Neighborhood · Windermere, Florida
Isleworth
Guard-Gated Lakefront Living Minutes From Orlando
17
Homes for sale
$5,500,000
Median list price
$944
Avg price / sqft
57
Median days on market
Isleworth is the address people picture when they think of luxury in Windermere — a guard-gated enclave wrapped around the Butler Chain of Lakes, where estates sit on generous lots behind manicured hedges and private drives. Life here runs on golf, water, and privacy, with the everyday conveniences of nearby communities like Keenes Pointe and Lakeside Village close at hand. Universal Orlando is about 14 minutes out, and both Walt Disney World and Orlando International are roughly 33 minutes away.
For a buyer today, this is a small, top-of-market inventory: 16 active listings with a median list price of $5,400,000 and asking prices running from $2,999,000 to $12,750,000. Homes are large — a median of 5,386 square feet at about $929 per square foot — and nearly every active listing is gated with a pool. Over the past year 19 homes sold at a median of $4,350,000, so serious sellers and serious buyers are both here, and neighboring Summerport and Butler Bay offer entry points nearby.
Isleworth is a community in Windermere, Florida.
Quick facts
$2,999,000 – $13M price range
5,471 sqft median home
$1,224/mo median HOA
$13,250/mo median rent
19 sold in 12 months
Drive times
On the market now
Homes for sale in Isleworth
View all 17 →
$12,350,000
9312 BLANCHE COVE DR, WINDERMERE
7 bd · 9.5 ba · 11,465 sqft
$6,650,000
9921 LAKE LOUISE DRIVE, WINDERMERE
5 bd · 6 ba · 6,970 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
$5,300,000
5199 LATROBE DR, WINDERMERE
6 bd · 6.5 ba · 4,665 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
$11,900,000$12,500,000
9323 GLADYS GARDEN COURT, WINDERMERE
6 bd · 8 ba · 9,770 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
19
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
≈ $33,213/mo
$5,500,000 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
$13,250/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 Windermere's most established luxury communities, built around the Butler Chain of Lakes and known for privacy and space. Assigned schools include Windermere Elementary, Chain Of Lakes Middle, and Olympia High, and neighboring communities like Keenes Pointe add nearby options. The parks and the airport are all reachable in roughly 15 to 35 minutes.
Is Isleworth expensive?+
Yes — this is the high end of the Windermere market, with a median list price of $5,400,000 and every one of the 16 active listings priced above $1 million. Over the past year, homes sold at a median of $4,350,000. If you want a lower entry point in the area, communities like Summerport are worth a look.
What do homes cost in Isleworth?+
Active listings run from $2,999,000 to $12,750,000, with a median of $5,400,000 and an average of about $929 per square foot on a median home size of 5,386 square feet. Rentals are equally premium, with a median around $15,000 a month.
How is the Isleworth market right now?+
It's a small, deliberate market: 16 homes are active and 19 sold over the past 12 months, with a median of 52 days on market. Sellers are getting about 93% of asking on average, so well-priced homes trade but there's still room to negotiate.
What about HOA fees and property taxes?+
The median HOA here runs about $1,224 per month, which supports the gated, guard-controlled setting most listings share. Property taxes are substantial at a median of roughly $34,520 per year, in line with the estate-level pricing across the community.
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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