Neighborhood · Windermere, Florida
Isleworth
Guard-gated golf living on the Butler Chain of Lakes
19
Homes for sale
$5,300,000
Median list price
$930
Avg price / sqft
57
Median days on market
Isleworth sits on the Butler Chain of Lakes in Windermere, the kind of guard-gated address where estate homes open onto private water and championship fairways. Life here is quiet and deliberate — long lots, boat docks, and a country-club rhythm that keeps residents close to home while Keenes Pointe and Butler Bay round out the surrounding luxury-community landscape. Universal Orlando is about 14 minutes away, with Walt Disney World and Orlando International Airport each roughly 33 minutes out.
For a buyer today, this is a top-tier luxury market with real scarcity: just 19 active listings, all of them above $1M, and a median list price of $5.3 million. Homes are large — a median of 5,301 square feet at about $930 per square foot — and they take time to trade, with a median 57 days on market. Over the past year 20 homes sold at a median of $4,365,000, with sellers netting around 94% of asking, so there's room to negotiate at this level.
Isleworth is a community in Windermere, Florida.
Quick facts
$2,999,000 – $14M price range
5,301 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 19 →
$12,350,000
9312 BLANCHE COVE DR, WINDERMERE
7 bd · 9.5 ba · 11,465 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
$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
$7,999,000
9317 GLADYS GARDEN COURT, WINDERMERE
6 bd · 7.5 ba · 8,038 sqft
$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
$4,450,000
9144 ISLEWORTH GARDENS DRIVE, WINDERMERE
3 bd · 4 ba · 5,004 sqft
$6,499,999$6,950,000
6462 DEACON CIR, WINDERMERE
5 bd · 5 ba · 7,178 sqft
$4,390,000$4,590,000
4906 AVIVA GARDEN COURT, WINDERMERE
3 bd · 4.5 ba · 6,236 sqft
$3,299,999$3,499,999
5001 LATROBE DRIVE, WINDERMERE
5 bd · 4.5 ba · 4,417 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
20
Sold, last 12 months
$4,365,000
Median sold price
94%
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
▼ 9.6% 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
≈ $31,897/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
$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.
On the calendar
Near Isleworth
Jul
12
Sun
Rumba Brunch
11:30am
Every Sunday, attendees have the opportunity to immerse themselves in the authentic rumba music played live by wandering guitarists and vocalists. To accompany the riveti…
Jul
12
Sun
Walt Disney World Park Meetup
The Orlando Social Network (OSN) is a vibrant community that facilitates adults in meeting, connecting, and building friendships through a variety of fun events, includin…
Jul
12
Sun
Vibe, Sip, and Make Jewelry
Wanda Taylor, a seasoned craftswoman, invites the community to a workshop where she'll share her expertise in creating a wide range of handcrafted items. Attendees will h…
Jul
12
Sun
Bite30
Bite30 in Orlando, FL, USA, is a culinary celebration that spotlights the creativity and talent of Central Florida’s top chefs and restaurants. For a set price, diners ca…
Jul
12
Sun
Bands, Brew, and BBQ
Bands, Brew, and BBQ brings together live country and rock music with delicious food and refreshing drinks for a lively summer experience at SeaWorld Orlando. You can enj…
Jul
12
Sun
Cirque du Soleil: Drawn to Life
1:30pm
Drawn to Life is a Cirque du Soleil and Disney collaboration featuring acrobatics, animation, and theatrical magic. The show brings classic Disney drawings to life in a d…
Straight answers
Isleworth FAQs
Is Isleworth a good place to live?+
It's one of Central Florida's premier guard-gated communities, built around the Butler Chain of Lakes and a country-club lifestyle. Sixteen of the current listings are gated and eighteen have private pools, so privacy and resort-style amenities come standard. Families also draw on well-regarded assigned schools including Olympia High and Windermere Elementary.
Is Isleworth expensive?+
Yes — this is a luxury enclave where every one of the 19 active listings is priced above $1 million and the median list price is $5,300,000. Homes run from roughly $2,999,000 to $13,900,000, averaging about $930 per square foot. It sits at the top end of the broader Windermere market.
What do homes cost in Isleworth?+
The median list price is $5.3 million for a home of about 5,301 square feet, while homes that actually sold over the past year closed at a median of $4,365,000. That gap reflects negotiation room — sellers here average about 94% of asking. Expect large estate-scale properties rather than starter homes.
How is the market right now?+
It's a slower, high-value market: 19 homes are active and 20 sold over the past 12 months, so inventory turns roughly once a year. The median days on market is 57, and sellers net about 94% of their asking price. Nearby luxury options like Keenes Pointe give buyers additional comparison points.
What about HOA fees and property taxes?+
Carrying costs match the address — the median HOA runs about $1,224 per month, and median annual property tax is around $30,452. Those figures cover the gated infrastructure and community services typical of an estate community like this. Budget for them alongside the purchase price when comparing homes.
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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