Casabella
A small Tuscan-inspired enclave behind Windermere's quieter gate.
Live the MaxLife.
$2.9M
Median Price
$2M – $4.5M
50
Homes
$480–$1450
Monthly HOA
2005
Established
Dr. Phillips Elementary School
School Zone
Search Homes for Sale in Casabella
Stellar MLS · 2026-04-26 · 1 closed sale
Recent market data
Median sold
$3,500,000
$3500K – $3500K
Median DOM
328
days on market
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Background
A brief history
Casabella was platted in the mid-2000s as a small Mediterranean and Tuscan-inspired community on a parcel of former groves off the quieter end of Windermere. Roughly 50 lots were subdivided, most of them between one and two acres, with the developer enforcing a single architectural vocabulary — tile roofs, stucco and stone elevations, arched loggias. Most homes were built between 2005 and 2015, largely as one-off customs by a handful of Central Florida luxury builders. The community didn't chase scale; it chased coherence. Nearly twenty years later, that discipline is why Casabella reads as a single integrated neighborhood rather than a collection of builder-spec plans.
The feel
What it's like to live here
Casabella is quiet in a way that larger gated communities rarely are. With only 50 homes, there's no through-traffic and almost no school drop-off congestion. The streets are narrow and curving, lined with queen palms and mature oaks. Residents tend to know each other by first name. Lots are generous — one to two acres, with most homes sited well back from the road — and privacy hedging between lots is standard. The Tuscan-Mediterranean palette is enforced by the architectural covenants: tile roofs, stone and stucco, earth-tone paint, and wood or iron entry doors. Even recent rebuilds have largely stayed inside that vocabulary.
The details
What to expect
Architecture & Lots
Mediterranean and Tuscan exclusively, enforced by covenants. Main houses 5,000–8,500 square feet. Lots 1 to 2 acres. Tile roofs required; flat or low-slope modern roofs prohibited. Stucco and stone elevations. Pools, summer kitchens, and detached casitas are common.
Lifestyle & Amenities
Casabella is amenity-light by design — no pool, no clubhouse, no golf. The trade-off is lower HOA dues and larger lots. Residents typically carry social or golf memberships at Isleworth, Keene's Pointe's Golden Bear Club, or Bay Hill nearby.
HOA Rules & Fees
Monthly HOA $480–$1,450 depending on property (confirmed via public listing data, Apr 2026). Covers grounds maintenance, community roads, security, and common area taxes. Architectural review required for all exterior changes, with strict adherence to the Mediterranean palette. No short-term rentals. Commercial vehicle parking restricted.
Schools
Zoned for Windermere Elementary, Bridgewater Middle, and Olympia High. Private options within 10 minutes include Windermere Prep.
Access & Commute
Ten minutes to Restaurant Row, 25 minutes to downtown Orlando, 30 minutes to MCO, 12 minutes to Disney. Easy 429 access for trips north.
Community
Amenities
- Gated entrance (code-accessed, not manned)
- 1–2 acre lots with mature landscaping
- Architecturally coherent Tuscan/Mediterranean community
- Proximity to Isleworth and Keene's Pointe club memberships
Know Before You Buy
HOA rules worth knowing
- HOA: $480–$1,450/month depending on property — confirmed via public listing data, Apr 2026
- Covers grounds, roads, security, common area taxes
- Mediterranean/Tuscan architectural palette strictly enforced
- Tile roofs required; flat or modern roofs prohibited
- Short-term rentals prohibited
- ARB approval required for all exterior changes
Education
School assignments
- Dr. Phillips Elementary School
- Southwest Middle School
- Dr. Phillips High School
- Windermere Prep (private)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Current median sale sits in the $2.5M–$3.5M range, with the upper end pushing to $4.5M for the largest estates. Square-footage range is relatively tight (5,000–8,500), so pricing is driven more by finish level, lot orientation, and whether the home has been recently updated. Given only 50 total homes, inventory can go months with nothing listed — then three homes at once. Off-market activity is meaningful; we've placed buyers here through direct-to-owner approaches more than once.
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Homes available in Casabella
2 homes currently listed in Casabella.
Also Worth Seeing
Related communities
Windermere
Keene's Pointe
Windermere's guard-gated Jack Nicklaus community on the Butler Chain.
$900K – $5M · 1,100 homes
Explore Keene's Pointe →
Windermere
Isleworth
Arnold Palmer's Windermere legacy — Florida's most private address.
$2M – $40M · 660 homes
Explore Isleworth →
Windermere
Reserve at Lake Butler Sound
Windermere's intimate lakefront enclave on Lake Butler.
$2M – $15M · 150 homes
Explore Reserve at Lake Butler Sound →
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Listings courtesy of Stellar MLS as distributed by MLS GRID
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.
Based on information submitted to the MLS GRID as of June 3, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA