01
Entry
$650K - $900K
Homes in communities adjacent to Windermere proper. Good school zones, established neighborhoods. Some gated communities.
Windermere
Lakefront luxury with a relaxed pace
LuxuryLakefrontSpaciousGated
$700K - $5M+
Price Range
20-35 minutes
Downtown
25-35 minutes
Airport
10-15 minutes
Disney
“Windermere is space and water.”
The Lifestyle
Weekend mornings on the boat, kids playing in big backyards, dinner at home with the sunset over the lake. It's quieter than most of Orlando's popular neighborhoods and that's exactly the point. The town of Windermere itself is charming – a few blocks of small shops and restaurants that feel like old Florida.
The Highlights
- 01
Butler Chain of Lakes access
- 02
Windermere Preparatory School
- 03
Close to Disney and major attractions
- 04
Gated communities with large lots
Best For
- Families who want large lots and top schools
- Executives and professionals seeking privacy
- Boating and water sports enthusiasts
- Buyers relocating from high-cost markets who want space
Not Ideal For
- Buyers who want walkability or urban convenience
- Budget-conscious buyers under $650K
- Those who prefer newer, master-planned communities
Price Points
$700K - $5M+
What it costs to live in Windermere, from entry-level to premium.
02
Mid-Range
$900K - $1.5M
Gated communities like Keenes Pointe and Belmere. 4-5 bedrooms, community amenities, some with lake or conservation views.
03
Premium
$1.5M - $5M+
Lakefront estates on the Butler Chain. Custom builds, large lots, private docks. Isleworth, Bay Hill, and direct lakefront properties.
New Construction
Building new in Windermere
New construction in Windermere is primarily custom builds on remaining lots and a few newer communities on the outskirts. The core of Windermere is established, but surrounding areas like Horizon West offer extensive new construction options with Windermere mailing addresses.
Builders
Toll BrothersDream Finders HomesRyan HomesAshton WoodsElement Home Builders
Active Communities
- Saddlecrest at Windermere
- Palms at Windermere
- Lake Cawood Cove
- Sanctuary at Lakes of Windermere
Schools
Education in Windermere
Windermere High School
(highly rated)
Windermere Elementary
(A-rated)
Windermere Preparatory School
(private, PreK-12)
Bay Meadows Elementary
(A-rated)
Dining
Where to eat
Yellow Dog Eats
eclectic American, Windermere staple
My French Cafe
European bakery and cafe
Bella Tuscany
Italian, downtown Windermere
Restaurant Row in Dr. Phillips
10 minutes away
Local Tips
Nicole's Windermere notes
Nicole Mickle
30 years in Orlando
01
The Butler Chain of Lakes is one of Florida's most pristine lake chains – boat access is a genuine lifestyle upgrade
02
Windermere's downtown has a farmers market and community events worth checking out
03
Horizon West is the fast-growing area adjacent to Windermere – new construction at lower price points
04
The West Orange Trail is nearby in Oakland and Winter Garden for biking and running
Interested in Windermere?
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.