Neighborhood · Windermere, Florida
Isleworth
Guard-gated luxury on the Butler Chain of Lakes
21
Homes for sale
$5,300,000
Median list price
$946
Avg price / sqft
76
Median days on market
Isleworth is one of the most recognizable addresses in Windermere, a private, guard-gated community wrapped around the Butler Chain of Lakes and its own championship golf. Homes here run large and estate-scaled — the median floor plan is nearly 6,000 square feet, and every active listing has a pool. It's a community built for people who want space, privacy, and water access without leaving the west Orlando footprint, with Universal Orlando about 14 minutes out and both Disney and MCO roughly a half hour away.
For a buyer, this is a rarefied slice of the market. All 21 active listings ask $1M-plus, with a median list price of $5.3 million and a range that stretches from $2.8 million to $19.5 million. Inventory is thin and moves deliberately — median days on market sits at 76, and over the last year sellers collected about 93% of asking, so there's real room to negotiate at this price point. If Isleworth's numbers stretch the budget, nearby communities like Keenes Pointe and Summerport offer other ways into the same corner of Windermere.
Isleworth is a community in Windermere, Florida.
Quick facts
$2,800,000 – $20M price range
5,993 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 21 →
$19,500,000
5192 VARDON DRIVE, WINDERMERE
6 bd · 9 ba · 13,494 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
$18,750,000
5036 LATROBE DRIVE, WINDERMERE
6 bd · 8 ba · 15,337 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
$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
$4,999,500$5,500,000
5138 FAIRWAY OAKS DR, WINDERMERE
4 bd · 5 ba · 4,330 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
≈ $32,312/mo
$5,300,000 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
$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 a private, guard-gated community on the Butler Chain of Lakes with golf, pools on every property, and a genuinely central west-Orlando location. Universal Orlando is about 14 minutes away and both Disney and MCO airport sit around 33 minutes out. Assigned schools include Windermere Elementary, Chain of Lakes Middle, and Olympia High.
Is Isleworth expensive?+
Yes — this is one of Central Florida's top-tier luxury addresses, and all 21 active listings are priced above $1 million. The median list price is $5.3 million, with individual homes ranging from $2.8 million up to $19.5 million. Buyers exploring the broader area may find more entry points among Windermere homes for sale outside the gates.
What do homes cost in Isleworth?+
The median list price is $5.3 million, and homes trade at roughly $946 per square foot on a median footprint of about 5,993 square feet. Over the past 12 months, 17 homes sold at a median price of $4,287,500.
How is the Isleworth market right now?+
It's a slow, deliberate luxury market with 21 active listings and a median 76 days on market. Sellers took in about 93% of asking on average over the last year, so a well-prepared buyer has genuine negotiating leverage at these price points.
What are the HOA fees and property taxes?+
The median HOA runs about $1,224 per month, which reflects the guard-gated, amenity-heavy nature of the community. Median annual property tax is roughly $35,432, in line with the multimillion-dollar values here.
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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