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73 Whippoorwill Lake RoadChappaqua, NY 10514

For Sale

$1,999,000

Smart Buyer Rebate $19,990

Experience modern luxury and timeless sophistication in this stunning contemporary, beautifully sited on over an acre of park-like property in Chappaqua’s sought-after Whippoorwill neighborhood. Set on a quiet cul-de-sac with a majestic approach and newly resurfaced Belgian block–lined driveway, this home is surrounded by mature trees and lush landscaping, creating a private oasis with level play areas and serene natural views backing to a protected nature preserve. This dramatic residence features soaring ceilings, expansive windows, gorgeous hardwood floors and sophisticated modern design throughout. A bold double-door entry opens to a sun-drenched foyer and gallery-like living spaces. The vaulted dining room with floor-to-ceiling windows flows seamlessly into an oversized living room with a fireplace and sliders to expansive wraparound decks—perfect for indoor/outdoor entertaining. The beautifully renovated chef’s kitchen showcases high-end stainless steel appliances (SubZero, Bosch, Thermador), custom cabinetry, and a breakfast area with sliders for effortless alfresco dining. The main level also includes a spacious home office (or playroom) with a second fireplace, a guest bedroom suite, updated full bath, laundry area, and an attached two-car garage. Upstairs, the luxurious primary suite offers a fireplace, private balcony, dual walk-in closets, and an ensuite bath. Three additional bedrooms include one with an en-suite bath and two sharing a stylishly updated hall bath. The walk-out lower level provides a large recreation room, home gym, storage, and access to the expansive yard and surrounding landscape. Recent updates include: new roofs (2019 & 2024), new hot water heater, alarm and sprinkler systems, above-ground oil tanks, electric car charger, and more. Offering a rare combination of architectural drama, flexible living space, and resort-like grounds, this exceptional home delivers the best of modern living in a peaceful Whippoorwill setting within the award-winning Chappaqua School District.

Listed by Cindy Glynn

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Compass Greater NY, LLC

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914-238-0676

Last updated October 22, 2025

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Source: OneKey #926237

Listing Facts

  • TypeSingle-family
  • NeighborhoodNew Castle
  • Bedrooms5
  • Bathrooms5
  • Days on PrevuNew Today
  • HOA/Maint. Fees$1,200/annual
  • Taxes$36,400.75/year
  • Size4,839 sqft
  • Price per sqft$413

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

10/22/2025
Listed by Compass Greater NY, LLC
$1,999,000

Property Details for 73 Whippoorwill Lake Road

Association

Amenities

  • Community Features: Other

Fees

  • Association Fee: $1,200.00 Annually
  • Association Fee Includes: Common Area Maintenance

Exterior

Construction

  • Property Condition: Actual
  • Window Features: Floor To Ceiling Windows, Oversized Windows, Wall Of Windows
  • Year Built: 1980
  • Architectural Style: Contemporary, Modern
  • Construction Materials: Frame
  • Exterior Features: Basketball Hoop

Features

  • Patio And Porch Features: Deck, Patio, Wrap Around

Measurements

  • Building Area Total: 5,589
  • Building Area Units: Square Feet
  • Lot Size Acres: 1.16
  • Lot Size Square Feet: 50,530

Financial

Taxes

  • Parcel Number: 3600-101-006-00002-000-0004
  • Tax Annual Amount: $36,400.75
  • Tax Assessed Value: $218,845.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Dishwasher, Dryer, Electric Range, Gas Oven, Gas Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Oil Water Heater
  • Fireplace Features: Bedroom, Living Room, Wood Burning
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Flooring: Hardwood
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Central Vacuum, Chandelier, Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entertainment Cabinets, Entrance Foyer, Formal Dining, High Ceilings, His And Hers Closets, Open Floorplan, Recessed Lighting

Measurements

  • Living Area: 4,839
  • Living Area Source: Public Records

Rooms

  • Basement: Partially Finished, Walk-Out Access
  • Has Basement: Yes
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 5
  • Rooms Total: 12

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes
  • Parking Features: Attached, Driveway, Electric Vehicle Charging Station(s), Garage, Garage Door Opener

Schools

Elementary School

  • Elementary School: Douglas G Grafflin School
  • Elementary School District: Chappaqua

High School

  • High School: Horace Greeley High School
  • High School District: Chappaqua

Middle or Junior School

  • Middle Or Junior School: Robert E Bell School
  • Middle Or Junior School District: Chappaqua

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Baseboard, Oil
  • Laundry Features: Laundry Room
  • Sewer: Septic Tank
  • Utilities: Cable Connected, Electricity Connected, Phone Connected, Trash Collection Public, Water Connected
  • Water Source: Public

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey™ MLS. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. Information Copyright 2025, OneKey™ MLS. All Rights Reserved.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.