Neighborhood · Windermere, Florida
Isleworth
Guard-gated luxury on the Butler Chain of Lakes
20
Homes for sale
$4,700,000
Median list price
$901
Avg price / sqft
67
Median days on market
Isleworth is the address that put Windermere on the map — a private, guard-gated golf-and-lake community where estate homes sit on generous lots and the Butler Chain of Lakes shapes daily life. The pace is quiet and deliberate: pool decks, mature landscaping, and a level of privacy that draws executives and pro athletes alike. It's tucked among Windermere's most established enclaves, a short hop from the Lakeside Village core and the family-friendly streets of Summerport and Lake Burden South.
This is a genuine top-tier market, so buyers should read the numbers before falling for a listing. There are 20 active homes with a median list price of $4,649,750, ranging from $2.8M up to $12.35M, and properties tend to take their time — a median of 76 days on market. Over the last year 18 homes sold at a median of $4,318,750, with sellers collecting about 94% of asking, which tells you there's room to negotiate if you come prepared. If Isleworth stretches the budget, it's worth comparing against nearby Keenes Pointe and the broader field of Windermere homes for sale.
Isleworth is a community in Windermere, Florida.
Quick facts
$2,800,000 – $12M price range
5,732 sqft median home
$1,224/mo median HOA
$21,750/mo median rent
17 sold in 12 months
Drive times
On the market now
Homes for sale in Isleworth
View all 20 →
$12,350,000
9312 BLANCHE COVE DR, WINDERMERE
7 bd · 9.5 ba · 11,465 sqft
$7,200,000
5373 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE
5 bd · 5.5 ba · 5,993 sqft
$3,500,000
5524 WORSHAM COURT, WINDERMERE
4 bd · 6 ba · 7,669 sqft
$3,189,000
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE
4 bd · 4.5 ba · 3,365 sqft
$3,400,000
5379 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE
4 bd · 3.5 ba · 3,872 sqft
$6,650,000
9921 LAKE LOUISE DRIVE, WINDERMERE
5 bd · 6 ba · 6,970 sqft
$6,900,000$7,000,000
6055 LOUISE COVE DRIVE, WINDERMERE
5 bd · 5.5 ba · 7,158 sqft
$6,500,000
9316 GLADYS GARDEN CT, WINDERMERE
5 bd · 6.5 ba · 5,471 sqft
$3,900,000$4,100,000
5151 LATROBE DR, WINDERMERE
4 bd · 4.5 ba · 5,301 sqft
$5,300,000
5199 LATROBE DR, WINDERMERE
6 bd · 6.5 ba · 4,665 sqft
$11,750,000$12,750,000
9832 LAUREL VALLEY DRIVE, WINDERMERE
6 bd · 8.5 ba · 11,100 sqft
$2,800,000$2,999,000
5073 LATROBE DR, WINDERMERE
4 bd · 5 ba · 4,706 sqft
Every active listing inside the Isleworth boundary
Open full map search →Find your fit
Browse Isleworth
By feature — on the live map
The numbers that matter
The Isleworth market
17
Sold, last 12 months
$4,287,500
Median sold price
93%
Sale-to-list ratio
What sellers actually get vs asking
30 days
Median time to sell
Isleworth vs Windermere
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 9.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Isleworth boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Isleworth is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Isleworth home
≈ $29,195/mo
$4,700,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$1,224/mo
Median HOA
From current listings inside the boundary
$21,750/mo
Median rent
Homes for rent inside the boundary
Population
630
Median age
58
Median income
$151,250
Beyond the listings
Living in Isleworth
Food & Drink
Top 2% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Food & Drink
Top 4% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
Relationships
Top 5% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Entertainment
Top 5% in the U.S.Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Lifestyles
Top 6% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Attitudes
Top 6% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
Straight answers
Isleworth FAQs
Is Isleworth a good place to live?+
It's one of Central Florida's most established luxury communities — guard-gated, quiet, and built around the Butler Chain of Lakes with private pools on nearly every property. Assigned schools include Windermere Elementary, Chain Of Lakes Middle, and Olympia High. You're about 14 minutes from Universal Orlando and 33 from both Walt Disney World and Orlando International Airport.
Is Isleworth expensive?+
Yes — this is the top of the Windermere market. Every one of the 20 active listings is priced above $1M, with a median list price of $4,649,750 and a ceiling of $12.35M. Buyers looking for a slightly lower entry point often explore nearby Keenes Pointe.
What do homes cost in Isleworth?+
Active listings run from $2.8M to $12.35M, with a median of $4,649,750 and an average of about $901 per square foot. Over the past 12 months, 18 homes sold at a median price of $4,318,750, so real closings track close to current asking levels.
How is the Isleworth market right now?+
It's a patient market where quality commands a premium but buyers hold leverage. Homes take a median of 76 days to sell, and over the last year sellers averaged about 94% of their asking price — meaning there's typically room to negotiate on an Isleworth estate.
What about HOA fees and property taxes?+
Expect a median HOA of around $1,224 per month, which supports the guarded gate and community upkeep. Property taxes run a median of roughly $34,520 per year, in line with the community's estate-level valuations.
Keep exploring
More Windermere neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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