2025 Compare Cities Overview:
Leonardtown, MD vs Winchester, VA

Are people in Winchester older or younger than people in Leonardtown?
- The Median Age in Winchester is 4.3 years older than in Leonardtown.

Are housing costs cheaper in Winchester or Leonardtown?
- Winchester housing costs are 26.0% less expensive than Leonardtown housing costs.

Which city has a longer commute, Winchester or Leonardtown?
- The average commute for residents of Winchester is 5.2 minutes shorter than it is for residents of Leonardtown.

Things to do in Leonardtown?
Leonardtown, MD is a wonderful place to live. With its small-town charm and close-knit community, the town is a great place for families to settle down. It has plenty of outdoor activities to enjoy such as fishing, boating and swimming in the beautiful Patuxent River. There are also lots of great restaurants, shops and galleries that make it easy to have an enjoyable time exploring the area. For those who enjoy history, there are plenty of historic sites and buildings such as Leonard Hall Plantation and St. George's Episcopal Church that offer insight into the area's past. The town also has several parks where you can relax in nature or take part in a variety of activities like tennis and disc golf. All in all, Leonardtown is a wonderful place to call home!

Things to do in Winchester?
Winchester is located in the northern Shenandoah Valley of Virginia. It's a historically significant city known for its rich Civil War history and architectural attractions like Winchester National Cemetery, as well as its numerous outdoor activities like hiking, kayaking, and fishing. The city also boasts an array of art and cultural offerings, with events such as the annual Hillbilly Festival taking place throughout the year.