01
Entry
$450K - $650K
Condos, townhomes, and smaller single-family homes. Often in adjacent areas like Maitland or Hannibal Square.
Winter Park
Tree-lined charm meets cultural sophistication
WalkableCulturalLakefrontDining
$450K - $3M+
Price Range
10-15 minutes
Downtown
25-30 minutes
Airport
30-40 minutes
Disney
“Winter Park is where you go when you want walkability, culture, and character.”
The Lifestyle
Saturday mornings at the farmer's market, afternoon strolls along Park Avenue, evening dinners at chef-driven restaurants. The pace is relaxed but the community is active. It's the kind of place where you run into your neighbors at the coffee shop and actually want to.
The Highlights
- 01
Park Avenue shopping and dining district
- 02
Rollins College campus and cultural events
- 03
Chain of lakes with scenic boat tours
- 04
Top-rated public and private schools
Best For
- Families who prioritize top-rated schools
- Professionals who value walkability and culture
- Relocators from Northeast cities who want a similar urban-village feel
- Empty nesters downsizing from larger suburban homes
Not Ideal For
- Buyers looking for new construction – most homes are established
- Those who need quick access to the attractions corridor
- Budget-conscious buyers under $400K
Price Points
$450K - $3M+
What it costs to live in Winter Park, from entry-level to premium.
02
Mid-Range
$650K - $1.2M
Updated 3-4 bedroom homes in established Winter Park neighborhoods. Some lakefront access. Top school zones.
03
Premium
$1.2M - $3M+
Lakefront estates, historic homes, and custom builds on large lots. Via Tuscany, Palmer Avenue, and lakefront properties.
New Construction
Building new in Winter Park
New construction in Winter Park proper is limited due to the established nature of the community. Most new builds are custom homes on infill lots or tear-down rebuilds. Adjacent areas like Winter Park Village and parts of Maitland offer some new townhome developments.
Builders
Phil Kean Design GroupDavid Weekley HomesSurrey HomesCahill HomesFG Schaub Custom Homes
Active Communities
- Custom infill lots throughout Winter Park
Schools
Education in Winter Park
Winter Park High School
(highly rated)
Brookshire Elementary
(highly rated)
The Geneva School
(private, classical Christian)
Trinity Preparatory School
(private, grades 6-12)
Lake Highland Preparatory School
(private, PreK-12, nearby)
- Rollins College campus community
Dining
Where to eat
Prato
Italian, Park Avenue staple
The Ravenous Pig
gastropub, Michelin-recognized
Hillstone
upscale American, lakefront views
The Parkview
seasonal American, Park Avenue
Local Tips
Nicole's Winter Park notes
Nicole Mickle
30 years in Orlando
01
The Winter Park Farmer's Market on Saturdays is a community institution – go early
02
The Scenic Boat Tour on Lake Osceola is the best way to see the historic lakefront homes
03
Park Avenue during the holidays is worth the visit even if you don't live here yet
04
The Morse Museum houses the world's most comprehensive collection of Tiffany glass – free on Friday evenings from November through April
Interested in Winter Park?
I can tell you what it's really like to live here, what the market looks like right now, and whether it's the right fit for your lifestyle.