19 High Street, Chester, NY 10918 - DeSimone Real Estate

$1,195,000

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… Read More 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. Read Less

Listing Courtesy of Keller Williams Realty.

Listing Snapshot

Days Online

Last Updated

May 18, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

4,965

Year Built

1850

Property Tax

$19,292

MLS Number

995148

30 Days Snapshot Of 10918

$300k

-38%

(avg) sold price

-85%

home sold

-32%

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

Description: "Dishwasher", "Dryer", "Gas Range", "Microwave", "Oven", "Range", "Refrigerator", "Stainless Steel Appliance(s)", "Washer", "Gas Water Heater"

Basement

Description: "Full", "Storage Space", "Unfinished"

Building

Area: 4965, Architecture: "Colonial", "Farmhouse", "Victorian", Building Area: 4965, Construction Materials: "Blown-In Insulation", "Frame", "Vinyl Siding", Year Built: 1850

Cooling

Details: "Wall/Window Unit(s)"

Exterior Features

Features: "Balcony", "Garden", "Lighting", "Mailbox", "Rain Gutters", Patio Features: "Covered", "Deck", "Patio", "Terrace"

Fireplaces

Total Fireplaces: 2

Floors

Flooring: "Hardwood", "Tile", "Vinyl", "Wood"

Heating

Heating: "Electric", "Natural Gas", "Steam"

Laundry

Description: "In Basement", "Multiple Locations"

Lot

Features: "Back Yard", "Cleared", "Corner Lot", "Front Yard", "Garden", "Historic District", "Landscaped", "Near Public Transit", "Near School", "Paved", "Private", "Secluded", Acres: 2.7

Parking

Parking Total: 12

Pool

Features: "Fenced", "In Ground", "Outdoor Pool", Private Pool

Utilities

Sewer: "Public Sewer", Water Source: "Public", Utilities: "Cable Available", "Electricity Available", "Electricity Connected", "Natural Gas Available", "Natural Gas Connected", "Sewer Available", "Sewer Connected", "Trash Collection Public", "Water Available", "Water Connected"

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