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1923 Map of Pasadena-On-The-Gulf
1925 Entrance to Pasadena Estates (Central Ave near 64th St) Trolley Line
A Stroll Through Historic Old Pasadena’s Past
Picture it—Florida, 1914. The air was thick with the scent of saltwater and orange blossoms, and the shores of Boca Ciega Bay were quiet but brimming with possibility.
Two visionaries, Frank A. Davis and H. Walter Fuller, began carving out a new community they called Davista. At the time, it reached only as far north as 7th Avenue North, but it was already attracting dreamers who saw more than just sand and sea.
Frank Davis and H. Walter Fuller
Back then, visiting the barrier islands meant braving a ferry ride. That changed in 1919 when W.D. “Bill” McAdoo built the very first bridge from the mainland to Long Key—today’s St. Pete Beach—and Pass-a-Grille.
The wooden bridge stretched from the end of Villa Grande across open bay waters, landing near what is now 87th Avenue. Without the modern fill that shapes our shoreline today, it was a remarkable feat. But Mother Nature had other plans—the 1921 hurricane ripped it away and it had to be rebuilt, only to be torn down when the new Corey Causeway Bridge was constructed in 1927.
Just a year later, in 1922, a tall, dashing New Yorker named “Handsome” Jack Taylor arrived with big ideas and even bigger pockets. He bought 1,800 acres, including a large part of Davista, and launched his grand vision: Pasadena Estates—Pasadena on the Gulf.
Inspired by the elegance of the Mediterranean Revival style, Jack Taylor lined the streets with red-tiled roofs, stucco walls, and arched doorways. He wasn’t just selling homes—he was selling a lifestyle.
Sunset Hotel 1918
Some of those treasures still stand today. The Sunset Hotel (Central and Park Street), built in 1915 by Walter Fuller, now lives on as the Crystal Bay Hotel.
Golf legend Walter Hagen, who lived at 320 Park St. So., whose 11 major championships put him in the record books behind only Nicklaus and Woods, managed Jack Taylor’s Bear Creek Golf Course.
Babe Ruth once lived here too, his home on Sunset Drive was part of the original Pasadena-on-the-Gulf. Even Hollywood found its way to our shores—silent film star Annie Russell lived at 7210 3rd Ave. So. from 1924 to about 1930.
By 1926, Pasadena’s streets were renumbered, its neighborhoods were bustling, and landmark buildings dotted the landscape—the Rolyat Hotel (now Stetson Law School), Pasadena Fundamental School on its original site, and the Pasadena Community Church, which held its first service in 1925 in what would later become a beloved gathering place.
There is even an artesian well at Villa Grande and Sunset Drive, advertised in a 1923 brochure as providing “wonderful drinking water” for residents.
Pasadena has always been more than just a collection of homes—it’s been a place where visionaries took risks, where community grew out of both hardship and celebration, and where history still lingers in the architecture, the street names, and the stories passed down. Over a century later, its Mediterranean charm, sense of community, and love of the water remain the heartbeat of the neighborhood.
1926 – 72nd Street looking north at 4th Ave. So.