| Winter Springs to Shelbyville (Tennessee) | 559.56 mi (900.53 km) |
| Winter Springs to Shelton (Connecticut) | 984.67 mi (1,584.67 km) |
| Winter Springs to Shelton (Washington) | 2,572.31 mi (4,139.74 km) |
| Winter Springs to Shenandoah (Louisiana) | 596.60 mi (960.14 km) |
| Winter Springs to Shepherdsville (Kentucky) | 690.86 mi (1,111.83 km) |
| Winter Springs to Sheridan (Wyoming) | 1,792.82 mi (2,885.27 km) |
| Winter Springs to Sherman (Texas) | 968.47 mi (1,558.60 km) |
| Winter Springs to Sherrelwood (Colorado) | 1,551.61 mi (2,497.07 km) |
| Winter Springs to Sherwood (Arkansas) | 769.72 mi (1,238.74 km) |
| Winter Springs to Sherwood (Oregon) | 2,529.53 mi (4,070.88 km) |
| Winter Springs to Shiloh (Illinois) | 842.86 mi (1,356.45 km) |
| Winter Springs to Shiloh (Ohio) | 787.05 mi (1,266.63 km) |
| Winter Springs to Shiloh (Pennsylvania) | 820.16 mi (1,319.91 km) |
| Winter Springs to Shirley (New York) | 961.51 mi (1,547.40 km) |
| Winter Springs to Shively (Kentucky) | 706.98 mi (1,137.77 km) |
