Harbor Bluffs, on the water’s edge

By: Carla Kerns

Harbor Bluffs, although now part of unincorporated Pinellas County, was once inside Largo's boundaries, and its history, growth, and development closely parallel that of our city.

The written history of Harbor Bluffs dates back to 1856 when 40 acres of wooded land, sitting high on a bluff overlooking the Intracoastal waters, was homesteaded by Moses Powledge of Georgia. Phillip (P .J.) Bayly, a New Zealand native, purchased the property in 1883 and for many years thereafter, it was known as "Bayly's Bluff". Bayly's citrus trees survived the freezes of 1894-95 and 1898 which devastated many other groves in Florida. Growers came from afar to get budwood from Bayly's "Sandsfoot" grove in order to replant what had been lost. .

An anonymous "old timer" recalled his visits fo Bayly's Bluff around the turn of the century. "I remember when there was just the Bayly mansion and a couple of fishing shacks down by the water. The rest was woods and a sort of jungle where a kid with a .22 could have a lot of fun. When I got a bit older, I used to work all week, save my money to hire a horse and buggy to drive there on Saturday evening. It was some place to take your gal to ... "

In 1918, the land was purchased by Timothy 0'Leary, a New York stockbroker, who built a home there. After World War II, a group of investors bought 236 acres from O'Leary and platted a subdivision, but never developed it. It wasn't until 1953 that another group, known as the Harbor Bluffs Development Corporation, began construction of the first homes. In 1966, these concrete block ranch-style homes sold for $18,000 to $30,000. Dredging in the late 1950s and 196os created "fingers" which made many more waterfront lots available for building. The subdivision's appeal to both retiring northerners and local families meant that by the early 1980s only a few undeveloped lots remained.

As Pinellas County and the Largo area became more densely populated, the interest in Harbor Bluffs increased due to its location near the water, spacious lots, and abundance of majestic live oak trees. A surge in upscale home renovation and remodeling began in the 1990s. An increasing number of modest-sized homes have been torn down and replaced with larger, more elaborate residences, some of which sell for millions of dollars. Pinellas County, Largo, and especially Harbor Bluffs, have come a long way since the days of dense woods, orange groves, and fishing shacks.

Source: Largo, then 'till...; Pinellas Counselor, August 1910; Harbor Bluffs Magazine, 1956; Sparkling Clearwater-Largo
Realtor brochure, 1966; Harbor Bluffs Homeowners Association Directory, 2002-2003.