A new town center is taking shape along Simpson Road in Kissimmee, where developers are planning roughly 130,000 square feet of shops, restaurants and neighborhood services wrapped around a live oak estimated to be more than 150 years old. The project, called The Village at Hilliard Isle, is designed to serve the sprawling residential community growing up around it, bringing grocery stores, fitness studios and dining options to an area that has seen rapid development in recent years.
According to WFTV, the town center is currently in the planning and permitting phase, with infrastructure work anticipated to begin in the first quarter of 2028 and the first commercial pads expected to be delivered by the third quarter of that year. Plaza Lakes, the developer behind the project, has selected SRS Real Estate Partners to lead leasing efforts for the site. The announcement did not identify any signed tenants, and no opening date has been set.
Plans call for a walkable town center featuring outdoor dining, pedestrian connections and a central gathering green built around the aging oak tree, the station's report notes. Commercial spaces are expected to range from smaller storefronts to larger sites and freestanding drive-thru locations, and the development team is seeking grocery, restaurant, coffee, fitness, wellness and specialty retail tenants along with other neighborhood services. A new traffic signal is also planned at the development's entrance on Simpson Road, per the announcement.
A Vision for Gathering and Shopping
Jaime Luis Fonalledas, speaking for the project, said Plaza Lakes envisions a thoughtfully designed town center for shopping, dining, gathering and enjoyment, the same account states. Plaza Lakes assembled and master-planned the larger property and has retained the town center and multifamily portions of the site, while an adjacent development by Pulte Homes includes approximately 2,000 homes. Hilliard Isle overall also includes planned multifamily residences, rounding out a community designed to house thousands of new residents.
A Winding Path to the Current Plan
The scope of Hilliard Isle's commercial component has shifted across different reports over the past year and a half. An Osceola News Gazette report, cited by aroundosceola.com, described city approval for a development with 3,000 residential units, 190,000 square feet of commercial space and 177 acres of conservation area, with primary and secondary entrances planned off Simpson Road. An August 2025 Orlando Sentinel report described the town-center site as 67 acres with entitlements for 620 multifamily units and 190,000 square feet of commercial use, while in the same report Kissimmee development director Craig Holland described the broader project as roughly 3,000 dwelling units with about 125,000 square feet of commercial space — a different figure from the entitlement number cited elsewhere in that article. The Sentinel also reported that a preliminary plat showed a larger 61-acre town-center parcel divided into three phases with a mix of retail uses and two apartment complexes. The evidence does not explain what accounts for these differing figures or whether the 61-acre and 67-acre descriptions refer to the same boundaries.
A February 2026 GrowthSpotter report said Empresas Fonalledas retained the 67-acre town-center site when the residential portion of Hilliard Isle changed hands. That same report, from GrowthSpotter, said Pulte paid $47.95 million for the residential portion, described as a 2,016-home master-planned community.
Growth Pressure Across Osceola County
The push to build new commercial hubs comes as Osceola County's population has grown rapidly. WESH reported the county's population had increased nearly 20 percent since 2020, a surge that has fueled demand for new rooftops and the retail to go with them. WESH also described Hilliard Isle as a 900-acre master-planned community, with Pulte Homes saying it would include single-family homes, townhomes, walkable trails, resort-style pools, clubhouses and a mixed-use town center.
For now, the oak tree at the heart of The Village at Hilliard Isle remains the project's most tangible landmark, a fixed point around which the rest of the plan is still being drawn. Whether grocery chains, restaurants or fitness studios ultimately sign on, and when the center might actually open its doors, are details that have yet to be announced.
