Inside Matt Damon’s Oscar-Worthy Property Portfolio

Matt Damon is embracing a new chapter in life—and his carefully curated real estate portfolio reflects the family-first priorities that have guided him for years.

Now, the Oscar-winning actor is adjusting to an emptier nest as two of his and wife Luciana Barroso’s four daughters head out into the world.

Reflecting on fatherhood, Damon—who shares kids Alexia, 27, Isabella, 20, Gia, 17, and Stella, 15, with Barroso—told People he has become more mindful of making the most of the time he has with his younger children while continuing to balance his Hollywood career.

“Having two older kids who are out of the nest and knowing how fast these final years go, we’re trying to be mindful of holding onto what we can,” he said.

The Massachusetts native has come a long way since making trips to Manhattan in pursuit of his Hollywood dream.

Looking back on his early years, Damon recalled traveling to New York with his childhood friend and fellow actor, Ben Affleck, in hopes of landing acting jobs.

"We were in our teens coming down to New York on the train or on the bus to audition for things, like 'The Mickey Mouse Club,'" he told the outlet.

His career has since soared to Oscar-winning heights, and away from the cameras, The Odyssey star has built an equally impressive real estate portfolio, with homes that range from a record-setting New York City penthouse to a secluded country estate and a contemporary California retreat.

The Brooklyn base

In 2018, Damon dropped $16.7 million on his most famous property: a 6,200-square-foot Brooklyn Heights penthouse.

Ideal for family life, the six-bedroom home features an expansive living space, a private rooftop, and panoramic views of the Manhattan skyline and New York Harbor.

He's also in good company: Emily Blunt and John Krasinski are neighbors, having snagged a full-floor apartment in the building for $11 million the following year.

A New York nest

When he's looking to escape the city, Damon can retreat to his estate in Bedford,NY.

Set on roughly 13 acres, the private property offers a peaceful setting surrounded by nature while remaining within easy reach of Manhattan.

He picked up the pad in 2022 for $8.5 million. The home comes complete with four bedrooms and 5.5 bathrooms.

Sprawling across 7,190 square feet, the lavish abode also boasts a saltwater pool, a tennis court, a greenhouse, an antique barn, a treehouse, and other features.

The actor reportedly purchased the property through an LLC attached to Pearl Street Films, the production company he shares with Affleck.

His Hollywood home

In 2024, he expanded his property portfolio by picking up an $8.5 million condo in West Hollywood.

Designed by acclaimed architecture firm Olson Kundig, the 2,900-square-foot residence features two bedrooms, 2.5 bathrooms, floor-to-ceiling glass walls, and a spacious terrace overlooking the Hollywood Hills.

The residence also boasts a 1,600-square-foot private terrace, which is one of the largest outdoor areas in the building.