In short: Winter Garden is mostly newer West Orange neighborhoods, where paver and concrete driveways are common and HOAs often set the look. Pavers typically run $10–$30 per square foot and concrete $8–$18, as estimates.
HOA rules first
Many Winter Garden communities require architectural approval for driveway changes, from the paver color to the border pattern. We provide the drawings, samples and product details your HOA asks for, and wait for approval before ordering.
Extensions and widening
A common job here is widening a driveway or adding a side pad for a third car, a boat or a trailer. Matching the existing pavers or concrete finish and tying in cleanly is most of the skill.
Older homes near downtown
Closer to the historic downtown, older homes often have asphalt or worn concrete drives ready for replacement. We price asphalt, concrete and pavers side by side so you can choose.
City or county permit?
Inside Winter Garden city limits, work that reaches the street, curb or sidewalk goes through the City of Winter Garden's right-of-way permit. Plenty of West Orange addresses with a Winter Garden mailing address are actually unincorporated, and those go to Orange County instead. We look up which one covers your lot first, so the HOA approval and the permit line up and the crew isn't left waiting on paperwork.
These prices are estimates. See the cost guide for every option.
Last reviewed October 8, 2026.