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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…
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…
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…
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…
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…
South Apopka Supply Company
Two men walking on Main Street past the South Apopka Supply Company in Winter Garden, Florida. Located at 32 South Main Street, the building was erected around 1915 and stood directly south of the 1912 Dillard and Boyd Building. The South Apopka…
South Intersection of Main Street and Plant Street, Winter Garden
A southward view of Main and Plant Street in Winter Garden, Florida, prior to the fires of 1909 and 1912. The large building on the right is A. B. Newton's Dry Good Store, which was later replaced by Dillard and Boyd General Merchandise Store. Behind…
Winter Garden Business District
The business district of Winter Garden, Florida, photographed prior to the 1909 and 1912 fires that destroyed all of the buildings pictured. Winter Garden's business district was located at the intersection of East Plant Street and North Main Street.…
Black Building
The Black Building, located at 101-121 West Plant Street in Winter Garden, Florida. This two-story brick Masonry Vernacular commercial building was constructed in 1921 by a businessman and citrus grower from Clermont named Robert E. Black. It…
12 West Plant Street, Winter Garden
The structure at 12 West Plant Street in Winter Garden, Florida, was the first brick commercial building built in 1912, after a 1909 fire destroyed all the downtown wood buildings. It was built by James Lafayette Dillard (1858-1943) and Benjamin T.…
126 West Plant Street, Winter Garden
This one-story commercial building in Winter Garden, Florida, was constructed in 1922 as part of land platted by J. D. McMillan in 1915. The building at 126 West Plant Street was originally owned by the McMillan-Bray Hardware Company. The store was…
Edgewater Hotel
The Edgewater Hotel, located at 99 West Plant Street in Winter Garden, Florida. The hotel is a part of the Winter Garden’s National Historic Register Business District, was completed in 1926 and opened in 1927 with 53 guestrooms available. At…
First Baptist Church of Winter Garden
The First Baptist Church of Winter Garden was originally organized in Ocoee, Florida, in August of 1888 with nine charter members. After eight years, the church voted to relocate to Winter Garden on land donated by James Lafayette…
RICHES Podcast Documentaries, Episode 18: Winter Garden's 20th Century: Boom, Bust and Rebirth
Episode 18 of RICHES Podcast Documentaries: Winter Gardens 20th Century: Boom, Bust and Rebirth. RICHES Podcast Documentaries are short form narrative documentaries that explore Central Florida history and are locally produced. These podcasts can…