| Winter Springs to Rome (New York) | 1,054.44 mi (1,696.96 km) |
| Winter Springs to Romeoville (Illinois) | 973.09 mi (1,566.03 km) |
| Winter Springs to Romulus (Michigan) | 942.49 mi (1,516.78 km) |
| Winter Springs to Ronkonkoma (New York) | 955.22 mi (1,537.28 km) |
| Winter Springs to Roosevelt (New York) | 935.58 mi (1,505.67 km) |
| Winter Springs to Rosamond (California) | 2,198.82 mi (3,538.66 km) |
| Winter Springs to Rosaryville (Maryland) | 741.41 mi (1,193.19 km) |
| Winter Springs to Roscoe (Illinois) | 1,042.88 mi (1,678.36 km) |
| Winter Springs to Rose Hill (Virginia) | 737.32 mi (1,186.61 km) |
| Winter Springs to Roseburg (Oregon) | 2,526.30 mi (4,065.69 km) |
| Winter Springs to Rosedale (California) | 2,255.33 mi (3,629.60 km) |
| Winter Springs to Rosedale (Maryland) | 783.63 mi (1,261.14 km) |
| Winter Springs to Roselle (Illinois) | 994.64 mi (1,600.71 km) |
| Winter Springs to Roselle (New Jersey) | 916.80 mi (1,475.44 km) |
| Winter Springs to Roselle Park (New Jersey) | 917.41 mi (1,476.42 km) |
