19 High St

Chester, NY 10918

$1,195,000
Price
9
Beds
4,965 Sq. Ft.
$241 / Sq. Ft.
4,965
Sq. Ft.
$241
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Guest House

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...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.
  1. Listed by Beth Palma • Keller Williams Realty
    P: (845)-928-8000 C: (917)-363-0234 bethpalma@kw.com
  2. Listed by Kevin M. Tuhy • Keller Williams Realty
    P: (845)-928-8000 C: -- kevin.tuhy@kw.com

Property Details for 19 High Street

City/Township
Chester Town
Architectural Style
Colonial, Farmhouse, Victorian
Waterfront
No
LISTING UPDATED: 05/03/2026 01:09 PM

Property Details for 19 High Street

StatusActive
MLS #992878
Days on Market4
Taxes$19,292 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeMulti Family
MLS TypeDuplex
Year Built1850
Lot Size2.70 AC / 117,612 SF
CountyOrange County
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Location

Listing Courtesy of Keller Williams Realty
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Building Information for 19 High Street

Stories-Residences2Year Built1850Building Size-Lot Size2.70 AC / 117,612 SF

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$7,625 per month

30 year fixed, 6.46% Interest

Principal and Interest

$6,017

Property Taxes

$1,608

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 19 High Street

Summary
Location and General Information
  • Village: Chester Village
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: Detached
  • State Or Province: NY
  • Water Access YN: No
School Information
  • School District: Chester
  • Elementary School District: Chester
  • Elementary School: Chester Elementary School
  • Middle Or Junior School District: Chester
  • Middle Or Junior School: Chester Academy-Middle/High School
  • High School District: Chester
  • High School: Chester Academy-Middle/High School
Unit Information
Unit 1 Information
  • Unit Type Beds Total: 7
  • Unit Type Baths Total: 7
Unit 2 Information
  • Unit Type Beds Total: 2
  • Unit Type Baths Total: 1
Unit Information
  • Number Of 1 Bedrooms: 0.0
  • Number Of 2 Bedrooms: 1.0
  • Number Of 3 Bedrooms: 0.0
  • Number Of 4 Bedrooms: 1.0
  • Building Units Total: 2
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 332201-102-000-0001-062.200-0000
  • Tax Assessed Value: $255,900.00
  • Included In Taxes: Sewer, Trash
  • Tax Source: Municipality
  • Tax Year: 2025.0
Interior and Exterior Features
Interior Features
  • Amenities: Balcony, Barn(s), Breakfast Bar, Built-in Features, Cabana, Chandelier, Colonial, Covered, Crown Molding, Deck, Drapes, Eat in Kitchen, Family Room, Farmhouse, Fenced, Floor to Ceiling Windows, Formal Dining, Garden, Guest House, Hardwood Floors As Seen, High Ceilings, In Basement, In Ground, Kitchen Island, Lighting, Mailbox, Multiple Locations, Original Details, Outdoor Pool, Oversized Windows, Patio, Pool House, Primary Bathroom, Public, Rain Gutters, Residence, Screens, Shutters, Soaking Tub, Stable(s), Terrace, Tile, Victorian, Vinyl, Walk In Closet, Walk Through Kitchen, Wood, Wood Burning Stove
  • 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)
  • Basement: Full, Storage Space, Unfinished
  • Attic Description: Partial
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Fireplace Features: Family Room, Wood Burning Stove
  • Location Amenities: Balcony, Wood Burning Stove, Hardwood Floors As Seen, Eat in Kitchen, Formal Dining Room, High Ceilings, Island Kitchen, Original Details, Soacking Tub, Walk Through Kitchen, Walk In Closet, Garden, Privacy, Barn(s), Deck, Patio, Terrace, In Ground Pool, Pool Outdoor, Oversized Windows
  • Laundry Features: In Basement, Multiple Locations
  • Spa: Yes
  • Window Features: Drapes, Floor to Ceiling Windows, Oversized Windows, Screens, Shutters
  • Flooring: Hardwood, Tile, Vinyl, Wood
  • Basement: Yes
Exterior Features
  • Exterior Features: Balcony, Garden, Lighting, Mailbox, Rain Gutters
  • Exterior Property Features: Balcony, Garden, Lighting, Mailbox, Rain Gutters, Fenced, In Ground, Outdoor Pool, Covered, Deck, Patio, Terrace, Detached, Driveway, Oversized, Drapes, Floor to Ceiling Windows, Oversized Windows, Screens, Shutters, Back Yard, Cleared, Corner Lot, Front Yard, Historic District, Landscaped, Near Public Transit, Near School, Paved, Private, Secluded
  • Elevation Certificate: No
  • Patio And Porch Features: Covered, Deck, Patio, Terrace
  • Construction Materials: Blown-In Insulation, Frame, Vinyl Siding
  • Road Responsibility: Public Maintained Road
  • Other Structures: Barn(s), Cabana, Guest House, Pool House, Residence, Stable(s)
  • Pool Private: Yes
  • Pool Features: Fenced, In Ground, Outdoor Pool
  • Pool Details: Fenced,In Ground,Outdoor Pool
Lot Information
  • Lot Features: Back Yard, Cleared, Corner Lot, Front Yard, Garden, Historic District, Landscaped, Near Public Transit, Near School, Paved, Private, Secluded
  • Additional Parcel: No
  • Site Features: Back Yard, Cleared, Corner Lot, Front Yard, Garden, Historic District, Landscaped, Near Public Transit, Near School, Paved, Private, Secluded
  • Building Area Units: Square Feet
Parking
  • Parking Features: Detached, Driveway, Oversized
  • Parking Total: 12.00
  • Garage: No
  • Carport: No
Utilities
  • Cooling: Wall/Window Unit(s)
  • Heating: Electric, Natural Gas, Steam
  • Heat Fuel Type: Electric, Natural Gas, Steam
  • Sewer: Public Sewer
  • Water Source: Public
  • Utilities: Cable Available, Electricity Available, Electricity Connected, Natural Gas Available, Natural Gas Connected, Sewer Available, Sewer Connected, Trash Collection Public, Water Available, Water Connected
Green Features
  • Green Features: Drapes, Floor to Ceiling Windows, Oversized Windows, Screens, Shutters, Electric, Natural Gas, Steam, Balcony, Garden, Lighting, Mailbox, Rain Gutters, Fenced, In Ground, Outdoor Pool
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 19 High Street

DateEvent & SourcePriceAppreciation
Apr 30, 2026

Withdrawn

ONEKEY #972335

$1,295,000—
Apr 30, 2026

Listed (Active)

ONEKEY #992878

$1,195,000—
Jun 6, 2024

Expired

ONEKEY #H6251644

$995,000—
DateEvent & SourcePrice
04/30/2026

Withdrawn

ONEKEY #972335

$1,295,000
04/30/2026

Listed (Active)

ONEKEY #992878

$1,195,000
06/06/2024

Expired

ONEKEY #H6251644

$995,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 19 High Street

Taxable ValueLand$89,100Additions$166,800Total$255,900
Tax Record2021$3,769 ($314 / month)
Home Facts
Baths3Total Finished SqFt3,615 SqFtAbove Grade Finished SqFt3,615 SqFtStories2Lot Size117,612 SqFtStyleDuplexYear Built1850ZoningRSCountyORANGEAPN332201 102-1-62.2Fireplace TypeHas Fireplace

Schools near 19 High Street

This home is within Chester Union Free School District.
Rating
School
Type
Grades
Distance
Chester Elementary School
Public - PK to 5
Chester Academy Middle High School
Public - 6 to 12
Rating
School
Distance
Chester Elementary School
PublicPK to 5

Chester Academy Middle High School
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 19 High Street, Chester, NY 10918

19 High Street is a multi-family home for sale in Chester, NY 10918. This property was listed for sale on April 30, 2026 by Keller Williams Realty, it's currently listed at $1,195,000. It has been on the market for a total of 4 days and was last sold on April 14, 2022. This listing's school district is Chester Union Free School District. Nearby schools include Chester Elementary School and Chester Academy Middle High School. 19 High Street is a 9-bed, 8-bath, 4,965 sqft multi-family home built in 1850.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Keller Williams Realty

Based on information submitted to the MLS GRID as of 05/03/2026 01:09 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.