The gates of 1209 Westway Drive in Lido Shores open to a procession of palm trees, a Turkish white shell-stone wall, and, beyond, the azure blue waters of the Gulf. Inside, the house spreads out with confidence—vaulted ceilings, glass panes framing the horizon, and a family room that has been remade more than once.

For William M. “Bill” Isaac, the former chairman of the Federal Deposit Insurance Corporation (FDIC), this home was never just a residence; it was a long-term commitment. Isaac bought the property in 2000 for $2.7 million, tore through its interiors, and remade it room by room, even carving out a sauna back at a time when most Sarasota homes had only pools. (He has a pool, too, plus almost 250 feet of beachfront.)

Isaac, now 81, is candid about how he ended up in town. “I came to Sarasota because I heard it was a nice place, stayed at the Longboat Key Club and fell in love,” he says. He lived all over and traveled the world, but it was the easy confluence of beach, weather, and habit that pulled him into Sarasota’s orbit. A condo at the Longboat Key Club came first, then a penthouse, then marriage, children and the search for a family home. “That brought us to Lido Shores,” he says, where he and his wife raised their children amid the enclave of Sarasota School of Architecture homes and other modernist residences.

The house is a survivor; one of two original buildings on the property. The other, a guest house, sustained significant storm damage last year and was torn down. Isaac admits that loss nudged him toward selling.

“We figured if we sell the lot, we should sell the main [house], too,” he says. Spared by storm surge thanks to its high perch, the home is intact—6,800 square feet, six bedrooms, eight baths, high-windowed and newly remodeled. “The kitchen is brand new. The dining area, too," Isaac says. "The bedrooms are new. The whole thing is new."

Family life remains inscribed there. A bedroom painted with clouds on a powder blue ceiling was for Isaac's daughter, who is now at Columbia Law School. There's a “shark room” for his son, now attending the University of Southern California. A stand-up bass and piano his daughter once played still sit in the family room, where Isaac spent the most time.

The home is on the market for $26 million, placing it near the top of Sarasota’s current listings. But Isaac is matter-of-fact about the calculus. “It’s a lovely home. It will attract a lot of people,” he says. A recent $30.3 million cash closing on Longboat Key didn’t surprise him. “[That sale] gave us incentive to look at our options,” he says.

In the rarefied tier of the Gulf-front luxury real estate market, downturns hardly register. Sarasota’s mid-priced market may be softening, but at the high end, insulated wealth continues to trade in the eight figures. Isaac’s house now joins a short roll of Westway addresses on the market for more than $20 million. Nearby, a newly built home is listed at $22.5 million; another, larger home hovers at $20 million.

Isaac's career has been as expansive as the Gulf views from his terrace. Born in Bryan, Ohio, and trained as a lawyer, he was appointed to the FDIC board by President Jimmy Carter at age 34. Two years later, Ronald Reagan named him chairman of the board—the youngest chair in the agency’s history. He presided over the banking upheavals of the early 1980s, when thousands of institutions failed, earning a reputation as a steady hand in an unsteady era. “It’s a tough world, but very rewarding," he says of finance. "I would do it again.”

After leaving Washington, Isaac founded the Secura Group, a consulting firm later acquired by FTI, and went on to chair Fifth Third Bancorp, advise governments and banks across the globe, and publish his book Senseless Panic: How Washington Failed America, an insider’s chronicle of financial crises. In Sarasota, he chairs the board of Sarasota Private Trust and serves on boards ranging from Emigrant Bank to Ringling College of Art and Design.

The Westway sale will be less a departure than a pivot—another transaction on the long ledger of a life spent balancing risk and security.

Until then, the Gulf still fills Isaac's windows. The pool still spills into its waterfall edge. Lido Shores, with its midcentury grid and short walk to St. Armands Circle, is still what it was when Isaac first saw it: convenient, delightful, a place to stay put.

Interested? Contact Gordon Menninger of Engel & Völkers at (727) 405-7476.