19 High Street, Chester, NY 10918
Local realty services provided by:ERA Caputo Realty
Listed by: beth palma, kevin m. tuhy
Office: keller williams realty
MLS#:995148
Source:OneKey MLS
Price summary
- Price:$1,145,000
- Price per sq. ft.:$230.61
About this home
Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses.
Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a rare blend of historic grandeur, modern comfort, and income-producing potential. The main residence features seven bedrooms and four and a half baths, showcasing timeless Victorian craftsmanship throughout, including soaring ceilings, original hardwood floors, intricate moldings, marble fireplaces, pocket doors, and elegant architectural details that have been carefully preserved.
Expansive living and entertaining spaces flow seamlessly into outdoor areas, ideal for gatherings, events, or quiet enjoyment of the serene setting. Enhancing the property’s versatility is a second detached building featuring a well-appointed two-bedroom apartment, ideal for guest accommodations, rental income, or on-site management.
A separate pool house with a full bathroom and sauna introduces a resort-style element, creating a private retreat perfect for relaxation, wellness, or entertaining. The current owner has taken exceptional care in maintaining and improving the property, including significant updates to major mechanical systems and the roof, ensuring both historic integrity and modern reliability. This thoughtful stewardship allows the next owner to enjoy the property with confidence while preserving its legacy.
With strong potential as a hospitality property, the estate presents flexible opportunities for use as a bed and breakfast, short-term rental, private residence, or boutique event venue. Its rich provenance, combined with strong visual appeal and a unique story, creates a standout offering that cannot be easily replicated in today’s market.
Situated in close proximity to local amenities, transportation, and the charm of the surrounding area—and just 40 miles from Manhattan—the property offers both privacy and accessibility. Whether you are seeking a distinctive primary residence, a lifestyle investment, or a legacy property with unmatched historical significance, the Hambletonian House represents a truly rare opportunity....
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Home facts
- Year built:1850
- Listing ID #:995148
- Added:59 day(s) ago
- Updated:June 29, 2026 at 12:28 AM
Rooms and interior
- Bedrooms:9
- Total bathrooms:7
- Full bathrooms:6
- Half bathrooms:1
- Rooms Total:18
- Flooring:Hardwood
- Dining Description:Eat-In Kitchen, Formal Dining
- Bathrooms Description:Soaking Tub
- Kitchen Description:Dishwasher, Eat-in Kitchen, Kitchen Island, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Walk Through Kitchen
- Basement:Yes
- Basement Description:Full, Unfinished
- Living area:4,965 sq. ft.
Heating and cooling
- Heating:Electric, Natural Gas, Steam
Structure and exterior
- Year built:1850
- Building area:4,965 sq. ft.
- Lot area:2.7 Acres
- Lot Features:Cleared, Corner Lot, Garden, Historic District, Near Public Transit, Paved, Private, Secluded
- Architectural Style:Colonial, Farmhouse, Victorian
- Construction Materials:Blown-In Insulation, Frame, Vinyl Siding
- Exterior Features:Balcony
Schools
- High school:Chester Academy-Middle/High School
- Middle school:Chester Academy-Middle/High School
- Elementary school:Chester Elementary School
Utilities
- Water:Public, Water Available
- Sewer:Public Sewer, Sewer Available
Finances and disclosures
- Price:$1,145,000
- Price per sq. ft.:$230.61
- Tax amount:$19,292 (2025)
Features and amenities
- Appliances:Dishwasher, Dryer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry features:Dryer, Washer
- Amenities:High Ceilings, Walk-In Closet(s)
- Pool features:In Ground, Outdoor Pool
Parking
- Total parking spaces:12
- Parking description:Detached, Driveway
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