Orange County · Central Florida
Winter Park blends a historic college-town character with a polished, walkable downtown. Park Avenue's boutiques and restaurants face a shaded central park, and a short walk leads to canals and lakes.
Arts and culture run deep here: the city is home to several respected museums and gardens, and Rollins College adds lectures, performances, and a youthful energy.
You'll find a broad mix — 1920s-era bungalows and Mediterranean Revival homes, mid-century ranches, lakefront estates, and newer townhomes and condos near downtown. Established, tree-lined neighborhoods are a big part of the appeal, and many homes are within walking or biking distance of shops and parks.
Winter Park sits just north of downtown Orlando, which can make commutes to downtown offices, the hospital districts near downtown, and parts of Maitland manageable. SunRail has a stop in Winter Park. Commutes to the airport, Lake Nona, or the theme parks are longer and depend heavily on time of day.
Winter Park's signature street of independent shops, cafés, and restaurants faces Central Park's lawns and oaks. Spend an afternoon browsing or grab a seat outdoors and people-watch.
Visit Official Website for Park Avenue & Central Park (opens in new tab)
Home to an extraordinary collection of works by Louis Comfort Tiffany, including the reconstructed Tiffany Chapel. It's a must-see for visitors and a point of pride for locals.
Visit Official Website for Charles Hosmer Morse Museum of American Art (opens in new tab)
A narrated pontoon cruise through Winter Park's lakes and narrow, tree-lined canals, passing historic homes and Rollins College. A relaxing way to see the city from the water.
Visit Official Website for Winter Park Scenic Boat Tour (opens in new tab)
A natural garden with boardwalks, a butterfly garden, greenhouse, and an outdoor amphitheater. It hosts community events and offers a peaceful escape close to town.
Visit Official Website for Mead Botanical Garden (opens in new tab)
The former home and studio of sculptor Albin Polasek, set on lakeside grounds with gardens and sculpture. A quiet, beautiful stop for art lovers.
Visit Official Website for Albin Polasek Museum & Sculpture Gardens (opens in new tab)Hours, admission, and event schedules change — please check each official website before visiting.
Get local guidance on pricing, neighborhoods, and next steps from Jennifer.