# 19 High Street, Chester, NY 10918 > **TL;DR:** 9bd/7ba single family, $1,145,000 ($231/sqft), built 1850, 4,965 sqft. > Pool, Spa, Fireplace, Hardwood. Est. $6,124/mo. Listed 175 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,145,000 | | Price/sqft | $231 | | Bedrooms | 9 | | Bathrooms | 6 full, 1 half | | Square Feet | 4,965 | | Year Built | 1850 | | Lot Size | 117,612 sqft (2.70 acres) | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 175 | ## Why This Home Stands Out - **Pool** - Deck, Patio - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $5,790 | | Estimated Insurance | $334 | | **Total** | **$6,124** | ## Nearby Schools - **Elementary:** Chester Elementary School - **Middle:** Chester Academy-Middle/High School - **High:** Chester Academy-Middle/High School ## Key Amenities - Pool - Spa - Fireplace - Hardwood - A/C ## Property Highlights - Built in 1850 - 2.70 acre lot - 12 parking spaces - Private pool - Fireplace ## Description ### Agent 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 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. ## Location - **Address:** 19 High Street, Chester, NY 10918 - **County:** Orange County - **Coordinates:** 41.363087, -74.274271 - **Google Maps:** https://www.google.com/maps?q=41.363087,-74.274271 ## Virtual Tour & Media - **Video Tour:** https://iframe.videodelivery.net/ac7f35cfb85d7c002be3b6b05013c32c ## Listing Agent - **Name:** Beth Palma - **Brokerage:** Keller Williams Realty - **Broker Phone:** (845) 928-8000 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/19-High-St_Chester_NY_10918_M47843-49552?f=listhub&s=MLSLINY&m=995148&c=propsimple) ## Photos ![19 High Street - Photo 1](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f4195610758r.jpg) ![19 High Street - Photo 2](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3258018682r.jpg) ![19 High Street - Photo 3](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3054396030r.jpg) ![19 High Street - Photo 4](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f146599955r.jpg) ![19 High Street - Photo 5](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f303327770r.jpg) ![19 High Street - Photo 6](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3631918402r.jpg) ![19 High Street - Photo 7](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f2407975019r.jpg) ![19 High Street - Photo 8](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3892573287r.jpg) ![19 High Street - Photo 9](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1611945526r.jpg) ![19 High Street - Photo 10](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f46160972r.jpg) ![19 High Street - Photo 11](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3157554002r.jpg) ![19 High Street - Photo 12](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f939809760r.jpg) ![19 High Street - Photo 13](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f2268255046r.jpg) ![19 High Street - Photo 14](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3375095521r.jpg) ![19 High Street - Photo 15](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f2908682006r.jpg) ![19 High Street - Photo 16](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f648783893r.jpg) ![19 High Street - Photo 17](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f677884278r.jpg) ![19 High Street - Photo 18](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f926857716r.jpg) ![19 High Street - Photo 19](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f4503809r.jpg) ![19 High Street - Photo 20](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f2048769576r.jpg) ![19 High Street - Photo 21](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1046230929r.jpg) ![19 High Street - Photo 22](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1533815226r.jpg) ![19 High Street - Photo 23](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1328183333r.jpg) ![19 High Street - Photo 24](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1946858147r.jpg) ![19 High Street - Photo 25](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3692860472r.jpg) ![19 High Street - Photo 26](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f906887302r.jpg) ![19 High Street - Photo 27](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f722957410r.jpg) ![19 High Street - Photo 28](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1073184421r.jpg) ![19 High Street - Photo 29](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3987499581r.jpg) ![19 High Street - Photo 30](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3005131077r.jpg) ![19 High Street - Photo 31](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1535594079r.jpg) ![19 High Street - Photo 32](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3118689857r.jpg) ![19 High Street - Photo 33](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f529559534r.jpg) ![19 High Street - Photo 34](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f2304285962r.jpg) ![19 High Street - Photo 35](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f431244493r.jpg) ![19 High Street - Photo 36](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f4237258306r.jpg) ![19 High Street - Photo 37](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3971415939r.jpg) ![19 High Street - Photo 38](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3878757990r.jpg) ![19 High Street - Photo 39](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3578955674r.jpg) ![19 High Street - Photo 40](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f2193273878r.jpg) ![19 High Street - Photo 41](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3842323537r.jpg) ![19 High Street - Photo 42](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1499675026r.jpg) ![19 High Street - Photo 43](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1095111709r.jpg) ![19 High Street - Photo 44](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f918694394r.jpg) ![19 High Street - Photo 45](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f1258511281r.jpg) ![19 High Street - Photo 46](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3614420014r.jpg) ![19 High Street - Photo 47](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f60790202r.jpg) ![19 High Street - Photo 48](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f2473634545r.jpg) ![19 High Street - Photo 49](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f3303410129r.jpg) ![19 High Street - Photo 50](http://lh.rdcpix.com/ba3f94f8953f93865b35c5338cc23ed9l-f537851935r.jpg) --- **MLS#:** 995148 | **Updated:** 2026-10-22 **Source:** listhub *Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/19-high-street-chester-ny-10918-c2b4cb586c6f431ca8b5804fa5336769) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/19-high-street-chester-ny-10918-c2b4cb586c6f431ca8b5804fa5336769#listing", "url": "https://staging.propertysimple.ai/listing/19-high-street-chester-ny-10918-c2b4cb586c6f431ca8b5804fa5336769", "name": "19 High Street, Chester, NY 10918", "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 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. 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