Winter Park LGBTQ City Guide

Winter Park is a beautiful, smaller-sized city located just north of Orlando. It’s well known for its beautiful parks, tree-lined streets and charming downtown area packed full of unique boutiques, restaurants, and shops. It's also home to Rollins College, many great schools, plenty of unique neighborhoods, and many friendly people, including a smaller, but thriving LGBTQ community. If you’re thinking of finding your next home in Winter Park, chances are, you’ll find plenty about it to love!

A Look at Winter Park's History

Winter Park was first officially chartered in 1887 when the city was originally developed as a winter resort for wealthy Northerners who were seeking a break from harsh New England winters, and a warm, beautiful place to rest and relax. The city was first given the name Lakeview in 1858 and was subsequently renamed Osceola in 1870. Eleven years later, the name Winter Park was selected by its founders, Loring Chase and Oliver Chapman, who after some discussion about the matter, decided they wanted the name to center around the idea of a beautiful park in winter. From the time of its founding through the present, the city has played an important role as a center of higher education, a tourist destination, and a beautiful, friendly area with a relaxed vibe, diverse neighborhoods, and much to see and do.

A Few Fun Facts About Winter Park

  • Rollins College, the oldest college in Florida, is located in Winter Park. It was founded in 1885 by New England Congregationalists who wanted to bring their style of liberal arts education to Florida. It continued to have a highly esteemed reputation as an excellent liberal arts college to this day.
  • Famed children’s show host Fred Rogers, better known as Mr. Rogers of Mr. Roger’s Neighborhood, was a graduate of Rollins College, and for many years, spent his winters in Winter Park.

Read more fun facts about Winter Park here.

Winter Park’s LGBTQ Community                                

Winter Park is a city that loves and supports its LGBTQ community with a variety of resources, including:

PFLAG Orlando

PFLAG Orlando is the Winter Park area’s local chapter of the national PFLAG organization, which is the largest grassroots organization of its kind in the country. PFLAG is well-known for its mission of supporting LGBTQ people, friends, family, and allies across the country in a wide variety of ways. With 500 chapters and more than 200,000 members in the United States, PFLAG plays a critical role in providing advocacy, support, and resources to the LGBTQ community.

The Center - Orlando

The Center, founded in 1978, is one of the oldest in the country established to support and empower LGBTQ individuals. The mission of The Center is, “To promote and empower the LGBT Community and its allies through information, education, advocacy, and support."

What's the Weather Like in Winter Park?

Those who live in Winter Park can expect plenty of warm weather, sunshine, and rain for most of the year. Typically, the hottest and rainiest season tends to be from mid-May through mid-September, while October through April weather tends to be warmer and drier. Throughout the year, temperatures can range from an average low of around 49°F in January to an average high-temperature of around 92°F in July.

Can’t-Miss Events in Winter Park

Winter Park Sidewalk Art Festival

The Winter Park Sidewalk Art Festival is one of the most popular and well-attended events in the city each year, typically drawing crowds of more than 250,000 people. The festival features stunning sidewalk chalk art by local and national artists, plenty of great food, live music, and lots of fun.

Come Out With Pride Orlando

Come Out With Pride, typically in October, is Orlando's LGBTQ weeklong-pride event that brings LGBTQ individuals, friends, family, and allies together to celebrate. The mission of Come Out With Pride Orlando is to produce an annual pride event that fosters a sense of community, encourages LGBTQ+ citizens to live openly and with pride, and educates the general public of our shared cultural heritage.

The Best Neighborhoods in Winter Park

Unlike some larger cities that tend to have one specific “gayborhood” where most of the LGBTQ community lives, the LGBTQ population in Winter Park is a bit more spread out. This isn’t a bad thing though – it simply means that there are many wonderful neighborhoods to choose from, each friendly and unique in its own way.

There are a wide variety of home styles available in different price ranges, many of which are characterized by the unique Spanish-style architecture in the area. Homes in Winter Park tend to be on the more expensive side, but if a more expensive home is in your budget, there are plenty of wonderful options to choose from. The median list price of homes currently for sale in the Winter Park area is around $727,000.

Arts and Entertainment

The Enzian

The Enzian Theater is a nonprofit arthouse movie theater in Maitland, Florida, a suburb of Orlando. Each year, the theater hosts the Florida Film Festival and several other local film festivals as well. There is definitely something for any film fan to enjoy. 

Annie Russell Theatre

The Annie Russell Theatre is the oldest continuously operating theatre in Florida and is included on the National Register of Historic Places. The theatre, located on the campus of Rollins College, was named after the English-born actress Annie Russell. Throughout the year, the theatre puts on a wide variety of shows and performances – don’t miss the chance to enjoy one for yourself!

Parks and Recreation

Park Avenue

Park Avenue is quintessential Winter Park. This beautiful, cobblestoned, tree-lined street weaves right through the middle of town and offers residents and visitors alike a wonderful selection of boutiques, shops, restaurants, and nightspots to enjoy. It also passes right by the town's beautiful Central Park, which boasts plenty of green space and a beautiful fountain, and is a wonderful spot to stop and relax on a beautiful Winter Park day!

Scenic Boat Tours

Many people associate Florida with its beautiful beaches, but often don’t realize that it’s a state filled with many beautiful lakes and fresh waterways as well – and this is nowhere more evident than in Winter Park. The city has several interconnected lakes and waterways, and taking a scenic boat tour on a beautiful day is a great way to enjoy nature’s beauty, and learn a bit about the history of the area as well.

Winter Park Nightlife

Parliament House

Parliament House is a unique piece of the history of the Winter Park and greater Orlando area. An LGBTQ landmark in Orlando since 1975, Parliament House has 7 uniquely different bars, as well as a hotel, swimming pool, inside and outside stages, a café, and Orlando’s largest LGBTQ dance floor.

Fiddler's Green

Though not specifically an LGBTQ bar, Fiddler's Green is a longstanding and very popular Winter Park nightspot and a great place to enjoy a night out with friends. This classic Irish pub offers cozy seating, excellent food, strong drinks, and friendly crowds.

Contact a Winter Park Gay Realtor Today

If you're ready to make a move to Winter Park, at, we're here to help you take the first step toward finding an agent who knows and loves the community, and who can help you find a home and a neighborhood you'll love. We're proud to have a network of excellent realtors in Winter Park, and we would love to help connect you with the right one. Contact a Winter Park gay realtor today for a free, no-obligation consultation!

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