The Matthews Team

William Raveis Lifestyles Realty

371 Whippoorwill RoadChappaqua, NY 10514Sale Price: $2,250,000

  • Sale Price: $2,250,000
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Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $2,250,000Sale Price
  • 5Bedrooms
  • 5Bathrooms
  • 2.76Acreage
  • 6,410Square Feet
Sold

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This spectacular farm-house colonial with welcoming front porch designed by noted architect David Graham with Shoreline Pool, spa, custom pool house and waterfall is perfectly situated on 2.76 acres on a private road in the prestigious Whippoorwill area. This well-crafted 5 BR. 4.5 bath home is flooded with sunlight. A gracious entry foyer with vaulted ceilings opens to a formal dining room with Butler's Pantry and formal living room with fireplace. In addition, there is a tranquil, relaxing sunroom, an office with custom bookcases and powder room. The gourmet kitchen with a windowed breakfast area features Christopher Peacock Cabinetry, quartzite counters and backsplash, Wolf 6 burner range, Viking wall oven, Subzero refrigerator, Miele dishwasher. The kitchen opens to a sun filled family room with wood burning stone fireplace and French doors leading to an outdoor deck and pool. Second floor boasts the primary en-suite bedroom with marble bath and walk in closets; 4 additional bedrooms and 3 full baths, bonus gathering/playroom or nanny's suite, laundry room, and sundeck. A fully finished basement with over 2000 sq ft offers plenty of space for entertaining, recreation, exercise and woodworking. Multiple upgrades include new roof, new above ground oil tanks, full home generator, freshly painted exterior. Perfectly maintained and well suited for today's discerning buyer, conveniently located to train, shopping and schools. Additional Information: Amenities:Dressing Area,Marble Bath,Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,

Property Details of 371 Whippoorwill Road

Property Details

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Community

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Listed by Wendy Nolan of Houlihan Lawrence Inc. (914-238-4766)

Listing Sold by Ginnel Real Estate

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of May 17, 2026 8:49 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. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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