Close Menu


407.622.1111 439 Lake Howell Road, Maitland FL 32751 20 S. Main Street, Winter Garden FL 34787

Main Content

Winter Park

Winter Park is a city in Florida and consists of 6 neighborhoods. There are 431 homes for sale, ranging from $75K to $12.5M.

  • Avg list price: $415,000
  • Avg home value: $351,558
  • Home Value 2021: Winter Park home values have gone up 9.1% over the past year.
  • Avg price per sqft: $249
  • Avg Mortgage Rate: 2.73%
  • Area’s population: 30,522

Perhaps one of Central Florida’s best-kept secrets is the authentically beautiful City of Winter Park. This picturesque neighborhood just north of Orlando was established in the late 1800s as a winter playground for wealthy snowbirds seeking refuge from the harsh colder months up north. Still known today for its charming cobblestone streets, thriving cultural scene and impressive homes, this affluent community continues to be one of the best places to live in the Orlando area.

Winter Park has the perfect mix of old and new, with custom-built and historic colonial-style mansions offering lakefront living with incredible views. Beyond these sprawling estates with perfectly manicured lawns and private pools, you’ll also discover spacious mid-size family homes and bungalows with just as much Florida charm as their grand neighbors.

The beating heart of Winter Park is Park Avenue, the historic main street and coveted address that truly put the area on the map. Its Central Park greenspace with a rose garden, trickling fountains and shady tree-lined paths is the perfect place for a lazy afternoon stroll or family picnic. It’s also the site of many popular events throughout the year, including the biannual Winter Park Sidewalk Art Festival and live concerts from local jazz and orchestra groups. Just steps away from it all sits the main bricked thoroughfare with upscale boutiques, brand-name shops, trendy restaurants and wine bars coupled with a nearby golf course and Saturday farmer’s market.

Park Avenue’s crowning jewel is Rollins College, Florida’s oldest college, which remains a prominent private institution to this very day. Other prestigious schools in the area include the Crealde School of Art and Full Sail University, both a testament to Winter Park’s vibrant arts scene. Local culture is also very much alive at the area’s diverse museums and galleries, including the Morse Museum of American Art, the Albin Polasek Museum & Sculpture Garden, the Cornell Fine Arts Museum and Casa Feliz Historic House Museum to name just a few.

More than 70 parks and outdoor spaces call Winter Park home, each offering an idyllic spot to make the most of the abundant sunny days that grace the city. You’ll find plenty of solace at Mead Botanical Garden and Kraft Azalea Garden, the latter of which boasts a spectacular display of its namesake flowers at the start of spring. And if you’re a boater, you’ll have no trouble making a splash on the various sparkling lakes in town, many of which are adjoined by serene canals shaded with ancient Live Oak trees and tropical flora. Regardless of your budget, you’ll undoubtedly enjoy window-shopping the stately homes that flank the shore, which you can do aboard the famous Winter Park Scenic Boat Tour; perhaps the best way to imagine yourself as a permanent resident here.

Sorry we are experiencing system issues. Please try again.