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Land with Home for Sale in Chester, New York

19 High St, Chester, NY 10918

$1,145,000
2.7 acres
Active sale
$50k drop
Est $7,458/mo

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, executive 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.

4,965
Sq feet
9
Beds
6
Full baths
1
1/2 bath
1850
Built

Location

Street address
19 High St
Zip code
10918
School district
Chester
Elevation
517 feet
Coordinates
41.3631, -74.2743

Property details

Acreage
2.7 acres
MLS #
MLSLI 995148
Posted

Property taxes

2025
$19,292

Parcels

  • 332201-102-000-0001-062.200-0000

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Franchise
Keller Williams Realty

Lot

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

Exterior

Parking Spaces
12
Parking
Driveway, Oversize
Pool
Deck, Patio
Hot Tub
Yes
Structures
Cabana
Features
Balcony, Lighting, Mailbox, Rain Gutters

Structure

Style
Colonial, Victorian
Basement
Full, Storage Space, Unfinished
Water
Public
Sewer
Public Sewer
Heating
Electric, Natural Gas, Steam
Cooling
Wall/Window Unit(s), Window Unit(s)
Materials
Blown-In Insulation, Frame, Vinyl Siding
Windows
Drapes, Screens, Shutters

Interior

Room Count
18
Rooms
Basement, Bathroom x 7, Bedroom x 9, Dining Room
Flooring
Hardwood, Tile, Vinyl, Wood
Appliances
Dishwasher, Dryer, Gas Range, Gas Water Heater, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Features
Breakfast 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)

Property utilities

CategoryTypeStatus
GasNatural GasConnected

Nearby schools

NameTypeDistrict
Chester Elementary SchoolElementaryChester
Chester Academy-Middle/High SchoolMiddleChester
Chester Academy-Middle/High SchoolHighChester

Listing history

DateEventPriceChangeSource
June 26, 2026Price drop$1,145,000$50,000 -4.2%MLSLI
Apr 30, 2026New listing$1,195,000MLSLI
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This 2.7-acre property is located at 19 High St in Chester, NY 10918. The property is available for sale, priced at $1,145,000. It has a 4,965 square foot 9-bedroom, 6.5-bath house built in 1850.

Listed by Keller Williams Realty, (845) 928-8000

Checked 1 hour agoUpdated Source

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