150 Old Farm RD Chappaqua, NY 10514 Active

UPDATED: 03/02/2026 10:01 AM ON MARKET: 12 days on market

$4,500,000

5 Beds7 Baths7,608 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 7,608 sqft

Price per Sqft $591

MLS Listing ID 950756

Style Carriage House

Bedrooms 5

Full Baths 5

Half Baths 2

HOA Y/N No

Rental Info No

Year Built 1906

Annual Tax Amount $56,819

Lot Size 4.450 Acres

Acres 4.45

Property Sub-Type Single Family Residence

Source onekey2

Property Description

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!