Ever since the motorcade left the White House for the last time, people have been obsessed with one question: where do Obamas live now that they don't have a 132-room mansion on Pennsylvania Avenue? Honestly, it’s not just one place. While most former presidents head back to their home states and fade into the woodwork, Barack and Michelle have built a lifestyle that spans from the heart of D.C. to the shores of Massachusetts and even the tropical breeze of Hawaii. It’s a portfolio that reflects a post-presidency that is anything but "retired."
The short answer? They still call Washington, D.C. their primary base, but they’ve basically created a triangle of homes that allow them to balance work, privacy, and their love for the water.
The Kalorama Command Center
The Obamas didn't leave D.C. after the 2017 inauguration. They moved about two miles away.
Located in the exclusive Kalorama neighborhood, their primary residence is an 8,200-square-foot Tudor-style mansion that they originally rented from Joe Lockhart (Bill Clinton’s former press secretary) before buying it for $8.1 million in late 2017. It’s a massive brick house with nine bedrooms and eight and a half bathrooms. You’ve probably seen the exterior in paparazzi shots—it has that classic, stately Washington vibe with a gated courtyard that can fit a dozen Secret Service SUVs.
Inside, it’s all about understated luxury. We’re talking marble countertops, a sprawling terrace, and formal gardens. Michelle Obama once joked on Ellen that Barack got "shortchanged" with the smallest room for his office, but let’s be real—it’s still a workspace most of us would kill for. The neighborhood is a literal "who’s who" of power; they’ve lived down the street from Jeff Bezos and around the corner from various foreign ambassadors.
Living here allowed their younger daughter, Sasha, to finish high school at Sidwell Friends without an interstate move. Even now, in 2026, it remains their tactical headquarters for their various projects with the Obama Foundation and Higher Ground Productions.
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Summering on Martha's Vineyard
When the humidity in D.C. gets unbearable, the family heads north.
In 2019, the Obamas dropped $11.75 million on a stunning estate in Edgartown, Martha’s Vineyard. This isn't just a "summer cottage." It’s a 29-acre property sitting right on the edge of the Edgartown Great Pond. The house itself is nearly 7,000 square feet with seven bedrooms and a bunch of stone fireplaces that probably feel great during those chilly Atlantic evenings.
What’s interesting is the history. Before they bought this place, they used to rent a property called Blue Heron Farm. That house actually just sold recently to billionaire Les Wexner for a whopping $37 million. But the Obamas' current Vineyard home is much more secluded. It’s tucked away at the end of a long, private drive, giving them the kind of peace that’s hard to find when you’re one of the most famous couples on the planet.
- Acreage: 29.3 acres of privacy.
- Water Access: Direct views of the barrier beach and the ocean.
- Fun Fact: The home was sold to them by Wyc Grousbeck, the owner of the Boston Celtics. (No word on if a basketball court was included in the closing costs, but Barack probably insisted on one nearby).
The Hawaii Retirement Plan
You can take the man out of Hawaii, but you can't take Hawaii out of the man.
For years, rumors swirled about a "Magnum, P.I." house on Oahu. Well, it’s more than a rumor now. In 2026, the Obamas' beachfront compound in Waimanalo, Hawaii is finally a reality. The project has been a long time coming. The land was originally purchased back in 2015 by Marty Nesbitt, a close friend of the former president, and the development has been a massive undertaking involving three separate houses and two pools.
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It hasn't been without controversy, though. Local environmentalists have been vocal about a century-old seawall on the property. These walls can cause beach erosion, and while the developers used a legal loophole to keep it, it’s been a point of contention with the local community. Despite the drama, the compound is designed to be their ultimate "forever home," a place where Barack can body-surf and Michelle can enjoy the Pacific sunsets away from the D.C. grind.
What Happened to the Chicago House?
You might be wondering about the house that started it all—the Georgian revival on Greenwood Avenue in Chicago’s Kenwood neighborhood.
They still own it.
Even though they haven't lived there full-time in nearly two decades, the Chicago house remains a symbol of their roots. It’s the place where they raised their girls before the world knew their names. With the Obama Presidential Center set to open in Chicago's Jackson Park in June 2026, the family will likely be spending a lot more time in the Windy City. The center is a massive 60,000-square-foot campus featuring a museum, a library, and even an NBA-regulation basketball court (aptly named "Home Court").
Why This Real Estate Portfolio Matters
Looking at where the Obamas live tells a story of how they’ve transitioned from public servants to global icons. They haven't just bought houses; they've built fortresses of privacy and productivity.
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If you're trying to keep track:
- Washington, D.C.: The work hub.
- Martha's Vineyard: The summer retreat.
- Hawaii: The tropical sanctuary.
- Chicago: The legacy home.
They’ve essentially mastered the art of the "multi-hyphenate" lifestyle. They are authors, producers, and philanthropists, and their homes reflect that. You’ve got the urban sophistication of Kalorama for meetings, the rugged isolation of the Vineyard for writing, and the island vibes of Oahu for actual relaxation.
Actionable Insights for the Curious
If you're planning a trip to see these spots, remember: privacy is the priority.
- Kalorama: You can walk the streets, but expect a heavy Secret Service presence. It’s a public neighborhood, but don't expect to get anywhere near the front door.
- Chicago: The Kenwood house is visible from the street, but the block is often restricted. Your best bet for an "Obama experience" is visiting the Presidential Center once it opens this summer.
- Martha's Vineyard: The estate is completely invisible from the road. If you want a glimpse, you’d literally need to be on a boat in the Great Pond, and even then, the trees do a lot of heavy lifting.
The Obamas have designed a life that allows them to be everywhere and nowhere all at once. Whether they’re hosting a dinner in D.C. or paddle-boarding in Hawaii, they’ve clearly decided that one home just isn't enough to contain the next chapter of their lives.
Next, you might want to look into the specific visiting hours and ticket information for the Obama Presidential Center opening in Chicago this June.
Sources:
- The Vineyard Gazette, "President Obama Buys Home on Edgartown Great Pond."
- Realtor.com, "Inside the Obamas' D.C. Mansion."
- ProPublica, "The Loophole Protecting the Obama Hawaii Seawall."
- Obama.org, "Construction Updates for the Presidential Center 2026."