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5 Beds
7 Baths
7,608 sqft

$4,500,000

150 Old Farm Road N, Chappaqua NY, 10514

Price per sqft$591.48
Built in1906
Property size7,608 sqft
Property typeResidential
Courtesy of Julia B Fee Sothebys Int. Rlty, Joanna Rizoulis Listing Contact: 917-359-7885

Overview

Active

Listed Mar 1, 2026

Updated 6h ago

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

$29,939/mo

Est. mortgage payment based on a $4,500,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
950756

Interior Features

Bedrooms
5
Bathrooms
7
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
4.45 Acres

Other Property Details

Taxes
$57,712
Tax Frequency
Annually
Garage
Yes
View
Yes
Pool
Yes
55+/Senior Community
No

Listings courtesy of OneKey MLS as distributed by MLS GRID

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Based on information submitted to the MLS GRID as of 1:32 PM UTC on 9/15/2026. 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.

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