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This building has changed little since its 1921 construction by J. Davis "Jeter" McMillan, Robert E. Black and Alvah Cohen Bray. Throughout its life, the structure has housed a variety of shops and offices. Early on, it was referred to as the Clinic Building, most likely because several physicians leased space in the upstairs offices. From 1933 to 1953, the Winter Garden Post Office operated out of space on the first floor.

After McMillan and Bray sold their property shares to Black, a citrus grower and Clermont businessman, the structure was called the Black Building. L. Eugene Cappleman, Sr. and Ed Fischer purchased the building in 1968, and the Cappleman family acquired Fischer's share at his death. In 2012, the family renamed the building, in recognition of the 100th anniversary of the arrival of brothers William and Thurlow Cappleman to Winter Garden, and the opening of their grocery store, the first of many local businesses owned and operated by family members.

— Winter Garden Heritage Foundation, 2012

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