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Corner of Main Street and Plant Street
A gathering of Winter Garden citizens on the corner of Main Street and Plant Street around 1913. To the right of the image by the car is a few of James Lafayette Dillard's (1858-1943) family. Dillard migrated to Central Florida from Virginia with his…
Train at the Atlantic Coast Line Railroad Depot in Winter Garden
An Atlantic Coast Line (ACL) Railroad Company train coming in to the depot located at 1 North Main Street in Winter Garden, Florida, around 1915. Aspects of the downtown business district of Winter Garden are noticeable in this photograph, such as…
Aerial View of Downtown Winter Garden
This aerial view from the Winter Garden water tower highlights the business district of Downtown Winter Garden, Florida, and some of it's prominent buildings in the 1920s. Those buildings include the First Baptist Church, South Apopka Supply Company,…
Tavares & Gulf Railroad Depot in Winter Garden
This photograph highlights the Tavares & Gulf Railroad Depot, a water tower, and Winter Garden Light & Water Company around 1913. This depot replaced the original 1889 structure in 1913, at a cost of $1,765. The western portion, built of…
Construction of the Shelby Hotel
James Lafayette Dillard (1858-1943) built the Shelby Hotel in 1913 on 1 West Plant Street in Winter Garden, Florida. In this photograph, it is evident that construction was still in progress. The hotel was located a block away from both the Tavares…
Arthur Bullard Newton's Fourth Store
Arthur Bullard Newton's fourth store in Winter Garden, Florida, the 1920s. Over the years other businesses would take root in the building. However, in the early 1920s the store's interior was burned. Until it was repaired, Newton worked at a…
First National Bank of Winter Garden
The First National Bank of Winter Garden, located at the corner of Plant Street and Boyd Street around 1919. The bank opened on the previous location of Arthur Bullard Newton's dry goods store, which was built in 1909. In 1919, Newton served as the…
Arthur Bullard Newton's Dry Goods Store
The building in the photograph is the third incarnation of Arthur Bullard Newton's dry goods store, which was built at 14 South Main Street in Winter Garden, Florida, in 1909. Across the building is advertising the merchandise sold at his store.Often…
Arthur Bullard Newton, 1909
Arthur Bullard Newton in 1909. Often called "Mr. First," Newton moved to Winter Garden, Florida, in 1892 where he was continually busy with varied pursuits in business, politics, and services. In his long line of being first, he established the first…
Winter Garden City Station, 1924
The City Station, located at the southeast corner of Dillard Street and Plant Street in Winter Garden, Florida, in 1924. Built by James Lafayette Dillard (1858-1943), this building was a combination of a gas station and a grocery store with upstairs…
Bank of Winter Garden, 1912
The Bank of Winter Garden, located on the corner of Main Street and Plant Street in Winter Garden, Florida, in the early 1900s. In 1908, James Lafayette Dillard (1858-1943) founded the Bank of Winter Garden. He would later become the Director and…
Intersection of Plant Street and Main Street in Winter Garden Before the Fire of 1912
The intersection of Plant Street and Main Street in Winter Garden, Florida. This photograph was taken in the winter of 1912, before the infamous fire that same year. The fire occurred on March 12, destroying several bushiness such as the wood…
Main Street in Winter Garden After Fire of 1912
A revitalized Main Street after being rebuilt from two devasting fires devastating fires in 1909 and 1912 in Winter Garden, Florida. Taken around 1912, this photograph shows the new Bank of Winter Garden (1908-1929) and, on the right, the Dillard…
Construction of the First Baptist Church of Winter Garden
The construction of the First Baptist Church of Winter Garden, Florida, around 1922. The congregation was originally organized in Ocoee, Florida, in August of 1888 with nine charter members. After eight years, the church voted to relocate to 125 East…
Orange Hotel
One of Winter Garden's first hotels was the Orange Hotel, located on the east side of South Main Street. The hotel had various types of guests, such as fishermen, salesmen, and regular visitors. The hotel burned down in the fire of 1912.