Word around the island is that the Obamas, who’ve rented a place on the Vineyard for the past several summers, are looking to buy. The former first family has many friends on Martha’s Vineyard — Harvard professors Henry Louis “Skip” Gates and Charles Ogletree , and former Obama adviser Valerie Jarrett , to name just a few — and they would like to own a place of their own on the island.

Chicago will always be former President Obama ’s hometown — that’s where the Obama Presidential Center is being built — but it looks like he may be spending a lot more time on Martha’s Vineyard in the future.


The 44th president and his wife, Michelle, are believed to be focused “up island,” looking at homes or buildable lots in the rural communities of Aquinnah, Chilmark, and West Tisbury. (It’s worth noting that the Obamas have always rented “up island,” including for a two-week stay this summer.)

No one’s talking, least of all realtors, but we’re told that one property that may be getting a long look is a magnificent waterfront outpost in Aquinnah owned by Caroline Kennedy and her husband, Edwin Schlossberg. A few years ago, the couple, who inherited from Jacqueline Kennedy Onassis the 377-acre Red Gate Farm overlooking the Atlantic Ocean, subdivided the property and put two parcels on the market.

Both are still available — but they don’t come cheap. Sotheby’s International Realty is listing a 75-acre parcel for $15 million, and a second 40-acre parcel for $12 million. The descriptions for each read like something out of a fairytale: “The vast acreage and exquisite dune-fringed sands give the sense of a world apart in an idyllic landscape which has remained virtually unchanged over the centuries. Perched on a southwest-facing ridge, the potential homesite commands glorious views to the ocean’s brilliant blue waters and sunsets in the midst of this sublime seaside paradise of pastoral coastal heathlands and high dunes.”

The listing broker, George Ballantyne of Gibson Sotheby’s International Realty, declined to talk to us. The properties appear on multiple sites, including Hancock Real Estate and Sand Piper Realty, which are both located on the Vineyard. We contacted Deborah Hancock of Hancock Real Estate Tuesday, but she hung up as soon as we uttered the name “Obama.”

“Goodbye,” she said. Click.

Of course, Martha’s Vineyard is home to more than a few celebrities, who enjoy the island for the privacy it affords. David Letterman, Meg Ryan, Carly Simon, Kenneth Cole, Larry David, Seth Meyers, and Bill Murray, among many others, all have homes there. (Murray was Obama’s golf partner at Farm Neck Golf Club last Friday, BTW.) Former secretary of state John Kerry and his wife, Teresa Heinz, recently paid $11.75 million for a house on 18 acres at Seven Gates Farm, a historic property overlooking Vineyard Sound in Chilmark. Former President Clinton doesn’t own a place, but he and Hillary Clinton are frequent visitors to the island, including last week on the occasion of his 71st birthday.