Nestled in the heart of Armonk sits 69 Whippoorwill Rd, a timeless 1790 antique gem set on 1.4 lush green acres. Brimming with historic character and modern comforts, the main home is a beautifully preserved 3-bedroom abode that lives like a 5-bedroom with unmatched charm throughout - original doors, wide plank floors, and hand-hewn exposed wooden beams honor the home’s rich heritage. The first floor offers seamless transition between the kitchen, living area and dining room with an attached screened-in porch perfect for enjoying afternoon tea and a summer's breeze. A bedroom with full bath off the kitchen provides a bonus space perfect for a guest room and/or home office. Upstairs you'll find a primary suite with a fully renovated bath and access to the finished 3rd floor. Additionally, a generously sized 2nd bedroom, fully renovated hall bath and sunny sitting room complete this floor. The detached garage which encompasses the historic charm of what once was the chauffeur's quarters from its original build includes a fully finished guest cottage with its own full bath—perfect for visitors, a home office, or creative retreat. This gorgeously landscaped property dotted with specimen trees and curated plantings borders the Fordham University Louis Calder Center, offering panoramic tranquility and land that gently slopes toward Calder Lake. Whether sipping coffee on the porch, relaxing on the tree swing or exploring the nature trails just beyond your backyard, this is a property that invites serenity and inspiration. A must-see Whippoorwill classic.