50 Overlook Drive

Chappaqua, NY 10514

REINTRODUCING 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, and beautiful staging, 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.

Listing courtesy of Houlihan Lawrence Inc. wnolan@houlihanlawrence.com


Based on information submitted to the MLS GRID as of 2025-06-14 10:22 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.