50 Hambletonian Avenue
Chester, NY, 10918 $ 624,900
Bedrooms3 Baths2.0 Sq 1,583 Monthly Estimate*
$ 3,946
for $624,900 with 3 bedrooms and 2 full baths. This 1,583 square foot home was built in 2001 on a lot size of 4.
Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Chester Academy and the Heritage Trail, this property provides easy access to walking, biking, running, local events, and community amenities while offering the peaceful retreat of your own private acreage. Set on 4 private acres, this home is a nature lover’s dream. The expansive property offers the perfect balance of open space and natural beauty, providing endless opportunities for outdoor enjoyment, family adventures, gardening, recreation, and creating your own private oasis. The large yard gives children plenty of room to play, explore, and connect with nature, while offering the space and flexibility for a hobby farm, gardens, chickens, outdoor activities, or other homesteading dreams. The entire home has been thoughtfully renovated within recent years, offering a fresh, updated feel throughout. A new HVAC system provides added comfort, efficiency, and peace of mind. The home also offers excellent future expansion potential with a full walk-out basement ready to be finished—perfect for a recreation room, guest suite, home gym, office, playroom, or media area. A standout feature is the oversized garage, providing exceptional space for vehicles, storage, hobbies, a workshop, or additional workspace. Step outside and enjoy the wrap-around back porch, the perfect place to relax, entertain, and take in the peaceful surroundings of your expansive yard. Whether enjoying morning coffee, hosting friends and family, or watching kids explore the outdoors, this space truly embraces the best of country-style living with village convenience. Property Highlights • Beautifully renovated home with modern updates • Just steps from Chester Academy and the Heritage Trail • Prime Village of Chester location close to schools, shops, and amenities • 4 private acres with beautiful natural surroundings • Perfect property for nature lovers and outdoor enthusiasts • Large yard ideal for kids to play, explore, and create memories • Endless possibilities for gardens, recreation, and hobby farming • New HVAC system • New roof • Full walk-out basement with finishing potential • Oversized garage with ample storage and workspace • Wrap-around back porch overlooking the property A rare opportunity to own a move-in ready home with land, updates, and endless possibilities—all in one of Chester’s most convenient locations. Whether you’re looking for space to grow, room for your family to explore, or the opportunity to create your own private retreat, 50 Hambletonian Ave offers the lifestyle you’ve been searching for.
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FeaturesInteriorInterior Amenities First Floor Bedroom First Floor Full Bath Ceiling Fan(s) Double Vanity Entrance Foyer High Ceilings Marble Counters Open Kitchen Primary Bathroom Recessed Lighting Smart Thermostat Soaking Tub Storag
Basement Finished Full Walk-Out Access
Flooring Hardwood Tile
Total Fireplaces 1
Basement Features Finished Full Walk-Out Access
Basement (Y/N) Y
Fireplace Y/N Y
Half Baths 0
Total Bedrooms 3
Total Baths 2
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GeneralSewer Public Sewer
Heating Natural Gas
Cooling Central Air
Utilities Cable Connected Electricity Connected Natural Gas Connected Sewer Connected Trash Collection Public Water Available
Appliances Dishwasher Disposal Freezer Gas Cooktop Gas Oven Gas Range Microwave Oven Refrigerator Stainless Steel Appliance(s) Washer Gas Water Heater Water Purifier Owned
Garage Spaces 2
Patio/Porch Features Covered Deck Porch Wrap Around
Architectural Style Raised Ranch
Security Features Security Lights Video Cameras
Construction Materials Vinyl Siding
Year Built 2001
View Open Trees/Woods
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 332289-002-000-0001-042.000-0000
County Orange County
Property Type Residential
HOA N
Garage Y/N Y
Total Rooms 5
Full Baths 2
Directions From NY 17 N take the Chester exit drive through two traffic lights left at the stop sign on to Main St. Drive 1 mile and veer left to High St. Drive 1/2 mile and take left onto Hambletonian Ave. Dri
High School Chester Academy-Middle/High School
City Chester Town
Senior Community Y/N N
High School District Chester
Carport Spaces 2
Carport Y/N Y
Elementary School Chester Elementary School
Property Attached Y/N N
Tax Annual Amount 13121.22
Middle/Junior High School Chester Academy-Middle/High School
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Chester
Elementary School District Chester
Tax Assessed Value 196000
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ExteriorExterior Amenities Lighting Mailbox Playground Rain Gutters
Fencing Back Yard
Parking Features Detached Driveway Garage Garage Door Opener Oversized Private Detached Driveway Garage Garage Door Opener Oversized Private
Water Source Well
Foundation Details Block
Waterfront Y/N N
Horse Y/N N
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* Excluded FeaturesList ByDerek J. GreeneListing Agent
Greene Realty GroupBroker
Affordability Calculator
- Monthly Principal & Interest
- $3,946
- Monthly Property Taxes
- $1,093
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Chester, NY
Average List Price $815,331
Percent of Sale Price 30%
About Chester, NY 3,423 Population
-5% Since 2002
$ 54,539 Median Income
50.03 Median Age
26% Households with Children
Trends Information provided by ATTOM Data Solutions.
4100324 Elementary School
4100290 Middle School
Chester Academy-Middle/High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 7/23/2026 | $624,900 | | Listed Price |