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1 Winding Trail

Chester, NY 10918

Name: Open House: 1pm-4pm
Start: 2025-06-22T13:00:00
End: 2025-06-22T16:00:00
Location: 1 Winding Trail

3 beds
3 baths
2,040 sqft
~1 acre lot
$269 per sqft
1991 build
– on site

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!

Listing courtesy of ONEKEY / Howard Hanna Rand Realty

Last checked: Checking… • Last updated Jun 13, 2025 •

MLS# 857601 —

Upcoming Open Houses

Sunday, 6/22
1pm-4pm

The Building

Year Built:

1991
Basement:

true
Architectural Style:

Splanch, Split Level
Construction Materials:

Wood Siding
Patio And Porch Features:

Deck, Patio
Building Area Units:

Square Feet
Building Area Total:

2040
Building Area Source:

Public Records
Laundry Features:

In Basement
Attic:

Pull Stairs

Interior

Living Area:

2040
Total Rooms:

8
Interior Features:

Cathedral Ceiling(s), Central Vacuum, Eat-in Kitchen, Formal Dining, His and Hers Closets, Washer/Dryer Hookup
Fireplace Features:

Family Room
Fireplaces Total:

1
Fireplace:

true
Flooring:

Hardwood
Living Area Source:

Public Records
# of Kitchens:

1

Financial & Terms

Lease Considered:

false

The Property

Lot Features:

Level
Lot Size Acres:

1.2
Parcel Number:

332289-005-000-0001-091.100-0000
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size SqFt:

52,272 Sqft
Property Attached:

false
Property Condition:

Actual
Additional Parcels:

false
Waterfront:

false
Horse:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Source:

Municipality
Tax Annual Amount:

12837.49
Tax Lot:

9.11
Included In Taxes:

Trash

Beds

Total Bedrooms:

3

Baths

Full Baths:

2
Half Baths:

1
Total Baths:

3

The Listing

Special Listing Conditions:

None

Heating & Cooling

Heating:

Oil
Cooling:

Central Air

Utilities

Sewer:

Septic Tank
Utilities:

Cable Connected, Electricity Connected, Trash Collection Public
Water Source:

Well
Electric Company:

Orange & Rockland

Appliances

Appliances:

Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Water Softener Owned

Schools

High School:

Monroe Woodbury High School
Elementary School:

North Main Street
High School District:

Monroe Woodbury
Middle School:

Monroe-Woodbury Middle School

The Community

Association:

false
Senior Community:

false
Additional Fees:

No
Pool Private:

false
Spa:

false

Parking

Parking Features:

Driveway
Garage:

true
Garage Spaces:

2
Carport:

false

Monthly cost estimate

Asking price

$549,000

Expense	Monthly cost
Mortgage	$2,939
Taxes	$1,069
Insurance	$150
Utilities	$331 See report
Total	$4,489/mo.^*
	^*This is an estimate

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Sale history

Date	Event	Source	Price	% Change
6/3/25 Jun 3, 2025	Price Changed	ONEKEY	$549,000	-8.3%
5/28/25 May 28, 2025	Listed / Active	ONEKEY	$599,000

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This house located in Chester, NY 10918 is currently for sale for $549,000. 1 Winding Trail is a 2,040 square foot house with 3 beds and 3 baths that has been on Estately for 18 days.

Listing Courtesy of: ONEKEY and Howard Hanna Rand Realty.

IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.

Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

1 Winding Trail

Chester, NY 10918