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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.
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,
www.SouthwestOrlandoBulletin.com x February 16 - March 1, 2017 x 7
FEATURE
A Historical Look at Winter Garden
Cherishing the Past While Progressing Into the Future
by Debra Wood
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
Dillard-Boyd 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
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