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!
Pending
Price cut: $50K (6/3)
$549,000
1 Winding Trail, Chester, NY 10918
3beds
2,040sqft
Single Family Residence, Residential
Built in 1991
1.2 Acres Lot
$-- Zestimate®
$269/sqft
$-- HOA
What's special
Private backyardGenerous storage spaceVaulted ceilingsHardwood floorsLarge sized eat-in kitchen
- 79 days
- on Zillow |
- 227 |
- 3 |
Likely to sell faster than
Zillow last checked: 7 hours ago
Listing updated: July 03, 2025 at 12:07am
Listing by:
Howard Hanna Rand Realty 845-928-9691,
Donald L Serotta 914-772-2468
Source: OneKey® MLS,MLS#: 857601

Travel times
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Heating
- Oil
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Water Softener Owned
- Laundry: Washer/Dryer Hookup, In Basement
Features
- Cathedral Ceiling(s), Central Vacuum, Eat-in Kitchen, Formal Dining, His and Hers Closets
- Flooring: Hardwood
- Basement: Partial,Unfinished
- Attic: Pull Stairs
- Number of fireplaces: 1
- Fireplace features: Family Room
Interior area
- Total structure area: 2,040
- Total interior livable area: 2,040 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Deck, Patio
Lot
- Size: 1.2 Acres
- Features: Level
Details
- Parcel number: 3322890050000001091.1000000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Splanch
- Property subtype: Single Family Residence, Residential
Materials
- Wood Siding
Condition
- Actual
- Year built: 1991
Utilities & green energy
- Sewer: Septic Tank
- Utilities for property: Cable Connected, Electricity Connected, Trash Collection Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Chester
Financial & listing details
- Price per square foot: $269/sqft
- Tax assessed value: $191,800
- Annual tax amount: $12,837
- Date on market: 5/28/2025
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
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