35 Overlook Drive, Chappaqua, NY 10514
Local realty services provided by:Better Homes and Gardens Real Estate Shore & Country Properties



35 Overlook Drive,Chappaqua, NY 10514
$2,699,000
- 4 Beds
- 7 Baths
- 5,354 sq. ft.
- Single family
- Pending
Listed by:cindy glynn
Office:compass greater ny, llc.
MLS#:859784
Source:One Key MLS
Price summary
- Price:$2,699,000
- Price per sq. ft.:$504.11
About this home
Welcome to this timeless and sophisticated Colonial, perfectly sited on meticulously landscaped grounds in one of Chappaqua’s most coveted neighborhoods. Just minutes from town, train, and top-rated schools, this exceptional residence seamlessly blends classic architectural charm with modern luxury. This fully renovated and expanded home offers 4 spacious bedrooms (lives like 5), 6.1 beautifully updated baths, and a thoughtfully designed layout filled with natural light. Gleaming hardwood floors, walls of windows, and elegant millwork create a warm and inviting atmosphere throughout. The stunning Chef’s kitchen is a true showpiece, featuring Christopher Peacock custom cabinetry, oversized center island with Carrera marble top, Pietra del Cadoso limestone kitchen countertops, top-of-the-line stainless appliances (Bosch, Thermador, Viking) and an open flow ideal for entertaining.
The main level enjoys multiple formal and informal living spaces including an expansive family room open to the kitchen, a versatile first floor office, a second office/library, full bath and a serene screened sun porch. The second level features a luxurious primary bedroom suite and three additional huge bedrooms, one with an en-suite bath and a hall bath. The walkout lower level adds even more functionality with room for recreation, fitness, or guests. Recent mechanical upgrades include a high efficiency GE front-loading washer and dryer, NEW (May 2025) Energy Kinetics System 2000 High-Efficiency Boiler designed to reduce oil consumption, and above-ground oil tanks, ensuring comfort and efficiency for years to come. The exterior is equally captivating: clapboard siding, a hand split cedar shake roof, copper gutters, bluestone walkways, an expansive rear patio with built-in grill and stone walls, a Mahogany deck, and a manicured, level lawn with vibrant gardens, professional landscaping and an irrigated vegetable garden. Additional highlights include an oversized driveway, a two-car garage, and an adjacent garage bay-sized storage room perfect for bicycles, equipment, or hobbies. A rare offering that effortlessly combines grace, comfort, and convenience — 35 Overlook Drive is an extraordinary opportunity for the discerning buyer.
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Home facts
- Year built:1952
- Listing Id #:859784
- Added:72 day(s) ago
- Updated:July 13, 2025 at 07:43 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:7
- Full bathrooms:6
- Half bathrooms:1
- Living area:5,354 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Hydro Air, Oil
Structure and exterior
- Year built:1952
- Building area:5,354 sq. ft.
- Lot area:1.22 Acres
Schools
- High school:Horace Greeley High School
- Middle school:Robert E Bell School
- Elementary school:Douglas G Grafflin School
Utilities
- Water:Public
- Sewer:Septic Tank
Finances and disclosures
- Price:$2,699,000
- Price per sq. ft.:$504.11
- Tax amount:$52,310 (2024)
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