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$1,195,000

  • For Sale
  • Active
  • Single Family
  • 9 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 4,965 Sq. Ft.
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Own a true piece of 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.

Full Property Details for 19 High St

General

  • Price: $1,195,000
  • Taxes: $19,292
  • Status: Active
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 995148
  • Updated: 5/5/2026
  • Added to Site: 24 day(s) ago

Interior

  • Number of Rooms: 18
  • 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)
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Family Room, Wood Burning Stove
  • Appliances: Dishwasher, Dryer, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater
  • Laundry Facilities: Yes
  • Flooring: Hardwood, Tile, Vinyl, Wood

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 6
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 9

Other Rooms

  • Laundry: In Basement, Multiple Locations

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Fenced, In-Ground, Outdoor Pool
  • Spa: Yes

Exterior

  • Exterior Features: Balcony, Garden, Lighting, Mailbox, Rain Gutters
  • Porch/Patio/Deck: Covered, Deck, Patio, Terrace

Parking

  • Total Spaces: 12
  • Parking Features: Detached, Driveway, Oversized

Location

  • County: Orange County

School Information

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

Heating & Cooling

  • Cooling Type: Wall/Window Unit(s)
  • Heating Type: Electric, Natural Gas, Steam

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Available, Electricity Available, Electricity Connected, Natural Gas Available, Natural Gas Connected, Sewer Available, Sewer Connected, Trash Collection Public, Water Available, Water Connected

Structural Information

  • Architectural Style: Colonial, Farmhouse, Victorian
  • Detached/Attached: Detached
  • Construction: Blown-In Insulation, Frame, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Full Basement, Storage Space, Unfinished
  • Windows: Drapes, Floor to Ceiling Windows, Oversized Windows, Screens, Shutters
  • Building Size: 4965
  • Square Feet: 4,965
  • Sq. Ft. Source: Public Records
  • Year Built: 1850

Additional Structures

  • Other Structures: Barn(s), Cabana, Guest House, Pool House, Residence, Stable(s)

Lot Features

  • Lot Size (Acres): 2.7
  • Lot Size (Sq. Ft.): 117,612
  • Road Maintenance: Public Maintained Road
  • Lot Features: Back Yard, Cleared, Corner Lot, Front Yard, Garden, Historic District, Landscaped, Near Public Transit, Near School, Paved, Private, Secluded

Financial Considerations

  • Taxes Include: Sewer, Trash
  • Tax Amount: $19,292

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 332201-102-000-0001-062.200-0000

Listed by Keller Williams Realty

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Listing agents

— 19 High St —

  • Keller Williams Realty

  • Keller Williams Realty

845-928-8000

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 19 High St

School District:Chester Union Free School District
NameGradesDistance
Chester Elementary School, Chester, NY
2 Herbert Drive, Chester, NY 10918
K-50.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 19 High St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/05/2026
Listed
$1,195,000
249.76%
MLS
4/14/2022
Sold
$341,661
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 19 High St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$18,476
390%
$255,900
—
2021
$3,769
-50%
$255,900
—
2021
$7,503
-54%
$255,900
—
2020
$16,473
5%
$255,900
—
2018
$15,757
3%
$255,900
—
2017
$15,346
1%
$255,900
—
2016
$15,178
2%
$255,900
—
2015
$14,917
-1%
$255,900
—
2015
$15,011
1%
$255,900
—
2013
$14,808
—
$255,900
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 19 High St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Keller Williams Realty

19 High Street, Chester, NY 10918 (MLS# 995148) is a Single Family property with 9 bedrooms, 6 full bathrooms and 1 partial bathroom. 19 High Street is currently listed for $1,195,000 and was received on May 05, 2026. Want to learn more about 19 High Street? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

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