Dana Robyn Chubb
Licensed Real Estate Salesperson, PSA
PSA, REALTOR®
Delhi, NY
Office: (607) 746-7400 (518) 522-6779
social icon 

259 Westchester Avenue, Pound Ridge, NY 10576

26 Photos

Property Description

A live/work compound in the heart of Pound Ridge, 259 Westchester Avenue brings together a sophisticated street-level showroom, designed three-bedroom residence, separate two-story studio barn, landscaped grounds, and off-street parking lot-directly across from The Inn at Pound Ridge by Jean-Georges. Originally built in 1860 as the Samuel Parker House, this property has been transformed into a flexible commercial and residential offering with the character, infrastructure, and versatility to support a wide range of owner-user, investment, and creative business uses.The property presents an opportunity for an owner-user, luxury retail or design brand, creative entrepreneur, studio or gallery operator, or investor seeking both income potential and long-term flexibility. Rather than a conventional commercial building, 259 Westchester Avenue offers multiple complementary components that can function together or independently: a prominent street-level commercial space, a three-bedroom residence above, and a separate heated and air-conditioned two-story barn.The street-level commercial space is currently configured as an elevated retail showroom, with wide-plank flooring, architectural ceilings, custom lighting, fitting room, office, design workspace, powder room, and kitchen. Its open, finished layout lends itself to a variety of commercial uses and provides a strong platform for retail, showroom, design, creative, office, gallery, or other owner-user concepts. The space offers flexibility for a future owner.Above the commercial space is a three-bedroom residence with soaring vaulted beamed ceilings, abundant natural light, a great room, appointed kitchen with soapstone countertops, primary suite with walk-in closet, two additional bedrooms, and thoughtfully designed baths. The residential component creates the opportunity to live directly above the business while maintaining separation between the two uses.A separate two-story barn further expands the property's commercial potential. Heated and air-conditioned, the barn offers a first level suitable for a showroom, studio, workshop, business use, inventory, receiving, storage, entertaining, or other permitted use, along with a second-level studio or office. The separation between the main commercial space, residence, and barn provides flexibility rarely found in a property of this scale and location.Professionally landscaped grounds, private garden and intimate outdoor entertaining areas provide additional space for client gatherings, private events, prod

259 Westchester Avenue | MLS# 1019874

This single family home located at 259 Westchester Avenue, Pound Ridge, NY 10576 is currently listed for sale with an asking price of $2,350,000. This property was built in 1860 and has 3 bedrooms and 2 full and 1 partial baths with 4250 sq. ft. Westchester Avenue is located within the Bedford school district. Search Pound Ridge real estate on dana-chubb.timberlandproperties.com today.

Gallery

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Unfinished
Cooling: Central Air
Fenced: Yes
Heating: Forced Air, Propane
Home Style: Other
Lot Size: 0.27 Acres
Taxes: $23,961
Year Built: 1860

Amenities

Beamed Ceilings
Galley Type Kitchen
High Ceilings
Open Floorplan
Soaking Tub
Stone Counters
Storage
Walk-In Closet(s)
Washer/Dryer Hookup
Awning(s)
Garden

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Range
Attic: Pull Stairs
Days on Site: 76
Exterior: Frame
Fencing: Fenced
Flooring: Hardwood
Laundry: Electric Dryer Hookup, Washer Hookup
Number Of Kitchens: 1
On Market Date: 2026-07-22
Other Structures: Barn(s)
Parcel Number: 4600-000-000-09820-032
Parking Features: Assigned, Detached, Driveway
Rental Term: Monthly
Rooms Total: 8
Security Features: Video Cameras
Sewer: Septic Tank
Utilities: Electricity Connected
Water: Well

Local Schools

High School: Fox Lane High School
Middle School: Fox Lane Middle School
Elementary School: Pound Ridge Elementary School
School District: Bedford

Estimate Your Payment

Estimated Payment

$ 7,912.25 per month $5,230.08 Principal & Interest $1,996.75 Property Tax $685.42 Homeowner's Insurance

Change Payment Information

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

Demographics

Listed By / Shown By

Listing By

Agency Name: Compass Greater NY, LLC
Agency Contact: 914-238-0676

Shown By

Agent Name: Dana Robyn Chubb
Agent Phone: (518) 522-6779
Agency Title: Timberland Properties

IDX logo

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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 on this site was last updated 10/07/2026. The listing information on this page last changed on 10/07/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 10/07/2026 12:00:47 AM EST) or Global MLS (last updated Tue 10/06/2026 8:13:18 AM EST) or New York State Alliance MLS (last updated Tue 10/06/2026 11:58:57 PM EST) or Hudson Valley Catskill Region MLS (last updated Tue 10/06/2026 11:51:15 PM EST) or OneKey MLS (last updated Tue 10/06/2026 11:53:19 PM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.




All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

Privacy Policy / DMCA Notice / ADA Accessibility

Login to My Homefinder