OneKey® MLS
  • Buy
  • Rent
  • Commercial
  • Find an Agent
  • Fair Housing Notices
  • Language
    Price range
    $
    $
    Bedrooms
    Bathrooms
    Home type
    Square feet
    Lot size
    Heating
    Cooling
    Parking spots
    Garage
    Basement
    Year built
    Max HOA
    Down payment assistanceDown payment assistance
    Tours
    View
    More amenities
    1 home
    1 home available
    50 Overlook Drive, Chappaqua, NY 10514
    $2,250,000
    6beds
    4 full, 2 halfbath
    5,234sqft
    1.2acres
    House for Sale

    50 Overlook Drive, Chappaqua, NY 10514

    Listing by: Houlihan Lawrence Inc.
    1 - 1 of 1 results
    Copyright © 2025 OneKey® MLS LLC
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Equal opportunity
    Membio
    OneKey® MLS
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    50 Overlook Drive, Chappaqua, NY 10514
    $2,250,000
    6beds
    4full,2half bath
    5,234sqft
    1.2acres

    50 Overlook Drive, Chappaqua, NY 10514

    City/Town:Chappaqua   Post Office: Chappaqua     

    House for Sale by Wendy NolanHoulihan Lawrence Inc..

    Data checked -. Listing last updated 4 days ago.
    1. Overview
    2. Details
    3. More 

    Elegant 6-Bedroom Colonial Tudor on One of Chappaqua’s Most Coveted Streets. Grandly sited on a beautiful tree-lined street, this stately 6-bedroom Colonial Tudor exudes timeless elegance and historic charm. Built in 1929, this meticulously maintained brick residence showcases a classic tile roof, soaring ceilings, intricate period moldings, and expansive sunlit interiors. Set on a beautifully landscaped and level 1.2-acre lot, the property boasts stunning specimen plantings and an exquisite stone patio with a charming bridge leading to a park-like setting—a landscape masterpiece designed by renowned architect Ned Baldwin. Designed for both grand entertaining and comfortable living, the spacious living and dining rooms seamlessly flow into a sun-drenched sunroom and a serene screened-in porch, creating the perfect blend of indoor and outdoor living. This is a rare opportunity to own a distinguished home in one of Chappaqua’s most desirable neighborhoods. Experience the perfect balance of classic architecture and modern luxury in this extraordinary residence.

    Details
      Property type
    Residential
      Year built
    1929
      Heating
    Hot Water, Steam, Radiant Floor
      Cooling
    Central Air
      Total rooms
    15
      Garage
    Yes (2 space)
      City/Town
    Chappaqua
      Post Office
    Chappaqua
      Parking spots
    -
    818295
    MLS ID
    Active
    Status
    02/21/2025
    On Market Date
      Laundry features
    Electric Dryer Hookup, Laundry Room
      Flooring
    Hardwood, Tile
      Fireplace
    Yes
      Pets allowed
      Architectural Style
    Colonial, Tudor
      View
    Interior 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, Washer/Dryer Hookup
    Exterior features
    Garden, Lighting, Mailbox, Rain Gutters
    Lot features
    Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Near School, Near Shops, Private
    Appliances included
    Other
    Construction materials
    Brick
    Monthly taxes
    $3,888
    Yearly taxes
    $46,656.72
    Community Features
    -
    School district
    Chappaqua
    Schools
    Douglas G Grafflin School, Robert E Bell School, Horace Greeley High School
    Senior community
    No
    Common Charges
    -
    Maintenance
    -
    Additional Fees
    -
    Open Houses
    In-Person
    No upcoming in-person open houses
    Virtual
    No upcoming virtual open houses
    Contact Agent
    Wendy Nolan
    Wendy Nolan
    Real Estate Salesperson, Houlihan Lawrence Inc.
    Direct Number 
     
    Location
    For Sale Nearby
    9 Caruso Place, Armonk, NY 10504
    $1,451,800
    3beds
    3.5bath
    3,379sqft
    acres
    House for Sale

    9 Caruso Place, Armonk, NY 10504

    Listing by: Houlihan Lawrence Inc.
    27 Neustadt Lane, Chappaqua, NY 10514
    $2,475,000
    4beds
    4bath
    4,974sqft
    acres
    House for Sale

    27 Neustadt Lane, Chappaqua, NY 10514

    Listing by: William Raveis-New York, LLC
    32 Langeland Drive, Mount Kisco, NY 10549
    $850,000
    4beds
    1bath
    2,050sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    32 Langeland Drive, Mount Kisco, NY 10549

    Listing by: William Raveis Real Estate
    8 Kitchel Road, Mount Kisco, NY 10549
    $2,260,000
    4beds
    3.5bath
    5,376sqft
    acres
    House for Sale

    8 Kitchel Road, Mount Kisco, NY 10549

    Listing by: Compass Greater NY, LLC
    17 Byram Hill Road, Armonk, NY 10504
    $775,000
    2beds
    2bath
    1,431sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    17 Byram Hill Road, Armonk, NY 10504

    Listing by: Houlihan Lawrence Inc.
    215 Bedford Banksville Road, Bedford, NY 10506
    $3,912,750
    5beds
    7.5bath
    8,356sqft
    acres
    House for Sale

    215 Bedford Banksville Road, Bedford, NY 10506

    Listing by: Douglas Elliman Real Estate
    2 Brook Lane, Chappaqua, NY 10514
    $975,000
    3beds
    2bath
    1,819sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    2 Brook Lane, Chappaqua, NY 10514

    Listing by: Compass Greater NY, LLC
    117 Smith Avenue, Mount Kisco, NY 10549
    $485,000
    3beds
    2.5bath
    2,400sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    117 Smith Avenue, Mount Kisco, NY 10549

    Listing by: YourHomeSold Guaranteed Realty
    13 White Birch Road, Pound Ridge, NY 10576
    $845,001
    4beds
    3.5bath
    3,516sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    13 White Birch Road, Pound Ridge, NY 10576

    Listing by: Keller Williams NY Realty
    260 West Street # 6B, Mount Kisco, NY 10549
    $125,000
    1beds
    1bath
    700sqft
    acres
    Co-op for Sale
    Down payment assistanceDown Payment Help

    260 West Street # 6B, Mount Kisco, NY 10549

    Listing by: RE/MAX Town & Country
    Recently Sold
    Closed May 7
    9 Caruso Place, Armonk, NY 10504
    $1,451,800
    3beds
    3.5bath
    5,663sqft
    acres
    House for Sale

    9 Caruso Place, Armonk, NY 10504

    Listing by: Houlihan Lawrence Inc.
    Closed May 6
    27 Neustadt Lane, Chappaqua, NY 10514
    $2,475,000
    4beds
    4bath
    89,734sqft
    acres
    House for Sale

    27 Neustadt Lane, Chappaqua, NY 10514

    Listing by: William Raveis-New York, LLC
    Closed May 5
    32 Langeland Drive, Mount Kisco, NY 10549
    $850,000
    4beds
    1bath
    45,738sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    32 Langeland Drive, Mount Kisco, NY 10549

    Listing by: William Raveis Real Estate
    Closed May 2
    8 Kitchel Road, Mount Kisco, NY 10549
    $2,260,000
    4beds
    3.5bath
    63,598sqft
    acres
    House for Sale

    8 Kitchel Road, Mount Kisco, NY 10549

    Listing by: Compass Greater NY, LLC
    Closed May 1
    17 Byram Hill Road, Armonk, NY 10504
    $775,000
    2beds
    2bath
    54,014sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    17 Byram Hill Road, Armonk, NY 10504

    Listing by: Houlihan Lawrence Inc.
    Closed Apr 29
    215 Bedford Banksville Road, Bedford, NY 10506
    $3,912,750
    5beds
    7.5bath
    141,570sqft
    acres
    House for Sale

    215 Bedford Banksville Road, Bedford, NY 10506

    Listing by: Douglas Elliman Real Estate
    Closed Apr 29
    2 Brook Lane, Chappaqua, NY 10514
    $975,000
    3beds
    2bath
    12,196.8sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    2 Brook Lane, Chappaqua, NY 10514

    Listing by: Compass Greater NY, LLC
    Closed Apr 29
    117 Smith Avenue, Mount Kisco, NY 10549
    $485,000
    3beds
    2.5bath
    6,308sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    117 Smith Avenue, Mount Kisco, NY 10549

    Listing by: YourHomeSold Guaranteed Realty
    Closed Apr 29
    13 White Birch Road, Pound Ridge, NY 10576
    $845,001
    4beds
    3.5bath
    sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    13 White Birch Road, Pound Ridge, NY 10576

    Listing by: Keller Williams NY Realty
    Closed Apr 23
    260 West Street # 6B, Mount Kisco, NY 10549
    $125,000
    1beds
    1bath
    38,730sqft
    acres
    Co-op for Sale
    Down payment assistanceDown Payment Help

    260 West Street # 6B, Mount Kisco, NY 10549

    Listing by: RE/MAX Town & Country
    50 Overlook Drive, Chappaqua, NY 10514, is a 6 bedroom, 4 bathroom, 5234 sqft. Single Family Residence built in 1929. This property is currently available for sale and was listed on OneKey® MLS on 2-21-2025. The MLS# for this Single Family Residence is MLS# 818295.
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Copyright ©2025
    BESbswy