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150 Old Farm Road N

Chappaqua, NY 10514

  • $4,500,000
  • 5 Beds
  • 5/2 Baths
  • 7,608 Sqft
  • 4.45 Acres
  • 1906 Built

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!

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Property Highlights
  • BUYER BROKER COMPENSATIONInfo : 2.5%
  • SCHOOL DISTRICT : Chappaqua
  • ELEMENTARY : Douglas G. Grafflin
  • STYLE : Carriage House
  • MUNICIPALITY : Chappaqua
  • VIEW : Mountain(s), Panoramic
  • PRICE/SQFT : $591
  • DAYS ON MARKET : 8
  • MLS : 950756
  • TAXES : $56,820
  • Joanna Rizoulis

    Joanna Rizoulis

    Licensed Associate Real Estate Broker
    M
    View My Profile
  • Amy Smith-Sroka

    Amy Smith-Sroka

    Licensed Associate Real Estate Broker
    M
    View My Profile

Additional Information

ADDITIONAL INFORMATION
  • DAYS ON MARKET: 8
  • ELEMENTARY SCHOOL: Douglas G Grafflin School
  • ELEMENTARY SCHOOL DISTRICT: Chappaqua
  • HIGH SCHOOL: Horace Greeley High School
  • MIDDLE SCHOOL: Robert E Bell School
  • ON MARKET DATE: 2026-03-01
  • SEWER: Septic Tank
  • STYLE: Carriage House
  • TYPE: Residential
  • UTILITIES: Electricity Connected, Water Connected
  • VIEW: Mountain(s), Panoramic
  • YEAR BUILT: 1906
INTERIOR FEATURES
  • APPLIANCES INCLUDED: Cooktop, Dishwasher, Dryer, Gas Cooktop, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
  • BEDS: 5
  • COOLING: Central Air
  • FLOORING: Carpet, Ceramic Tile, Hardwood, Tile
  • FULL BATHS: 5
  • HEAT: Forced Air, Oil
  • INTERIOR FEATURES: Beamed Ceilings, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chandelier, Entrance Foyer, High Ceilings, Kitchen Island, Open Floorplan, Recessed Lighting, Soaking Tub, Storage, Walk-In Closet(s), Wet Bar
  • LIVING AREA SQFT: 7608
  • ROOMS: 14
EXTERIOR FEATURES
  • CONSTRUCTION MATERIALS: Stone
  • EXTERIOR FEATURES: Courtyard, Tennis Court(s), Deck, Patio, Terrace, Pool (In Ground, Pool/Spa Combo, Private)
  • PARKING: Attached, Driveway, Garage, Heated Garage
ASSESSED VALUE AND TAXES
  • TAX AMOUNT: $56,819

Listing Courtesy of Joanna Rizoulis of Julia B Fee Sothebys Int. Rlty (914.234.0200).

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Location for 150 Old Farm Road N, Chappaqua, NY

Community

Chappaqua>

Chappaqua

Westchester County, New York

Chappaqua, a quiet residential hamlet in the midpoint of Westchester County, is noted for its wooded winding roads and privately situated Westchester County real estate offerings. Located in the town of...

Request More Info for 150 Old Farm Road N, Chappaqua, NY

  • Joanna Rizoulis

    Joanna Rizoulis

    Licensed Associate Real Estate Broker
    M
    View My Profile
  • Amy Smith-Sroka

    Amy Smith-Sroka

    Licensed Associate Real Estate Broker
    M
    View My Profile
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