Xavier Cherniak
Licensed Real Estate Salesperson
REALTOR®
Sidney, NY
Office: (607) 604-4394 (607) 429-9989

259 Westchester Avenue , Pound Ridge, NY 10576

New - 4 Hours Ago

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Property Description

Originally built in 1860 as the Samuel Parker House, this extraordinary property has been thoughtfully transformed into a one-of-a-kind luxury live/work compound featuring a main residence, a street-level showroom, and a heated, air-conditioned barn with a private studio above. Set in the heart of Pound Ridge's charming hamlet, directly across from The Inn at Pound Ridge by Jean-Georges, it offers a rare blend of historic character, modern functionality, and exceptional lifestyle appeal.Following a complete, no-compromise 2019 renovation under acclaimed New York interior designer Jenny Wolf of The Huntress, every element, infrastructure, mechanical systems, and all interiors alike - was reimagined to honor the homes history while delivering modern luxury. The result adapts effortlessly to almost any life: full time residence, weekend retreat, designer showroom, creative studio, gallery, or true live/work estate, creating a home that is as functional as it is beautiful. The beautifully finished street-level space offers remarkable flexibility and may continue as an inspiring showroom or seamlessly become part of the residence, creating expansive living and entertaining areas.The private upper-level home is filled with warmth and character, where soaring vaulted beamed ceilings, abundant natural light, and timeless architectural details create an atmosphere of understated elegance. A spacious great room anchors the residence, complemented by a beautifully appointed kitchen with soapstone countertops, a serene primary suite with a walk-in closet, two additional bedrooms, and thoughtfully designed baths that reflect the home's refined aesthetic.Adding to the property's exceptional appeal is a heated and air-conditioned barn offering endless possibilities. With an expansive first level ideal for a showroom, studio, workshop, entertaining, business use, or storage, and a spacious second-level studio or office, it is a rare complement to an already extraordinary offering.Life here extends far beyond the property itself. Spend mornings walking the picturesque hamlet, enjoy world-class dining just steps away at The Inn at Pound Ridge by Jean-Georges, explore nearby hiking trails, nature preserves, and equestrian estates, or simply embrace the quiet beauty and timeless charm that define Pound Ridge. Located within the highly regarded Katonah-Lewisboro School District and just over an hour from Manhattan, this is a rare opportunity to experience a lifestyle where history, design, creativity, and modern luxury exist

259 Westchester Avenue | MLS# 1029454

This commercial property located at 259 Westchester Avenue , Pound Ridge, NY 10576 is currently listed for sale with an asking price of $2,350,000. Westchester Avenue is located within the Bedford school district. Search Pound Ridge real estate on xavier-cherniak.timberlandproperties.com today.

Gallery

Property Features

Property Type: Commercial - Multiple
Basement: Yes
Basement: Unfinished
Cooling: Central Air
Fenced: Yes
Heating: Forced Air, Propane
Lot Size: 0.27 Acres
Taxes: $23,961
Year Built: 1860

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Range
Building Area Total: 4225
Business Type: Retail
Exterior: Frame
Fencing: Fenced
Flooring: Hardwood
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
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

Demographics

Listed By / Shown By

Listing By

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

Shown By

Agent Name: Xavier Cherniak
Agent Phone: (607) 429-9989
Agency Title: Timberland Properties

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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 07/22/2026. The listing information on this page last changed on 07/22/2026. 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 07/22/2026 12:02:19 AM EST) or Global MLS (last updated Tue 07/21/2026 11:52:27 PM EST) or New York State Alliance MLS (last updated Tue 07/21/2026 11:58:58 PM EST) or Hudson Valley Catskill Region MLS (last updated Wed 07/22/2026 12:01:12 AM EST) or OneKey MLS (last updated Wed 07/22/2026 12:00:27 AM 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.

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