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$540,000

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,040 Sq. Ft.
  • 2 Car Garage
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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!

Full Property Details for 1 Winding Trail

General

  • Sold For: $540,000
  • Taxes: $12,837
  • Status: Closed
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 857601
  • Added to Site: 234 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Cathedral Ceiling(s), Central Vacuum, Eat-in Kitchen, Formal Dining, His and Hers Closets, Washer/Dryer Hookup
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Family Room
  • Appliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Water Softener Owned
  • Laundry Facilities: Yes
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Basement

Exterior

  • Porch/Patio/Deck: Deck, Patio

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Driveway

Location

  • County: Orange County
  • Cross Streets: Bull Mill Road
  • Driving Directions: Route 17M to Bull Mill Road to 1 Winding Trail

School Information

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

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Oil

Utilities

  • Sewer: Septic Tank
  • Water: Well
  • Utility Description: Cable Connected, Electricity Connected, Trash Collection Public

Structural Information

  • Architectural Style: Splanch, Split Level
  • Detached/Attached: Detached
  • Construction: Wood Siding
  • Basement: Yes
  • Basement Desc.: Partial, Unfinished
  • Building Size: 2040
  • Square Feet: 2,040
  • Sq. Ft. Source: Public Records
  • Year Built: 1991

Lot Features

  • Lot Size (Acres): 1.2
  • Lot Size (Sq. Ft.): 52,272
  • Lot Features: Level

Financial Considerations

  • Taxes Include: Trash
  • Tax Amount: $12,837.49

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 332289-005-000-0001-091.100-0000
  • Block: 5
  • Lot Number: 9.11

Listed by Howard Hanna Rand Realty
Sold by Keller Williams Realty

Listing agent

— 1 Winding Trail —

  • Howard Hanna Rand Realty

845-928-9691

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1 Winding Trail

School District:Monroe-Woodbury Central School District
NameGradesDistance
Monroe Woodbury Middle School
199 Dunderberg Rd, Woodbury, NY 10917
6-85 mi
Monroe Woodbury High School
155 Dunderberg Rd, Woodbury, NY 10917
9-125.1 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1 Winding Trail

Date
Details
Price
Change
Source
8/28/2025
Sold
$540,000
-1.64%
MLS
6/03/2025
Price Reduced
$549,000
-8.35%
MLS
5/28/2025
Listed
$599,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Howard Hanna Rand Realty
Sold by Keller Williams Realty

1 Winding Trail, Chester, NY 10918 (MLS# 857601) is a Single Family property that was sold at $540,000 on August 28, 2025. Want to learn more about 1 Winding Trail? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.