Neighborhood · Windermere, Florida
Isleworth
Guard-gated golf living on the Butler Chain
18
Homes for sale
$4,800,000
Median list price
$902
Avg price / sqft
65
Median days on market
Isleworth is one of Central Florida's most established luxury addresses — a guard-gated community wrapped around a championship golf course and the Butler Chain of Lakes, minutes from downtown Windermere homes for sale. Homes here run large, private, and pool-centered, with a good share of waterfront estates and mature landscaping that separates this community from the newer builds nearby. Buyers weighing it against neighborhoods like Keenes Pointe or Summerport are usually after the privacy, the space, and the lifestyle that comes with it.
The market reflects that tier: 18 homes are active with a median list price of $4.8M, ranging from just under $3M to $12.75M, and pricing lands around $902 per square foot on a median 5,153-square-foot house. Over the past year 20 homes sold at a median of $4,375,000, with sellers collecting about 94% of asking — so there's room to negotiate at this level. With a median 64.5 days on market, this is a patient, considered buy rather than a bidding-war environment.
Isleworth is a community in Windermere, Florida.
Quick facts
$2,999,000 – $13M price range
5,153 sqft median home
$1,224/mo median HOA
$13,750/mo median rent
20 sold in 12 months
Drive times
On the market now
Homes for sale in Isleworth
View all 18 →
$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
20
Sold, last 12 months
$4,375,000
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
48 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
≈ $29,393/mo
$4,800,000 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 a good fit if you want space, privacy, and an established luxury setting — 16 of 18 active homes are gated and 17 have pools, on a median lot-and-home footprint of 5,153 square feet. Families also value the school assignments to Windermere Elementary, Chain of Lakes Middle, and Olympia High. The location keeps you close to it all, with Universal Orlando roughly 14 minutes away.
Is Isleworth expensive?+
Yes — this is a top-tier market with a median list price of $4,800,000 and active homes running from just under $3M to $12.75M. Pricing works out to about $902 per square foot, well above most of the surrounding Windermere homes for sale. Carrying costs are meaningful too, with median property taxes around $32,030 a year.
What do homes cost in Isleworth?+
The 18 active listings carry a median list price of $4.8M, and over the last 12 months 20 homes sold at a median of $4,375,000. Expect large floor plans — the median home is 5,153 square feet — at roughly $902 per square foot. Buyers comparing options often also look at Keenes Pointe for a similar gated lifestyle.
How is the market right now?+
It's a steady, patient market rather than a frenzy: the median days on market is 64.5, and sellers are getting about 94% of asking on average. That 6% gap means there's genuine room to negotiate at these price points, especially with 18 homes currently available to choose from.
What about HOA fees and property taxes?+
Plan for a median HOA of about $1,224 per month, which covers the guard-gated infrastructure this community is known for. Property taxes run around $32,030 a year at the median, reflecting the high assessed values. If you're renting first, the median lease here is about $13,750 per month.
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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