150 Old Farm Road N • Chappaqua, NY 10514

$4,500,000 • Beds: 5 • Baths: 5 full 2 partial • Sq. Feet: 7608 • MLS ID: 950756 • Subdivision: • School Dist: Chappaqua
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! View this listing at: http://kathleenmyers.laffey.com/mls=950756

Property Features

  • Garage: 2
  • Taxes: $56,819
  • Fenced: Yes
  • Formal Dining: Yes
  • Swimming Pool: Yes
  • Exterior: Stone
  • Special View Info: Mountain(s),Panoramic
  • Lot Size: 4.45 Acres
  • Heating: Forced Air,Oil
  • Cooling: Central Air
  • Year Built: 1906
  • Fireplaces: 2
  • Security: yes
  • Water: Public
  • Sewer: Septic Tank
  • On Market Date: 2026-03-01
  • Appliances: Cooktop,Dishwasher,Dryer,Gas Cooktop,Microwave,Oven,Refrigerator,Stainless Steel Appliance(s),Washer
  • Building Area Total: 11603
  • Exterior Features: Courtyard,Tennis Court(s)
  • Fencing: Fenced
  • Fireplace Features: Family Room,Gas,Living Room,Masonry,Wood Burning
  • Fireplace Y/N: Yes
  • Flooring: Carpet,Ceramic Tile,Hardwood,Tile
  • GarageY/N: Yes
  • Interior Features: Beamed Ceilings,Built-in Features,Cathedral Ceiling(s),Ceiling Fan(s),Chandelier,Entrance Foyer,Formal Dining,High Ceilings,Kitchen Island,Open Floorplan,Primary Bathroom,Recessed Lighting,Soaking Tub,Storage,Walk-In Closet(s),Wet Bar
  • Laundry: Laundry Room
  • Lot Features: Back Yard,Cul-De-Sac,Front Yard,Landscaped,Near School,Secluded,Views,Waterfront
  • Other Structures: Pergola
  • Parcel Number: 3489-099-016-00002-010-0000
  • Parking Features: Attached,Driveway,Garage,Heated Garage
  • Patio And Porch: Deck,Patio,Terrace
  • Pool Features: In Ground,Pool/Spa Combo
  • Rental Term: Monthly
  • Rooms Total: 14
  • Security Features: Fire Alarm,Security System,Smoke Detector(s),Video Cameras
  • Spa Y/N: Yes
  • Utilities: Electricity Connected,Water Connected
  • Waterfront Features: Pond

School Information

  • High School: Horace Greeley High School
  • Middle School: Robert E Bell School
  • Elementary School: Douglas G Grafflin School
  • School District: Chappaqua
Printed March 05, 2026

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