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$2,000,000

  • Sold
  • Closed
  • Single Family
  • 6 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 5,234 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 50 Overlook Dr

General

  • Sold For: $2,000,000
  • Taxes: $47,202
  • Status: Closed
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 877002
  • Added to Site: 215 day(s) ago

Interior

  • Number of Rooms: 15
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Wood Burning
  • Appliances: Other
  • Laundry Facilities: Yes
  • Flooring: Hardwood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 4
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 6

Other Rooms

  • Laundry: Electric Dryer Hookup, Laundry Room

Additional Information

  • Security/Safety: Security System, Smoke Detector(s)

Exterior

  • Exterior Features: Garden, Lighting, Mailbox, Rain Gutters
  • Porch/Patio/Deck: Patio, Porch, Screened

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Attached, Driveway

Location

  • County: Westchester County

School Information

  • High School District: Chappaqua
  • Elementary School: Douglas G Grafflin School
  • Middle School: Robert E Bell School
  • High School: Horace Greeley High School

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Hot Water, Steam, Radiant Floor
  • Heating Zones: 2

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Trash Collection Public, Water Connected

Structural Information

  • Architectural Style: Colonial, Tudor
  • Detached/Attached: Detached
  • Construction: Brick
  • Basement: Yes
  • Basement Desc.: Full Basement, Partially Finished, Storage Space
  • Windows: ENERGY STAR Qualified Windows, Screens
  • Building Size: 5234
  • Square Feet: 5,234
  • Sq. Ft. Source: Public Records
  • Year Built: 1929

Lot Features

  • Lot Size (Acres): 1.2
  • Lot Size (Sq. Ft.): 52,272
  • Road Maintenance: Public Maintained Road
  • Lot Features: Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Near School, Near Shops, Private

Financial Considerations

  • Tax Amount: $47,202.49

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 3600-093-017-00004-000-0003

Listed by Houlihan Lawrence Inc.
Sold by Compass Greater NY, LLC

Listing agent

— 50 Overlook Dr —

  • Houlihan Lawrence Inc.

914-238-4766

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 50 Overlook Dr

School District:Chappaqua Central School District
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 50 Overlook Dr

Date
Details
Price
Change
Source
10/29/2025
Sold
$2,000,000
—
MLS
7/30/2025
Price Reduced
$2,000,000
-10.11%
MLS
6/15/2025
Listed
$2,225,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Houlihan Lawrence Inc.
Sold by Compass Greater NY, LLC

50 Overlook Drive, Chappaqua, NY 10514 (MLS# 877002) is a Single Family property that was sold at $2,000,000 on October 29, 2025. Want to learn more about 50 Overlook Drive? Do you have questions about finding other Single Family real estate for sale in Chappaqua? You can browse all Chappaqua real estate or contact a Coldwell Banker agent to request more information.