Windsor Hills Homes for Sale

About Windsor Hills Neighborhood

Windsor Hills Resort is a master-planned, fully gated vacation resort community situated along N. Old Lake Wilson Road (SR-545) in the heart of Kissimmee's Westside corridor. Development began in 2004 and was completed by approximately 2010, creating a cohesive, resort-caliber environment across nearly 1,000 individually owned units. The community sits in Osceola County's coveted 34747 ZIP code — the same postal district that places residents and guests within a remarkably short drive of every major Central Florida theme park and attraction.

The community's property mix is one of its defining strengths. Windsor Hills offers 320 condominiums (two- and three-bedroom configurations), 210 townhomes (three bedrooms, three bathrooms), and 469 single-family pool homes with four, five, or six bedrooms. Living spaces range from approximately 1,081 square feet in the condominium buildings up to roughly 2,832 square feet in the largest single-family layouts. Every single-family home features its own private screened pool and spa, while the townhome sub-association covers exterior maintenance for those properties.

What sets Windsor Hills apart from comparable resort communities is its short-term rental zoning — every property type within the community is approved for vacation rental use under Osceola County's rules. This makes Windsor Hills equally attractive as a permanent primary residence, a second home used personally and rented during off periods, or a purely investment-oriented vacation rental managed by any of the numerous professional companies operating within the gates. The community's long track record of high occupancy and strong rental demand makes it one of the most frequently searched resort neighborhoods in the greater Kissimmee market.

The crown jewel of the community is its 10,000-square-foot clubhouse, which recently underwent a major renovation to its water park amenities. The updated waterpark features two large dueling water slides, a children's splash park with water cannons, and a beach-entry pool alongside the original 140,000-gallon lagoon pool with hot tub. The clubhouse interior houses a fitness center, movie theater, video arcade, billiards, and a sundry shop. Outside, residents enjoy lighted basketball, tennis, and sand volleyball courts, a modern children's playground, and a dedicated putting green.

Windsor Hills Location & Connections

Windsor Hills sits along N. Old Lake Wilson Road (SR-545) in the Westside corridor of Kissimmee, positioned between Teascone Boulevard and Livingston Road. The community's main entrance is just off US-192 (W. Irlo Bronson Memorial Highway) — one of Kissimmee's primary commercial corridors — and connects to the broader regional highway network via nearby SR-429 (Daniel Webster Western Beltway), which provides fast access north toward Orlando or south toward I-4.

The positioning is genuinely exceptional for theme park proximity: Walt Disney World's main gate is approximately 1.5 miles (roughly 3–4 minutes by car via Lake Wilson Road) — making Windsor Hills one of the closest resort communities to Disney in all of Osceola County. The broader US-192 corridor places virtually every Central Florida attraction, outlet mall, and entertainment district within a short drive, while SR-429 gives commuters a clean path to Orlando International Airport without navigating local traffic.

Windsor Hills Amenities & Lifestyle

Life at Windsor Hills operates on two distinct tracks — and that duality is its greatest asset. Owner-residents enjoy the security and exclusivity of a 24-hour gated environment while accessing a full suite of resort amenities that most primary residential communities simply cannot match. The renovated waterpark, movie theater, fitness center, and sports courts mean there is always something to do without leaving the gates. Meanwhile, the surrounding Kissimmee Westside corridor provides immediate access to world-class theme parks, outlet shopping, lakefront dining, and entertainment options of every variety.

For investors and second-home buyers, Windsor Hills offers a proven rental platform. The community's short-term rental zoning, professional property management ecosystem, and proximity to Disney World have created one of the highest-demand vacation rental destinations in Central Florida. Many owners enjoy personal use during peak travel seasons while generating rental income throughout the remainder of the year. The community's on-site welcome center and 24/7 security team provide peace of mind whether the owner is in residence or the home is rented to guests.

How Windsor Hills Compares

Windsor Hills occupies a unique position in the Kissimmee resort market. As one of the closest vacation-eligible communities to Walt Disney World in the entire county, it commands premium attention from buyers seeking both investment potential and resort-quality living. Compared to newer resort communities further from the park gates, Windsor Hills' location advantage is difficult to replicate. Compared to older communities along US-192, Windsor Hills' recently renovated waterpark and comprehensive clubhouse represent a significant amenity upgrade.

Windsor Hills HOA & CDD Information

Windsor Hills operates under a master homeowners association (HOA) that governs the entire community, with additional sub-associations for each of the three property types: single-family homes (The Enclave), townhomes (The Vistas), and condominiums (The Ventura). Each property owner pays both the master association fee and the applicable sub-association fee. The master HOA covers the shared amenities — including the waterpark, clubhouse, courts, guard gate, and common areas — while sub-association fees address property-type-specific maintenance such as lawn care, roofing, or building exteriors.

Windsor Hills has no Community Development District (CDD). This is a meaningful financial benefit for buyers comparing resort communities in Osceola County, many of which carry CDD assessments that can add thousands of dollars per year to ownership costs. To learn more about what CDDs are and how they affect ownership, visit our What's a CDD guide.

HOA dues at Windsor Hills cover an extensive range of services. The master association covers cable/internet, landscaping of common areas, clubhouse amenities, 24-hour guard-gated security, sports courts, roadways, sidewalks, and insurance for common facilities. Sub-association fees provide additional coverage specific to each property type, which is one of the reasons Windsor Hills properties remain so consistently well-maintained.

Frequently Asked Questions