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150 Old Farm Road N

$4,500,000

Est. $27,175/mo

Chappaqua, NY 10514 · Westchester County

Beds
5
Baths
6
Sqft
7,608
Status
Active
On site
200 days

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About this home

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!

Listed with Julia B Fee Sothebys Int. Rlty · Joanna Rizoulis · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 3:09 PM ET. ©2026 One Key MLS.

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$27,175.15Total / mo

Estimated Monthly Payment

Principal & interest
$22,165.82 (81.6%)
Taxes
$4,809.33 (17.7%)
Insurance
$200.00 (0.7%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

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Market Insights

The market around Chappaqua, NY

Current Listings

New in the last 30 days

8

Sep 2026

Average Price

Active listings

$1,857,441

Sep 2026

Average Days on Market

Active listings

92 days

Sep 2026

Computed from 34 active OneKey MLS listings in Chappaqua, NY.

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