Winter Park
FL
Average Sales Price
$1,085,519
Median Sales Price
$631,225
Population
72,388
Total Listings
476
Discover Life in Winter Park with Matthew Buckley
Local Perspective
If I were walking a client through Winter Park, I’d point out how this area truly stands apart in the Central Florida market. Winter Park offers a rare blend of historic charm and modern convenience, making it a perennial favorite for those looking to settle somewhere with character and a strong sense of community. I often recommend Winter Park to clients who appreciate walkability, mature tree-lined streets, and a vibrant local culture—qualities that are increasingly hard to find in newer developments. In my experience, Winter Park’s unique mix of established neighborhoods, lakes, and thriving downtown makes it a standout choice for buyers who want both lifestyle and long-term value.
Neighborhood Highlights
Winter Park has an unmistakable atmosphere—think relaxed sophistication, with a creative edge. The area is known for its picturesque parks, brick-lined streets, and a downtown that buzzes with boutique shops, art galleries, and top-notch dining. You’ll notice a slower pace here compared to busier nearby areas, but there’s always something happening, from farmers’ markets to cultural festivals. What sets Winter Park apart is its blend of old Florida elegance with a youthful, active community spirit—perfect for those who want the best of both worlds.
Homes & Architecture
The housing in Winter Park is as diverse as its residents. You’ll find everything from stately historic homes with classic Mediterranean or Colonial Revival architecture, to updated mid-century ranches and sleek, newer construction. Many properties feature spacious lots, mature landscaping, and inviting porches or patios—ideal for outdoor living. Townhomes and condos are also available, especially closer to downtown, offering lower-maintenance options without sacrificing style or location. The architectural variety is one of Winter Park’s biggest draws, appealing to buyers who value both tradition and thoughtful updates.
Demographics
Data provided by Attom Data
Population
Employment
Population
72.4K
72.4K in 2020
Density
3.2K
per square mile
Households
32.1K
22 With Children
Gender
49% / 51%
Men Vs Women
Occupancy
54% / 46%
Owned Vs Rented
Age Median: Years
Education Level
Educational Environment
Elementary Schools (21)Middle Schools (14)High Schools (14)
Name
Category
Grades
Library
Ratio
8/10
Lakemont Elementary School
901 N Lakemont Ave, Winter Park, FL 32792
Public
KG - 5
No
14:1 STUDENTS/TEACHERS
7/10
Brookshire Elementary School
2500 Cady Way, Winter Park, FL 32792
Public
PK - 5
No
12:1 STUDENTS/TEACHERS
6/10
Aloma Elementary School
2949 Scarlet Rd, Winter Park, FL 32792
Public
PK - 5
No
14:1 STUDENTS/TEACHERS
6/10
Killarney Elementary School
2401 Wellington Blvd, Winter Park, FL 32789
Public
KG - 5
No
14:1 STUDENTS/TEACHERS
5/10
Eastbrook Elementary School
5525 Tangerine Ave, Winter Park, FL 32792
Public
PK - 5
No
14:1 STUDENTS/TEACHERS
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Amenities & Attractions
Featured Listings
For Sale (483)
For Sold (10266)
Active5 Beds3 Baths2,300 SqFt5354 LANYARD CT, Winter Park, FL 32792
Listed by Johanna Chandler LPT REALTY, LLC
Active
Active3 Beds2 Baths1,765 SqFt1133 BELLA LAGO CV, Winter Park, FL 32792
Listed by Hang Kendall LPT REALTY, LLC
Active1 Bed1 Bath735 SqFt1000 S SEMORAN BLVD #715, Winter Park, FL 32792
Listed by Leticia Morales LPT REALTY, LLC
Active4 Beds3 Baths2,031 SqFt2054 EASTBROOK BLVD, Winter Park, FL 32792
Listed by Melissa Stalzer LPT REALTY, LLC
Active4 Beds3 Baths2,102 SqFt1946 STRATHAVEN RD, Winter Park, FL 32792
Listed by Youbel Montesino LPT REALTY, LLC
Winter Park Living: Your Local FAQ Guide
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
What types of homes are common in Winter Park?
Winter Park offers a mix of historic bungalows, charming cottages, and modern single-family homes. You’ll also find upscale condos and townhomes, especially closer to the downtown area. The architectural diversity is a real highlight, appealing to a broad range of preferences and lifestyles.
How convenient is the commute from Winter Park?
What’s the lifestyle and walkability like here?
How fast do homes typically sell in Winter Park?
What should I know about local schools?
Are there HOA fees or special assessments?
