Downtown Winter Park is the best, coziest, and happiest place to stroll, sit by the fountains, enjoy a cup of tea/coffee/drink, browse the internet, study, or chat. The area boasts great local stores, fun places to explore, and free parking lots. Visitors can enjoy the dining scene, browse the multitude of stores, and take in the wonderful atmosphere. The downtown is dog-friendly, and even more fun to explore by taking the Sunrail. With a lovely park for picnicking and a great overall ambiance, Downtown Winter Park is a delightful destination.
Charming town. Lots to see. A lot of food options. It's a vintage little town. Love the find!
June 2026
Is a beautiful place to have an evening with the family, your love. Is peaceful and quiet.
May 2026
A nice walkable town of shops and restaurants. The park located across the street as well as two other main parks within a reasonable car driving distance. Train station also located within walking distance. Can't believe I didn't take pictures. It was in and out after a meal. Next time.
Recommended as Best Shopping Because: Familiar brands and unique shops meld with colorful flowers and cobbled lanes. Park Avenue isn't just great shopping, it's great sightseeing, too.
Best for Christmas Shopping Because: Shopping doesn't get more pleasant than when you're perusing the picturesque purveyors of Park Ave.
