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259 Westchester AvenuePound Ridge, NY 10576

For Sale

$2,350,000

Smart Buyer Rebate $23,500

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 in perfect harmony.

Properties of this caliber rarely come to market. Rich in history, impeccably renovated, and genuinely unlike anything else available today, this is a singular opportunity to own one of Pound Ridge's most distinctive homes.

Listed by Jan Pierre Chavez

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Compass Greater NY, LLC

·

914-238-0676

Listed by Nicole Biello

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Compass Greater NY, LLC

Last updated September 15, 2026

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Source: OneKey #1019874

Listing Facts

  • TypeSingle-family
  • NeighborhoodPound Ridge
  • Bedrooms3
  • Bathrooms3
  • Days on Prevu55
  • Taxes$23,961.86/year
  • Size4,250 sqft
  • Price per sqft$553

Amenities

  • Dishwasher
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

08/18/2026
Status changed to Active
$2,350,000
08/14/2026
Status changed to Canceled
$2,350,000
08/12/2026
Status changed to Temporarily Off Market
$2,350,000
07/22/2026
Listed by Compass Greater NY, LLC
$2,350,000
  1. 08/18/2026$2,350,000
    Status changed to Active
  2. 08/14/2026$2,350,000
    Status changed to Canceled
  3. 08/12/2026$2,350,000
    Status changed to Temporarily Off Market
  4. 07/22/2026$2,350,000
    Listed by Compass Greater NY, LLC

Property Details for 259 Westchester Avenue

Exterior

Construction

  • Property Condition: Updated/Remodeled
  • Year Built: 1860
  • Architectural Style: Other
  • Construction Materials: Frame
  • Exterior Features: Awning(s)

Features

  • Fencing: Fenced
  • Other Structures: Barn(s)

Measurements

  • Building Area Units: Square Feet
  • Lot Size Acres: 0.27
  • Lot Size Square Feet: 11,761

Financial

Taxes

  • Parcel Number: 4600-000-000-09820-032
  • Tax Annual Amount: $23,961.86
  • Tax Assessed Value: $165,700.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Dishwasher, Dryer, Electric Range
  • Flooring: Hardwood
  • Interior Features: Beamed Ceilings, Galley Type Kitchen, High Ceilings, Open Floorplan, Soaking Tub, Stone Counters, Storage, Walk-In Closet(s), Washer/Dryer Hookup

Measurements

  • Living Area: 4,250
  • Living Area Source: Public Records

Rooms

  • Basement: Unfinished
  • Has Basement: Yes
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 3
  • Rooms Total: 8

Parking

Parking

  • Parking Features: Assigned, Detached, Driveway
  • Parking Total: 9

Schools

Elementary School

  • Elementary School: Pound Ridge Elementary School
  • Elementary School District: Bedford

High School

  • High School: Fox Lane High School
  • High School District: Bedford

Middle or Junior School

  • Middle Or Junior School: Fox Lane Middle School
  • Middle Or Junior School District: Bedford

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Forced Air, Propane
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Sewer: Septic Tank
  • Utilities: Electricity Connected
  • Water Source: Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 3 bedrooms and 3 bathrooms in this single-family home at 259 Westchester Avenue.

What schools are nearby to 259 Westchester Avenue?

Nearby schools include the Pound Ridge Elementary School, Fox Lane Middle School, and Fox Lane High School.

Does this single-family home have parking?

Yes, there are 9 parking spaces available for 259 Westchester Avenue.

What are the annual taxes for 259 Westchester Avenue?

Annual taxes for this single-family home are estimated at $23,961.

How does 259 Westchester Avenue compare to other single-family homes in Pound Ridge?

This single-family home is listed 22% below the average price for single-family homes in Pound Ridge and has been on the market for 12 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 4,250 sqft.

259 Westchester Avenue is a 3-bedroom, 3-bath single-family home for sale in Pound Ridge NY 10576. On Prevu for 55 days at $2,350,000. This home features 4,250 square feet of living space, located in Pound Ridge. The median listing price for single-family homes in this area is $2,504,495. Nearby schools include Pound Ridge Elementary School, Fox Lane Middle School, and Fox Lane High School. Additional amenities include dishwasher, air conditioning, parking, and washer/dryer. View other single-family home listings in Westchester County.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey™ MLS. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. Information Copyright 2026, OneKey™ MLS. All Rights Reserved.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.