63-73 Old Chester rd Old Chester Road

A Rare Multi-Generational Compound with Verified Historic Pedigree — Goshen, New York Set on 10.4 rolling acres in the heart of Orange County's storied horse country, this remarkable six-residence compound offers a truly singular combination of history, character, and income diversity rarely found in the Hudson Valley market. Anchored by a main dwelling dating to 1860 and a beautifully preserved two-story barn built in 1861, the property carries a documented pedigree that few estates can claim: it was once home to legendary Parisian art dealer Paul Rosenberg, the internationally renowned champion of modern art and dealer to Picasso, Braque, and Matisse, and later to Henry Herman Westinghouse, engineer, industrialist, and brother of inventor George Westinghouse — a legacy reflected in the property's own name, Westinghouse Farm. Spanning over 12,000 square feet across six thoughtfully maintained and appointed residences, the compound blends timeless architectural character — original wood exterior, hand-hewn barn framing, hot water steam heat, and classic period details — with the kind of ongoing care and updates that today's buyers expect. Each residence has been maintained to a high standard, and the grounds reflect the same attention to detail throughout. What truly distinguishes this offering is its diversified and resilient income profile. Four of the six residences (#67, #69, #71, and #73) have been home to long-term tenants for years, providing the kind of dependable, established rental history that speaks to strong financial character and low turnover risk. The remaining two residences (#63 and #65) operate as licensed short-term rentals under an active Orange County Hotel and Motel Occupancy Tax Certificate of Authority, with a well-documented multi-year booking history on major platforms. Rounding out the offering are two additional income components — the Butterhouse Storage building and the Doghouse Shop, the latter offering clear upside potential as a future rental conversion. This is a compound built for flexibility. It will appeal equally to the sophisticated investor seeking a diversified, multi-stream income property with a compelling historic story, and to the owner-operator who envisions living in one of the residences while continuing — and potentially expanding — the established short-term rental business across the balance of the property. Either path offers a rare opportunity to own a piece of documented Hudson Valley history with a proven, adaptable income foundation beneath it. Ideally located in Goshen — home to LEGOLAND New York and long known as the "Cradle of the American Trotting Horse" — the property offers easy access to Route 17 and the NY State Thruway, with Manhattan roughly an hour's drive away and Metro-North's Port Jervis Line accessible via the nearby Middletown-Town of Wallkill station. Few properties on the market today offer this rare intersection of verified history, architectural character, and genuine income diversity — all within reach of New York City.