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Ann Glynn
Licensed RE Salesperson
REALTOR®
Cell: (516) 972-5677

1 Winding Trail , Chester, NY 10918

Sold: 540000
Sold on: Aug 28th, 2025
$ Per Square Foot: $265
Sold: 540000
Sold on: Aug 28th, 2025
$ Per Square Foot: $265
BEDS3 BATHS2 full 1 partial SQUARE FEET2,040 MLS#857601
STATUSClosed REPRESENTEDSeller PROPERTY TYPEResidential - Single Family SCHOOLMonroe-Woodbury


Property Description

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 homes 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 Valleys 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, dont hesitate because this amazing property will not last!

Property Features

Basement: Partial, Unfinished
Basement: Yes
Cooling: Central Air
Days on Market: 92
Fireplaces: 1
Garage: 2
Heating: Oil
Lot Size: 1.20 Acres
Taxes: $12,837
Year Built: 1991

Amenities

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

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Water Softener Owned
Attic: Pull Stairs
Building Area Total: 2040
Exterior: Wood Siding
Fireplace Features: Family Room
Fireplace Y/N: Yes
Flooring: Hardwood
Formal Dining: Yes
GarageY/N: Yes
Included In Taxes: Trash
Laundry: In Basement
Lot Features: Level
Number Of Kitchens: 1
On Market Date: 2025-05-28
Parcel Number: 332289-005-000-0001-091.100-0000
Parking Features: Driveway
Patio And Porch: Deck, Patio
Rental Term: Monthly
Rooms Total: 8
Sewer: Septic Tank
Utilities: Cable Connected, Electricity Connected, Trash Collection Public
Water: Well

Local Schools

High School: Monroe-Woodbury High School
Middle School: Monroe-Woodbury Middle School
Elementary School: North Main Street
School District: Monroe-Woodbury

Listed By / Sold By

Listed By

Agency Name: Howard Hanna Rand Realty
Agency Phone: 845-928-9691

Shown By

Agent Name: Ann Glynn
Agent Phone: Cell: (516) 972-5677
Agency Title: Laffey Real Estate

Sold By

Agency Name: Keller Williams Realty
Agency Phone: 845-928-8000
Agent Name: Robert Addon

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/22/2026. The listing information on this page last changed on 04/22/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 04/22/2026 12:01:18 AM EST) or OneKey MLS (last updated Tue 04/21/2026 11:53:11 PM EST). Real estate listings held by brokerage firms other than Laffey Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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