19 High St
Description
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...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.
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...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.
- Listed by Beth Palma • Keller Williams RealtyP: (845)-928-8000 C: (917)-363-0234 bethpalma@kw.com
- Listed by Kevin M. Tuhy • Keller Williams RealtyP: (845)-928-8000 C: -- kevin.tuhy@kw.com
Property Details for 19 High Street
City/Township
Chester Town
Architectural StyleColonial, Farmhouse, Victorian
WaterfrontNo
LISTING UPDATED: 07/15/2026 07:05 PM
Property Details for 19 High Street
| Status | Active |
|---|---|
| MLS # | 995148 |
| Days on Market | 71 |
| Taxes | $19,292 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Single Family |
| Year Built | 1850 |
| Lot Size | 2.70 AC / 117,612 SF |
| County | Orange County |
Location
Listing Courtesy of Keller Williams Realty
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Building Information for 19 High Street
Stories-Year Built1850Building Size-Lot Size2.70 AC / 117,612 SF
Payment Calculator
$7,313 per month
30 year fixed, 6.36% Interest
Principal and Interest
$5,706
Property Taxes
$1,608
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property 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
Rental
Rental
- Lease Considered: No
Unit Information
Unit Information
- Building Units Total: 1
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
- Association: No
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)
- Appliances: Dishwasher, Dryer, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater
- Total Rooms: 18
- Basement: Full, Storage Space, Unfinished
- Attic Description: Partial
- Fireplace: Yes
- Fireplaces Total: 2
- Fireplace Features: Family Room, Wood Burning Stove
- Location Amenities: Stainless Steel Appliances, 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
- Living Area: 4,965.00
- 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, Dishwasher, Dryer, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater, Electric, Natural Gas, Steam, Balcony, Garden, Lighting, Mailbox, Rain Gutters, Fenced, In Ground, Outdoor Pool
Virtual Tour
- Virtual Tour URL Unbranded: https://iframe.videodelivery.net/ac7f35cfb85d7c002be3b6b05013c32c
Agent
Payment and Rate
- Down Payment Resource: No
Property History for 19 High Street
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Jun 26, 2026 | Price Change ONEKEY #995148 | $1,145,000 | — |
| May 5, 2026 | Listed (Active) ONEKEY #995148 | $1,195,000 | — |
| May 5, 2026 | Withdrawn ONEKEY #992878 | $1,195,000 | — |
| 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 | — |
| Jun 5, 2023 | Listed (Active) ONEKEY #H6251644 | $995,000 | — |
| Apr 14, 2022 | Sold (Public Record) Public Record #1495065794 | $341,661 | -36.1% / yr |
| Nov 13, 2020 | Sold ONEKEY #H6046010 | $650,000 | — |
| Nov 5, 2020 | Sold (Public Record) Public Record #692508226 | $650,000 | +149.7% / yr |
| Aug 26, 2020 | Pending ONEKEY #H6046010 | — | |
| Jul 18, 2020 | Listed (Active) ONEKEY #H6046010 | $669,000 | — |
| Jul 23, 2018 | Sold (Public Record) Public Record #636784933 | $80,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 06/26/2026 | Price Change ONEKEY #995148 | $1,145,000 |
| 05/05/2026 | Listed (Active) ONEKEY #995148 | $1,195,000 |
| 05/05/2026 | Withdrawn ONEKEY #992878 | $1,195,000 |
| 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 |
| 06/05/2023 | Listed (Active) ONEKEY #H6251644 | $995,000 |
| 04/14/2022 | Sold (Public Record) Public Record #1495065794 | $341,661 -36.1% / yr |
| 11/13/2020 | Sold ONEKEY #H6046010 | $650,000 |
| 11/05/2020 | Sold (Public Record) Public Record #692508226 | $650,000 +149.7% / yr |
| 08/26/2020 | Pending ONEKEY #H6046010 | — |
| 07/18/2020 | Listed (Active) ONEKEY #H6046010 | $669,000 |
| 07/23/2018 | Sold (Public Record) Public Record #636784933 | $80,000 |
For completeness, we 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 |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| 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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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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 07/15/2026 07:05 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.
