19 High ST, Chester, NY 10918
19 High ST, Chester, NY 10918
19 High ST, Chester, NY 10918
19 High ST, Chester, NY 10918
19 High ST, Chester, NY 10918
19 High ST, Chester, NY 10918
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$ 1,195,000
Est. payment | /mo

9 Beds

8 Baths

2.7 Acres Lot


$ 1,195,000
Est. payment | /mo

9 Beds

8 Baths

2.7 Acres Lot

Open House

Sun May 03, 11:00am - 1:00pm

Key Details

Property Type Multi-Family

Sub Type Duplex

Listing Status Active

Purchase Type For Sale

MLS Listing ID 992878

Style Colonial,Farmhouse,Victorian

Bedrooms 9

Full Baths 8

Rental Info No

Year Built 1850

Annual Tax Amount $19,291

Lot Size 2.700 Acres

Acres 2.7

Property Sub-Type Duplex

Source onekey2

Property Description

Own a true piece of American 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.

Location

State NY

County Orange County

Rooms

Basement Full, Storage Space, Unfinished

Interior

Interior 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)

Heating Electric, Natural Gas, Steam

Cooling Wall/Window Unit(s)

Flooring Hardwood, Tile, Vinyl, Wood

Fireplaces Number 2

Fireplaces Type Family Room, Wood Burning Stove

Fireplace Yes

Laundry In Basement, Multiple Locations

Exterior

Exterior Feature Balcony, Garden, Lighting, Mailbox, Rain Gutters

Parking Features Detached, Driveway, Oversized

Pool Fenced, In Ground, Outdoor Pool

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

Total Parking Spaces 12

Garage false

Private Pool Yes

Building

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

Sewer Public Sewer

Water Public

Structure Type Blown-In Insulation,Frame,Vinyl Siding

Schools

Elementary Schools Chester Elementary School

Middle Schools Chester Academy-Middle/High School

High Schools Chester

School District Chester

Others

Senior Community No

Special Listing Condition None

Virtual Tour https://iframe.videodelivery.net/ac7f35cfb85d7c002be3b6b05013c32c

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
Listed by Keller Williams Realty • Beth Palma

Nearby Locations

GET MORE INFORMATION

Morreale Real Estate
Morreale Real Estate

Licensed Real Estate Broker | Lic# 10311210108

+1(845) 796-3707

95 Glen Wild Road Suite 205 Rock Hill, NY, 12775

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19 High ST