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
- 19 days |
- 4,704 |
- 177 |
Zillow last checked: 7 hours ago
Listing updated: March 02, 2026 at 02:01am
Listing 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
Tour with a local agent
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, Kitchen Island, Open Floorplan, Primary Bathroom, Recessed Lighting, Soaking Tub, Storage
- 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: 20 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
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
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 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
BuyAbility℠ payment
Estimated monthly payment
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Neighborhood: 10514
Nearby schools
GreatSchools rating
- 8/10Robert E Bell SchoolGrades: 5-8Distance: 0.8 mi
- 10/10Horace Greeley High SchoolGrades: 9-12Distance: 2.1 mi
- 8/10Douglas G Grafflin SchoolGrades: K-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.
Local experts in 10514
- New York
- Westchester County
- Chappaqua
- 10514
- 150 Old Farm Road N
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