by RH Advisors

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Chester 10918
19 High Street
$1,145,000
↓ $50K (4.2%)
● House - For Sale

19 High Street

Chester Town, NY 10918
bedrooms
9 Beds
bathrooms
6 Baths, 1 Half Bath
square feet
4,965 Ft²
$7,230
Est. Monthly

About This Property

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.
Unit Size
4,965 Ft²
Days on Market
191 days
Land Size
2.70 acres
Price per sqft
$231
Property Type
House
Property Taxes
$1,608
HOA Dues
-
Year Built
1850

Listed By

Beth Palma
Keller Williams Realty
Kevin Tuhy
Keller Williams Realty

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Last updated: 4 months ago (OneKey MLS #KEY995148)

Price History

Date / Event Date Event Price
Jun 27, 2026 Price Decreased $1,145,000
↓ $50K (4.2%)
Price Decreased
May 5, 2026 Listed by Keller Williams Realty $1,195,000
Listed by Keller Williams Realty
Oct 1, 2023 In contract -
In contract
Jun 5, 2023 Listed $995,000
Listed
May 3, 2022 Sold
Sold
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Property Highlights

Garage
Fireplace
Parking Details
Has Open Parking
Parking Features: Detached, Driveway, Oversized
Interior Details
Half Bathrooms: 1
Full Bathrooms: 6
Interior Features: Breakfast Bar, Built-in Features, Chandelier, Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen Island, Soaking Tub, Walk-In Closet(s), Formal Dining, Original Details, Primary Bathroom, Walk Through Kitchen
Appliances: Dishwasher, Dryer, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater
Flooring Type: Hardwood, Tile, Vinyl, Wood
Laundry Features: In Basement, Multiple Locations
Rooms: 18
Has Fireplace
Fireplace Features: Family Room, Wood Burning Stove
Fireplaces: 2
Basement: Full, Storage Space, Unfinished
Exterior Details
Square Footage: 4965
Square Footage Source: $0
Architectural Style: Colonial, Farmhouse, Victorian
Year Built: 1850
Building Area Total: 4965
Other Structures: Barn(s), Cabana, Guest House, Pool House, Residence, Stable(s)
Building Area Units: Square Feet
Window Features: Drapes, Screens, Shutters, Floor to Ceiling Windows, Oversized Windows
Construction Materials: Blown-In Insulation, Frame, Vinyl Siding
Patio and Porch Features: Covered, Deck, Patio, Terrace
Pool Features: Fenced, In Ground, Outdoor Pool
Pool is Private
Lot Features: Back Yard, Cleared, Corner Lot, Front Yard, Garden, Landscaped, Near Public Transit, Paved, Private, Secluded, Historic District, Near School
Lot Size Area: 117612
Lot Size Units: Square Feet
Lot Size Acres: 2.7
Lot Size Square Feet: 117612
Water Source: Public
Financial Details
Tax Assessed Value: $255,900
Tax Annual Amount: $19,292
Utilities Details
Cooling Type: Wall/Window Unit(s)
Heating Type: Electric, Natural Gas, Steam
Sewer : Public Sewer

Building Info

Overview

    General

  • Year Built: 1850
  • Effective Year Built: 1850
  • Total Rooms: 10
  • Bedroom Count: 4
  • Bathroom Count: 3
  • Full Bathrooms: 3
  • Partial Bathrooms: 3
  • Building Condition: 6
  • Building Quality: 4
  • Construction Type: 0
  • Building Style: 1
  • Exterior Walls Type: 17
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 0
  • Floor Count: 200
  • Floor Cover: 0
  • Basement Type: 6
  • Basement Area: 0
  • Garage Type: 10
  • Garage Square Area: 960
  • Parking Space Count: 7
  • Patio Type: 0
  • Porch Type: 6
  • Pool Type: 8

    Dimensions

  • Lot Size Square Feet: 117,612
  • Lot Size Depth Feet: 1,830
  • Lot Size Frontage Feet: 2,750
  • Total Building Area: 3,615
  • Gross Building Area: 3,615
  • Building Area: 3,615
  • Building Area Measurement: T

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 0
  • Heating: 10
  • Heated Square Feet: 3,125
  • Heating Fuel Type: 3

    Utilities

  • Sewer System: 1
  • Water Service: 2

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000002700
  • Standard Land Use Code: 1101
  • County Land Use Code: 220
  • Legal Description 1: LT 2 HULSE SURVEY MP 4804

Neighborhood

  • School District Name: Chester Union Free School District
  • School Tax School District: CHESTER
  • Census Tract: 014301

Zoning

  • Zoning: RS

Geography

  • Account Number: 102-1-62.2
  • District: 332201
  • Section: 102.00
  • Parcel: 332201 102-1-62.2
  • Block: 1
  • Lot: 62.200
  • Municipality: CHESTER
  • Latitude: 41.3629
  • Longitude: -74.2742

    Address

  • Full Address: 19 High St
  • Address - House Number: 19
  • Address - Street Name: High
  • Address - Suffix Type: St
  • State: NY
  • City Name: Chester
  • Carrier Code: C001
  • 4-Digit Zip Code: 1230
  • Zip Code: 10918

Valuation

    Tax

  • Tax Year: 2023
  • Tax Amount: $1,750,628
  • Tax Rate Code Area: 332201

    Appraisal Valuation

  • Standard Deviation: 0.1198
  • Valuation Date: Feb 07, 2024
  • Confidence Score: 87
  • Final Value: 1,028,498
  • High Value: 1,151,734
  • Low Value: 905,263

    Market Valuation

  • Market Total Value: $624,100
  • Market Land Value: $217,301
  • Market Improvement Value: $406,799

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $255,900
  • Assessed Land Value: $89,100
  • Assessed Improvements Value: $166,800

    Sales

  • Current Sale Contract Date: Apr 14, 2022
  • Current Sale Recording Date: May 03, 2022
  • Current Sale Price:
  • Current Sale Document Type: 27
  • Current Sale Input Document Number: 20220033312
  • Previous Sale Recording Date: Dec 17, 2020
  • Previous Sale Contract Date: Nov 05, 2020
  • Previous Sale Amount: $650,000
  • Previous Sale Document Type: 27
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Chester


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Nearby Rentals

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Unit for rent at 37 Main Street, Chester, NY, 10918

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37 Main Street #2, Chester, NY, 10918 Listing by James Feldhaus


Frequently Asked Questions

When was property at 19 High Street built and last sold?
The property at 19 High Street was built in 1850 and last sold on Apr 14, 2022 for $341,661.
How much is this home worth?
The estimated value of the home located at 19 High Street is $1,149,490.
What are some comparable homes to 19 High Street?
There are currently no comparable homes to 19 High Street.