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Premier Sotheby's International Realty · Orlando, FL

Windermere FL Homes for Sale
Butler Chain of Lakes Luxury Real Estate

Windermere (34786) is Florida's most exclusive address — guard-gated Isleworth and Keene's Pointe estates on the 13-lake Butler Chain from $700K to $15M+. Celebrities, PGA Tour players, and Fortune 500 executives call the Town Among the Lakes home.

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Windermere Market Data · 2026

Median Price

$0

Price / Sq Ft

$300 – $900

YoY Growth

0%

Avg Days on Market

0

Price Range

$700,000 – $15,000,000+

HOA Fees

$200 – $800/month

Primary ZIP

34786

School District

Orange Co. · A-Rated

Community Overview

About Windermere

Some addresses carry a gravitational weight that requires no explanation, and Windermere is one of them. The Town Among the Lakes (34786) has drawn PGA Tour professionals, Fortune 500 executives, entertainers and investors to its guard-gated enclaves for four decades, and the reason is always the same: there is simply nowhere else in Central Florida that delivers this combination of privacy, prestige and natural beauty. Isleworth Golf and Country Club, where Tiger Woods and Mark O'Meara once called home and Jack Nicklaus's Signature course hosts members who understand exactly where they have arrived, anchors the community's identity as one of the most exclusive addresses in the Southeast. Keene's Pointe surrounds The Golden Bear Club, another Nicklaus design, with estates that begin where most luxury markets end. The Butler Chain of Lakes, all 13 interconnected lakes of it, provides a waterway system with exceptional water clarity and no-wake zone conservation that makes every sunrise from a private dock feel like a private moment. The median home price in Windermere is approximately $1,200,000 in 2026, with waterfront estates on the Butler Chain ranging from $700,000 to $15,000,000 and beyond. For buyers relocating from Greenwich, the Hamptons, Beverly Hills or Palm Beach, Windermere offers comparable privacy and prestige at 60 to 70% below what those markets now demand, with zero Florida state income tax added to the equation.

Top Schools

Orange Co. · A-Rated

Nearest Hospital

AdventHealth · 8 mi

Downtown Orlando

15 miles / 22 minutes via SR-408

Airport (MCO)

22 miles / 28 minutes via SR-528

Notable Communities

Isleworth Golf & Country Club, Keene's Pointe / Golden Bear Club, Windermere Sound, Cypress Row

Major Employers

Universal Orlando (12 mi), Walt Disney World (12 mi), Lockheed Martin (20 mi)

Flood Zone

Butler Chain waterfront properties require individual flood zone determination. Non-waterfront Windermere homes are predominantly Zone X.

New Construction

Yes — luxury custom builds on available lots; some spec homes in newer communities

Search by Lifestyle

Windermere Homes by Lifestyle

Windermere Golf Front Homes

Golf community living with fairway views and country club amenities.

Windermere Lakefront Homes

Waterfront estates with private docks and stunning lake views.

Windermere Luxury Estates Over $2M

Ultra-premium estates with the finest finishes and amenities.

Windermere 55+ Resort Style Living

Low-maintenance luxury with resort amenities for active adults.

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Live MLS updated daily — every active listing in Windermere.

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Frequently Asked Questions

Windermere Real Estate — Answered

What is the average home price in Windermere FL in 2026?
The median home price in Windermere is approximately $1,200,000, with waterfront estates on the Butler Chain ranging from $700,000 to $15,000,000 and above.
What communities are in Windermere FL?
Windermere's most prestigious communities include Isleworth Golf and Country Club, Keene's Pointe (The Golden Bear Club), Belmere, Chase Reserve, Cypress Isle, and numerous other guard-gated and private enclaves surrounding the Butler Chain of Lakes.
What is Isleworth in Windermere FL?
Isleworth Golf and Country Club is Windermere's most prestigious guard-gated community, featuring Jack Nicklaus Signature and Arnold Palmer-designed golf courses on the Butler Chain. Tiger Woods and Mark O'Meara are among its most famous residents. Estates begin around $3,000,000.
What is the Butler Chain of Lakes in Windermere?
The Butler Chain is a system of 13 interconnected freshwater lakes spanning from Windermere south through Dr. Phillips. It features exceptional water clarity, no-wake conservation zones, and private dock access through communities like Isleworth and Keene's Pointe.
How far is Windermere from Orlando?
Windermere is approximately 12 miles southwest of downtown Orlando, accessible via SR-535 and SR-408 in approximately 22 to 28 minutes. Disney World is approximately 12 to 15 minutes via SR-535.
What schools serve Windermere FL?
Windermere is served by Orange County Public Schools, feeding into Windermere Elementary, Bridgewater Middle School, and West Orange High School (A-rated). Windermere Preparatory School is a private option nearby.
Is Windermere FL a good investment?
Yes. Windermere has maintained consistent appreciation of approximately 5.2% year-over-year with exceptional stability through market cycles. Butler Chain waterfront is structurally scarce, supporting long-term value.
What is the property tax rate in Windermere FL?
Orange County property taxes apply to Windermere at approximately 1.0 to 1.2% of assessed value. Florida's zero state income tax saves buyers from northeastern markets $15,000 to $130,000+ annually.
How far is Windermere from Disney World?
Windermere is approximately 12 to 15 minutes from Walt Disney World via SR-535, one of the closest luxury communities to Disney's campus.
What is Keene's Pointe in Windermere?
Keene's Pointe is a 24/7 guard-gated luxury golf community surrounding The Golden Bear Club, a Jack Nicklaus Signature course on the Butler Chain. Estates range from $700,000 to $5,000,000+.
Are there waterfront homes for sale in Windermere?
Yes. Butler Chain waterfront estates with private docks begin around $1,500,000 and extend to $15,000,000 and above in communities like Isleworth and Keene's Pointe.
What makes Windermere different from other Orlando luxury markets?
Windermere's combination of the Butler Chain of Lakes, Jack Nicklaus and Arnold Palmer golf courses, 24/7 guard-gated privacy, and established prestige creates an address no other Central Florida community can replicate. It is the only market where PGA Tour professionals and Fortune 500 executives have chosen to live for four consecutive decades.
What is the commute from Windermere to downtown Orlando?
The commute from Windermere to downtown Orlando is approximately 22 to 28 minutes via SR-535 and SR-408 in standard traffic.
Is Windermere gated?
Major Windermere communities are guard-gated. Isleworth and Keene's Pointe are 24/7 guard-gated. The historic Town of Windermere itself is not gated.
How does Windermere compare to Dr. Phillips for luxury buyers?
Both offer Butler Chain access. Windermere has a higher median ($1.2M vs $850K) but more privacy and exclusivity. Dr. Phillips offers Restaurant Row dining and slightly lower entry points. Budget and lifestyle priorities determine the best fit.
What are the best luxury communities in Windermere?
The best luxury communities in Windermere are Isleworth (from $3M, PGA Tour golf, Butler Chain), Keene's Pointe (from $700K, Nicklaus golf, gated), Belmere (from $700K, gated, lakefront), and Chase Reserve (custom estates).

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