52 Piping Rock Road, Locust Valley, NY, 11560

Conceived in 1929 for Vanderbilt heir Aldred Coster Schermerhorn, Buttonball Hill is a masterwork of Georgian architecture set amid sweeping manicured grounds. The classic red brick and clapboard exterior — crowned by a slate roof and crisp black shutters — announces itself with quiet authority.

Inside, a double-height foyer with hand-carved moldings and a gracefully curved staircase sets the tone. Soaring ceilings and a natural flow make the principal rooms equally suited to intimate daily liv...