Isleworth
Arnold Palmer's Windermere legacy — Florida's most private address.
Live the MaxLife.
$5.3M
Median Price
$2M – $40M
660
Homes
$863–$1163
Monthly HOA
1984
Established
Windermere Elementary School
School Zone
Search Homes for Sale in Isleworth
Stellar MLS · 2026-04-26 · 5 closed sales
Recent market data
Median sold
$3,550,000
$2750K – $4475K
$/sqft
$793
Median DOM
114
days on market
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Background
A brief history
Isleworth opened in 1984 on a peninsula between Lake Louise, Lake Bessie, and Lake Tibet — land Arnold Palmer had scouted personally and later lived on for the rest of his life. Palmer designed the original 18 in the mid-1980s; Steve Smyers did a full redesign in 2005 that pushed the course into national rankings. The community's tall perimeter walls and heavy setbacks were an intentional design choice from day one: Palmer wanted the feel of a European country estate rather than a conventional Florida subdivision, and that restraint is part of why the neighborhood has aged as well as it has. The roster of former and current residents includes Tiger Woods (before Keene's Pointe), Shaquille O'Neal, Ken Griffey Jr., and Wesley Snipes — but even the non-household names tend to be founders, funds, and C-suites, and the community treats the privacy of all of them equally seriously.
The feel
What it's like to live here
Isleworth is the quietest luxury community in Central Florida — deliberately. You don't see homes from the main road. You don't see homes from neighboring homes, most of the time. Lots run from 0.5 acre on the interior up to 4-plus acres on the lakefront, and mature hedging, custom walls, and dense landscape buffers mean most estates are effectively invisible from the street. The architectural vocabulary is Mediterranean, Georgian, and transitional — no Florida-generic anywhere. Homes are predominantly custom builds, and the average main house is 7,000 to 15,000 square feet. Isleworth Country Club membership is typically sold separately from the home — when you buy a house here, you buy the right to apply for a membership, not the membership itself, and the club controls that process.
The details
What to expect
Architecture & Lots
Mediterranean, Georgian, transitional, and a small but growing minority of modern-contemporary. Main houses typically 7,000–15,000 square feet, with separate guest houses on many lakefront lots. Lots run 0.5 to 4 acres. Every exterior change — paint, roof tile, windows, landscape walls — requires architectural review board approval, and the ARB here is stricter than most neighborhoods in the state.
Lifestyle & Amenities
Isleworth Country Club (separate application and membership) offers the Steve Smyers/Arnold Palmer course, a 38,000-square-foot clubhouse, tennis, fitness, spa, fine dining, and wine cellar. The community itself maintains private parks, lake access points, and walking trails. A community boat ramp provides Butler Chain access for members.
HOA Rules & Fees
HOA $863/month ($2,589/quarter) for standard Isleworth; $1,163/month if in the Gardens of Isleworth section (additional $900/quarter) — confirmed via tjcosgrove.com, Apr 2026. Includes 24-hr manned gate, security patrols, landscaping, street maintenance, community park/trails, cable TV. Country club membership is NOT required — application-based, separate initiation. No short-term rentals. No signage, including political. Fencing heavily restricted.
Privacy & Security
24-hour manned gate with license-plate recognition, roving security patrols, and a secondary staffed gate on the club side. Residents receive custom decals; guests are cleared individually. Pre-arranged deliveries go to a central receiving point.
Access & Commute
Main gate is off Chase Road, same corridor as Keene's Pointe. Fifteen minutes to Restaurant Row, 25–40 minutes to downtown Orlando depending on I-4, 35 minutes to MCO, 15 minutes to Walt Disney World. The 429 Western Beltway is a five-minute drive for trips north.
Community
Amenities
- Isleworth Country Club — Steve Smyers/Arnold Palmer 18-hole course
- 38,000 sq ft clubhouse with dining, spa, and wine cellar
- Private tennis center and fitness facility
- Community boat ramp with Butler Chain access
- Private parks and walking trails
- 24-hour manned gate with LPR and roving patrols
Know Before You Buy
HOA rules worth knowing
- HOA $863/month ($2,589/qtr) standard; $1,163/month in Gardens of Isleworth section — confirmed Apr 2026
- Includes 24-hr gate/patrols, landscaping, street maintenance, cable TV, common areas
- Country club membership is OPTIONAL — application required, not automatic with purchase
- All exterior changes require architectural review board approval
- Short-term rentals prohibited
- Signage (including political) prohibited
- Landscape-buffer privacy preferred over solid fencing
- Centralized receiving for deliveries
Education
School assignments
- Windermere Elementary School
- Chain of Lakes Middle School
- Olympia High School
- Windermere Prep (private)
- The First Academy (private)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
The market has two distinct tiers. Interior homes on half-acre-plus lots trade in the $2M–$5M band and move in a reasonable timeframe when priced correctly. The lakefront tier — homes on Lake Butler, Lake Louise, or Lake Bessie with 100-plus feet of frontage and private docks — trades from $8M to $40M+ and moves slowly and privately. A meaningful share of lakefront sales here never touch MLS. Expect off-market inventory to be two to three times what you see publicly at any given moment. Teardowns are common on older interior lots; a 1990s 6,000-square-foot home on a 0.8-acre lot may trade at land value if it hasn't been kept up, then come back 24 months later as a $10M custom build.
Active MLS Inventory
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Homes available in Isleworth
12 homes currently listed in Isleworth.
$7,250,000
5074 Isleworth Country Club Dr
Windermere, FL 34786
5 bd · 7 ba · 7,099 sqft
Isleworth
MLS# O6373191
$4,450,000
9144 Isleworth Gardens Dr
Windermere, FL 34786
3 bd · 5 ba · 5,004 sqft
Isleworth
MLS# O6397842
$3,299,999
5001 Latrobe Dr
Windermere, FL 34786
5 bd · 5 ba · 4,417 sqft
Isleworth
MLS# O6389183
$5,300,000
5199 Latrobe Dr
Windermere, FL 34786
6 bd · 7 ba · 4,665 sqft
Isleworth
MLS# O6409961
$6,950,000
6462 Deacon Cir
Windermere, FL 34786
5 bd · 6 ba · 7,178 sqft
Isleworth
MLS# O6407107
$11,900,000
9323 Gladys Garden Ct
Windermere, FL 34786
6 bd · 10 ba · 9,770 sqft
Isleworth
MLS# O6381880
Also Worth Seeing
Related communities
Windermere
Keene's Pointe
Windermere's guard-gated Jack Nicklaus community on the Butler Chain.
$900K – $5M · 1,100 homes
Explore Keene's Pointe →
Windermere
Reserve at Lake Butler Sound
Windermere's intimate lakefront enclave on Lake Butler.
$2M – $15M · 150 homes
Explore Reserve at Lake Butler Sound →
Windermere
Casabella
A small Tuscan-inspired enclave behind Windermere's quieter gate.
$2M – $4.5M · 50 homes
Explore Casabella →
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 3, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA