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: Owned by Henry Herman Westinghouse, engineer, industrialist, and brother of inventor George Westinghouse — a legacy reflected in the property's own name, Westinghouse Farm. 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.
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 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. There has been 7 years of continuous SUPER HOST STATUS ranked in the top 5% in guest reviews. 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 Campbell Hall Station and 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.
For sale
$2,999,999
63-73 Old Chester Road, Goshen, NY 10924
17beds
12,128sqft
Single Family Residence, Residential
Built in 1860
10.4 Acres Lot
$-- Zestimate®
$247/sqft
$-- HOA
What's special
Classic period detailsButterhouse storage buildingHand-hewn barn framingOriginal wood exteriorDoghouse shop
- 5 days
- 215
- 8
Zillow last checked:
Listing updated:
Listed by:
Hudson Valley Realty & Busines 845-629-2223,
Steven Brown 845-629-2223
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1051458
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 17
- Bathrooms: 10
- Full bathrooms: 9
- 1/2 bathrooms: 1
Heating
- Oil
Cooling
- Ductless, Multi Units
Appliances
- Included: Other, Range, Refrigerator
Features
- Beamed Ceilings, Natural Woodwork, Original Details
- Basement: See Remarks
- Attic: See Remarks
- Has fireplace: Yes
Interior area
- Total structure area: 12,182
- Total interior livable area: 12,128 sqft
Property
Parking
- Parking features: Private
Features
- Has view: Yes
- View description: Mountain(s), Panoramic
Lot
- Size: 10.4 Acres
- Features: Near School, Near Shops, Private, Rolling Slope, See Remarks, Views
- Residential vegetation: Partially Wooded
Details
- Parcel number: 3330890080000001009.2120000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Farmhouse
- Property subtype: Single Family Residence, Residential
Materials
- Other
- Foundation: Other
Condition
- Updated/Remodeled
- Year built: 1860
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Connected, Electricity Connected, Propane, See Remarks
Community & HOA
HOA
- Has HOA: No
Location
- Region: Goshen
Financial & listing details
- Price per square foot: $247/sqft
- Annual tax amount: $24,843
- Date on market: 9/16/2026
- Cumulative days on market: 5 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 9/16/2026 | Listed for sale | $2,999,999$247/sqft |
Source: | ||
Public tax history
Tax history is unavailable.
Monthly payment
Climate risks
Neighborhood: 10924
Nearby schools
Schools provided by the listing agent
- Elementary: Chester Elementary School
- Middle: Chester Academy-Middle/High School
- High: Chester Academy-Middle/High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.



