Written by Featured image: cartoony concept art for a planned Eastport-area shopping hub (not a photo of the unfinished site).
The Villages Development Company has filed a state stormwater permit for the Live Oak Shopping Center in the Villages of Southern Oaks. The proposed grocery-anchored hub would sit in the Eastport area — near Long Prairie and a short drive from Middleton.
Southwest Florida Water Management District records show the Environmental Resource Permit application (No. 1002345) was received Oct. 29 for “VOSO – Live Oak Shopping Center,” covering about 32.8 acres in Sumter County. As of Nov. 4 the application was listed as Incomplete, which is typical while reviewers ask for more information. No construction start or opening date has been announced.
What’s planned
The Villages announced Live Oak in August alongside Tribute Recreation Complex, which is planned directly across from the shopping center in the Village of Long Prairie. Per the developer’s announcement, Live Oak is planned to include:
- A local grocery store as the anchor
- A fuel station
- Health and wellness businesses
- Waterside restaurants
- Open green spaces and pedestrian pathways
No tenants have been named yet. Tribute is planned for a sports pool, pickleball, shuffleboard, pavilions, a dog park, and a Fit Club, with trails linking the two sites. District records also show related trail groundwork was already permitted in late 2025 for a Live Oak multimodal path.
Why it matters for Middleton: Eastport is the growth edge closest to many Middleton and southern Villages neighborhoods. A grocery-anchored center with trails to recreation would change everyday errands and golf-cart trips for nearby residents — once permits clear and construction starts.
Sources: Gazette News The Villages (SWFWMD ERP application 1002345); The Villages — Announcing Tribute Recreation & Live Oak Shopping Center (Aug. 13, 2026). Checked Nov. 6, 2026.
Planning a weekly grocery run from Middleton once this opens — or still headed to Brownwood / Lake Sumter Landing? Tell us in the comments.