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Topography of Winter Garden. The exact coordinates for the City of Winter Garden is located at (28.560328, –81.584069 [22]According to the United States Census Bureau, the city has a total area of 15.6 square miles (40.4 km 2), of which 15.4 square miles (39.9 km 2) is land and 0.19 square miles (0.5 km 2) (1.28%) is water.