$1,145,000
 $6,147 est/mo Sourced by Back At You

19 High Street,Chester, NY 10918

Chester, NY 10918

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Description

Own One of America's Great Equestrian LandmarksSteeped 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 10the 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, executive retreat, or premier destination rentaloffering 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.

Details

MLS #995148
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive
Year1850
Days On Site115
Listing Provided ByKeller Williams Realty | Beth Palma

Features

Bed(s)9
Bath(s) 7 Total
SQ Feet4,965
BasementY
PoolYes
Acreage2.70

Interior

CoolingWall/Window Unit(s)
HeatingElectric, Natural Gas, Steam
Interior FeaturesBreakfast Bar, Built-in Features, Chandelier, Crown Molding, Eat-in Kitchen, Formal Dining, High Ceilings, Kitchen Island, Original Details, Primary Bathroom, Soaking Tub, Walk Through Kitchen, Walk-In Closet(s)
Window FeaturesDrapes, Floor to Ceiling Windows, Oversized Windows, Screens, Shutters
AppliancesDishwasher, Dryer, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater

Exterior

Exterior FeaturesBalcony, Garden, Lighting, Mailbox, Rain Gutters
Construction MaterialsBlown-In Insulation, Frame, Vinyl Siding
Lot FeaturesBack Yard, Cleared, Corner Lot, Front Yard, Garden, Historic District, Landscaped, Near Public Transit, Near School, Paved, Private, Secluded

Parking

Garage Yes / NoNo
Parking FeaturesDetached, Driveway, Oversized

Utilities

UtilitiesCable Available, Electricity Available, Electricity Connected, Natural Gas Available, Natural Gas Connected, Sewer Available, Sewer Connected, Trash Collection Public, Water Available, Water Connected
SewerPublic Sewer

Taxes

Tax Year2025
Tax Assessed Value255900
Tax Annual Amount19292

Area Information

StateNY
CountyOrange County
CityChester
Zip Code10918
School DistrictChester Academy-Middle/High Scho
Elementary SchoolChester Elementary School
High SchoolChester Academy-Middle/High Scho
Listing VS Median (in 10918)
Price:
$1,145,000
low | high
Med:
$549,950
100% of Average
sqft:
4,965
low | high
Med:
2,118
100% of Average
$ / sqft:
$231
low | high
Med:
$260
37.397063110626% of Average
On site:
115
low | high
Med:
58.5
100% of Average
Sourced by Back At You

Market Activity 10918

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Learn More About This Property

StateNY
CountyOrange County
CityChester
Zip Code10918
School DistrictChester Academy-Middle/High Scho
Elementary SchoolChester Elementary School
High SchoolChester Academy-Middle/High Scho
Listing VS Median (in 10918)
Price:
$1,145,000
low | high
Med:
$549,950
100% of Average
sqft:
4,965
low | high
Med:
2,118
100% of Average
$ / sqft:
$231
low | high
Med:
$260
37.397063110626% of Average
On site:
115
low | high
Med:
58.5
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $858K - $1.431M
sqft: 3,500 - 6,000
Nearby Listings Property ImageNearby Listings Details
38 Main Street 36 E Property Photo 1
$1,500
38 Main Street 36 E
Chester, NY 10918
Listing Updated: July 15, 2026 at 6:38:38 PM PDT