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Sold for $2,000,000
  • $2,000,000

    50 Overlook Drive, Chappaqua, NY 10514

    6beds
    5,234sqft
    Single Family Residence, Residential
    Built in 1929
    1.2 Acres Lot
    $2,059,400 Zestimate®
    $382/sqft
    $9,850 Estimated rent

    Home value

    $2,059,400

    $1.85M - $2.29M

    $9,850/mo

    Zestimate® history
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    What's special

    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Wendy Nolan 914-610-6334,

    Houlihan Lawrence Inc. 914-238-4766

    Bought with:

    Lori Hoffman, 10301212865

    Compass Greater NY, LLC

    Usha Subramaniam, 10301215449

    Compass Greater NY, LLC

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 877002MLS Logo

    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: 1.20 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 & neighborhood

    Security
    • Security features: Security System, Smoke Detector(s)
    Location
    • Region: Chappaqua

    Other

    Other facts
    • Listing agreement: Exclusive Right To Sell

    Price history

    DateEventPrice
    10/29/2025Sold$2,000,000$382/sqft
    Source: OneKey® MLS as distributed by MLS GRID #877002 Report a problem
    8/25/2025Pending sale$2,000,000$382/sqft
    Source: OneKey® MLS as distributed by MLS GRID #877002 Report a problem
    7/30/2025Price change$2,000,000-10.1%$382/sqft
    Source: OneKey® MLS as distributed by MLS GRID #877002 Report a problem
    6/15/2025Listed for sale$2,225,000-1.1%$425/sqft
    Source: OneKey® MLS as distributed by MLS GRID #877002 Report a problem
    5/30/2025Listing removed$2,250,000$430/sqft
    Source: OneKey® MLS as distributed by MLS GRID #818295 Report a problem
    2/21/2025Listed for sale$2,250,000$430/sqft
    Source: OneKey® MLS as distributed by MLS GRID #818295 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025-- $285,000
    2024-- $285,000
    2023-- $285,000
    2022-- $285,000
    2021-- $285,000
    2020-- $285,000
    2019-- $285,000
    2018-- $285,000
    2017-- $285,000
    2016-- $285,000 +2.3%
    2015-- $278,500
    2014-- $278,500
    2013-- $278,500
    2012-- $278,500
    2011-- $278,500
    2010-- $278,500
    2009-- $278,500
    2008-- $278,500
    2007-- $278,500
    2006-- $278,500
    2005-- $278,500 +5.1%
    2004-- $265,000
    2003-- $265,000
    2002-- $265,000
    2001-- $265,000
    2000-- $265,000
    1999-- $265,000

    Find assessor info on the county website

    Neighborhood: 10514

    Nearby schools

    GreatSchools rating
    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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    Estimated market value
    $2,059,400
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $2,059,400