Sands of Time : A Walk through Estero Island History

Sands of Time : A Walk through Estero Island History


Part Eight : Land boom (and bust, and boom)

To 21st-century visitors and residents, tourism and construction may appear to be the eternal mainstays of Fort Myers Beach. But after the native Calusa people were killed or run out of southwest Florida by the 1700’s, this 7.5-mile island on Estero Bay remained an uninhabited, transient fishing outpost for nearly 200 years.

In 1865 only the Ellis family officially resided on Crescent Beach – as Estero Island was then known – farming their homestead around the Mound House. Other homesteaders trickled in through the first decade of the 20th century.

Although sparsely settled, the island welcomed its first hotel in 1912: the grand, 3-storey Winkler Hotel. Guests arrived and left by boat and dined at the only local restaurant, in the hotel. The island’s modest popularity as a vacation spot likely traced to early Fort Myers seasonal resident and avid fisherman, Thomas Edison.

Organized development began slowly, as the original homesteaders sold off portions of their holdings. Wrote Rolfe Schell in his 1980 History of Forty Myers Beach Florida:

Connecticut Avenue, looking north over the Case subdivision to the Swing Bridge at Matanzas Pass on Fort Myers Beach. The Mound House is in the foreground. Circa 1950’s.

“In 1911 the first semblance of development, as we know it today, was started by Harold C. Case. It was about a mile and a half wide piece of property with Connecticut Avenue in its center. At that time, the shell road ended at Connecticut Avenue. In order to travel farther southward you turned onto the beach, which at low tide could accommodate six-lane traffic.”

In 1919 homesteaders E.E. Damkohler and C.S. Fickland started the Seagrape Subdivision on Mango and Chapel Streets. An airfield, built on the site of the now-defunct Fort Myers Beach Golf Club, opened to fly-in tourism on a micro-scale. Whispers of a land boom began.

The Matanzas Pass Swing Bridge in 1978. Photos courtesy of the Estero Island Historic Society.

The first bridge to Crescent Beach opened in May 1921: a wooden lift bridge to allow boats to pass through. Only one car at a time could traverse the narrow span, at an eyebrow-raising toll of 50 cents per car plus 15 cents per passenger.

That year Captain Jack DeLysle, a flamboyant entrepreneur and rum runner, built a 3-storey resort and the Seminole Sands Casino and dance pavilion on the Gulf side of Connecticut Street. In July 1921, local Tom Phillips and Chicagoan Harry Fiedler dug the island’s first canal at First and Crescent Streets.

A story in the Fort Myers News-Press in early October 1921 proclaimed: “Crescent Beach Center of Most Intense Development in Florida Today.” The island’s population was pegged at just 62 souls.


Winds of change

On October 26, 1921 a severe hurricane lashed the island; perhaps the worst since 1873.

Wrote Rolfe Schell:

“The grassland at the Beach was pushed back a hundred feet and considerable damage was done to the few buildings located on the island. The Seminole Sands Casino and bathhouse were ruined, as were several cottages. The road on the mainland which paralleled the shore, was destroyed.”

After 18 months of rebuilding, the island was back on its feet. In June 1923, over 200 cars passed over the Matanzas Pass Bridge in a single day. The Miramar and Gulf Heights Subdivisions launched in 1925.

But the 1920s’ almost yearly tropical storms kept taking bites out of the boom. Hurricanes in ’24 and ’26 left the lift bridge so damaged that it was replaced in 1928 by a 50-year-old, second-hand swing bridge with a hand-cranked (and cranky) mechanism.

The 1926 storm blasted out Hurricane Pass (creating San Carlos Island) and demolished a budding subdivision called San Carlos on the Gulf.

According to Jean Gottlieb’s book, Coconuts & Coquinas:

“The boom bubble burst right after the 1928 hurricane wiped out most of the flimsy buildings on the Beach. There was very little development after the hurricane until 1934-35.”

Wrote Rolfe Schell: “In 1935 at Canal 1 they had a sale of lots…but nobody would bid the necessary $50 per lot. So they closed the auction because the highest bid they got was $35.”

Shortly after that, Schell purchased a double lot on Delmar Street for $2 per foot; a total of $160.

“The beach was like a place that might come to you in a dream,” recalled the late Connie Brigham (in Coconuts & Coquinas), whose family moved to the island in the late 1930’s. “Everything was slow, relaxed, and sunshine, white sand, gulls and porpoises…a number of the cottages out here were owned by Fort Myers people and they would occupy them during the summer and then rent them out to tourists in the winter.”

The island held so few buildings that houses had no addresses and were designated by the names of their owners. Everyone who owned a place here pretty much knew everyone else.

The late 1930s’ peak season population was estimated at 400.


Cottage courts, hotels and motels

Silver Sands was the island’s first cottage court motel, built in 1921. Beachside and bayside cottages and fish camps popped up over the next four decades as popular tourist lodgings.

The massive Commodore Hotel – built of whitewashed coquina-rock blocks, with imposing pillars and a grand lobby – appeared on the shore in 1938, on the site of today’s Smuggler’s Cove condo. It was the 4th island hotel after the Beach (formerly Winkler) Hotel, Gulf Shore Inn and Pelican Hotel.

The Estero Island Historic Society website recounts the prominence of the Commodore Hotel in the 1940’s:

“During the WWII years the Commodore Hotel was a hub of activity when busloads of military were brought to the beach for R&R. On Sunday afternoons, buses left directly for the airbases in Fort Myers, and the Commodore provided bathhouses, ice cold sodas and beer, chili and cheese hotdogs and hamburgers, while dancing was always popular on the gulf-front patio.”

With the war, new visitors arrived on Estero Island: soldiers and airmen. The airfield at Buckingham became a gunnery school; Page Field in Fort Myers was a flying school. A number of military officers and their families stayed out on “The Beach,” where wartime regulations froze rents as low as $45 per month, all-inclusive.

Airplanes soared from Page Field over the Gulf of Mexico while the Coast Guard patrolled for German submarines. A rumored sighting of a German submariner buying groceries on the island was never proved, or disproved.

In 1946 the wartime rent freeze thawed, rationing disappeared and tourists flowed in growing numbers onto the quiet island paradise.

The Skyline and Rancho del Mar motels opened in 1949. Developers dredged canals and used the muck to create higher ground for more cottages and motels. Calusa Indian mounds fell to bulldozers, their contents crushed into fill for the growing network of roads. Archaeology and historic preservation weren’t yet on the radar.

By 1950 the Estero Island population stood at 711. Development continued apace, with little long-term planning or vision. In 1959 the Privateer opened as the first three-story “high-rise” co-op apartment building. It later changed to interval ownership, as did the Sandpiper and Neptune Inn motels.

As of 1960, the island’s population reached 2,464. More restaurants and shopping centers appeared. The south-end Big Carlos Pass Bridge to Lovers’ Key, Bonita and Naples opened in 1968. Traffic increased and growth accelerated.

Estero Island’s population was 4,305 in 1970 when Leonardo Arms opened as the first condo at the south end, followed by Island Towers in 1971 at the north. The 65-foot-high Matanzas Pass Skybridge opened in 1979, sparing millions a wait for the balky swing bridge to function. But it did not spare the island from seasonal traffic back-ups.

By the turn of the 21st century the Fort Myers Beach permanent population reached 6,844, of which 5,614 were housed in condo units in 2013. Visitors swelled the numbers in season to over 45,000.

The most recent land bust that started with the 2007 recession reversed course in the past three years. Property values are rising again and the good times roll on.

Until the next turn of the cycle?


Janet Sailian

This is the final column of Sands of Time for the season. Any local-history topics you would like us to explore in fall 2017? Please e-mail