19 High Street, Chester, NY 10918

• 9 beds |
• 7 baths |
• 4,965 sqft

Property Description

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 45 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.

Listing Status:

Active

Data Last Updated:

May 11, 2026 at 5:22AM

Listing Office:

Keller Williams Realty : 845-928-8000

MLS ID:

995148

Interior

• General: Breakfast BarBuilt-in FeaturesChandelierCrown MoldingEat-in KitchenFormal DiningHigh CeilingsKitchen IslandOriginal DetailsPrimary BathroomSoaking TubWalk Through KitchenWalk-In Closet(s)
• Appliances: DishwasherDryerGas RangeMicrowaveOvenRangeRefrigeratorStainless Steel Appliance(s)WasherGas Water Heater
• Laundry: In BasementMultiple Locations
• Basement: FullStorage SpaceUnfinished
• Flooring: HardwoodTileVinylWood
• A/C: Wall/Window Unit(s)
• Heating: ElectricNatural GasSteam
• Fireplace: Family RoomWood Burning StoveFireplaceFireplaces: 2

Exterior

• General: BalconyGardenLightingMailboxRain Gutters
• Style: ColonialFarmhouseVictorian
• Other Structures: Barn(s)CabanaGuest HousePool HouseResidenceStable(s)TerraceDeckPatioCovered
• Pool: FencedIn GroundOutdoor Pool
• Parking: DetachedDrivewayOversizedParking spaces: 12

Construction

• Windows: DrapesFloor to Ceiling WindowsOversized WindowsScreensShutters

Location

• Originating MLS: onekey2
• School District: Chester
• County: Orange County

Lot

• Zoning: 332201-102-000-0001-062.200-0000

Utilities

• Utilities: Cable AvailableElectricity AvailableElectricity ConnectedNatural Gas AvailableNatural Gas ConnectedSewer AvailableSewer ConnectedTrash Collection PublicWater AvailableWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: onekey2