Before hitting it big in Hollywood, Affleck and Damon rented the enchanting Egasse-Braasch House located in a northeastern Los Angeles neighborhood called Eagle Rock. This hilltop gem was dubbed The Castle by the childhood besties, and fondly referred to as the Good Will Hunting house by neighbors because the pair wrote the film’s Oscar-winning script while living there. Designed by French architect Jean L. Egasse for Eagle Rock pioneer Albert Braasch in 1923, the 2,187-square-foot residence, along with the accompanying detached cottage, was declared a Historical-Cultural Monument by the city of Los Angeles in 2013. It was granted city landmark status not because of its two former A-list residents, but because it embodies whimsical storybook-style architecture with multiple gables, inlaid stone, and stained glass windows. In a 1923 interview, Egasse said he drew inspiration from “Norman lines” of the Vikings, and that Saxony and Northern Italian designs informed the exterior. The uniquely executed asymmetrical curves and arches “are all geometrically related, in order to create an ensemble of harmonious lines suggestive of spiritual truths,” which equates to a uniquely straight-out-of-a-fairytale aesthetic.
The Georgia estate
Affleck was captivated by Savannah’s charm while filming Forces of Nature in the late 1990s and bought a sprawling 87-acre estate on a 4,000-acre island called Hampton Island Preserve about 35 miles south of the city for $7.11 million in 2003. “I live down this long dirt road, and people are very respectful of people’s privacy,” Affleck once said about the neighborhood.
The compound, completed in 2000, comprises three structures: the Big House, a 6,360-square-foot Greek Revival–style main house, reflective of typical antebellum plantation houses; Oyster Cottage, a 10,000-square-foot camp-style structure with six bunk-style bedrooms and two main suites; and Summer House, a structure with screened in living and dining spaces and interior and exterior fireplaces for shrimp boils.
In 2022—nearly 20 years after their first infamous breakup—Affleck and Jennifer Lopez wed at the property. While Affleck once praised the estate’s tranquility, mentioning that he felt calm and happy there, he and Lopez caught some flack from the public for making it their wedding venue, given the area’s history of slavery and the home’s contemporary take on Civil War–era design. The area formerly hosted several 19th-century rice plantations, and an unmarked burial site for enslaved people reportedly lies somewhere on the property grounds. Affleck put the estate on the market in 2018, but removed the listing in 2020. He presumably still owns the home today.
The hacienda
Before Affleck reconnected with Lopez, he married Jennifer Garner in 2005 and moved into her romantic Spanish-style Brentwood hacienda shortly after. Built in 1929, the five-bedroom, five-bathroom home was surrounded by leafy landscaping, and fronted by a courtyard and fountain canopied by mature trees. The backyard featured a pool, fireplace, olive trees, and a detached guesthouse. The house comes with a ton of star wattage, as Cindy Crawford once lived there, as did Reese Witherspoon’s character in the 2017 rom-com Home Again. The couple moved out in 2009 when Garner sold the historic property for $6.25 million.
The family compound
From the Brentwood hacienda, the Affleck/Garner family paid $17.6 million to upgrade to a sprawling three-acre property in the Pacific Palisades. A Cliff May–designed historic estate developed in the 1930s, this compound came with roughly 20,000 square feet of living space—a five-bedroom, eight-bathroom main house and a separate cottage that housed an office, gym, art studio, and two bathrooms. There was also a subterranean guesthouse that spanned the size of the enormous backyard and is reportedly where Ben lived for two years after the couple separated in 2015. In addition, a huge swimming pool was part of the backyard entertainment, and Garner set up a farm on the property, complete with vegetable gardens, a beehive, and chickens. In 2018, the same year the couple finalized their divorce, the estate was sold to Maroon 5 lead singer Adam Levine and his model wife, Behati Prinsloo. AD toured the home before they sold the property for $51 million.
Bachelor pad
Affleck paid $19 million for the ultimate bachelor pad in 2018. The newly built East Coast traditional-style mansion, which was a few blocks from Garner’s new home in the Pacific Palisades, spanned 13,000 square feet and had seven bedrooms and nine bathrooms scattered throughout. The property came packed with luxe amenities like a guest cottage, movie theater, wine cellar, full bar, gym, swimming pool and spa, well-manicured landscaping, and wellness room. It also sat across the street from the neighborhood’s posh Riviera Country Club. The Argo star sold the property for $28.5 million in October of 2022, promptly after his summer nuptials to Lopez. The sale was the neighborhood’s third-highest for the year up until that point.
