Windsor Hills

Windsor Hills Resort was developed by Pulte Homes and built in phases between approximately 2004 and 2010, purpose-designed as a short-term rental community from the ground up. The location — at the intersection of US Highway 192 and Old Lake Wilson Road in Osceola County, just two miles from Walt Disney World's Animal Kingdom gate — was chosen deliberately to capture the Disney-area vacation rental market that was booming in the mid-2000s. At build-out the community encompasses 999 individually owned units including condominiums, townhomes, and single-family villas ranging from three to eight bedrooms, almost all with private pools.

Unlike some communities that evolved into vacation rentals after the fact, Windsor Hills was zoned and permitted as a short-term rental resort from day one, which has protected it legally from the STR restrictions that have complicated ownership in neighboring communities. Osceola County's permissive vacation rental framework, combined with the community's proximity to Disney, established Windsor Hills as one of the most recognized brand names in the Central Florida vacation rental market — a status it has maintained for two decades.

The community weathered the 2008–2012 foreclosure cycle — which hit STR-heavy Osceola County particularly hard — and emerged with a more professionally managed inventory as institutional and experienced individual investors absorbed distressed inventory. Today the community is substantially mature, with most capital improvements to the clubhouse and common areas already undertaken, and it operates as a well-established resort product rather than a development-phase community.