Find Your Dream Home in Winter Park: Discover Exclusive Real Estate Listings for Sale
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In June 2025, Winter Park home prices were up 1.7% compared to last year, selling for a median price of $750K. On average, homes in Winter Park sell after 19 days on the market compared to 38 days last year. There were 41 homes sold in June this year, down from 46 last year.
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A Guide To
Winter Park, FL, is best known for its charming downtown, lush parks, scenic lakes, and historic architecture—making it a top destination for buyers looking for single family homes for sale in Winter Park. From the iconic Casa Feliz Historic Home Museum to Rollins College, one of the nation’s leading liberal arts institutions, Winter Park blends culture, education, and natural beauty.
The city’s famous chain of lakes enhances the lifestyle appeal of its residential areas, offering homeowners opportunities for boating, fishing, and water recreation right outside their door. Its walkable streets, vibrant arts scene, and family-friendly atmosphere make it ideal for those seeking a forever home in one of Central Florida’s most desirable locations.
Explore top amenities, school districts, and neighborhood features—and browse the latest listings of Winter Park single family homes for sale in the map-based guide by Toni Marie Cafferty.
Winter Park, just north of Orlando, is one of Central Florida’s most desirable locations for single family homes for sale. With easy access to I-4, the Florida Turnpike, and Orlando International Airport, Winter Park offers a seamless blend of convenience and upscale residential charm—ideal for families, professionals, and retirees.
Winter Park’s close-knit, vibrant community is a major draw for homebuyers. Events like the Sidewalk Art Festival and the weekly Farmer’s Market make it an ideal setting for those searching for single-family homes in a friendly, culturally rich environment.
Homeowners in Winter Park enjoy access to upscale dining at local favorites like Prato, Ravenous Pig, and Seito Sushi. Whether you prefer casual cafes or fine dining, the area complements the lifestyle of Winter Park single-family home residents with culinary excellence.
Families seeking single-family homes in Winter Park benefit from access to some of Orange County’s best schools. Winter Park High School and nearby private institutions like Rollins College enhance the area’s reputation as a top choice for families prioritizing education and quality living.
Winter Park offers a wide variety of single family homes, ranging from charming historic properties to newly built residences in quiet neighborhoods. Whether you’re drawn to tree-lined streets, lakefront homes, or established communities, Winter Park has the perfect home for every lifestyle. Buyers looking for Winter Park single family homes for sale will find abundant high-end options with timeless appeal.
Winter Park is known for its walkability and bike-friendly infrastructure. Residents of single family homes for sale in Winter Park can take advantage of free shuttle services, SunRail connectivity, and local Lynx routes for convenient commuting and exploring.
Meet our team.
Winter Park
Toni Marie Cafferty | December 15, 2023
Winter Park, Florida: A Hidden Gem for Property Investors.
Winter Park
Toni Marie Cafferty | June 9, 2022
From market trends to where to buy groceries, everything you need to know about Winter Park.
Winter Park
Toni Marie Cafferty | July 27, 2022
Winter Park, Windermere, and Golden Oak all have restaurants to please every palate!