From the quiet estates at the northern end of the street to the sprawling compound to the south, every address tells a story. Whether it’s the one about the now-vanished menagerie that included a joke-playing dolphin and a temperamental panther, or the one about the annoying neighbor whose fellow Drive residents finally saw him led away in handcuffs (although not, alas, for his code violations), there are innumerable tales to tell. These are a few.

1188 Gordon Drive
Novelist and social observer Tom Wolfe once noted that the real rich live in neighborhoods with hardwood trees. (Poseurs are doomed to brush pine needles off their cars.) What might Wolfe make of the awesome banyan and mahogany canopy that shelters part of Gordon Drive?
This brace of stately trees, nature’s testament to man-made wealth, stretches southward from a modest clapboard home built in 1918 by N.P. Sloan, the town’s first realtor. The 2,300-square-foot landmark is sheltered by an enormous banyan planted around the same time by Sloan’s young son. Although some of Sloan’s descendants reside in the historic cottages ringing the property, this is now the studio of Paul Arsenault, an artist who fell in love with Naples decades ago and made a career of depicting the city’s charms.

2100 Gordon Drive to the Port Royal Club
Except for the Gulf of Mexico in their back yards, the residents who live on this stretch of Gordon might as well be squires in the English countryside, dwelling on three-plus acre parcels with space for guest homes and elaborate landscaping. Seen from the air, the individual addresses in this stretch resemble nothing so much as miniature villages.

Technically, the largest tract of land at 10-plus acres encompasses a couple of addresses. The main estate boasts what is either Gordon’s ugliest duckling or its most beautiful swan, depending on how the observer feels about a Japanese, pagoda-style residence dropped into the middle of the subtropics. A favorite slow-down spot for sightseers, it has two tennis courts, an elaborate koi pond (lake might be a better word), and what city documents call "a non-habitable tea house."
Most homes are set safely back from the road, away from prying eyes, an ideal setting for a street whose residents are described as "mostly private." "Famously private" might be the better term for Miles Collier, descendant of the county’s namesake, and Arthur Allen, global software magnate. Both step out for business deals or good causes, but they resist interest in their private lives with a zeal normally expressed by ants being fried under a magnifying glass.

But high-profile deals reap high profiles, even if only temporary ones, and the bashful businessmen made news together in spring 2007 when Collier sold a four-plus acre estate to Allen for a record-setting $40 million. Allen is said to be "renovating" the home, built in 1994. (If busy construction traffic is any indication, the difference between "renovating" and "gutting" lies in the eye of the beholder.)

Fortunately for Allen, the estate comes with built-in protection from rolling shutterbugs and pedestrian gawkers: a wall fronting Gordon. This edifice is what remains of the estate as it was when it was owned in the 1930s by the Uihlein family, of Schlitz Brewery fame. (What made Milwaukee famous lives discreetly in Naples: Pabst heirs also own property on Gordon Drive.) Call them the pioneers of panache: Port Royal wasn’t even a gleam in developer John Glen Sample’s eye when the Uihleins and their friends the Briggses (of Briggs & Stratton engines) moved to Gordon Drive, rendering the address instantly fashionable.

2900 Gordon Drive: The Port Royal Club
Although it’s now dwarfed by the 45,000-square-foot residence of Sandra and Alan Gerry, farther south on Gordon, for decades the Port Royal Club was the biggest kid on the block. Still the center of a lively social scene, the club, at 33,000-plus-square-feet, opened in 1959. Seated on five acres of land, it was personally financed by developer John Glen Sample, to the tune of $1 million, as part of his vision for Port Royal.

Sample, who had made his fortune in advertising, was president of the club for its first seven years (one- to two-year terms have been the norm since), and some of its bylaws still bear the hallmark of the man who believed no vision was too big to carry out and no detail too small to micromanage.
Naples native Sherrill Dixon remembers riding in Sample’s Jeep as a seven-year-old, down what was then a shell road, while the developer described to her father the dredging that would turn the southern end of Gordon Drive into saleable beach-front parcels. The earth moved—literally—to accommodate Sample’s scheme: Mary Watkins recalls that the developer had Gordon Drive itself shifted slightly east, south of the Port Royal Club, so that the residential lots on the Gulf side would fit his specifications.

Lots of developers before and since have kicked themselves for not having Sample’s drive and vision, but those qualities came at an arguable cost.

It’s true that he saw the potential in a piece of swampland others overlooked, but as the late Marjory Stoneman Douglas so eloquently points out in The Everglades: River of Grass, the best potential use of a piece of swampland is in its natural role as part of Florida’s delicately balanced eco-system. In theory, and some of our region’s recent golf developments to the contrary, Sample’s wholesale remake of the landscape would be federally prohibited today.

Sample left an unintended legacy in environmental circles: Alarmed by the dredging and filling, and the destruction of the mangroves, some leading members of the community were galvanized into action, coming together to buy land for preservation and to found some of the Gulfshore’s most prominent conservation groups.

Sample personally approved the architectural plans for every home, and he insisted that no two homes be alike. But, priding himself on being a great judge of character, Sample also personally approved every buyer. Although he rejected many for quirky and unclear reasons, there is some suggestion that he also turned away "diverse" residents, even those with cash in hand. The result was that his Gordon Drive was populated by men and women who, for the most part, looked and thought and worshiped exactly the way Sample did.

Fortunately, on today’s Gordon Drive, there is a refreshing mix of personalities and demographics. From infants to the elderly, the street’s residents represent a variety of occupations, hometowns and religious faiths. Driving by a modern, minimalist home two houses down from a warm, Cape Cod-inspired one, you could say that Sample realized part of his vision—if not, thank goodness, the rest.

The 3000 Block: Much Buzz
Sample loved media coverage of Port Royal, so long as he could control it, but some stories have a life of their own. In Penny and Lee Anderson’s case, perhaps it’s the property itself, located in the 3000 block of Gordon, that’s the source of the inadvertent buzz. Just as Sedona, Ariz., has its magical vortices, this is an estate where anything can happen—and has.

As early as the 1960s, an editorial in the city’s daily newspaper warned Port Royal residents to lock their doors, as out-of-town prowlers had been attracted to Naples by its reputation "as a playground for millionaires." In late 2002, two of these usual suspects stumbled onto some very unusual items at the Andersons’ 27,000-plus-square-foot villa.

Pulling a quick grab-and-go while no one was home, the thieves removed a couple of paintings they thought they could fence. Unfortunately, their taste in art was a bit too high-brow: They had stolen a Monet and a Renoir, museum-quality pieces that were valued together at around $6 million. International art-crime squads, the feds and the Naples police bore down on the culprits, who couldn’t wait to hand the hot art over during an undercover sting operation in Miami. (At a 300-plus-person charity lunch at the Anderson home in the spring of 2003, the genial host pointed lines of curious guests to the paintings, by then safely rehung.)

There was also a thrilling moment under a previous owner, John Slater, when his panther hurled himself out of the front picture window and tore down the street. (Although perhaps it happened so often the neighbors got used to it.) It wasn’t as though the cat didn’t get enough fresh air—the sight of Slater walking his exotic pet on a leash through Old Naples and into a local bar was a common one.

The panther was just one member of the menagerie owned by Slater, who founded one of the country’s largest food service businesses. There was a miniature horse and a dolphin, rumored to be the sister of Flipper. She operated a sort of mini-ferry in a pond on the front lawn (now filled in), happily pulling a raft that took local children from one side to the other. (Apparently Slater’s dolphin was so well trained that it even shared his memorably twisted sense of humor: Lavern Gaynor remembers Slater encouraging her, at the house with her children, to go for a ride across the pond. She did, whereupon the dolphin got halfway across, dropped the leads to the raft, and swam back to shore without her.)

The 3400 Block and Beyond: Something to Talk About
Forget the tear-down—how about the "move-over?" In the 3400 block of Gordon, the massive home owned by Sandra and Alan Gerry sits on a lot once occupied by a smaller abode. Rather than destroy that one, however, Gerry had it hauled to a nearby address, where it’s now owned by his son. (It’s one of several pieces of property that, although they are interrupted by other residences and lots, make up a sort of loose Gerry "compound." The accumulated value of the property, $58 million plus, also makes the homeowner the city’s largest taxpayer besides Coastland Center.)

While the main Gerry home was under construction in 2001 and 2002, there were so many rubberneckers that the couple had to hire private security to direct traffic. Politely the guard answered questions as the curious parked their cars on or across the street and strolled over to oversee construction. Yes, the home does have a bowling alley, as well as two pools, a spacious hub for monitoring the estate’s mechanical operations, lots of outdoor living space, and plenty of room for friends and family. As befits the man who purchased the rights to the Woodstock festival, the couple is said to entertain frequently.

3630 Gordon Drive
Perhaps the only organization more fearsome than the Mob is the Neighborhood Association. In the late 1990s, Port Royal was abuzz with rumors that Anthony Marchiano, then residing at 3630 Gordon Drive, was, as they say, "connected." That didn’t stop a group of neighbors from banding together to sue the homeowner for his refusal to cut back the sea oats and other vegetation choking a common beach path. Marchiano, who was embroiled in a lengthy custody battle at the time, said he needed the greenery for privacy.

As it turned out, he had a lot to hide. In 1998, federal agents arrested Marchiano at the Fifth Avenue South headquarters of A.S. Goldmen, the boiler room brokerage he owned with his twin brother, Salvatore. In a court room in New York, the two were convicted in 2001 of cheating investors out of an estimated $100 million. The company’s chief financial officer was sentenced to an extra-long prison stint for a bungled murder-for-hire plot targeted at the judge who presided over the case.

As of this writing, the three-story, Bermuda-style home, which has had two owners since Marchiano, is listed for sale at $12.9 million. The path to the beach is clear.

100 Bay Road
Technically, John ("Jack") Donahue, founder of Federated Investors, doesn’t live on Gordon Drive, but his walled estate and a row of picturesque boathouses distinguish the southernmost tip of Gordon, where the street ends in a circular turnaround as the land runs out into Gordon Pass (a favorite spot for frisky dolphins).

Beyond Donahue’s gates lies a compound of structures, including a boathouse and the stately main home, all situated on Bay Road. From there it’s a short boat hop away to Keewaydin, an island with a storied history.

On the maritime maps you’ll find it listed as Key Island, but everyone calls it Keewaydin. Keewaydin was originally a chain of boys’ camps, but the Southwest Florida location was floundering when Chicagoan Lester Norris visited Naples and the Everglades during World War II. Norris fell in love with the island and purchased it as a retreat for family and friends. He let the native key deer roam free around the 1930s lodge while his wife amassed one of Southwest Florida’s most impressive seashell collections. (The late Dellora Norris is the "Delnor" in Delnor-Wiggins Pass State Park—another favored shelling spot.)

Off-island errands required sailing into Naples, and a family member remembers that once during one of their day trips into town, a chimpanzee that Lester Norris had been given locked the island’s groundskeeper in his cage and turned a garden hose on him. Upon the Norris’ return, they rescued the man, damp but none the worse for wear.

The Norrises and their guests traveled back and forth to Keewaydin, using a private marina at the south end of the street. But after part of the property passed into other private hands, use of the lodge "intensified," to quote from a 1994 meeting of the city’s planning advisory council. When the owner asked for additional parking, dozens of Port Royal residents, representing as many as 150 other petitioners, turned out to spin a dark vision of the fume-spewing tour buses, loud out-of-towners, and careless flower-bed trampers they would be held captive to if the use was granted.
It wasn’t. Parts of Key Island deemed "environmentally sensitive" were put into public hands, and a large portion of the private parcel is owned by a company affiliated with Donahue and his family. Rumors of pending high-end development on the island are always rampant.

A generous donor to the Catholic Church, Donahue was also one of President Bush’s super-fundraisers during the 2004 campaign. The New York Times’ Elisabeth Bumiller (once the Naples’ correspondent for the Miami Herald) covered a lunch Donahue threw for Bush that year, during which journalists reporting on the lunch were kept in the guesthouse, away from the action, and protesters were carefully kept several hundred yards north of the Donahue home.

Truthfully, the area around Gordon Pass has always been a magnet for the hoi polloi. It was once the site of Gordon Fish Camp, where transients used tents and trailers as the home base for some prime fishing. The late Larry Brown, an otherwise distinguished resident of Palm Cottage during the 1950s, organized cock fights at the pass, at which the high and mighty and the rough and rowdy bet with and against one another. (Brown also began the Old Naples’ tradition of running up a flag to signal happy hour to the neighbors, so perhaps he wasn’t that dignified.)

Then there are the bicyclists. To hear some residents tell it, the only thing worse than hobos gathering to watch roosters battle to the death are these suited and helmeted health nuts on their two-wheeled terror-mobiles. Greeting each other at the Port Royal Club or the Phil, the cyclists nod to the non-cyclists like the friendly neighbors they are. But riding to the southern end of Gordon each morning, they might as well be Hell’s Angels.

The bikers won a victory in late 2007, when the city repainted the eight-foot-wide bike lane, a safety boon for them, a garish desecration to others. Public opinion split roughly 50-50 on the need for the markings, but all are in agreement that traffic on Gordon is too heavy.

"It’s like walking down I-75 in the morning," says one longtime resident. She’s not entirely wrong: City statistics show that traffic on Gordon is extraordinarily heavy for a dead-end street with a relatively sparse population.

Service vehicles (caterers, construction crews, landscapers, yoga instructors) make up much of that traffic, but many of these are drivers cruising to see what’s new. What’s going up? What’s coming down? Which house just sold? Who bought it? Will the pink house ever sell so long as it’s pink? (Maybe not at $23.9 million.)

The question that most propels these drive-bys: How is the other half living today? Those who ask it feel an absolute freedom to traverse Gordon in search of the answer. Within certain limits, and with a token amount of grumbling, residents don’t begrudge them their curiosity. They understand that although it’s the city’s most exclusive address, in many ways Gordon Drive is Everyman’s Street.