Ashlyn Ouimet
Licensed Real Estate Salesperson
REALTOR®
Sidney, NY
Office: (607) 604-4394
(607) 316-3923
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!
150 Old Farm Road N | MLS# 950756
This single family home located at 150 Old Farm Road N, Chappaqua, NY 10514 is currently listed for sale with an asking price of $4,500,000. This property was built in 1906 and has 5 bedrooms and 5 full and 2 partial baths with 7608 sq. ft. Old Farm Road N is located within the Chappaqua school district. Search Chappaqua real estate on ashlyn-ouimet.timberlandproperties.com today.
Gallery
Property Features
Property Type: Residential - Single Family
Cooling: Central Air
Fenced: Yes
Fireplaces: 2
Garage: 2
Heating: Forced Air, Oil
Home Style: Carriage House
Lot Size: 4.45 Acres
Taxes: $56,819
Year Built: 1906
Amenities
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
Courtyard
Tennis Court(s)
Feature Descriptions
Appliances: Cooktop, Dishwasher, Dryer, Gas Cooktop, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
Building Area Total: 11603
Days on Site: 4
Exterior: Stone
Fencing: Fenced
Fireplace Features: Family Room, Gas, Living Room, Masonry, Wood Burning
Fireplace Y/N: Yes
Flooring: Carpet, Ceramic Tile, Hardwood, Tile
Formal Dining: Yes
GarageY/N: Yes
Laundry: Laundry Room
Lot Features: Back Yard, Cul-De-Sac, Front Yard, Landscaped, Near School, Secluded, Views, Waterfront
On Market Date: 2026-03-01
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: yes
Security Features: Fire Alarm, Security System, Smoke Detector(s), Video Cameras
Sewer: Septic Tank
Spa Y/N: Yes
Special View Info: Mountain(s), Panoramic
Swimming Pool: Yes
Utilities: Electricity Connected, Water Connected
Water: Public
Waterfront Features: Pond
Local Schools
High School: Horace Greeley High School
Middle School: Robert E Bell School
Elementary School: Douglas G Grafflin School
School District: Chappaqua
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150 Old Farm Road N, Chappaqua, NY 10514
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Estimated Payment
$ 16,062.47 per month $10,015.05 Principal & Interest $4,734.92 Property Tax $1,312.50 Homeowner's InsuranceChange Payment Information
Demographics
Listed By / Shown By
Listing By
Agency Name: Julia B Fee Sothebys Int. Rlty
Agency Phone: 914-234-0200
Shown By
Agent Name: Ashlyn Ouimet
Agent Phone: (607) 316-3923
Agency Title: Timberland Properties
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150 Old Farm Road N, Chappaqua, NY 10514
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