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150 Old Farm Rd N

chappaqua, NY 10514

$4,500,000

  • 5 BR
    5 BA, 2 HALF BA
    approx. 7,608 SF

Interested? Let's Connect

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!

Details

7,608 Sq Ft

4.45 Private Acres Lot Size

single family home

$4,735 Monthly Tax

Built in 1906

MLS/Listing ID 950756

Amenities & Features

Style - Carriage House

Ceiling Fans

Lot - Back Yard

Lot - Near School

Septic System

Public Water

Tennis Courts

Courtyard

Fenced

Wood Burning Fireplace

Masonry Fireplace

Living Room Fireplace

Gas Fireplace

Family Room Fireplace

Tile

Hardwood

Ceramic Tile

Carpet

Stone

Heating - Oil

Heating - Forced Air

Wet Bar

Walk-in Closets

Storage

Soaking Tub

Recessed Lighting

Open Floor Plan

Washer

Refrigerator

Oven

Microwave

Gas Cooktop

Dryer

Dishwasher

Cooktop

Construction - Stone

Cooling - Central Air

Lot - Cul-de-sac

Lot - Front Yard

Lot - Landscaped

Lot - Secluded

Lot - Views

Lot - Waterfront

Parking - Heated Garage

Parking - Garage

Parking - Driveway

Parking - Attached

Terrace

Patio

Deck

Pool Spa Combo

Pool - Inground

Panoramic View

Mountains View

Pond

Laundry Room

Beamed Ceilings

Built-in Features

Cathedral Ceilings

Chandelier

Entrance Foyer

High Ceilings

Kitchen Island

Stainless Steel Appliance(s)

Estimate my mortgage

TOTAL MONTHLY COST

$0

  • PRINCIPAL & INTEREST

    $0

  • PROPERTY TAXES

    $0

  • Common Charges

    $0

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DOWN PAYMENT
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