Founders Loring Chase and Oliver Chapman knew their purchase of 600 acres for $13,000 in 1881 was a wise investment. Now, just over 140 years later, the City of Winter Park continues to offer ways for residents and guests to experience the community’s vast history, heritage and unique assets. The City, with its old-world charm and New England feel, has become known for its neighborhoods, historic homes, shopping, dining and cultural opportunities.

When the pandemic created unprecedented economic challenges, the City partnered with the business community by offering financial support and developing creative solutions to continue service in a socially distant manner. Now in 2022, the resiliency of the City’s businesses is demonstrated in a high occupancy rate for office and retail citywide. After the recent holiday season, the City received reports of sales increasing by up to 70% over last year. In addition, Winter Park’s lakes, vast parks system, extensive tree canopy and annual events, such as its spring and autumn art festivals, make the City’s 10 square miles a popular destination for residents and visitors.

The City continues to seek opportunities to further enrich the lives of its residents, businesses and guests. The City’s main street, Park Avenue, is the epicenter of the business community, offering more than 140 boutiques, museums/galleries and sidewalk cafes. Anchored on the southern end of Park Avenue is Rollins College, the No. 1 regional university in the South ranked by U.S. News & World Report for the 2021-22 school year. At the northern end, Park Avenue is surrounded by the City’s golf course, fondly referred to as the WP9. The WP9 was the first golf course in Florida to be listed on the National Register of Historic Places and has been rated one of the Top 10 nine-hole golf courses in the country.

Just a few blocks away from Park Avenue is the City’s newest 21st-century facility, the Winter Park Library and Events Center, which opened in December 2021. This project was designed by internationally acclaimed architect Sir David Adjaye, who also designed the Smithsonian Institution’s National Museum of African-American History and Culture on the National Mall in Washington, D.C. The Library and Events Center features a two-story library as well as a welcoming covered passageway at the entrance of both facilities. The events center has a spacious grand ballroom and rooftop terrace with views of Martin Luther King, Jr. Park and downtown Orlando’s skyline.


The Library and Events Center is also the new home to a majority of the Winter Park Sidewalk Art Festival’s “Best of Show” collection and three sculptures from the Albin Polasek Museum and Sculpture Gardens. Winter Park is known for its diverse and comprehensive arts and culture offerings including museums, galleries, festivals, performing arts, visual arts and education. In addition, an inclusive Arts and Culture Alliance was launched in 2017 to represent all nonprofit arts and culture organizations within the City.

For those who enjoy the outdoors, the City values its green- space and understands the importance of parkland to the environment and personal health. This year, the City approved the contract to purchase the Winter Pines Golf Course. This acquisition allows the City to preserve 93 acres as active greenspace and adds an 18-hole golf course to the City’s recreational portfolio.

The City is also transforming two places into new green spaces for respite and relaxation. Just a few streets south of Park Avenue, along the Orange Avenue commercial corridor, the City cleared 3.54 acres of land to create a park surrounded by seven newly planted large live oak trees.

With the City’s 2017 purchase of 43.34 acres of Howell Branch Preserve, there also is a place for birdwatchers, walkers, paddleboarders, canoers and kayakers. This year, the City began removing an invasive species to add passive trails and boardwalks. They will be lined with educational signs for those interested in learning about the natural surroundings.

Whether it’s adding parkland, more trees or building state-of-the-art community facilities, Winter Park works hard to improve the services it provides year-round.

By Clarissa Howard

Clarissa Howard is Director of Communications for the City of Winter Park. The City of Winter Park, population 29,795, is located in Orange County.