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Back 39 Winslow Road
Off Market

39 Winslow Road

New Haven County CT 06410

3
2
2
1758 sq. ft.
0.58 ac.
Single-Family
Last sold for $450,000
Joe SnellJoe Snell, last sold this property on 25 June 2026 after 1472 days on market.

Overview

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.

Features

3 bedrooms
2 bathrooms
2 carspaces
2 garage spaces
1758 sq. ft. floor area
0.58 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in New Haven County over the last 12 months, the estimated median property value of 39 Winslow Road is $490k.

Median value
$490k
Estimated value range
$251k - $1.07m
Median days on market
8
Estimated value trend
7%
increase over the last 12 months
Average days on market is based on recent, comparable sales in New Haven County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 39 Winslow Road

2026
Sold
$450,000
25 Jun 2026 by Joe Snell, of Luxe Realty LLC
2021
Sold
$330,000
25 Jun 2021 by Sarah Ashton, of Century 21 AllPoints Realty

Happy sellers in New Haven County

~%

We have insufficient information to provide an overview of customer satisfaction for New Haven County. Viewing the agent profiles, reviews and sales for New Haven County can provide insights for this location.

Local market activity for 3 bedroom single-family properties in New Haven County

In the last 12 months, 110 three-bedroom single-family properties similar to 39 Winslow Road, have been sold.

This represents a 16% decrease in three-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in New Haven County

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Jessica Danard

Jessica Danard is a recommended agent for New Haven County.  They have 3 local sales and collected 1 local review across the last 12 months.

  •   5   (6 reviews)
  •  1 Review in New Haven County
  •  3 Sales in New Haven County
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Ken Demirs

Sellers who recommend Ken Demirs have praised them for being local expert, clear communication, responsive, reliable, dedicated, patient, and supportive

  •   5   (72 reviews)
  •  1 Review in New Haven County
  •  1 Sale in New Haven County
View profile
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Brette Stern

Brette Stern is a recommended agent for New Haven County.  They have 11 local sales across the last 12 months.

  •  11 Sales in New Haven County
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Jason Helton

Jason Helton is a recommended agent for New Haven County.  They have 10 local sales across the last 12 months.

  •  10 Sales in New Haven County
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