About This Home

This 9-bedroom, 7-bathroom single family at 19 High Street in Chester, NY is listed for $1,145,000 ($231 per sqft). Built in 1850, the home offers 4,965 sqft of living space on a 2.70 acres lot.

Key Features

  • Built in 1850
  • 2.70 acre lot
  • 12 parking spaces
  • Private pool
  • Fireplace

Property Details

6 full, 1 half
12 spaces
1850

Amenities

PoolFireplaceSpaHardwoodA/C
Listing Description

Own One of America's Great Equestrian Landmarks Steeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10-the foundation sire of nearly every modern Standardbred racehorse.

More than a remarkable home, this is an opportunity to become the next steward of one of the most significant equestrian properties in history. Gracefully set atop a scenic knoll on nearly three private acres in the heart of Chester, New York, the estate offers exceptional privacy while remaining just 40 miles from Manhattan.

From the moment you arrive, the home's commanding presence, timeless architecture, and beautifully maintained grounds create an unforgettable first impression. The stately main residence features seven bedrooms and four-and-a-half bathrooms, where authentic Victorian craftsmanship has been meticulously preserved.

Soaring ceilings, original hardwood floors, intricate millwork, marble fireplaces, elegant pocket doors, and exquisite architectural details reflect the grandeur of a bygone era, while thoughtful modern updates provide today's expected comforts. Designed for both elegant entertainment and everyday living, the home's expansive gathering spaces flow

effortlessly to the surrounding grounds, creating an ideal setting for celebrations, family gatherings, or quiet evenings enjoying the beauty of the property. Adding to the estate's resort-style appeal is a separate pool house, complete with a full bathroom and private sauna, offering the perfect retreat for relaxation, wellness, or entertaining guests throughout the seasons.

One of the property's most compelling features is its detached second residence, offering a beautifully appointed two-bedroom apartment with exceptional flexibility. Beyond providing luxurious accommodation for guests or extended family, this separate living space creates an outstanding opportunity for additional income.

Whether utilized as a premium long-term rental, short-term vacation rental, executive housing, caretaker's residence, or owner's quarters while operating the main home as a hospitality property, it provides the versatility today's buyers are seeking. Beyond its architectural beauty, the property presents an exceptional opportunity to offset ownership costs through multiple revenue streams.

This rare combination of a landmark residence and an income-producing secondary dwelling makes the estate equally attractive to homeowners, investors, and entrepreneurs. With its iconic history, breathtaking setting, and expansive layout, The Hambletonian House is ideally suited as a luxury bed and breakfast, boutique inn, private event venue, exec

utive retreat, or premier destination rental-offering limitless possibilities for both lifestyle and investment. The current owner has invested extensively in preserving the estate's historic integrity while making significant improvements to major mechanical systems and the roof, ensuring modern reliability without compromising its timeless character.

This careful stewardship allows the next owner to enjoy the confidence of updated infrastructure while preserving a truly irreplaceable piece of history. Ideally located near the shops, restaurants, and conveniences of the Village of Chester, with easy access to major highways and the best of the Hudson Valley, the property offers the perfect balance of peaceful country living and metropolitan accessibility.

Properties of this significance rarely become available. Combining rich history, exceptional architecture, income-producing potential, and an irreplaceable legacy, The Hambletonian House represents a once-in-a-generation opportunity to own one of the most celebrated equestrian landmarks. Some homes are purchased. Others become part of history. This is one of them.

Monthly Cost Estimate

$6,124/mo

20% down · 6.5% · 30 years

Principal$828
Interest$4,962
Insurance$334

Estimates only. Actual payments may vary.

Location

19 High Street

Chester, NY 10918

Features & Amenities

Interior Features

Breakfast BarBuilt-in FeaturesChandelierCrown MoldingEat-in KitchenFormal DiningHigh CeilingsKitchen IslandOriginal DetailsPrimary BathroomSoaking TubWalk Through KitchenWalk-In Closet(s)

Exterior Features

BalconyGardenLightingMailboxRain Gutters

Property Details

Flooring

VinylHardwoodTileWood

Construction

Blown-In Insulation Frame Vinyl Siding

Pool Features

Pool

Outdoor Features

DeckPatio

Parking

DrivewayOversize

Heating

Natural GasSteamElectric (Heating)

Cooling

Wall/Window Unit(s)Window Unit(s)

Appliances

DishwasherDryerGas RangeMicrowaveOvenRangeRefrigeratorStainless Steel Appliance(s)WasherGas Water Heater

Questions & Answers

This 9-bedroom, 7-bathroom single family at 19 High Street is listed at $1,145,000 ($231/sqft). The estimated monthly payment is $6,124 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1850, 2.70 acre lot, 12 parking spaces, Private pool, Fireplace. Interior Features: Breakfast Bar, Built-in Features, Chandelier. Exterior Features: Balcony, Garden, Lighting.

This property is listed by Beth Palma.

BP

Beth Palma

Agent at Keller Williams Realty

Listed by Keller Williams Realty · Broker phone: (845) 928-8000 · View on Broker Site · Broker website

MLS# 995148· Source: OneKey MLS· 174 days on PropertySimple

Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

19 High Street, Chester, NY 10918

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