Neighborhood · Windermere, Florida
Isleworth
Guard-gated luxury living on the Butler Chain
19
Homes for sale
$4,300,000
Median list price
$896
Avg price / sqft
72
Median days on market
Isleworth is one of the most established gated communities in Windermere, a private enclave built around golf, lakefront living, and a level of security that keeps its residents low-profile. Homes here run large — the typical property is just over 5,000 square feet — and life leans toward the water, with a handful of estates sitting directly on the Butler Chain of Lakes. If you're weighing nearby options, communities like Keenes Pointe and Lakeside Village share the same appeal for a slightly different budget.
The market here is thin and expensive by design. There are 19 active listings with a median list price of $4,300,000, and homes typically take about 72 days to sell — normal pacing for this price tier. Over the last year 21 homes closed at a median of $4,350,000, with sellers netting roughly 93% of asking, so there's real room to negotiate if you come prepared. Buyers comparing value should also look at Summerport and Butler Bay before committing.
Isleworth is a community in Windermere, Florida.
Quick facts
$2,999,000 – $13M price range
5,004 sqft median home
$1,224/mo median HOA
$13,750/mo median rent
21 sold in 12 months
Drive times
On the market now
Homes for sale in Isleworth
View all 19 →
$12,350,000
9312 BLANCHE COVE DR, WINDERMERE
7 bd · 9.5 ba · 11,465 sqft
$2,999,000
5073 LATROBE DR, WINDERMERE
4 bd · 5 ba · 4,706 sqft
$5,500,000
5138 FAIRWAY OAKS DR, WINDERMERE
4 bd · 5 ba · 4,330 sqft
$6,500,000
9316 GLADYS GARDEN CT, WINDERMERE
5 bd · 6.5 ba · 5,471 sqft
$12,750,000$13,900,000
9832 LAUREL VALLEY DRIVE, WINDERMERE
6 bd · 8.5 ba · 11,100 sqft
$3,900,000$4,100,000
5151 LATROBE DR, WINDERMERE
4 bd · 4.5 ba · 5,301 sqft
$7,999,000
9317 GLADYS GARDEN COURT, WINDERMERE
6 bd · 7.5 ba · 8,038 sqft
$6,499,999$6,950,000
6462 DEACON CIR, WINDERMERE
5 bd · 5 ba · 7,178 sqft
$5,300,000
5199 LATROBE DR, WINDERMERE
6 bd · 6.5 ba · 4,665 sqft
$3,299,999$3,499,999
5001 LATROBE DRIVE, WINDERMERE
5 bd · 4.5 ba · 4,417 sqft
$4,190,000$4,390,000
4906 AVIVA GARDEN COURT, WINDERMERE
3 bd · 4.5 ba · 6,236 sqft
$4,300,000$4,450,000
9144 ISLEWORTH GARDENS DRIVE, WINDERMERE
3 bd · 4 ba · 5,004 sqft
Every active listing inside the Isleworth boundary
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Browse Isleworth
By feature — on the live map
The numbers that matter
The Isleworth market
21
Sold, last 12 months
$4,350,000
Median sold price
93%
Sale-to-list ratio
What sellers actually get vs asking
37 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
≈ $26,891/mo
$4,300,000 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
$13,750/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 built for buyers who want privacy, space, and lake access — most homes are gated, pool-equipped, and average just over 5,000 square feet. The community feeds well-regarded schools including Olympia High, and you're about 14 minutes from Universal Orlando. If you like the setting but want more choices, Keenes Pointe offers a similar lifestyle.
Is Isleworth expensive?+
Yes — this is one of the top luxury markets in the Windermere area, with every active listing priced above $1 million and a median list price of $4,300,000. Prices run from $2,999,000 up to $12,750,000, and the average is about $896 per square foot. It's a genuine high-end market, not an entry point.
What do homes cost in Isleworth?+
The median list price is currently $4,300,000, and over the past 12 months 21 homes sold at a median of $4,350,000. At roughly $896 per square foot on a typical 5,004-square-foot home, you're paying for size, security, and lake proximity. Nearby Summerport offers lower price points if the budget needs flexibility.
How is the market right now?+
There are 19 active listings and homes are taking a median of 72 days to sell, which is normal for this luxury tier. Sellers are averaging about 93% of asking price, so there's meaningful negotiating room for a prepared buyer. With only 21 sales in the past year, inventory turns slowly and each listing matters.
What about HOA fees and property taxes?+
The median HOA runs about $1,224 per month, which reflects the gated infrastructure and community services here. Property taxes are substantial given the price point, with a median around $33,607 per year. Budget for both when comparing Isleworth to other Windermere communities.
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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