Neighborhood Guides
That is the question I hear most, and the honest answer is that it depends on what you are ultimately trying to accomplish. Winter Park is small enough that the difference between neighborhoods comes down to character, not convenience. Here is the lay of the land, the way I describe it to clients.
01 A lane in Olde Winter Park · morning light
The areas
Homes across these neighborhoods typically run from $500K to $2.5M+, with the emphasis on luxury and $1M+ properties. The price differences within Winter Park are about the street, the lot, and the water, more than the neighborhood itself.
Walkable · historic core · culture
The historic heart of the city. Brick paved Park Avenue is lined with boutiques, galleries, restaurants and the Morse Museum, and the chain of lakes is steps away. Saturday mornings the farmers market fills the old train depot grounds. Condos, townhomes and classic houses, priced for the convenience.
Lakeside · prestige · brick lanes
Winter Park’s storied lakeside enclave along Lake Maitland. Italian sounding street names, brick paver streets, and Mediterranean and Colonial revival homes from the 1920s and 1940s. One of the most protected, most collected addresses in Central Florida.
Historic · tree lined · renovated
A historic neighborhood dating to the 1920s with tree lined streets and a mix of bungalow, Mediterranean and Tudor revival homes. It has a private lakefront park and has seen a thoughtful wave of luxury renovations and new builds.
Established · calm · convenient
Well established and carefully kept, with mature trees and easy access to the city’s shops and schools. A favorite for buyers who want the Winter Park address with a quieter, settled feel.
Character · architecture · history
Historic character in spades, with Mediterranean and Colonial revival homes that reward buyers who appreciate architecture with a story. A neighborhood where older Winter Park is still visible in the rooflines.
Lakefront · luxury · waterfront
A lakefront community along the shores of the Winter Park chain of lakes, with some of Central Florida’s most desirable waterfront addresses. The definition of lakefront living in Winter Park.
Close in · residential · established
A close in, residential pocket of Winter Park that I know street by street. The personality here is best described in person, over coffee, because it changes block to block. Ask me and I will tell you what the right block would mean for you.
Family friendly · established · green
Developed in the 1960s, lush landscaping, a serene atmosphere, and the Cady Way Trail nearby. A community where families have a way of staying for decades, which says more than any brochure.
The right neighborhood depends on what you want the next chapter to look like. If you tell me about your life, I will tell you which streets to start on. That is the neighborhood expertise clients describe when they leave a review.
Tell me what you're looking forA life in Winter Park
Winter Park was planned in 1881 as a resort town, literally named for a park in winter, and it still lives at that unhurried pace. Six lakes are joined by hand dug canals, and the Scenic Boat Tour has run along them since 1938. Rollins College, Florida's oldest, anchors the south end; the Morse Museum holds the world's most comprehensive collection of Louis Comfort Tiffany.
The places below are real, and they are the ones I send friends to. Consider them a starting point for your own list.
On the water
Culture
Park Avenue tables
Green spaces
Tell me how you want to live and I will show you the streets that match. That is the neighborhood expertise working for you.
