Hillsborough
South of CR 466A DistrictThe Villages, FL
The Village of Hillsborough is named after Hillsborough County (home to Tampa) and is located in the South of CR 466A area of The Villages. With approximately 1,900 residents, Hillsborough is one of the larger individual villages in the Brownwood Paddock Square community. The neighborhood straddles the Sumter and Marion county border along CR 466A. Eisenhower Regional Recreation Center provides military-themed recreation, and Brownwood Paddock Square delivers Old Florida entertainment with nightly live music and dining. Homes are single-story with screened lanais, garages, and golf cart connectivity. Hillsborough's size means more street variety and home options for renters compared to smaller villages.
Recreation Centers
- Eisenhower Regional Recreation Center
Nearby Town Squares
- Brownwood Paddock Square
Frequently Asked Questions
What year was the Village of Hillsborough built?
Hillsborough homes were built in 2015 using block and stick-built construction. The village features patio villas, cottage homes, and designer homes with contemporary styling.
What recreation center serves Hillsborough?
Eisenhower Regional Recreation Center is the primary facility, with a patriotic military-history theme, sports pool, gym, pickleball and tennis courts, and community event spaces. The Hillsborough neighborhood also has its own adults-only pool.
How does Hillsborough connect to the rest of The Villages?
Golf cart paths link Hillsborough to Brownwood Paddock Square, Sawgrass Grove, and Lake Sumter Landing. Golf carts are the primary transportation for most daily activities.
What makes Hillsborough a good rental location?
Hillsborough sits in a sweet spot between Brownwood and Sawgrass Grove, giving renters access to two entertainment and dining areas. The 2015 construction means homes have newer fixtures and layouts.
Is Brownwood the only entertainment option near Hillsborough?
No. Sawgrass Grove to the south is a growing dining and entertainment area. Lake Sumter Landing, while farther, offers waterfront dining and a different atmosphere. All are reachable by golf cart.
What is the vibe of the Brownwood area compared to other town squares?
Brownwood Paddock Square has a rustic, Western cattle-town theme that is distinct from the Spanish-colonial feel of Spanish Springs or the lakefront setting of Lake Sumter Landing. Entertainment runs nightly on the outdoor Log Cabin Stage.