Calabria Homes for Sale

About Calabria Neighborhood

Calabria — known formally as Calabria at Westside — is a small, distinguished enclave of approximately 70 single-family homes situated on the western side of Westside Boulevard in the Four Corners area of Kissimmee. The community's eastern lots back to Old Lake Davenport, a natural lake stretching roughly a mile from north to south, while western-facing lots overlook protected conservation woodlands and wetlands, giving virtually every home in the community a private natural backdrop. This combination of lake and conservation views within a small-scale neighborhood is genuinely rare in the Westside resort corridor.

D.R. Horton developed Calabria beginning in 2007, with construction completing around 2013. Homes are generously proportioned, ranging from approximately 2,059 to 6,312 square feet of living space — a range that speaks to the variety of floor plans available, from family-sized four-bedroom homes to expansive five-bedroom layouts well-suited for vacation rental configuration. The architectural style is Mediterranean-influenced throughout, with tile roofs, stucco exteriors, and covered lanais that blend into the lush Florida surroundings. Many homes feature private heated pools, game rooms, and large open-plan interiors that work equally well as primary residences or income-producing vacation properties.

The community holds short-term rental approval, making it one of the smaller STR-eligible communities in the Westside corridor. Unlike large resort communities nearby, Calabria's intimate scale — roughly 70 homes — creates a quieter, more residential atmosphere even as it accommodates vacation guests. Homeowners here enjoy lawn maintenance included in the HOA, along with cable and internet service, reducing day-to-day upkeep. The neighborhood's palm-lined entry and well-maintained common areas reflect a community that takes pride in its presentation.

Westside Boulevard connects Calabria directly to US 192 (W. Irlo Bronson Memorial Highway) approximately one mile to the north, placing residents within immediate reach of the full range of dining, retail, and entertainment that lines the Kissimmee tourism corridor. The SR-429 Daniel Webster Western Beltway interchange is also close by, providing fast connections to Interstate 4, Orlando International Airport, and points across Central Florida.

Calabria Location & Connections

Calabria is located in the Four Corners area of Kissimmee, positioned along Westside Boulevard approximately one mile south of US 192 (W. Irlo Bronson Memorial Highway). The community sits at the boundary of Osceola and Polk Counties in the geographic "Four Corners" area where Orange, Osceola, Polk, and Lake Counties converge — one of the most intensely developed tourism and resort-residential corridors in Central Florida.

The SR-429 Daniel Webster Western Beltway runs just east of the community, providing direct toll-road access to Orlando International Airport, the western I-4 interchange, and points north toward Apopka and Sanford. This layered road network — Westside Boulevard to US-192 to SR-429 to I-4 — gives Calabria residents exceptional regional connectivity despite being nestled in a quiet residential pocket well removed from highway noise.

Calabria Amenities & Lifestyle

Life in Calabria offers a dual character unique to the Westside corridor: a quiet, residential pace within the community's intimate lake-view streets, combined with immediate access to the full energy of Central Florida's tourism and entertainment landscape just minutes away on US 192. Residents here can step into their backyard to watch sunset over Old Lake Davenport, then be at the gates of Walt Disney World in under 15 minutes — a balance that few communities in Osceola County can match.

The neighborhood's short-term rental approval attracts a mix of investors and full-time residents, creating a community dynamic that accommodates multiple lifestyles. Those using their Calabria home as a primary residence appreciate the HOA-maintained lawn care, cable, and internet included in fees, reducing ownership friction. Investors appreciate the proven rental demand generated by the community's proximity to Disney, Universal, and the broader Orlando theme park market.

How Calabria Compares

Calabria occupies an interesting position in the Westside resort market — it offers larger single-family homes with natural lake and conservation views at price points generally below the larger branded resort communities in the same corridor. The combination of STR approval, no CDD, and a genuinely intimate neighborhood scale makes it a standout option for buyers who want investment flexibility without the institutional resort-community feel.

Calabria HOA & CDD Information

Calabria at Westside is governed by a homeowners association that manages the community's common areas, entrance, sidewalks, and shared standards. The HOA is a meaningful value-add here because it includes lawn maintenance, cable television, and internet service as part of the monthly fee — reducing the out-of-pocket operating costs for both primary residents and vacation rental investors. The community has no Community Development District (CDD) fee, which is an important financial differentiator from many comparable communities in the Westside resort corridor. To learn more about what CDDs are and how they affect your property taxes, see our guide to what a CDD is.

Short-term rental use is permitted within Calabria, making this one of the smaller STR-approved communities in Kissimmee. Owners considering vacation rental use should confirm current HOA rental rules, minimum stay requirements, and any applicable restrictions directly with the HOA management company before closing.

Frequently Asked Questions