Oprah Winfrey Sells Vast Montecito Estate for $17.2 Million

In a move that reaffirms her status as a titan of celebrity luxury property, Oprah Winfrey has officially offloaded a prime four-acre slice of her legendary Montecito compound, "The Promised Land."

The transaction, which closed in December 2025, saw the media mogul sell the Spanish-style estate to Maroon 5 frontman Adam Levine and his wife, Behati Prinsloo, for a staggering $17.3 million. The deal marks a masterclass in real estate appreciation; Winfrey originally purchased the parcel from Hollywood veteran Jeff Bridges in 2019 for $6.85 million, effectively more than doubling her investment in just six years.

A strategic downsize?

While the sale may seem like a significant departure, it is a calculated move for the 71-year-old billionaire. This "micro-downsizing" allows Winfrey to streamline her holdings while maintaining the core of her $100 million primary residence, which still spans over 60 contiguous acres in California’s most exclusive enclave.

Levine and Prinsloo, who recently sold their own nearby estate for $60 million, were reportedly drawn to the 1919 Spanish Revival dwelling for its "irresistible" historical charm. The 3,500-square-foot main house—quaint by Montecito standards—is expected to undergo an extensive, year-long renovation to transform it into a family-focused retreat.

Even with the four-acre reduction, "The Promised Land" remains the gold standard of ultra-luxury real estate.

Features of the estate

- The Neo-Georgian mansion: A 23,000-square-foot masterpiece serving as the property's anchor.
- Seamair farm: The adjacent 23-acre equestrian estate Winfrey added in 2016 for nearly $29 million.
- The ‘Quiet Luxury’ aesthetic: Interiors designed with a palette of taupe's and sage greens, prioritizing "spiritual flow" over traditional opulence.

By moving into a portion of Winfrey's former land, Levine and Prinsloo join an elite neighbourhood that has become a fortress for A-list privacy. Current residents now include Prince Harry and Meghan Markle, Gwyneth Paltrow, and Kendall Jenner, who recently purchased her own $23 million compound directly adjacent to the Winfrey estate.

For luxury investors, the "Oprah Effect" remains potent. As the median home price in Montecito climbs past $5.4 million, Winfrey’s ability to flip secondary parcels for eight-figure profits highlights the enduring demand for celebrity-owned estates with proven provenance.