50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see.
Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can offer. Homes built to this quality are a rare find. Constructed in 1929, the home is also graced with soaring ceilings, intricate period moldings, and expansive sunlit interiors.
Designed for both grand entertaining and comfortable living, this spacious home is roaring with charm and can suit a variety of tastes and living styles. The first floor offers a living room with fireplace, an all seasons sunroom, a bright and airy dining room, a kitchen with pantry and wet-bar, a half bath, and an in-law or au pair suite with a full bath. Upstairs features 5 bedrooms and 3 full baths, a grand hallway, and attic access. Additional recreational space is provided in the finished basement, with a family room, a gym, and large mudroom, a half-bath, and a utility room.
The beautifully landscaped 1.2-acre lot boasts stunning specimen plantings and a private stone patio adjacent to the all-seasons sunroom. There is also a charming bridge, designed by renowned architect Ned Baldwin, leading to a park-like setting in the backyard.
This is an incredible opportunity to own a truly distinguished home in one of Chappaqua’s most desirable neighborhoods. Experience the perfect balance of classic architecture and modern luxury in this extraordinary residence, in a home that is built to stand the test of time.
For sale
Price cut: $225K (7/30)
$2,000,000
50 Overlook Drive, Chappaqua, NY 10514
6beds
5,234sqft
Single Family Residence, Residential
Built in 1929
1.2 Acres Lot
$-- Zestimate®
$382/sqft
$-- HOA
What's special
- 50 days
- on Zillow |
- 2,645 |
- 125 |
Zillow last checked: 7 hours ago
Listing updated: July 31, 2025 at 06:54am
Listing by:
Houlihan Lawrence Inc. 914-238-4766,
Wendy Nolan 914-610-6334
Source: OneKey® MLS,MLS#: 877002

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 6
- Full bathrooms: 4
- 1/2 bathrooms: 2
Heating
- Hot Water, Steam
Cooling
- Central Air
Appliances
- Included: Other
- Laundry: Washer/Dryer Hookup, Electric Dryer Hookup, Laundry Room
Features
- First Floor Bedroom, First Floor Full Bath, Built-in Features, Chandelier, Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, His and Hers Closets, Marble Counters, Primary Bathroom, Original Details, Pantry, Storage, Walk Through Kitchen
- Flooring: Hardwood, Tile
- Windows: ENERGY STAR Qualified Windows, Screens
- Basement: Full,Partially Finished,Storage Space
- Attic: Full,Pull Stairs
- Number of fireplaces: 1
- Fireplace features: Wood Burning
Interior area
- Total structure area: 5,234
- Total interior livable area: 5,234 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Driveway
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Three Or More
- Patio & porch: Patio, Porch, Screened
- Exterior features: Garden, Lighting, Mailbox, Rain Gutters
Lot
- Size: 1.2 Acres
- Features: Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Near School, Near Shops, Private
Details
- Parcel number: 3600093017000040000003
- Special conditions: None
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Tudor
- Property subtype: Single Family Residence, Residential
Materials
- Brick
Condition
- Actual
- Year built: 1929
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Connected, Electricity Connected, Trash Collection Public, Water Connected
Community & HOA
Community
- Security: Security System, Smoke Detector(s)
HOA
- Has HOA: No
Location
- Region: Chappaqua
Financial & listing details
- Price per square foot: $382/sqft
- Tax assessed value: $285,000
- Annual tax amount: $47,202
- Date on market: 6/15/2025
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
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