Scotts Road (Southampton Residence)

A historic oak tree on a one-acre site in the country was the starting point for a new 6,100-square-foot residence in Southampton, NY. A previously unremarkable house from the 1980s was demolished, but the tree remained. It was honored for its legacy, natural beauty, and shade. With the tree as the focal point, the courtyard shape is concentric on the tree’s canopy, where nearly all of the room’s windows and doors aim towards it from different angles. The courtyard establishes indoor-outdoor connections between the rooms as a unified outdoor space. This modern house has flat roofs and white walls to counter the forested setting. From the road, it’s a contemporary castle on a hill with its façade geometry derived from its angled shape rather than from angled roofs or windows. Although the house is shaped around the tree, many rooms look back to the front with views of forests or water in the winter when the leaves have fallen. Since the house is narrow, many rooms are see-through.

The entry is directly aligned with the tree, with spaces branching out in both directions. The first floor is an open plan with areas for cooking, dining, socializing, and connecting to the outdoors visually and physically. A guest suite for live-in guests is at the far end of the first floor. The second floor is split into two wings, each with its own stair. In one direction is the master suite, which extends from the entry side of the house back to the courtyard with a private deck. This is meant to be an oasis. The other wing is for the grown children who visit and occasional guests. It has three bedrooms aligned with doors and windows based on where they occur and the axial layout. A full basement includes a lounge, additional bedroom, wine room, storage, and mechanical.

Owners Fairley Pilaro and Joe Messina are long-time, year-round residents of Southampton. Joe is a builder and built the house, and together they designed the interior. Every room features paintings and sculptures from their collection, primarily from artists based in the Hamptons and their world travels.