David Letterman is widely reported to split his time between his longtime estate in North Salem, New York, a ranch in Montana, and a home base in his native Indiana, rather than one single full‑time residence.

Main home base

Public interviews and recent coverage suggest that Letterman has intentionally stepped away from a full‑time Hollywood or Manhattan lifestyle and “relocated” in spirit back to Indiana, where he feels more grounded and connected to everyday life. At the same time, reports note that Indiana is part of a small group of places he considers home, not his only address.

North Salem, New York estate

Biographical sources describe Letterman and his family as residing on a large estate in North Salem, New York, an area in Westchester County known for quiet, rural-style properties within reach of New York City. The property has been reported as about 108 acres, giving him considerable privacy and space away from city life.

Montana ranch

Letterman also owns a ranch near Choteau, Montana, where he has spent significant time since the late 1990s. He and his wife Regina Lasko were married in a small civil ceremony there, and the location is often mentioned in profiles as one of his primary retreats.

Indiana connection

Recent articles highlight that, after leaving late‑night television, Letterman spends more time back in Indiana, the state where he grew up and began his broadcasting career. This return is often framed as part of his desire for a simpler, more grounded life and a stronger sense of “humanity” away from Hollywood.

Privacy note

Exact street addresses or highly specific location details are not shared here out of respect for Letterman’s safety and privacy, and reputable sources typically mention only the state or town level when describing where he lives. Public information therefore supports the view that he divides his time among Indiana, his New York estate, and his Montana ranch rather than maintaining a single, fully disclosed residence.