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$449,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,758 Sq. Ft.
  • 2 Car Garage
  • Updated 10 hours ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 5/9 11:00 AM - 1:00 PM

39 Winslow Road,Cheshire, CT 06410

39 Winslow RoadCheshireCT06410

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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.

Full Property Details for 39 Winslow Rd

General

  • Price: $449,900
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24168914
  • Updated: Today (5/7/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 9
  • Rooms/Areas: Foyer, Laundry Room, Sitting Room, Workshop
  • Appliances: Oven/Range, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Full Bath: Main

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom, Main
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper

Other Rooms

  • Living Room: Living Room - Bay/Bow Window, Main
  • Family Room: Family Room - Ceiling Fan, Upper
  • Kitchen: Kitchen - Remodeled, Tile Floor, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Office: Office - Balcony/Deck, Upper
  • Laundry: Lower Level

Exterior

  • Exterior Features: Balcony, Deck

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: New Haven
  • Driving Directions: GPS Friendly

School Information

  • Elementary School: Doolittle
  • Middle School: Dodd
  • High School: Cheshire

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding, Wood
  • Basement Desc.: Full, Partially Finished
  • Roof: Fiberglass Shingle
  • Square Feet: 1,758
  • Above Ground: 1,758 Sq. Ft.
  • Year Built: 1956

Lot Features

  • Lot Size (Acres): 0.58
  • Zoning: R-20
  • Lot Description: Lightly Wooded

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Assessment Amount: $212,590
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1079181

Listed by Luxe Realty LLC, Joe Snell

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Listing agent

— 39 Winslow Rd —

  • Joe Snell

    Luxe Realty LLC

Agent Contact: (860) 839-8331 Office Contact: (860) 839-5035

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 39 Winslow Rd

School District:Cheshire School District
NameGradesDistance
Doolittle School
735 Cornwall Avenue, Cheshire, CT 06410
1-62.9 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-82.7 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-123.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 39 Winslow Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/07/2026
Listed
$449,900
36.33%
MLS
6/25/2021
Sold
$330,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 39 Winslow Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,322
8%
$212,590
—
2023
$5,838
7%
$212,590
37%
2023
$5,442
2%
$155,100
—
2022
$5,323
2%
$155,100
—
2021
$5,230
2%
$155,100
—
2020
$5,152
—
$155,100
—
2019
$5,152
3%
$155,100
1%
2018
$5,022
2%
$153,950
—
2017
$4,917
2%
$153,950
—
2016
$4,802
2%
$153,950
—
2015
$4,725
1%
$153,950
—
2014
$4,657
-2%
$153,950
-11%
2011
$4,768
—
$172,760
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 39 Winslow Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Luxe Realty LLC, Joe Snell

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39 Winslow Road, Cheshire, CT 06410 (MLS# 24168914) is a Single Family property with 3 bedrooms and 2 full bathrooms. 39 Winslow Road is currently listed for $449,900 and was received on May 07, 2026. Want to learn more about 39 Winslow Road? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

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