With a net worth of $300 million, we’d be buying up properties left and right, too.

It’s only natural that Leonardo DiCaprio, an IRL Wolf of Wall Street/Jay Gatsby hybrid, has swapped real estate these past three decades as often as he switches girlfriends (all under 25, until recently). The Academy Award–winning actor—who once shared a raft in freezing waters with Kate Winslet and has been adored worldwide ever since his splashy Hollywood entrance with What’s Eating Gilbert Grape—currently owns properties in locations from California to New York to a private island in Belize. Casual.

To help you make sense of where Leo might be at any given time (he did star in Catch Me If You Can, after all) and of homes he has parted ways with over the years, here’s a breakdown of his most notable real estate purchases.

9045 ORIOLE WAY ESTATE, LOS ANGELES

9045 Oriole Way—which DiCaprio originally got his hands on in the 1990s, marking his first foray into Hollywood real estate—is worth a double (or in this case, quadruple) take. It’s a compound now made up of four adjoining properties, the first of which DiCaprio bought from Madonna for $2.5 million. Life there was so good, apparently, that he proceeded to absorb the adjoining houses. The compound boasts multiple pools (spanning the plunge and full-size varieties), solar panel add-ons, lots of hedges and trees for privacy, and a basketball court that famously landed DiCaprio in court (pun not intended). Since the millionaire’s Oriole Way estate covers five land parcels across five acres (per Mansion Global), only time will tell if he’ll decide to snap up house #5: yet another potential location for an election night bash or a place to rent out to fellow Hollywood big shots who are on his good side.

1675 ANGELUS AVENUE, LOS ANGELES

Alex Zarour

Leo DiCaprio’s former Silver Lake abode is a study in the art of house flipping. He purchased this 4,006-square-foot Spanish hacienda residence in 1999, for a seemingly normal $769,500. Twenty years later, however, the Killers of the Flower Moon star sold it and made a tidy profit of $785,500 (all that method acting as Jordan Belfort must have paid off). The new owners laid a heavy hand on its original period details, according to Curbed Los Angeles: Gone was the Spanish and Art Deco tilework adorning select bathrooms and fireplaces, the outdoor pavilion’s tin ceiling, and the original kitchen, among other less depressing casualties. Whoever is presently on the deed (the property changed hands twice since DiCaprio’s time there) can now enjoy an exposed brick kitchen backsplash, multiple wine rooms, and the four bedrooms’ shiny, whitewashed aesthetic—as well as bragging rights that they own the former stomping grounds of an Oscar winner.

BLACKADORE CAYE, BELIZE

Courtesy Of Google Maps

In 2005, DiCaprio purchased this island off the coast of Belize—undoubtedly his most astounding investment—with the goal of creating a retreat devoted to ecological restoration. He employed the help of architect Jason McLennan, a champion of eco-friendly building, to transform the 104 acres into a haven replete with 68 overwater villas, 48 private homes, infinity pools, and other peak-of-luxury amenities. Blackadore Caye was set to open to guests in 2018, but, six years later, it’s still very much in its “pardon our dust” phase. Only time will tell if DiCaprio’s lofty aspirations—mainly, to completely reverse the island’s overfishing, erosion, and deforestation, while also pleasing uber-picky and uber-wealthy visitors—will truly come to fruition.

2 RIVER TERRACE, NEW YORK

Courtesy Of Google Maps

Inaugurating his bicoastal era, Leonardo DiCaprio purchased a $3.67 million apartment in Manhattan’s Battery Park City back in 2008—part of a development designed by industry heavy hitter David Rockwell that’s all about clean, conscious living—and then liked it so much he bought an adjoining unit six years later, as reported by The Real Deal. Both purchases were kept under wraps, bypassing public listings. 2 River Terrace’s residents are treated to stunning Hudson River views and serious perks like twice-filtered air, nontoxic materials, and lower-than-average energy costs. Additional amenities include a lap pool, yoga studio, kids’ playroom, and (yes) a dog spa. DiCaprio, as the bachelor that he is, doesn’t have to worry about the playroom. For now.

432 WEST HERMOSA PLACE, PALM SPRINGS, CALIFORNIA

Nextrecord Archives/GETTY

Palm Springs—a mecca for celeb A-Listers and the A-List designers who help beautify their lives—was too tempting for DiCaprio to resist, apparently. He beat the FOMO by investing in a $5.2 million estate built by the late architect Donald Wexler, who in the course of his illustrious career became synonymous with Palm Springs’ flavor of midcentury modernism. 432 West Hermosa Place might look unassuming on the outside, but a step inside reveals striking wood paneled ceilings in the living room; floor-to-ceiling windows that put palm trees and the majestical San Jacinto mountains in the limelight; glass and stone details throughout; a grand piano; a steam shower; and similarly glorious markers of living the good life. If all of this feels out of reach, it shouldn’t—anyone can rent the Leo-owned home for a cheerful sum of $3,750 per night.

66 EAST 11TH STREET, NEW YORK

Nina Poon

2014 seemed to be a fortunate year for DiCaprio, as this was when he bought not one, not two, but four properties, including a $10 million condo in New York City’s coveted Greenwich Village neighborhood. The building uniquely provides the benefit of a wellness concierge service by Donna Karan—called Urban Zen—and (less uniquely) a full-time doorman. DiCaprio surely also felt “zenned out” thanks to features like vitamin C–infused showers, in-duct aromatherapy, posture-supportive flooring, and circadian rhythm lighting design. He kept this three-bedroom, two-and-a-half-bathroom real estate acquisition for a mere two years, according to House Beautiful, before selling it for $2 million less. You win some, you lose some, Leo!7

2566 ABERDEEN AVENUE, LOS ANGELES

Todd F. Goodman / LA Light Photo

One of Jack Dawson’s (… err Leonardo DiCaprio’s) more recent purchases is this Spanish Colonial beauty in L.A.’s trendy Los Feliz neighborhood, which he bought—for $7.1 million—from actor Jesse Tyler Ferguson and husband Justin Mikita back in 2021. The interior vibes are sexy and homey at the same time, a hard-to-nail combo achieved through the house’s curving terra-cotta staircase; wall niches; beamed ceilings; stained glass in the revamped library; as well as a jewel box color scheme that provides continuity between rooms. The hacienda-style home also has an exterior to gush over (think arched doorways, a pool with chic teal tiling, and a Juliet balcony overlooking an inner courtyard bedecked with fairy lights), so buying it was definitely one of DiCaprio’s wiser life choices.