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Dan Smalley
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63-73 Old Chester Rd Old Chester Road , Goshen, NY 10924

$2,999,999
  • 63-73 Old Chester Rd Old Chester Road , Goshen, NY 10924 Main Photo
New to the Market Active
BEDS17 BATHS9 full 1 partial SQUARE FEET12,128 MLS#1051458
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLChester

Property Description

A Rare Multi-Generational Compound with Verified Historic Pedigree - Goshen, New YorkSet 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 beneat

63-73 Old Chester Rd Old Chester Road | MLS# 1051458

This single family home located at 63-73 Old Chester Rd Old Chester Road , Goshen, NY 10924 is currently listed for sale with an asking price of $2,999,999. This property was built in 1860 and has 17 bedrooms and 9 full and 1 partial baths with 12128 sq. ft. 63-73 Old Chester Rd Old Chester Road is located within the Chester school district. Search Goshen real estate on www.dansmalleyrealtor.com today.

Property Features

Property Type: Residential - Single Family
Basement: See Remarks
Cooling: Ductless, Multi Units
Heating: Oil
Home Style: Farmhouse
Lot Size: 10.40 Acres
Taxes: $24,843
Year Built: 1860

Amenities

Beamed Ceilings
Natural Woodwork
Original Details

Feature Descriptions

Appliances: Other, Range, Refrigerator
Building Area Total: 12182
Exterior: Other
Fireplace Y/N: Yes
Lot Features: Near School, Near Shops, Part Wooded, Private, Rolling Slope, See Remarks, Views
On Market Date: 2026-09-16
Parcel Number: 333089-008-000-0001-009.212-0000
Parking Features: Private
Rental Term: Monthly
Road Responsibility: Private Maintained Road
Rooms Total: 36
Sewer: Septic Tank
Special View Info: Mountain(s), Panoramic
Utilities: Cable Connected, Electricity Connected, Propane, See Remarks
Water: Well
Wooded: Yes

Local Schools

High School: Chester Academy-Middle/High School
Middle School: Chester Academy-Middle/High School
Elementary School: Chester Elementary School
School District: Chester

Estimate Your Payment

Estimated Payment

$ 18,114.88 per month $15,169.63 Principal & Interest $2,070.25 Property Tax $875.00 Homeowner's Insurance

Change Payment Information

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years/fixed
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yearly (est.)
(Payments are an estimate and may vary by lender)

Listed By / Shown By

Listing By

Agency Name: Hudson Valley Realty & Busines
Agency Phone: 845-629-2223

agent picture

Shown By

Agent Name: Dan Smalley
Agent Phone: Cell: (631) 469-8957
Agency Title: Coldwell Banker American Homes

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