Neighborhood · Windermere, Florida
Casabella
Gated luxury living minutes from Orlando's theme parks
5
Homes for sale
$3,599,000
Median list price
$621
Avg price / sqft
4
Median days on market
Casabella is a small, gated enclave in Windermere where estate-sized homes sit on generous lots — the median house here runs just over 6,000 square feet. It's a quiet, low-density pocket of southwest Orange County, close in character to neighbors like Keenes Pointe and Isleworth, and it's assigned to Windermere High, Bridgewater Middle, and Windermere Elementary. Despite the seclusion, Universal Orlando is about 21 minutes away and Walt Disney World roughly 23, so the parks are a genuine day-trip rather than a road trip.
This is a thin, high-end market: only 2 homes are active right now, both gated and both with pools, listed between $2.899M and $3.99M with a median around $3.44M. Over the past year 7 homes sold at a median of $3,075,000, with sellers netting about 93% of asking — so there's room to negotiate, but not a lot of inventory to negotiate over. If you're comparing options, it's worth looking at nearby communities like Summerport and Lakeside Village to understand where Casabella sits on price.
Casabella is a community in Windermere, Florida.
Quick facts
$2,899,000 – $4.0M price range
5,362 sqft median home
$537/mo median HOA
6 sold in 12 months
Drive times
On the market now
Homes for sale in Casabella
$3,700,000
4302 ISABELLA CIR, WINDERMERE
5 bd · 6.5 ba · 5,362 sqft
$3,290,000
4243 ISABELLA CIRCLE, WINDERMERE
5 bd · 6 ba · 5,502 sqft
$3,990,000$4,000,000
4201 ISABELLA CIRCLE, WINDERMERE
6 bd · 7 ba · 6,896 sqft
$3,599,000
3986 ISABELLA CIRCLE, WINDERMERE
5 bd · 6 ba · 5,342 sqft
$2,899,000
4303 ISABELLA CIRCLE, WINDERMERE
7 bd · 5 ba · 5,122 sqft
Every active listing inside the Casabella boundary
Open full map search →Find your fit
Browse Casabella
By feature — on the live map
The numbers that matter
The Casabella market
6
Sold, last 12 months
$3,037,500
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
119 days
Median time to sell
Casabella vs Windermere
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 8.9% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Casabella boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Casabella is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Casabella home
≈ $22,637/mo
$3,599,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$537/mo
Median HOA
From current listings inside the boundary
Population
295
Median age
46
Median income
$198,837
Median home value
$867,000
Beyond the listings
Living in Casabella
Emotional
Top 5% in the U.S.Awestruck
Great things are meant to be shared, and this population is eager to show others what they find to be amazing, beautiful and exciting.
Lifestyles
Top 10% 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.
Food & Drink
Top 15% 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.
Active
Top 17% in the U.S.Organized Sports
From tryouts and casual pick-up games, to varsity tournaments and intramural matches, this population includes people who participate in organized athletics. Often through schools or public recreational areas.
Attitudes
Top 19% 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.
Food & Drink
Top 19% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Straight answers
Casabella FAQs
Is Casabella a good place to live?+
It's a good fit for buyers who want a large gated home in a quiet corner of Windermere with easy access to Orlando's attractions. Homes are assigned to Windermere High, Bridgewater Middle, and Windermere Elementary, and the parks are 21 to 23 minutes away. It sits comfortably alongside established luxury neighbors like Keenes Pointe.
Is Casabella expensive?+
Yes — this is one of Windermere's higher-end enclaves, with active listings ranging from $2.899M to $3.99M and a median list price around $3,444,500. If that range is beyond your budget, communities like Summerport offer more accessible entry points in the same area.
What do homes cost in Casabella?+
The current median list price is about $3,444,500, and the average price works out to roughly $572 per square foot on a median home size near 6,009 square feet. Over the last 12 months, 7 homes sold at a median of $3,075,000.
How is the market in Casabella right now?+
Inventory is very tight, with just 2 active listings, but they move — the median days on market is only 17. Sellers have been getting about 93% of asking on average, so well-priced homes trade quickly while leaving some negotiating room.
What about HOA fees and property taxes?+
The median HOA runs about $509 per month, which covers the gated community's shared costs. Property taxes are significant at these price points — the median annual bill is around $30,171.
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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