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    1 home
      1 home available
      50 Overlook Drive, Chappaqua, NY 10514
      Closed Oct 29, 2025
      50 Overlook Drive, Chappaqua, NY 10514
      $2,000,000
      6beds
      4 full, 2 halfbath
      5,234sqft
      1.2acres
      House for Sale

      50 Overlook Drive, Chappaqua, NY 10514

      Listing by: Houlihan Lawrence Inc.
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      Copyright © 2026 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.
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      Membio
      OneKey® MLS
      50 Overlook Drive, Chappaqua, NY 10514
      Closed Oct 29, 2025
      $2,000,000
      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 124 days ago.
      1. Overview
      2. Details
      3. More 

      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.

      Internet Serviceability
      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
      -
      877002
      MLS ID
      Closed
      Status
      Oct 29, 2025
      Closed
        Laundry features
      Electric Dryer Hookup, Laundry Room
        Fireplace
      Yes
        Pets allowed
        Architectural Style
      Colonial, Tudor
        Basement
      Full, Partially Finished, Storage Space
        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, High Ceilings, His and Hers Closets, Marble Counters, Primary Bathroom, Original Details, Pantry, Storage, Walk Through Kitchen, Walk-In Closet(s), 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
      Flooring
      Hardwood, Tile
      Monthly taxes
      $3,934
      Yearly taxes
      $47,202.49
      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
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      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 6-15-2025. The MLS# for this Single Family Residence is MLS# 877002.
      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.
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