Stephen Chmil

19 High Street, Chester, NY 10918

$1,195,000
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New to the Market Active
BEDS9 BATHS6 full MLS#992878
STATUSActive PROPERTY TYPEMulti Unit - Multiple SCHOOLChester

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 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.

19 High Street | MLS# 992878

This multi-family property located at 19 High Street, Chester, NY 10918 is currently listed for sale with an asking price of $1,195,000. High Street is located within the Chester school district. Search Chester real estate on schmil.coachrealtors.com today.

Property Features

Property Type: Multi Unit - Multiple
Basement: Yes
Basement: Full, Storage Space, Unfinished
Cooling: Wall/Window Unit(s)
Fenced: Yes
Fireplaces: 2
Heating: Electric, Natural Gas, Steam
Home Style: Colonial, Farmhouse, Victorian
Lot Size: 2.70 Acres
Taxes: $19,291
Year Built: 1850

Amenities

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)
Balcony
Garden
Lighting
Mailbox
Rain Gutters

Feature Descriptions

Attic: Partial
Building Area Total: 4965
Exterior: Blown-In Insulation, Frame, Vinyl Siding
Fireplace Features: Family Room, Wood Burning Stove
Fireplace Y/N: Yes
Flooring: Hardwood, Tile, Vinyl, Wood
Formal Dining: Yes
Included In Taxes: Sewer, Trash
Laundry: In Basement, Multiple Locations
Lot Features: Back Yard, Cleared, Corner Lot, Front Yard, Garden, Historic District, Landscaped, Near Public Transit, Near School, Paved, Private, Secluded
On Market Date: 2026-04-30
Other Structures: Barn(s), Cabana, Guest House, Pool House, Residence, Stable(s)
Parcel Number: 332201-102-000-0001-062.200-0000
Parking Features: Detached, Driveway, Oversized
Parking Total: 12
Patio And Porch: Covered, Deck, Patio, Terrace
Pool Features: Fenced, In Ground, Outdoor Pool
Rental Term: Monthly
Road Responsibility: Public Maintained Road
Sewer: Public Sewer
Spa Y/N: Yes
Swimming Pool: Yes
Units: 2
Utilities: Cable Available, Electricity Available, Electricity Connected, Natural Gas Available, Natural Gas Connected, Sewer Available, Sewer Connected, Trash Collection Public, Water Available, Water Connected
Water: Public
Window Features: Drapes, Floor to Ceiling Windows, Oversized Windows, Screens, Shutters

Local Schools

High School: Chester Academy-Middle/High School
Middle School: Chester Academy-Middle/High School
Elementary School: Chester Elementary School
School District: Chester

Listed By / Shown By

Listing By

Agency Name: Keller Williams Realty
Agency Contact: 845-928-8000

Shown By

Agent Name: Stephen Chmil
Agent Phone: (516) 746-5511
Agency Title: Howard Hanna | Coach Realtors

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Estimated Payment

$ 7,088.14 per month $5,132.01 Principal & Interest $1,607.58 Property Tax $348.54 Homeowner's Insurance

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