Winter Park

Winter Park is a suburban city known for its artistic sensibility and beautiful outdoor spaces.

Winter Park, Florida Real Estate

Charming atmosphere meets luxury amenities

Winter Park is a suburban city known for its artistic sensibility and beautiful outdoor spaces. Home to just over 27,000 people, Winter Park sits directly northeast of Orlando, with only about a six-mile drive to the city’s center. For many years it was known as a luxury resort community for northerners, and has since expanded into a beautiful residential paradise. The area is deeply connected to Central Florida’s rich history as a citrus-growing, agricultural center. To this day, that history imbues the area with a sense of value for Florida’s natural beauty and wildlife.

Winter Garden homes for sale are a laid-back mix of old and newer homes. You'll find some vintage styles that nod to the town's history with citrus farming, sitting near more modern spots. The city's historic downtown is a testament to its past, with restored buildings and classic Florida bungalows, however, when venturing out a bit, the architecture transitions to include more recent developments, featuring amenities aligned with current trends and lifestyles. 

What to Love

  • One of the closest, most convenient suburbs in Orlando
  • Great connection to local history and preservation
  • Variety of museums to satisfy anyone’s interests
  • Hub for cultural tastemakers and artists
  • Beautiful parks to explore with your family
  • Charming, old-Florida atmosphere

Living in Winter Park, FL

Winter Park is a great place for those who value the roots of a community, making it an ideal choice for buyers who want more than just the right home. Residents are often passionate about the legacy of their city and making it a great place to live for years to come, and Winter Park’s many cultural and artistic institutions prove their commitment to fostering the creativity of this community. Winter Park is home to many families who enjoy its gorgeous scenery and the lush green surroundings found around every turn. The city is also home to Rollins College, a prestigious liberal arts college that was ranked #1 among regional universities in the South by the 2020 edition of Best Colleges. Though relatively small, the college is a top employer in the area and attracts many great young minds, some of whom go on to live and work in the Orlando area.

Winter Park, FL Restaurants

Winter Park has a range of great dining and shopping options. If you want to explore some of Winter Park’s flavor, try some Louisiana-style cuisine at Tibby's New Orleans Kitchen, a popular choice thanks to both its great food and lively atmosphere. Or for weekend brunch and creative cocktails, bring some friends along to local favorite The Parkview.

Winter Park, FL Shopping

For a day of shopping, check out Winter Park Village, an outdoor mall with great eateries, classic shops, and a movie theatre. If you want a more local shopping experience, head to Sultre Boutique, where you’ll find a selection of hand-picked clothing and accessories.

Things to Do in Winter Park, FL

Winter Park is an active community that offers an assortment of great events and experiences to enjoy. You can join the thousands of visitors who flock to the area each year for the Winter Park Sidewalk Art Festival, a long-running and highly prestigious annual outdoor art festival. Submit your own art for one of the many cash prize awards, visit the Children’s Workshop and let your kids make their own masterpieces, and bring home some art for yourself from one of the many vendors. Need to host an event of your own, like a birthday party or wedding? You can rent one of Orlando’s most gorgeous and intimate indoor/outdoor venues, Celebration Gardens.

On any of Winter Park’s many sunny days, you can take a slow stroll through the beauty of Olde Winter Park, where you can traverse winding brick streets under a lush covering of southern oak and camphor trees and hanging Spanish moss. You can also head over to the Winter Park Community Center, where you’ll find a fitness center, basketball courts, and an amphitheater overlooking one of the city’s great parks. Once you’ve had your fill of outdoor fun, take in some world-class live music by attending a performance of the Bach Festival Society of Winter Park, which regularly holds concerts in the Orlando area.

Read our featured blog for more insight on things to do in Winter Park.


Winter Park is served by the Orange County Public Schools District.

  • Winter Park High School
  • Edgewater High School
  • Maitland Middle School
  • Glenridge Middle School
  • Dommerich Elementary School

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