Winter Park, FL

Featured Listings


Winter Park, Orlando

People outside Orlando might confuse Winter Park with another Orlando neighborhood, Winter Garden. At 14 minutes away, Winter Park is nearer to the Central Business District compared to Winter Garden, which is 21 minutes away. And Winter Park is more established compared to Winter Garden.

Located 15 miles northeast of Downtown Orlando, via the FL-426 highway, you will find the neighborhood of Winter Park. Its history dates back to 1958 when David Mizell Jr. purchased an eight-acre property in the area, which he called the Lakeview. Three decades later, Oliver Chapman and Loring Chase purchased 600 acres of land, which then kick started the process of creating the town of Winter Park.

The name Winter Park was probably derived from the original purpose of this area. The community was first conceptualized as a winter resort area. The owners finally decided on the name of Winter Park in 1881.

Today, Winter Park is now a much sought after place to live.

One of Orlando’s Best Suburbs

Winter Park was named by as one of Orlando’s Best Suburbs for 2019. There are about 30,000 residents in this neighborhood. 

Both Walt Disney World and Universal Studios Orlando are less than half an hour’s drive from Winter Park. In addition, you have two college campuses located here.

The heart of the city is Park Avenue, which features 140 retail shops, cafes, restaurants, and more. It’s right next to Central Park with its canopy of mature oak trees, juxtaposed with the modern architectural design of the retail complex. Apart from shopping, Park Avenue also brings a lot of culture to the table. There are art shows, car shows, exhibits, fashion events, concerts, and other seasonal activities. This is also the place where residents mingle and catch up on each other’s lives.

There are also plenty of dining options in Park Avenue. Some of the restaurants in the complex include the Umi Japanese restaurant, Luma on Park, Barnie’s Coffee Kitchen, Antonio’s House of Pizza, Briar Patch Restaurant, Boca Winter Park, 310 Park South, Orchid Thai Cuisine, Prato, Power House Cafe, and Panera Bread.

If you like the outdoors, Winter Park has plenty of green spaces where you can get some fresh air. The Martin Luther Jr. Park stretches 23 acres of land, and almost every portion can be accessed via walkways and dirt paths. You will typically find toddlers and young kids at the big playground in the park.

A smaller space is the Kraft Azalea Garden over at Alabama Drive. The whole area covers just 5.22-acres, but there’s still plenty to do here. You can enjoy a picnic, explore the park, and you can even fish at the lake. There’s a dock that you can use and some people enjoy exercising with a kayak or paddleboard. It’s a nearby spot if you want a quick escape from the stress of everyday life.

Winter Park has plenty of fun activities to engage in. Some of these include: visiting the train station, going to the Winter Park farmers market, visiting the koi pond at the Paris Bistro restaurant, taking the famous one-hour Winter Park Scenic Boat Tour, and visiting Mead Botanical Garden.

What it’s Like Living in Winter Park?

Winter Park has a long history and is more well-established compared to the other neighborhoods in Orlando. You will find plenty of older neighborhoods with established patterns and rhythms. These neighborhoods have beautiful–manicured lawns with lots of space, mature trees that dot the paved walkways and roads.  Many of the residents grew up in the area.

Although the neighborhoods are older, the homes are not. Only a few homes in Winter Park are not renovated or upgraded to fit modern times. 

Drive around the different neighborhoods and it’s rare to find a house that is dilapidated.

Another nice feature is the size of the lawns. Many of them are spacious and beautiful.

Winter Park has been around for a long time, but many people are just now discovering this hidden gem of a neighborhood. Winter Park is a suburb that is near Downtown Orlando with access to modern conveniences, shopping, and entertainment.


Have More Questions About Winter Park, FL?

Scroll Up