A New Chapter at Promised Land: Adam Levine and Behati Prinsloo Buy a Piece of Oprah’s Montecito Estate

Montecito’s legacy estates rarely change hands—and when they do, it’s often quietly. In a recent off-market transaction, Adam Levine and Behati Prinsloo purchased a four-acre historic Spanish Revival ranch that had long been part of Oprah Winfrey’s iconic Promised Land estate, further reinforcing Montecito’s reputation as one of the most exclusive real estate markets in the country.

From Jeff Bridges to Oprah—and Now a New Generation

The four-acre property was originally purchased by Oprah in 2019 from Oscar-winning actor Jeff Bridges for $6.85 million, the same price he had paid years earlier. The ranch had previously been listed at a higher number, but Oprah ultimately acquired it at a discount and incorporated it into her broader Promised Land holdings in Montecito’s coveted Hedgerow District.

Fast forward to late 2025, and the property has quietly traded hands again—this time to Levine and Prinsloo—for approximately $17.2 million in an off-market deal, a testament to both Montecito’s appreciation and the value of privacy-driven transactions.

A Historic Spanish Revival with Deep Local Roots

Dating back to 1919, the ranch was originally designed by noted Santa Barbara architect James Osborne Craig, whose work helped define the region’s early architectural identity. Over the years, the property has been thoughtfully restored and updated while preserving its historic character.

The main residence spans roughly 3,500 square feet on a single level and features:

• Two bedrooms and four bathrooms

• Rich hardwood floors

• Soaring exposed-beam ceilings

• Leaded glass windows

• Five distinctive curved fireplaces

Classic Spanish Revival elements blend seamlessly with modern upgrades, creating a home that feels both timeless and livable.

Indoor–Outdoor Living at Its Best

French doors throughout the home open to beautifully landscaped grounds that include rolling lawns, mature gardens, and an expansive red-brick courtyard anchored by a fire pit. Additional highlights include a pool with spillover spa, multiple guesthouses, a barn, and horse stables—features that remain highly sought after in Montecito’s estate market.

The property’s layout and acreage offer a rare combination of privacy, usability, and historic charm, all within close proximity to Montecito’s village and coastline.

What This Sale Says About Montecito Real Estate

This transaction highlights several key truths about Montecito real estate today:

• Off-market sales remain common at the upper end of the market

• Architectural pedigree matters, especially when paired with land and privacy

• Legacy properties continue to attract high-profile buyers willing to pay a premium

• Values in Montecito remain strong, particularly for irreplaceable estates

When properties of this caliber trade hands, it’s often through long-standing relationships, discretion, and deep local knowledge—not public listings.

Final Thoughts

The sale of this historic ranch marks another evolution of Montecito’s most storied estates. From Jeff Bridges to Oprah Winfrey and now Adam Levine and Behati Prinsloo, the property’s lineage reflects the enduring appeal of Montecito as a place to live, invest, and create legacy.

If you’re curious about Montecito estates, off-market opportunities, or the nuances of buying or selling in this tightly held market, I’m always happy to share insight.