$1,145,000
- 9
- beds
- 6 full · 1 half
- baths
- 4,965
- sqft
- 1850
- year built
- 9
- beds
- 6 full · 1 half
- baths
- 4,965
- sqft
- 1850
- year built
- Status:
- Active
- MLS #:
- 995148
- County:
- Orange
- Listed By:
- Beth Palma - Keller Williams Realty
- Office Phone:
- (845) 928-8000
- Agent Email:
- bethpalma@kw.com
Sponsoring Broker: Steven Domber, Berkshire Hathaway HomeServices Hudson Valley Properties
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.
Highlights
- Residential
- Single Family Residence
- Built in 1850
- 2.7 Acre Lot
- 188 days on Market
-
- Bedrooms
- 9
-
- Bathrooms
- 6 full · 1 half
-
- Year Built
- 1850
-
- Architectural Style
- Farmhouse, Colonial, Victorian
-
- Construction Materials
- Frame, Vinyl Siding, Blown-In Insulation
-
- Parking Features
- Driveway, Oversized, Detached
-
- Living Area
- 4965.0
-
- Interior Features
- Eat-in Kitchen, Walk-In Closet(s), Kitchen Island, Breakfast Bar, High Ceilings, Crown Molding, Built-in Features, Soaking Tub, Chandelier
-
- Appliances
- Dryer, Dishwasher, Microwave, Refrigerator, Washer, Range, Gas Range, Oven, Gas Water Heater, Stainless Steel Appliance(s)
-
- Flooring
- Hardwood, Tile, Vinyl, Wood
-
- Exterior Features
- Lighting, Balcony, Rain Gutters, Garden
-
- Patio And Porch
- Covered, Patio, Deck, Terrace
-
- Pool Features
- Fenced, In Ground, Private, Outdoor Pool
-
- Cooling
- Wall/Window Unit(s)
-
- Heating
- Natural Gas, Electric, Wood Stove, Steam
-
- Basement
- Full, Unfinished, Storage Space
-
- Acres
- 2.7
-
- Lot Features
- Cleared, Corner Lot, Secluded, Private, Garden, Landscaped, Back Yard, Front Yard, Near Public Transit, Paved
-
- Utilities
- Cable Available, Sewer Available, Electricity Available, Water Available, Natural Gas Available, Natural Gas Connected, Electricity Connected, Sewer Connected, Water Connected
-
- Water
- Public
-
- County
- Orange
-
- City
- Chester
-
- Zip Code
- 10918
-
- High School
- Chester Academy-Middle/High School
-
- Middle School
- Chester Academy-Middle/High School
-
- Elementary School
- Chester Elementary School
-
Ask a Question
.png/){kind=logo}
ez Mortgage Calculator
Enter your details below to estimate your monthly mortgage payment with taxes, fees and insurance.
Please enter a valid number
Cost of the current home: $1145000
Please enter a valid number
Cash you pay when you close
Affects interest rates. 30- or 15- year loans are standard.
Default rate is illustrative, set internally by ez Home Search and updated periodically; actual rates vary by lender, credit score, and market conditions.
Please enter a valid number
Please enter a valid number
Typically 0.25% of home value per year.
Please enter a valid number
Homeowners association dues.
$ 0
Monthly
Principal and interest:
Property Taxes:
Homeowners Insurance:
HOA Dues:
$0 (0%)
$0 (0%)
$0 (0%)
$0 (0%)
The ez Mortgage Calculator is for educational purposes only. Real-world interest rates and payments can differ due to factors like market trends, location, and loan specifics. Calculations are based on your inputs and might not consider extra costs a lender may add, such as insurance, taxes, and fees; thus, actual repayments could surpass estimates. Please note, ez Home Search does not provide loans, and this tool does not promise lending.
Price History
| 11/02/2026 | Price Changed | $6,950 |
| Source: OneKey MLS #1060955 | ||
| 10/09/2026 | Listed | $7,250 |
| Source: OneKey MLS #1060955 | ||
| 06/26/2026 | Price Changed | $1,145,000 |
| Source: OneKey MLS #995148 | ||
| 05/05/2026 | Listed | $1,195,000 |
| Source: OneKey MLS #995148 | ||
| 04/30/2026 | Off Market | — |
| Source: OneKey MLS #992878 | ||
| 04/29/2026 | Off Market | — |
| Source: OneKey MLS #972335 | ||
| 11/10/2023 | Sold | $9,450 |
| Source: OneKey MLS #H6274513 | ||
| 10/19/2023 | Listed | $9,450 |
| Source: OneKey MLS #H6274513 | ||
| 10/19/2023 | Off Market | — |
| Source: OneKey MLS #H6274513 | ||
| 11/13/2020 | Sold | $650,000 |
| Source: OneKey MLS #H6046010 | ||
| 07/17/2020 | Listed | $669,000 |
| Source: OneKey MLS #H6046010 | ||
| 07/17/2020 | Off Market | — |
| Source: OneKey MLS #H6046010 | ||
Source: MLS Data
Deed History
| 05/03/2022 | Deed | $0 |
| 05/03/2022 | Deed | $341,661 |
| 12/17/2020 | Deed | $650,000 |
| 12/03/2013 | Deed | $0 |
Source: Public records via Constellation Data Labs
Mortgage History
| 05/03/2022 | Stand Alone Refi (Refinance of Original Loan) | $585,000 |
| 12/17/2020 | Purchase Money Mortgage | $585,000 |
| 09/20/2000 | Credit Line (Revolving) / HELOC | $100,000 |
Source: Public records via Constellation Data Labs
What's your home worth?
Calculate your current home value within seconds.
Frequently Asked Questions
How do I schedule a tour of 19 High St?
We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 19 High St.
They know residentials in the area well and can give you the guidance you need to buy with confidence.
How do I get more information about 19 High St?
Click Ask a Question to talk with our team. You already know it is a 9 bed, 6 bath, listed for $1,145,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Chester, and can even get you in to see the property quickly.
How do I get a virtual tour of 19 High St?
Yes! A virtual tour is available for 19 High St. Click here to view the full walkthrough and explore every room at your own pace. If you would like a guided virtual showing or have questions along the way, we can connect you with our local expert to walk you through it live.
How much is the monthly mortgage payment for 19 High St?
With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 19 High St at around $8,124. This includes estimated property taxes and insurance.
Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.
How do I get pre-approved to buy 19 High St?
Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.
Or, let us connect you with our preferred local lender in Orange County. They will give you all of your available financing options, based on your specific situation and what is available to you.
Can I negotiate the asking price for 19 High St?
In most cases, yes. Whether 19 High St is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Chester's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.
How do I make an offer on 19 High St?
We can handle that for you. Our preferred local agent specializes in residentials in Chester and can guide you through every step of the offer process.
You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.
What is the price per square foot for this home?
This home is listed at $1,145,000 with 4,965 sqft of space—that comes out to approximately $231 per square foot.
How long has this property been on the market?
19 High St was listed on May 05, 2026, which means it's been on the market for 188 days.
Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.
When was this house built?
This home was built in 1850, making it approximately 176 years old.
What is the lot size of this property?
19 High St sits on a 2.7-acre lot, which is 117,612 square feet.
What schools are assigned to this property?
Based on MLS info, this home is zoned for:
- Elementary: Chester Elementary School
- Middle: Chester Academy-Middle/High School
- High: Chester Academy-Middle/High School
Want to see how these schools compare? Check out our Orange County School Guide to see ratings, reviews, and more for the schools in the area.
What are the property taxes for 19 High St?
The most recent public record shows annual property taxes for 19 High St were approximately $19,292. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.
Is 19 High St still available for sale?
Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.
Source: ez Home Search, MLS Data
Popular Home Searches in Chester, NY
Open Houses Near Chester, NY
Land for Sale Near Chester, NY
Townhomes for Sale Near Chester, NY
Waterfront Homes for Sale Near Chester, NY
Waterfront Condos for Sale Near Chester, NY
Homes with Pools for Sale Near Chester, NY
Gated Community Homes for Sale Near Chester, NY
Homes with No Hoa for Sale Near Chester, NY
Homes in Adult Communities for Sale Near Chester, NY
Search Nearby Cities
Search Nearby Counties
Search Nearby Postal Codes
Listing information 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. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.
Last Updated: November 09, 2026 at 01:14PM | Source: OneKey MLS | MLS#: 995148
