Casabella Homes for Sale

About Casabella Neighborhood

Casabella sits in the southwestern quadrant of Windermere's 34786 ZIP, a guard-gated enclave developed by Toll Brothers and built out in stages from approximately 2013 through 2019. The community contains 79 single-family estate homes — small enough to feel exclusive, large enough to support a meaningful resale market. Mediterranean and transitional-modern architecture dominates, with tile roofs, paver drives, and stone-and-stucco façades that have weathered into the kind of established look that's increasingly rare among newer Windermere subdivisions.

Lot sizes are the headline differentiator. Where most contemporary luxury communities push homes onto 0.15–0.25 acre parcels, Casabella's homesites average roughly half an acre — providing room for screened pool enclosures, summer kitchens, side-load garages, and the kind of mature landscape buffers that make a 5,000+ square foot home feel right-sized rather than wedged in. Floor plans typically range from about 3,100 to 6,900 square feet, with four to seven bedrooms and three-car garages standard. The community has no Community Development District (CDD) — a meaningful annual savings versus newer Windermere and Horizon West developments.

The Butler Chain of Lakes is effectively next door, and the community's position on the western side of the Butler Chain corridor places it within minutes of The Grove at Isleworth, downtown Windermere, and Disney's eastern boundary along Vineland Road. Buyers drawn to Casabella tend to want the gated-luxury character of Isleworth or Keene's Pointe at a meaningfully lower entry point — without the country club initiation, without the CDD, and with the appeal of construction that's recent enough to require minimal updating.

Casabella Location & Connections

Casabella is positioned in southwest Windermere on the western edge of the Butler Chain of Lakes. The community sits within a tight cluster of guard-gated luxury enclaves — Chaine Du Lac, Bellaria, and Tildens Grove — that collectively define the Lake Burden / western Butler Chain corridor.

Access is via Conroy-Windermere Road and Winter Garden Vineland Road (CR 535), with SR 429 (Western Beltway) a few miles west providing the fastest connection south to Disney property and north to Apopka. The combination places Casabella within a 25-minute drive of downtown Orlando and the major theme parks while keeping the lake-luxury character of Windermere intact.

Casabella Amenities & Lifestyle

Casabella is an amenity-light community by design. Rather than building out a clubhouse, fitness center, and resort pool that would have required higher density and tighter lots, Toll Brothers concentrated the value in larger homesites and the guard-gated entry. Most residents build private screened pool enclosures, summer kitchens, and outdoor living spaces on their half-acre lots — and rely on the surrounding Windermere infrastructure for shopping, dining, recreation, and culture.

That trade-off works because Windermere's commercial and recreational footprint is unusually dense for a town this size. The Grove at Isleworth, Sand Lake Road's Restaurant Row, the historic Town Square, and Cornerstone at Summerport are all within a 5–15 minute drive.

How Casabella Compares

Casabella's value proposition becomes sharpest in direct comparison to the alternatives most buyers consider — newer master-planned luxury in Horizon West, country-club gated communities, and country-club estates. Casabella sacrifices club amenities and lakefront frontage to deliver larger lots, lower carrying costs, and tighter inventory.

Casabella HOA & CDD Information

Casabella is governed by a homeowners association that maintains the guard-gated entry, common-area landscaping, community streets, and architectural standards. The community is not in a Community Development District — there is no CDD assessment to consider beyond the HOA fee, which is a meaningful annual savings versus newer master-planned alternatives in Horizon West and similar developments.

Architectural review applies to exterior modifications, paint, landscaping changes, and additions. Buyers planning major exterior work — pool additions, summer kitchens, hardscape — should request the current ARC guidelines during due diligence.

Frequently Asked Questions