A Historical Look at Winter Garden

Cherishing the Past While Progressing Into the Future

by Debra Wood


One of the most successful efforts at embracing history in Central Florida, downtown Winter Garden has become an active, engaging area full of shops, restaurants, a hotel and a theater.

Men, women and children work the fields in the 1900s. (Photo courtesy of the Winter Garden Heritage Foundation)

The city formed a community redevelopment agency in 1992, the Winter Garden Heritage Foundation was created in 1994, and the History Research and Education Center opened in 2015.

“We are always asking residents to share their family history with us,” said James A. Crescitelli, WGHF program director.

The nearly 10-acre Winter Garden Downtown Historic District was listed on the National Register of Historic Places in 1996, as was the Winter Garden Historic Residential District, which includes the American Legion Hall. The Winter Garden Heritage Foundation, West Orange Trail and the city’s streetscape project in the 2000s deserve much credit for bringing the public and private sectors together to preserve this city’s rich history.

The commercial district developed at Plant and Main streets consists of 26 buildings, the oldest dating back to 1912, possessing significance for their architectural and historical characteristics. The 25-acre residential district contains 76 historical buildings bordered by Plant, Boyd and Tilden streets and Central Avenue. Most are in the Cooper/Sewell subdivision.

The city dates back further than its downtown. Winter Garden was settled in the 1850s, with scattered farms along the south shore of Lake Apopka. Early residents grew citrus and vegetables.

The Early Days

In the mid-1880s, the Orange Belt Railroad came through Oakland, providing an easy way to transport oranges to residents in northern states. The Tavares & Gulf Railroad came to Winter Garden in 1899, and citrus moved center stage. The post office opened in 1892, and the Winter Garden depot opened a year later. But the winter of 1894-95 was a difficult one, with two hard freezes. Ninety percent of the citrus trees were destroyed, and many settlers left. The price of land fell and opened opportunities for truck farming to develop.

The community continued to grow, and about 100 people lived in Winter Garden at the start of the 1890s. Amenities included a sawmill and turpentine stills.

The city incorporated in 1908, when about 191 people called Winter Garden home, and elected A.B. Newton as mayor. He was an agent for the Orange Belt Railway and then the postmaster and the publisher of the city’s first newspaper. He later served on the Orange County Commission and in state legislature.

The first residential subdivision, called Millers Plat of Winter Garden, formed in 1907, and the first telephone exchange and a bank arrived in 1908. By 1910, the population had grown to 351.

Early in the 20th century, a fire wiped out most of the wooden structures downtown, and the city was rebuilt with brick. One of the oldest surviving structures in downtown is the DillardBoyd Block, built in 1912, with a bakery and real estate office.

The Tavares & Gulf Railroad depot, at 101 S. Boyd St., opened in 1913 and cost $1,765. The Central Florida chapter of the National Railway Historical Society purchased it in 1982, kicking off local efforts to preserve Winter Garden’s history. It now serves as the Central Florida Railroad Museum and is operated by the Winter Garden History Foundation and owned by the city.

The first brick lodging property, the Shelby Hotel, opened around 1913, and an automobile repair shop a year later. Tonys Liquors now occupies the Shelby building.

The decade between 1910 and 1920 was marked by construction and large projects. The city’s first waterworks was built, as were an ice plant, electrical plant, streetlights and brick roads. The 1918 Atlantic Coast Line Depot is now the Winter Garden Heritage Museum.

The Florida Citrus Exchange was formed in the 1910s, and Luther Tilden served as director. He also operated a grocery store on Main Street and one of the first packing houses.

Tilden’s home, also known as Meadow Marsh, was built in 1910 and remains on the National Register of Historic Places. The wood-frame house later received additions for a kitchen, bedroom and parlor. Tilden died in 1929. The home was used as a bed and breakfast for a period of time, but now is a single-family residence.

Farmer Morgan Britt came to town in 1909. He grew vegetables and citrus and, in 1929, built a home on East Plant Street. He was considered one of the largest producers of lettuce in the 1920s, and two years later he started residential subdivisions. The Ort Law Firm purchased the Britt’s home in 2014 for nearly $1 million and has restored the building to its former glory.

The Roaring ’20s & Depressing ’30s

By 1920, Winter Garden’s population had reached 1,021. More than 300 new buildings were built between 1920 and 1926. The Winter Garden Rotary Club formed in 1926.

Commercial construction also continued, with the opening of a hardware store, theater and department store. The Winter Garden First Baptist Church built a new church on Plant Street in 1922. In 1926, the Pounds Motor Co. Building was finished. The Pounds family sold Ford cars and developed a tractor tire. The Roper Building was constructed in 1927 and contained a hardware store.

As with other parts of Florida, the 1920s was a period of great growth, which led to a building boom followed by a collapse. But Winter Garden’s citrus industry moderated the downturn, until fruit flies arrived in 1928 and curtailed the shipping of fruit.

The Historic Edgewater Hotel

The Historic Edgewater Hotel in Winter Garden opened in 1927 and reopened in 2003.

Construction began on the 52-room Edgewater Hotel at 99 W. Plant St. in 1924. A four-story hotel was planned, but the land bust curtailed the project. A group of investors completed it as a three-story building. It opened Jan. 26, 1927, and was considered one of the safest hotels in the country. It had a sprinkler system throughout and metal furniture. It also featured electric heat, telephones and private baths. The building also housed a barbershop, drugstore, telegraph office and a Pittman Jewelers, which is now located in Clermont. The dining room, called Evergreen, served traditional Southern meals. Local people would come to wander the halls and ride the elevator.

Works Progress Administration (WPA) funds brought a new city dock, boat basin, fire station, auditorium, city hall, sports fields, Tanner Hall, Lakefront Park and a municipal pool to the town during the 1930s. George Walker served as mayor during this period.

L. Frank Roper’s home was built on North Highland Avenue in 1937 (photo courtesy of the Winter Garden Heritage Foundation).

L. Frank Roper built an important home in 1937 at 220 N. Highland Ave. The Ropers grew citrus and processed it in town. According to the county, the home remains a single-family residence.

Fruit was packaged in packing houses in 1909 and 1910. In the 1940s, canning juice was popular, and in the 1950s, concentrate came into style.

Culture & Entertainment

Built in 1935 as a single-screen cinema, Garden Theatre was the first in Central Florida to show “talkies.” It closed in 1963 because of waning interest in films as television became popular. After it closed, the neighboring Pounds Motor Co. Inc. used the building as a storage space for tractors and other machinery. The interior was removed, and the sloped floor was covered with cement.

In 2003, the city of Winter Garden purchased the theater at 160 W. Plant St. and granted title to the Winter Garden Heritage Foundation in 2010, after it restored the theater to its original Spanish style. The Dr. P. Phillips Foundation and the Winter Garden Community Redevelopment Agency donated funds for the effort.

The foundation also upgraded the facility, bringing it up to modern building codes and hospitality standards. The theater reopened in February 2008 and provides a venue for plays, concerts and movies. The theater features the original building’s brick walls, tile courtyard and dark-blue ceiling with light shining through small holes, giving the illusion of a star-filled sky.

The 200-car StarLite Drive In opened in 1947 on East Plant Street. It featured an art deco style, but it closed in 1996 and was leveled in 1998.

Tourism Begins

The city of Winter Garden promoted Lake Apopka as a tourist stop during the 1930s. In 1936, the city built a 12-acre tourist camp called Trailer City in the northernmost spot in the Winter Garden Shores subdivision, also funded by WPA. Trailer City was popular with vacationers. It included boat basins, an auditorium, and a swimming pool and bathhouse.

In the 1930s, bass fishing on Lake Apopka attracts people to Winter Garden (photo courtesy of the Winter Garden Heritage Foundation).

Bass fishing on Lake Apopka also attracted people to the area. An early brochure called Winter Garden the “finest breeding place in the world for bass and pickerel.” Many folks, including Humphrey Bogart, Errol Flynn and Clark Gable, are said to have stayed at The Edgewater Hotel. An early hotel brochure said that it was common for fishermen to catch the daily limit within a few hours. During the late 1930s, the hotel added fish-cleaning stations with a refrigerator and sink on each of the three floors and marketed itself as a full-service fishing lodge in Field & Stream magazine. The hotel also maintained a houseboat and took guests out on the lake.

As agriculture began polluting Lake Apopka, the hotel’s fortunes changed, as did its success. The number of bass declined, and fisherman stopped coming. The U.S. Army housed soldiers at the hotel during World War II, and workers completing site work for Walt Disney World stayed there in the 1960s.

Gordon Dickerson became manager in 1948. He recently visited the hotel and recalled some of his fondest memories, including the six weeks that the Washington Senators stayed at the hotel during spring training.

The Edgewater Hotel closed in 1968 and fell into disrepair. Walls collapsed. Windows were boarded up, but still pigeons nested in the building and left decades worth of droppings. The current owners purchased the property in 1995 and set about fixing it up. Co-owner Mike Lanza and his team removed 72 tons of debris and then replaced walls with lath board and plaster, rather than sheetrock, to maintain historical integrity. The woodwork was restored as closely as possible to the original. The hotel was decorated with antique-style furniture to give guests a feel of what life may have been like early in the last century.

“It was a love of history and the town to honor its history,” Lanza said.

The Historic Edgewater Hotel’s first floor opened in 2000, and after a thorough renovation, the building began operating again as a bed-and-breakfast-style lodging in 2003. The manually operated Otis elevator remains in working order. It was one of the first elevators in the community. The person operating the lift must consider weight loads in order to slide the elevator to a proper stop at the appropriate floor, a job that takes some practice, so hotel employees, not guests, run the elevator. Guests can enjoy a 1920s experience with today’s comforts, such as air conditioning and internet access. People from more than 80 countries have stayed at the hotel, and it has received many honors.

Just as The Edgewater offers the latest amenities in a historic building, Winter Garden’s downtown envelops visitors in the feel and memories of an earlier time, when pioneers were settling Central Florida. 💓

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