The city is northeast of and adjacent to Orlando.
Elevation ranges between 66 and 97 feet (20 and 30 m) above sea level.

According to the United States Census Bureau, the city has a total area of 10.2 square miles (26.3 km²), of which 8.7 square miles (22.5 km²) is land and 1.5 square miles (3.9 km²) (14.62%) is water.
It is nestled among the Winter Park Chain of Lakes, a series of lakes interconnected by a series of navigable canals, which were originally created for flood control and to run logs to a sawmill on present-day Lake Virginia.
The lakes are popular for boating, watersports, fishing and swimming.

The city is traversed by the old East Florida and Atlantic Railroad ("Dinky Line") railroad bed, which until the 1960s had a stop at Lake Virginia/Rollins College at the city park now known as Dinky Dock.
Much of this right of way has been converted to a rail-trail pedestrian/biking path in the form of the Cady Way Trail, which leads from Cady Way Park toward the Baldwin Park neighborhood and downtown Orlando, and in the opposite direction to Oviedo and beyond (via the Florida Trail), due to a new pedestrian bridge spanning Semoran Boulevard (SR 436) in Orange County.

SunRail operates a rail line through Winter Park on the former Atlantic Coast Line, with an Amtrak and SunRail commuter rail station in downtown's historic Central Park.
The city is northeast of and adjacent to Orlando. Elevation ranges between 66 and 97 feet (20 and 30 m) above sea level.
According to the United States Census Bureau, the city has a total area of 10.2 square miles (26.3 km²), of which 8.7 square miles (22.5 km²) is land and 1.5 square miles (3.9 km²) (14.62%) is water. It is nestled among the Winter Park Chain of Lakes, a series of lakes interconnected by a series of navigable canals, which were originally created for flood control and to run logs to a sawmill on present-day Lake Virginia. The lakes are popular for boating, watersports, fishing and swimming.
The city is traversed by the old East Florida and Atlantic Railroad ("Dinky Line") railroad bed, which until the 1960s had a stop at Lake Virginia/Rollins College at the city park now known as Dinky Dock. Much of this right of way has been converted to a rail-trail pedestrian/biking path in the form of the Cady Way Trail, which leads from Cady Way Park toward the Baldwin Park neighborhood and downtown Orlando, and in the opposite direction to Oviedo and beyond (via the Florida Trail), due to a new pedestrian bridge spanning Semoran Boulevard (SR 436) in Orange County.
SunRail operates a rail line through Winter Park on the former Atlantic Coast Line, with an Amtrak and SunRail commuter rail station in downtown's historic Central Park.
Winter Park, Florida