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Back 1 Winding Trail
Off Market

1 Winding Trail

Chester NY 10918

3
3
2
2040 sq. ft.
52272 sq. ft.
Single-Family
Last sold for $540,000
Ann GlynnAnn Glynn, last sold this property on 28 August 2025 after 91 days on market.

Overview

Welcome to 1 Winding Trail in the Town of Chester. This well-maintained home sits on a picturesque 1.2 acre lot located in the desirable Bull Mill Road area with Monroe-Woodbury Schools. With an easy flow, the home’s first floor boasts a spacious family room with fireplace, an office/den and a half bath. Walk-up a few steps into the large living room and a formal dining room both of which contain hardwood floors and vaulted ceilings. There is a large sized eat-in kitchen accessed from the dining or living room. The slider off of the dining room opens to the 12x12 deck, which overlooks the private backyard and leads down onto a 1,100 sqft paver patio with a slider access into the family room. Up a few more stairs from the living room is the master bedroom with an ensuite bathroom. There are 2 additional bedrooms and another full bathroom. Hardwood floors throughout the entire upstairs. The basement level has laundry and generous storage space. There is an oversized free flowing 2 car garage. If you are looking for a year-round residence, or weekend retreat, Chester, NY is where you can enjoy the tranquility of the Hudson Valley’s suburban feel and the convenience to everything. Great commuter location, minutes to bus/train to NYC, shopping at Woodbury Commons, West Point, restaurants, and wonderful parks, recreation, and hiking trails. With inventory still so low, don't hesitate because this amazing property will not last!

Features

3 bedrooms
3 bathrooms
2 carspaces
2 garage spaces
2040 sq. ft. floor area
52272 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Chester over the last 12 months, the estimated median property value of 1 Winding Trail is $460k.

Median value
$460k
Estimated value range
$138k - $765k
Median days on market
29
Estimated value trend
-12%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Chester. 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 1 Winding Trail

2025
Sold
$540,000
28 Aug 2025 by Ann Glynn, of Howard Hanna Rand Realty

Happy sellers in Chester

90%
90% of sellers in Chester reported that their sale price either exceeded or met their price expectations.

Chester stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 4 reviews in Chester over the last 12 months.

Local market activity for 3 bedroom single-family properties in Chester

In the last 12 months, 14 three-bedroom single-family properties similar to 1 Winding Trail, have been sold.

This represents a 66% increase 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 Chester

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Claude Brischoux

Claude Brischoux is a recommended agent for Chester.  They have 2 local sales and collected 2 local reviews across the last 12 months.

  •   4.7   (3 reviews)
  •  2 Reviews in Chester
  •  2 Sales in Chester
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Claudia Lepore

Claudia Lepore is a recommended agent for Chester.  They have 2 local sales and collected 1 local review across the last 12 months.

  •   5   (5 reviews)
  •  1 Review in Chester
  •  2 Sales in Chester
View profile
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Kichka Pascaru

Sellers who recommend Kichka Pascaru have praised them for being local expert, responsive, patient, supportive, clear communication, detail-oriented, and reliable

  •   5   (49 reviews)
  •  1 Review in Chester
  •  1 Sale in Chester
View profile
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Shawn Larry

Shawn Larry is a recommended agent for Chester.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (1 review)
  •  1 Review in Chester
  •  1 Sale in Chester
View profile
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