08-05-2025
The Obamas' Former Martha's Vineyard Getaway Hits the Market for $39 Million
This iconic Martha's Vineyard estate—once the Obamas' go-to summer sanctuary—is back on the market, asking $39 million. Represented by Maggie Gold Seelig of MGS Group Real Estate and Brian Dougherty of Corcoran Property Advisors, the listing has both an architectural pedigree and presidential provenance.
Set on nearly 30 private acres in Chilmark, the estate hugs the shoreline of Tisbury Great Pond and delivers serious Vineyard magic: rolling lawns, meadows, and waterfront views. The Obama family rented the home for their summer getaways between 2009 and 2011, reportedly paying $50,000 a week, according to The Wall Street Journal. It's also where President Barack Obama addressed the nation after Hurricane Irene and honored the late Senator Ted Kennedy, Architectural Digest reported. Years later, the former first family would return to the island to put down more permanent roots, purchasing a $14.85 million estate in nearby Edgartown in 2019.
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At the heart of the property is a gracious 7,000-square-foot main house—classic New England on the outside, tailored luxury inside. Think vaulted ceilings, stone fireplaces, wraparound porches, and a dining room with knockout water views. Arrive via a gated drive, passing a 150-year-old Pennsylvania barn clad in cedar shingles, and it's hard not to feel like you've stumbled into an East Coast fairytale.
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But here's where it gets really interesting: the estate's current owner is none other than vaunted British architect Norman Foster, the mind behind London's Gherkin and Wembley Stadium. Foster was struck by the estate's pastoral approach and the authenticity of its architecture, describing it as a 'classic New England house that had grown from historic farming roots,' The WSJ reported. What made it special, he added, was its ability to feel remote and expansive while still sitting in the heart of Martha's Vineyard.
Since acquiring the property in 2011 for $22.4 million, Foster, the founder and chairman of Foster + Partners, has injected his signature style into the compound, most notably with the sleek, contemporary pool and poolhouse he designed to contrast the classic clapboard main home. Modernism meets Martha's Vineyard? Yes, indeed, and somehow, it works.
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Scattered across the grounds are a five-bedroom guesthouse, a boathouse with a private dock, a design studio, a gym, tennis and basketball courts, an apple orchard, equestrian paddocks, and staff housing. It's a compound built for both deep relaxation and active living—with just enough gravitas to host a head of state.
While Martha's Vineyard's luxury market has cooled since the pandemic peak, properties with notable provenance continue to draw interest. Case in point: Diane Sawyer's waterfront retreat sold for $23.9 million in late 2023 after just two months on the market and for just shy of its $24 million ask. Meanwhile, the island's median home price dipped to $1.1 million in April, down more than 30 percent from the previous of Robb Report
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