Sold
Last Sold Price
3 beds1,758 sqft$256/sqft
39 Winslow Rd, Cheshire, CT 06410
Single FamilyProperty Type
0.58 acresLot Size
1956Year Built
$256/sq ftPrice per sq ft
2 carsParking Spaces

Description

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...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 R Snell 860.839.8331 joesnellrealestate@gmail.com • Luxe Realty LLC
Listing closed: 06/25/2026 12:00 AM • Source: SMARTMLS, MLS#: 24168914

Location

Listing Courtesy of Luxe Realty LLC, Joe R Snell

Sold By KW Legacy Partners, Simonne E Corriveau

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Payment Calculator

$2,814 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,287

Property Taxes

$527

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 39 Winslow Road

Property Details
  • Taxes: $6,322 / year
  • MLS Type: Residential
  • Basement Description: Full, Partially Finished
  • Direct Waterfront: No
  • Expected Active Date: 05-07-2026
  • Garages Number: 2
  • Style: Cape Cod
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
  • Expected On Market Date: 05-07-2026
Building Information
  • Year Built: 1956
  • Lot Size: 0.58 AC / 25,264 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Doolittle
  • High School: Cheshire
  • Latitude: 41.53871
  • Longitude: -72.94147
  • Middle Jr High School: Dodd
  • Neighborhood Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Private School(s)
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $6,322
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Deck
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Dishwasher
  • Cooling System: Window Unit
  • Heat Type: Hot Water
  • Attic YN: No
  • Fireplaces Total: 0
  • Laundry Room Info: Lower Level
  • Rooms Additional: Foyer, Laundry Room, Sitting Room, Workshop
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Remodeled,Tile Floor
  • Room Level: Main
  • Room Type: Kitchen
Room 2
  • Room Entry Order: 10
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 2
  • Room Features: Bay/Bow Window
  • Room Level: Main
  • Room Type: Living Room
Room 4
  • Room Entry Order: 3
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 5
  • Listing Key: 4FFA458E3BC27E91E063E201100A4C19
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 6
  • Room Entry Order: 5
  • Room Level: Main
  • Room Type: Full Bath
Room 7
  • Room Entry Order: 6
  • Room Features: Ceiling Fan
  • Room Level: Upper
  • Room Type: Family Room
Room 8
  • Room Entry Order: 7
  • Room Features: Balcony/Deck
  • Room Level: Upper
  • Room Type: Office
Room 9
  • Listing Key: 4FFA458E3BC27E91E063E201100A4C19
  • Room Entry Order: 8
  • Room Level: Upper
  • Room Type: Full Bath
Room 10
  • Room Entry Order: 9
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding, Wood
  • Foundation Type: Block, Concrete
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Roof: Fiberglass Shingle
  • Year Built: 1956
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1758
Lot Information
  • Lot Description: Lightly Wooded
  • Parcel Number: 1079181
  • Sq Ft Est Heated Above Grade: 1758.0
  • Sq Ft Total: 1758.0
  • Zoning: R-20
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 39 Winslow Road

DateEvent & SourcePriceAppreciation
Jun 24, 2026

Closed (Public Record)

Public Record #1944523965

$464,235

+7.1% / yr

Jun 25, 2021

Closed (Public Record)

Public Record #1465584491

$330,000
DateEvent & SourcePrice
06/24/2026

Closed (Public Record)

Public Record #1944523965

$464,235

+7.1% / yr

06/25/2021

Closed (Public Record)

Public Record #1465584491

$330,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 39 Winslow Road

Taxable ValueLand$51,030Additions$161,560Total$212,590
Tax Record2025$6,322 ($527 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,758 SqFtAbove Grade Finished SqFt1,758 SqFtUnfinished Basement SqFt832 SqFtStories1Lot Size25,265 SqFtStyleSingle Family ResidenceYear Built1956Year Renovated1996ZoningR-20CountyNAUGATUCK VALLEYAPNCSHR M:24 B:54 L:

Schools near 39 Winslow Road

This home is within Cheshire School District.
Rating
School
Type
Grades
Distance
Public - K to 6
Public - 7 to 8
Public - 9 to 12
Rating
School
Distance
Doolittle School
PublicK to 6

Dodd Middle School
Public7 to 8

Cheshire High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Luxe Realty LLC, Joe R Snell

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.