Orange County · 34786

Windermere

Picturesque lakefront estates, tree-lined streets, and the true small-town feel of Central Florida's most coveted address on the Butler Chain of Lakes.

Live the MaxLife.

$1.5M–$5M+

Median Sale Price

$5M–$20M

Lakefront Range

~3,500

Population (town)

Isleworth

Top Community

Overview

Windermere, Florida is a picturesque town known for luxury lakefront estates, charming tree-lined streets, and a true small-town feel. Located west of Doctor Phillips, the area provides a peaceful retreat with easy access to Orlando's business centers, theme parks, and cultural attractions.

Schools

Windermere Elementary (highly rated), Bridgewater Middle (A-rated, STEM-focused), and Windermere High School (modern facilities, AP programs) serve the area. Private options include Windermere Prep and The First Academy.

Lifestyle & Recreation

Golf clubs include Isleworth Golf & Country Club and Keene's Pointe's Golden Bear Club. Parks include Central Park and Lake Street Park. Downtown Windermere offers cozy cafés, farm-to-table dining, and boutique shops along a quaint main street lined with historic buildings.

Location

25–35 minutes to Downtown Orlando, 20 minutes to Walt Disney World and Universal Orlando Resort, and 30 minutes to Orlando International Airport (MCO).

Real Estate Market

Median home price is approximately $1,050,000 for the broader area, with luxury lakefront estates ranging from $5M–$20M+. Inventory is limited and the market remains highly competitive, with waterfront and gated-community homes commanding the greatest premiums.

What Makes Windermere Special

  • Butler Chain of Lakes — 13 connected lakes for boating, skiing, and fishing
  • Keene's Pointe & the Golden Bear Club
  • Isleworth Golf & Country Club
  • The Reserve at Lake Butler Sound
  • Historic downtown Windermere main street
  • Windermere Prep and The First Academy

Around the neighborhood

Windermere luxury home exterior
Windermere residential street
Windermere neighborhood view
Windermere community
Windermere HDR landscape
Windermere estate view

Communities in Windermere

Keene's Pointe

Gated Jack Nicklaus golf community on Lake Tibet — the Golden Bear Club and estates with private boat access.

Isleworth

Central Florida's most prestigious private community — Arnold Palmer golf, 24-hour security, and multi-million-dollar estates.

Reserve at Lake Butler Sound

Ultra-exclusive gated enclave of custom estates on Lake Butler — some of the largest waterfront homes in Florida.

Downtown Windermere

Historic main street with coffee shops, boutiques, and community events — the heart of small-town Windermere.

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Thinking about buying or selling in Windermere?

MaxLife Realty is a boutique brokerage specializing in Windermere and the Butler Chain of Lakes. Let's talk about your next move.