Before Barack and Michelle Obama became household names, they were just two ambitious newlyweds carving out a life—and a little real estate—on Chicago’s South Side. Their journey together started in a Chicago law office, where a summer internship sparked a romance. By 1993, they were married and setting down roots, buying their first home and launching a life that would take them from Hyde Park to the White House and beyond. Over the next three decades, each move reflected a new chapter: raising daughters, climbing the political ladder, and eventually navigating the realities of life after the presidency.
Here’s every place Barack and Michelle Obama have called home.
Hyde Park Home (1993-2005)
Their love story began at a Chicago law firm in 1989, but their real estate story started four years later when the newlyweds dropped anchor in Hyde Park with a 2,200-square-foot condo purchase in 1993. The four-bedroom, three-and-a-half-bathroom first-floor unit in a 1910 building witnessed the birth of two future First Daughters and the makings of a future president.
The space featured original architectural details like wood trim, ceiling beams, tile floors, and a green tile fireplace that became the backdrop for Michelle’s Chicago Magazine photo shoot. For over a decade, this spot served as home base while Barack’s career trajectory shifted from community organizer to Illinois State Senator. The couple eventually sold the home to Grammy-winning jazz singer Kurt Elling and his wife in 2005, and when the Ellings listed it for $550,000 in fall 2024, it marked the first time the Obama family home had hit the market in nearly two decades.
Kenwood Mansion (2005-Present)
After Barack’s election to the Illinois State Senate, the Obamas purchased a $1.65 million Georgian Revival brick mansion in Chicago’s Kenwood neighborhood. Built in 1916, this 6,243-square-foot fortress has six bedrooms and six bathrooms. This purchase coincided with Barack’s rising political profile, and the heavily guarded property has since become a bit of a tourist destination, though the Obamas likely haven’t spent much quality time there since decamping to Pennsylvania Avenue in 2008. Still, they’ve held onto this property.
Capitol Hill Pad (2005-2008)
Barack needed a Washington base during his Senate years. Enter: an unglamorous $1,200-per-month rental along Stanton Park’s eastern edge. This 2,214-square-foot row house was split into two units, with Barack occupying the one-bedroom, one-bathroom space below a two-bedroom duplex. The entire building eventually sold for $1 million in 2023.
Kalorama Mansion (2017-Present)
In 2017, after Barack’s presidency, the Obamas made the unusual decision to stay in the capital (the only other president to stick around post-presidency was Woodrow Wilson in 1921), initially renting in the Kalorama neighborhood before purchasing their 8,122-square-foot mansion for $8.1 million. The nine-bedroom, eight-and-a-half-bathroom brick home required immediate security upgrades, including a protective wall. The home’s design aesthetic, glimpsed during Michelle’s podcast recordings, showcases quintessentially American style: white wooden floors, upholstered seating, rattan coffee tables, and leather sofas.
Martha’s Vineyard Retreat (2019-Present)
In 2019, the Obamas purchased their Martha’s Vineyard retreat for $11.75 million. Set on 29.3 acres along Edgartown Great Pond, the seven-bedroom, eight-and-a-half-bathroom estate was built in 2001. The property features vaulted ceilings, stone fireplaces, and a distinctive circular dining room with ocean views. Here, they’re regularly spotted engaging in delightfully normal activities: shopping, buying ice cream, biking, and golfing.
Julia Cancilla is the engagement editor (and resident witch) at ELLE Decor, where she oversees the brand’s social media platforms, covers design trends and culture, and writes the monthly ELLE Decoroscope column. Julia built her background at Inked magazine, where she grew their social media audiences by two million and penned feature articles focusing on pop culture, art, and lifestyle.
