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Land with Home for Sale in Chester, New York

19 High St, Chester, NY 10918

$1,195,000
2.7 acres
Active sale
ago
Est $7,339/mo

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 7 bedrooms and 4.5 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 to 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. Potential for a successful hospitality property, the estate presents flexible opportunities for continued use as a bed and breakfast, short-term rental, private residence, or boutique event venue. Its rich provenance, combined with strong visual appeal and unique story, creates a standout offering that cannot be easily replicated in today's market. Situated within close proximity to local amenities, transportation, and the charm of the surrounding area, also just 45 miles to 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.

Sq feet
9
Beds
6
Full baths
1850
Built

Location

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

Property details

Acreage
2.7 acres
MLS #
MLSLI 992878
Posted

Property taxes

2025
$19,292

Parcels

  • 332201-102-000-0001-062.200-0000

Open houses

DateBeginsEndsAppt neededRemarks
May 3, 202611:00 AM1:00 PMNoMichael Jenney

Details and features

Listing

Type
Residential Multi Family
Unit Count
2
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

Rooms
Basement, Bathroom x 6, Bedroom x 9, Dining Room
Flooring
Hardwood, Tile, Vinyl, Wood
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
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 for $1,195,000. It has a 9 bedroom, 6 bath house built in 1850.

Checked 2 hours ago — Updated

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