OneKey® MLS
  • Buy
  • Rent
  • Commercial
  • Find an Agent
  • NYS Fair Housing Notice
  • Language
    Price range
    $
    $
    Bedrooms
    Bathrooms
    Home type
    Square feet
    Lot size
    Heating
    Cooling
    Parking spots
    Garage
    Basement
    Year built
    Max HOA
    Down payment assistanceDown payment assistance
    Tours
    View
    More amenities
    1 home
      1 home available
      1 Winding Trail, Chester, NY 10918
      Closed Aug 28, 2025
      1 Winding Trail, Chester, NY 10918
      $540,000
      3beds
      2.5bath
      2,040sqft
      1.2acres
      House for Sale
      Down payment assistanceDown Payment Help

      1 Winding Trail, Chester, NY 10918

      Listing by: Howard Hanna Rand Realty
      1 - 1 of 1 results
      Copyright © 2025 OneKey® MLS LLC
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
      Equal opportunity
      Membio
      OneKey® MLS
      1 Winding Trail, Chester, NY 10918
      Closed Aug 28, 2025
      $540,000
      Down payment assistanceDown Payment Help
      3beds
      2full,1half bath
      2,040sqft
      1.2acres

      1 Winding Trail, Chester, NY 10918

      City/Town:Chester   Post Office: Chester     

      House for Sale by Donald L SerottaHoward Hanna Rand Realty.

      Data checked -. Listing last updated 118 days ago.
      1. Overview
      2. Details
      3. More 

      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!

      Internet Serviceability
      Details
        Property type
      Residential
        Year built
      1991
        Heating
      Oil
        Cooling
      Central Air
        Total rooms
      8
        Garage
      Yes (2 space)
        City/Town
      Chester
        Post Office
      Chester
        Parking spots
      -
      857601
      MLS ID
      Closed
      Status
      Aug 28, 2025
      Closed
        Laundry features
      In Basement
        Flooring
      Hardwood
        Fireplace
      Yes
        Pets allowed
        Architectural Style
      Splanch, Split Level
        Basement
      Partial, Unfinished
        View
      Interior features
      Cathedral Ceiling(s), Central Vacuum, Eat-in Kitchen, Formal Dining, His and Hers Closets, Washer/Dryer Hookup
      Exterior features
      Lot features
      Level
      Appliances included
      Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Water Softener Owned
      Construction materials
      Wood Siding
      Monthly taxes
      $1,070
      Yearly taxes
      $12,837.49
      Community Features
      -
      School district
      Monroe-Woodbury
      Schools
      North Main Street, Monroe-Woodbury Middle School, Monroe-Woodbury High School
      Senior community
      No
      Common Charges
      -
      Maintenance
      -
      Additional Fees
      -
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      DS
      Donald L Serotta
      Associate Real Estate Broker, Howard Hanna Rand Realty
      Direct Number 
       
      Location
      Route 17M to Bull Mill Road to 1 Winding Trail
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      1 Winding Trail, Chester, NY 10918, is a 3 bedroom, 2 bathroom, 2040 sqft. Single Family Residence built in 1991. This property is currently available for sale and was listed on OneKey® MLS on 5-28-2025. The MLS# for this Single Family Residence is MLS# 857601.
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
      Copyright ©2025