The city was founded as a resort community in the mid-1800s by wealthy northerners who were attracted to the place’s warm weather and natural beauty. Today, Winter Park is considered the first centrally-planned Florida community, retaining the charm and allure that has made it a haven for the rich and famous since its inception.
Winter Park is known for its brick-lined streets canopied by age-old, Spanish moss-draped oak and camphor trees. The city boasts scenic lakes, beautiful parks, historic buildings, art galleries, museums, theaters and stunning homes. Winter Park is also the site of the prestigious Rollins College, Florida’s oldest college founded in 1885.
Adjacent to Orlando, Winter Park serves as a bedroom community for the Theme Park Capital of the World. This status notwithstanding, Winter Park also gets its fair share of visitors who come to the city for its historic Southern charm and topnotch shopping, dining and leisure opportunities.
An affluent community, the housing stock in Winter Park is traditionally upscale, featuring a mix of historic and modern homes and estates in various architectural styles. However, you can also find plenty of affordable options in its many neighborhoods, some of which have been earmarked for affordable and workforce housing.
Winter Park neighborhoods
Winter Park is composed of old and new communities, reflecting the city’s growth and development over the decades.
Among its many historical neighborhoods are College Quarter Winter Park, Hannibal Square, Orwin Manor and Windsong. It is here where you will find the city’s well-preserved historic homes, mostly built between the 1920s and 1950s in various architectural styles, including Cape Cod, traditional, 1920s bungalow, and Spanish/Mediterranean.
Downtown Winter Park is the heart and soul of the city. The housing stock here is made up predominantly of luxury multi-family residences, including condos and townhomes with the finest appointments and top-of-the-line features.
Winter Park is also home to many newer subdivisions that offer everything from charming builder homes and condos to elegant custom homes with distinctive architecture. You can find spacious bungalows in very affordable prices to mid-range 2-story homes built in the 1960s and 1970s to contemporary luxury properties.
All around Winter Park’s Chain of Lakes are various communities like Lake Knowles and Osceola Shores that offer gorgeous lakefront properties, ranging from historic estates to modern condos.
Lifestyle, culture and recreation
- Park Avenue, downtown’s main street, is Winter Park’s primary shopping, dining and entertainment center. With its high-end shops and restaurants, Park Avenue is a favorite destination of the most discriminating residents in the region. Most restaurants in Park Avenue are fine dining, and the best ones include Bosphorous, Prato, The Bistro on Park Avenue and The Ravenous Pig.
- Downtown Winter Park is home to the 2,781 acre Chain of Lakes, which include Lake Virginia, Lake Osceola, Lake Maitland, Lake Mizell and Lake Minnehaha. These lakes are connected by narrow canals, allowing navigation from one to another. Pontoon boating, waterskiing and fishing are the most popular activities in these lakes.
- Winter Park boasts over 70 parks, many of which are located along the Chain of Lakes shores. Central Park in the downtown area is the “crown jewel of all parks” and is the site of many of the city’s major events and festivals. Other notable parks include the Kraft Azalea Garden on Lake Maitland, and the Dinky Dock, which has a community fishing pier and boat ramp.
- Winter Park is filled with historic and cultural treasures, including the Olde Winter Park historic district, the Mead Botanical Garden, the Polasek Museum & Sculpture Gardens, and the Charles Hosmer Morse Museum of American Art.
The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional Multiple Listing Service, Inc. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.