About this home

Soaring ceilings, a striking stone fireplace, and expansive windows overlooking mature trees define the character of 1 Whippoorwill Lake Road. Set on approximately 1.83 acres in Chappaqua, this five-bedroom contemporary offers approximately 3,423 square feet of living space, with natural materials and distinctive architecture creating a home of warmth and individuality. The living room is the architectural centerpiece. A towering stone fireplace anchors the space, while vaulted ceilings and an open upper gallery create a memorable sense of volume. Hardwood floors and rich wood detailing bring warmth to the airy interior, and sliding glass doors extend the living experience outdoors. The spacious eat-in kitchen pairs warm wood cabinetry with dark countertops, a paneled refrigerator, and a broad bank of windows that frames the surrounding greenery. There is room to linger over breakfast or gather while dinner comes together. A separate dining room, featuring an inviting window seat and generous windows, provides a welcoming setting for longer evenings around the table. Five bedrooms offer flexibility for guests, work, and personal pursuits. A skylit bathroom combines a substantial wood vanity, dual faucets, and classic black-and-white tile, adding another layer of character. A dedicated laundry room with extensive cabinetry, a utility sink, and counter space brings thoughtful practicality to the home. Outside, decks and a sheltered patio offer distinct places to dine, relax, and enjoy the landscape. Mature trees, flowering hydrangeas, stone-edged planting beds, and stretches of lawn soften the home's angular lines and provide a beautiful backdrop through the seasons. With Chappaqua's shops, dining, and Metro-North connections to Manhattan completing the setting, 1 Whippoorwill Lake Road offers space to gather, places to retreat, and a daily connection to nature.

Facts and features

Schools

• Horace Greeley High School

  high · 9-12 · 1.0 mi

  10

• Douglas G Grafflin School

  elementary · K-4 · 1.1 mi

  10

• Robert E Bell School

  elementary · 5-8 · 1.6 mi

  9

• The Karafin School

  high · 9-12 · 1.9 mi

• World Cup Nursery School & Kindergarten

  elementary · PK-K · 2.1 mi

• Roaring Brook School

  elementary · K-4 · 2.1 mi

  10

Price history

• Nov 3, 2026 · Listed$2,150,000
• Jan 11, 1993 · Sold$240,000

Tax history

• 2025$33,064 tax · $197,000 assessed
• 2024$32,443 tax · $197,000 assessed
• 2023$31,674 tax · $197,000 assessed
• 2022$30,954 tax · $197,000 assessed
• 2021$30,624 tax · $197,000 assessed
• 2020$30,149 tax · $197,000 assessed
• 2018$29,568 tax · $197,000 assessed
• 2017$27,864 tax · $197,000 assessed

Home value

$1,738,493

• Quantarium$1,738,493
• Collateral Analytics$1,926,000
• Cotality$1,707,800

Where it is