Skip To Content

Winter Park Area Guide and Home Search With beautiful public green spaces, high-end shopping venues, top-rated schools, and a vibrant art and culture scene, Winter Park has something for everyone.

Located just north of Downtown Orlando, Winter Park is known for its trendy sidewalk boutiques, beautiful green spaces, and popular brunch spots. Charming brick streets wind through the city under a canopy of mature trees draped in Spanish Moss, and the city is rich in history, art, culture, and architecture.

Search all Winter Park Homes for Sale
A server takes a drink order from two diners at a chic sidewalk cafe.

Winter Park at a Glance

This hidden gem is one of Orlando’s oldest cities and boasts gorgeous million-dollar estates, luxury high rises, and traditional suburban homes tucked in quiet, well-established neighborhoods. Central Florida’s innovative SunRail train runs right through downtown Winter Park, making it easy for locals to travel to and from the heart of Winter Park to local areas such as Maitland, Longwood, and Sanford.

Florida’s first four-year college, Rollins College, has a campus tucked along the bank of Lake Virginia in Winter Park. One of Rollins’ most notable students was Mister Rogers, an iconic childhood TV star, who donated his famous shoes and sweater to the school. 

Winter Park has an active and vibrant art community and hosts the Winter Park Sidewalk Art Festival every March. This outdoor festival brings over 250,000 art lovers to Central Park each year and is an opportunity to showcase the area’s most talented artists. 

Residents here are an eclectic mix of entrepreneurs, young professionals, college students, retirees, and growing families. With beautiful public green spaces, high-end shopping venues, top-rated schools, and a vibrant art and culture scene, Winter Park has something for everyone.

Things to Do in Winter Park

Park Avenue

Park Ave is where people in Winter Park go to see and be seen. This main stretch of road is lined with trendy shops, locally-owned boutiques, and the area’s most popular restaurants. Residents can enjoy sidewalk dining with a clear view of the heart of Winter Park, Central Park. This beautiful 11-acre green space features winding sidewalks, peaceful gardens, and tranquil water features. 

Winter Park Farmer’s Market

The Winter Park Farmers Market is one of the city’s most popular events and has been part of the Winter Park community for decades. Every Saturday, the streets of Winter Park are lined with local vendors selling fresh produce, homemade goods, art, jewelry, flowers, gourmet treats, and boutique-style clothing. The Farmer’s Market runs every Saturday from 7 am-1 pm and is one of the best reasons to get outside, get active, and shop local.

Winter Park Scenic Boat Tour

Woven through Winter Park is the pristine Winter Park chain of lakes, and a scenic boat tour is one of the best ways to experience them. The 18 passenger boats take guests through seven lakes and two man-made canals to see cranes, fish, alligators, and other wildlife tucked under mature palm trees, cypress trees, and lush ferns. Great for date nights, birthday parties, or a family experience outside, the boat tours allow residents to cruise the chain of lakes and enjoy breathtaking views of Winter Park’s natural beauty and lakefront estates.

Winter Park Golf Course

Golf enthusiasts from all over Central Florida come to Winter Park to play a round on the narrow, tree-lined fairways. This sunny 9-hole course is located in the heart of Winter Park is bordered by trees draped in Spanish moss, impressive residential estates, a historic cemetery, and train tracks to the east. The course is a 2480 yard par 35 and is one of the best short courses in the country. 

Kraft Azalea Garden

The Kraft Azalea Garden is a five-acre lakefront garden, open to the public. Commonly referred to as Winter Park’s secret garden, this public garden is home to towering cypress trees, gorgeous natural fauna, and is a popular wedding venue. This peaceful place is the perfect spot for a quiet walk at lunchtime or a romantic picnic lunch.

Mead Botanical Garden

The Mead Botanical Garden features a beautiful butterfly garden, winding bike trail, and boardwalk. This park has paths and trails for hiking, a community garden, and The Grove, a multi-purpose performance venue where you can watch shows and demonstrations. Here you can try bird watching or geocaching, or rent a pavilion for a gathering or celebration. Free to the public, Mead Botanical Garden is one of Winter Park’s best-kept secrets.

Hannibal Square Heritage Center

The Hannibal Square Heritage Center is a tribute to the contributions of the African American community in Winter Park. This modern museum allows visitors to take a walking tour through the city, led by a chief historian, to dive into Winter Park’s rich history. The center also includes photos of historic Winter Park and the African Americans that helped build it into the city that it is today. The Hannibal Square Heritage Center offers permanent and rotating exhibits, classes, workshops, and field trip opportunities.

Morse Museum of American Art

The Morse Museum of American Art is home to the world’s most comprehensive collection of works by Louis Comfort Tiffany. This art museum features everything from jewelry and pottery to artifacts from his famous Long Island home, Laurelton Hall. Artists and art enthusiasts can spend hours browsing the galleries and can take a self-guided audio tour through the museum to learn more about the art and the artist.

The Alfond Inn

The Alfond Inn is a historic landmark in Winter Park. What started as the luxurious Langford Hotel is now a teaching museum and venue for workshops and classes for the community. Owned by Rollins College, this hotel is the only inn in American that also serves as an extension of a formal art museum. The Alfond Inn has 112 guest rooms, 10,000 feet of meeting space, and high-end amenities.

What’s your Home Worth?

Winter Park Home Search

Notable Communities & Neighborhoods in the Area

  • Charmont
  • Comstock Park
  • Downtown Winter Park
  • Dixie Terrace
  • Dubsdread Heights
  • Kenilworth Shores
  • Lawndale
  • Maitland Shores
  • Osceola Shores
  • Sevilla
  • Virginia Heights
  • Whispering Waters
  • Windsong
  • Winter Park Pines

Winter Park Luxury Real Estate