Orange County · 34786
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
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.
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.
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.
25–35 minutes to Downtown Orlando, 20 minutes to Walt Disney World and Universal Orlando Resort, and 30 minutes to Orlando International Airport (MCO).
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.
Gated Jack Nicklaus golf community on Lake Tibet — the Golden Bear Club and estates with private boat access.
Central Florida's most prestigious private community — Arnold Palmer golf, 24-hour security, and multi-million-dollar estates.
Ultra-exclusive gated enclave of custom estates on Lake Butler — some of the largest waterfront homes in Florida.
Historic main street with coffee shops, boutiques, and community events — the heart of small-town Windermere.
Recent Work
6 homes representing $11.4M in recent Windermere volume.
Recently Sold$4,050,000
Sold Nov 2025 · List $4,200,000
9021 Lake Butler Blvd
Windermere, FL 34786
5 BD · 4.5 BA · 5,840 SF · 0.82 AC
Windermere
Recently Sold$3,400,000
Sold Oct 2025 · List $3,495,000
6217 Greatwater Dr
Windermere, FL 34786
5 BD · 5.5 BA · 5,840 SF · 0.7 AC
Windermere
Recently Sold$1,875,000
Sold Aug 2025 · List $1,895,000
11208 Bridge House Rd
Windermere, FL 34786
4 BD · 4.5 BA · 3,980 SF · 0.5 AC
Windermere
Recently Sold$2,125,000
Sold May 2025 · List $2,150,000
10433 Kensington Shore Dr
Orlando, FL 34786
5 BD · 4 BA · 4,210 SF · 0.44 AC
Windermere
Coming Soon$3,250,000
Keene's Pointe Estate
Windermere, FL 34786
5 BD · 5.5 BA · 5,420 SF · 0.68 AC
Windermere
Notable Home$8,500,000
Lake Butler Sound Estate
Windermere, FL 34786
6 BD · 7.5 BA · 9,420 SF · 1.5 AC
Windermere
4 Communities
Windermere's guard-gated Jack Nicklaus community on the Butler Chain.
$900K – $5M
1,100 homes
Explore Keene's Pointe →
Arnold Palmer's Windermere legacy — Florida's most private address.
$2M – $40M
660 homes
Explore Isleworth →
Windermere's intimate lakefront enclave on Lake Butler.
$2M – $15M
150 homes
Explore Reserve at Lake Butler Sound →
A small Tuscan-inspired enclave behind Windermere's quieter gate.
$2M – $4.5M
50 homes
Explore Casabella →
Two to three hand-picked matches per month — 48 hours before MLS.
Neighborhood
An exclusive golf and waterfront community offering world-class amenities, architectural excellence, and unrivaled prestige — one of Florida's most coveted addresses.
Explore Isleworth→
Neighborhood
Thirteen interconnected lakes — the most prestigious waterfront address in Central Florida, where private docks, sunset boat rides, and trophy bass fishing are everyday life.
Explore Butler Chain of Lakes→
Neighborhood
Luxury estates, A-rated schools, and Butler Chain lakefront living just minutes from Restaurant Row and Central Florida's finest attractions.
Explore Dr. Phillips→
MaxLife Realty is a boutique brokerage specializing in Windermere and the Butler Chain of Lakes. Let's talk about your next move.
