2026 Compare Cities Overview:
Leesburg, VA vs Winter Park, FL

Are people in Winter Park older or younger than people in Leesburg?
- The Median Age in Winter Park is 10.0 years older than in Leesburg.

Are housing costs cheaper in Winter Park or Leesburg?
- Winter Park housing costs are 33.0% less expensive than Leesburg housing costs.

Which city has a longer commute, Winter Park or Leesburg?
- The average commute for residents of Winter Park is 6.9 minutes shorter than it is for residents of Leesburg.

Things to do in Leesburg?
Leesburg, Virginia is a vibrant town located in the northern part of the state. The town was once the home of many prominent political figures and today serves as a hub for residents of Northern Virginia. With a population of nearly 48,000, Leesburg offers an ideal mix of small-town charm and big-city amenities. Residents can enjoy outdoor recreation opportunities at nearby parks and trails, or explore the many museums and historical sites throughout town. From shopping to fine dining to excellent schools, health care options and services, Leesburg provides something for everyone to love about this quaint yet bustling town.

Things to do in Winter Park?
Winter Park, FL is nestled between Orlando & Sanford offering magnificent mansions combined with vibrant street scenes fulls fabulous restaurants and boutique stores. Visitors here can enjoy swan boats cruising across Lake Virginia or find tranquility at Leu Gardens which offers breathtaking views no matter which season you visit during!