Water Private Well
Sewer Septic

Schools

Elem Doolittle
Middle Dodd
High Cheshire

Mortgage Calculator

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Est. Monthly Payment
Principal & Interest
Est. Property Tax $597/mo
Est. Home Insurance

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
May 6, 2026 Listed $449,900

Frequently Asked Questions

How much does 39 Winslow Road in Cheshire, CT cost?
This property is listed at $449,900, which works out to $256 per square foot.
How many bedrooms does 39 Winslow Road have?
This home has 3 bedrooms and 2 bathrooms.
What is the square footage of 39 Winslow Road?
The home is 1,758 square feet, situated on 0.58 acres.
When was 39 Winslow Road in Cheshire built?
This property was built in 1956.
Is 39 Winslow Road, Cheshire, CT still available?
The current MLS status of this property is "Coming Soon". Contact RYZE Realty Group for the latest availability.
What school district is 39 Winslow Road, Cheshire in?
This home is served by the Cheshire public school system, with Doolittle as the elementary school and Cheshire as the high school.
How do I schedule a tour of 39 Winslow Road, Cheshire, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Joe Snell · (860) 839-8331

Luxe Realty LLC · (860) 839-5035

MLS# 24168914 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated May 6, 2026 11:27 AM UTC