19 High Street, Chester, NY, 10918
About This Home
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.
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1850
Materials
- Construction materials: Blown-In Insulation,Vinyl Siding
Type & Style
- Home type: SingleFamily
- Architectural style: Colonial,Victorian
- Property subType: Single Family Residence,Residential
Interior
Appliances
- Appliances included: Dishwasher,Dryer,Gas Range,Microwave,Oven,Range,Refrigerator,Stainless Steel Appliance(s),Washer,Gas Water Heater
- Laundry features: In Basement,Multiple Locations
Basement
- Has basement: Yes
- Basement: Full,Storage Space,Unfinished
Bedrooms & Bathrooms
- Bedrooms: 9
- Bathrooms: 7
- Full bathrooms: 6
- 1/2 bathrooms: 1
Features
- Breakfast Bar,Built-in Features,Chandelier,Crown Molding,Eat-in Kitchen,Formal Dining,Kitchen Island,Original Details,Primary Bathroom,Soaking Tub,Walk Through Kitchen
- Window features: Drapes,Floor to Ceiling Windows,Oversized Windows,Screens,Shutters
- Flooring: Hardwood,Tile,Vinyl,Wood
- Number of fireplaces: 2
- Fireplace features: Family Room
- Fireplace: Yes
- Attic: Partial
Heating & Cooling
- Heating features: Electric,Steam
- Cooling features: Wall/Window Unit(s)
Interior Area
- Total structure area: 4,965
- Total interior livable area: 4,965 sqft
Property
Details
- Parcel number: 3322011020000001062.2000000
- Special condition: None
Features
- Private pool: Yes
- Pool features: Fenced,In Ground,Outdoor Pool
- Patio & porch: Covered,Deck,Patio,Terrace
- Exterior features: Garden,Lighting,Mailbox,Rain Gutters
- Has spa: Yes
Lot
- Lot size: 2.70 Acres
- Features: Back Yard,Cleared,Corner Lot,Front Yard,Garden,Historic District,Landscaped,Near Public Transit,Near School,Paved,Private,Secluded
Parking
- Total spaces: 12
- Parking features: Detached,Driveway,Oversized
- Has uncovered spaces: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Winter Weather
- Cold Wave
- Hurricane
- Inland Flooding
- Lightning
- Strong Wind
How This Home’s Risks Compare
FEMA Declared Disasters in Orange County and New York
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $5,789 | $69,468 |
| Home Insurance * | $344 | $4,128 |
| Property Taxes | $1,927 | $23,124 |
| Electricity | $820 | $9,846 |
| Total | $8,880 | $106,560 |
Income You'd Need if You Spent...
New York FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-05-05 | Listed for sale | $1,195,000 |
| 2026-05-05 | Listing removed | $1,195,000 |
| 2026-04-30 | Listed for sale | $1,195,000 |
| 2025-11-11 | Listing removed | $6,495 |
| 2025-10-02 | Listed for rent | $6,495 |
| 2023-11-12 | Listing removed | -- |
| 2023-10-21 | Listed for rent | $6,450 |
| 2023-07-01 | Listing removed | -- |
| 2023-06-05 | Listed for sale | $995,000 |
| 2022-12-28 | Listing removed | -- |
| 2022-11-28 | Listed for sale | $1,195,000 |
| 2022-10-05 | Listing removed | -- |
| 2022-09-28 | Listed for rent | $10,000 |
| 2022-08-05 | Listing removed | -- |
| 2022-06-27 | Listed for sale | $995,000 |
| 2022-05-03 | Sold | $341,661 |
| 2021-02-26 | Listing removed | -- |
| 2021-01-02 | Listed for rent | $12,500 |
| 2020-11-13 | Sold | $650,000 |
| 2020-07-18 | Listed for sale | $669,000 |
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