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!
For sale
$4,500,000
150 Old Farm Road N, Chappaqua, NY 10514
5beds
7,608sqft
Single Family Residence, Residential
Built in 1906
4.45 Acres Lot
$-- Zestimate®
$591/sqft
$-- HOA
What's special
Private tennis courtCentral islandCoveted first-floor private suiteVersatile five-bedroom layoutDramatic overhead skylightSoaring ceilingsFive-bedroom estate
- 160 days |
- 2,071 |
- 83 |
Zillow last checked:
Listing updated:
Listed by:
Julia B Fee Sothebys Int. Rlty 914-234-0200,
Joanna Rizoulis 917-359-7885,
Amy Smith Sroka 914-523-0678,
Julia B Fee Sothebys Int. Rlty
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 950756
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 5
- 1/2 bathrooms: 2
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Cooktop, Dishwasher, Dryer, Gas Cooktop, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry: Laundry Room
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
- Flooring: Carpet, Ceramic Tile, Hardwood, Tile
- Attic: None
- Number of fireplaces: 2
- Fireplace features: Family Room, Gas, Living Room, Masonry, Wood Burning
Interior area
- Total structure area: 11,603
- Total interior livable area: 7,608 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Driveway, Garage, Heated Garage
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Three Or More
- Patio & porch: Deck, Patio, Terrace
- Exterior features: Courtyard, Tennis Court(s)
- Has private pool: Yes
- Pool features: In Ground, Pool/Spa Combo
- Has spa: Yes
- Fencing: Fenced
- Has view: Yes
- View description: Mountain(s), Panoramic
- Waterfront features: Pond, Waterfront
Lot
- Size: 4.45 Acres
- Features: Back Yard, Cul-De-Sac, Front Yard, Landscaped, Near School, Secluded, Views
Details
- Additional structures: Pergola
- Parcel number: 3489099016000020100000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Carriage House
- Property subtype: Single Family Residence, Residential
Materials
- Stone
- Foundation: Stone
Condition
- Year built: 1906
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Electricity Connected, Water Connected
Community & HOA
Community
- Security: Fire Alarm, Security System, Smoke Detector(s), Video Cameras
HOA
- Has HOA: No
Location
- Region: Chappaqua
Financial & listing details
- Price per square foot: $591/sqft
- Tax assessed value: $22,000
- Annual tax amount: $56,819
- Date on market: 3/1/2026
- Cumulative days on market: 161 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 3/1/2026 | Listed for sale | $4,500,000$591/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #950756 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $22,000 |
| 2024 | -- | $22,000 |
| 2023 | -- | $22,000 |
| 2022 | -- | $22,000 |
| 2021 | -- | $22,000 |
| 2020 | -- | $22,000 |
| 2019 | -- | $22,000 |
| 2018 | -- | $22,000 |
| 2017 | -- | $22,000 |
| 2016 | -- | $22,000 |
| 2015 | -- | $22,000 |
| 2014 | -- | $22,000 |
| 2013 | -- | $22,000 |
| 2012 | -- | $22,000 |
| 2011 | -- | $22,000 |
| 2010 | -- | $22,000 |
| 2009 | -- | $22,000 |
| 2008 | -- | $22,000 |
| 2007 | -- | $22,000 |
| 1999 | -- | $22,000 |
Find assessor info on the county website
Monthly payment
Climate risks
Neighborhood: 10514
Nearby schools
GreatSchools rating
- 9/10Robert E Bell SchoolGrades: 5-8Distance: 0.8 mi
- 10/10Horace Greeley High SchoolGrades: 9-12Distance: 2.1 mi
- 10/10Douglas G Grafflin SchoolGrades: PK-4Distance: 0.8 mi
Schools provided by the listing agent
- Elementary: Douglas G Grafflin School
- Middle: Robert E Bell School
- High: Horace Greeley High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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