Winter Park


Welcome to Winter Park

The cultural hub of Orlando located along scenic waterways.
Approximately 20 miles northeast of downtown Orlando, Winter Park is a charming, green, cultural community known for its public displays of art, vast outdoor spaces, and quaint downtown streets reminiscent of previous times. Park Avenue is the vibrant beating heart of the community and home to several acclaimed eateries, boutiques, and museums. Nearby, residents can enjoy scenery and sunshine at one of the community’s many lakes, parks, or trails
First a rural indigenous community, Winter Park experienced rapid growth after the completion of the South Florida Railroad in 1880. Shortly after, the area was developed as a resort community for northern U.S. residents to retreat to during their brutal winter months. Today, Winter Park residents enjoy high performing schools, almost 3,000 acres of crystal blue waterways, luxurious homesteads, and award winning cuisine in one of Orlando’s cultural meccas.

What to Love

  • A well established, cultural hub
  • Award winning cuisine, modern art, and some of Orlando’s best shopping
  • Over 70 parks and nearly 3,000 acres of scenic waterways
  • Only 20 miles from downtown Orlando

Local Lifestyle

Winter Park residents enjoy easy access to modern amenities without sacrificing such close proximity to large scale outdoor recreation not often found in many sprawling urban neighborhoods. Park Avenue, the center of Winter Park, is home to more than 140 cafes, museums, and boutiques protected beneath a blanket of lush, green treetops. Seasonal art displays, concerts, and fashion shows often attract visitors from across Orlando. Just beyond downtown, a vast chain of lakes helps connect the community’s extensive network of communal parks, playgrounds, and botanical gardens.

Dining, Entertainment, and Shopping

In addition to the scenery and aesthetic of their picture perfect downtown district, Winter Park has become a favorite destination for shopping and dining in Orlando. Critically acclaimed eateries headed up by award winning chefs are plentiful and Winter Park locals are hardly ever left longing for ways to keep themselves entertained.
Beer, wine, and brunch: the three cornerstones of any successful American institution. They are all done very well at The Parkview, located on bustling Park Avenue. This intimate neighborhood institution is well known for its extensive drink list featuring a variety of difficult to find brews and vinos, which pair perfectly alongside elevated bar favorites like truffle mac and cheese, duck confit pizza, baked brie, and crab salad sandwiches. 
More casual American fare can be found just down the street at Garp & Fuss. A newer addition to Park Avenue, Garp & Fuss’ goal was to bring a variety of shareable plates to the people of Winter Park, with their own downhome twists. Buffalo cauliflower, bacon and fig flatbreads, and “brinner” (breakfast for dinner) have become beloved favorites in the community. 
With nearly 150 different businesses lining popular Park Avenue, it’s hard for locals to narrow their top choices down. If pressed, many would name Arabella or Writer’s Block at the top of their lists. Arabella is the ideal spot for Florida inspired decor, accessories, unique wardrobe additions with a quaint, European twist. Less than a quarter mile away at Writer’s Block, Orlando’s best known independent bookstore is a community icon with a steady stream of reader events, book fairs, and an endless selection of publications.

Things To Do

Winter Park’s community calendar is a never ending stream of fun filled events for all members of the community. Often held at one of their many local parks, some of these events include holiday gatherings, the annual tree lighting, museum open houses, public art displays, and movie nights in the park. These are usually held at lush Central Park, a sprawling 11 acre site with impeccable landscaping, including the continuous canopy of oak trees and the beautiful Rose Garden.


Several schools in Winter Park are among the best in the state. A few of these are:
  • Lake Highland Preparatory School, prekindergarten to 12th grade; the largest private school in Orlando is situated on 42 acres and ranks among the top 1% of Florida private schools
  • Audubon Park School, kindergarten to 8th grade; Audubon offers students the opportunity to join a number of clubs and athletic teams, with new organizations being added each year, such as tennis, orchestra, yoga, the mentoring club and more
  • Winter Park High School, grades 9 to 12; WPHS is a magnet school for the International Baccalaureate program

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