150 Old Farm Road N, Chappaqua, NY

$4,500,000

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5

Beds

7

Baths

7,608

Square feet

4.45

Acres

About 150 Old Farm Road N

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!

Features of 150 Old Farm Road N

MLS® # 950756
Price $4,500,000
Bedrooms 5
Bathrooms 7.00
Full Baths 5
Half Baths 2
Square Footage 7,608
Square Footage 193842
Acres 4.45
Year Built 1906
Type Residential
Sub-Type Single Family Residence
Style Carriage House
Status Active

Community Information

Address 150 Old Farm Road N
City Chappaqua
County Westchester County
State NY
Zip Code 10514

Amenities

Horse Property No
Utilities Electricity Connected, Water Connected
Parking Attached, Driveway, Garage, Heated Garage
# of Garages 2
View Mountain(s), Panoramic
Is Waterfront Yes
Waterfront Pond
Has Pool Yes
Pool In Ground, Pool/Spa Combo

Interior

Interior Carpet, Ceramic Tile, Hardwood, Tile
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
Appliances Cooktop, Dishwasher, Dryer, Gas Cooktop, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
Heating Forced Air, Oil
Cooling Central Air
Fireplace Yes
# of Fireplaces 2
Fireplaces Family Room, Gas, Living Room, Masonry, Wood Burning
Has Basement No

Exterior

Exterior Features Courtyard, Tennis Court(s)
Lot Description Back Yard, Cul-De-Sac, Front Yard, Landscaped, Near School, Secluded, Views, Waterfront
Construction Stone

School Information

District Chappaqua
Elementary Douglas G Grafflin School
Middle Robert E Bell School
High Horace Greeley High School

Additional Information

Date Listed March 1st, 2026
Days on Market 11
Taxes $56,820
Short Sale No
RE / Bank Owned No

Listing Details

OfficeJulia B Fee Sothebys Int. Rlty

Listing Map

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