In short: Winter Park's older homes and big oak canopy mean driveways often fail from roots and tired bases rather than surface wear. Asphalt replacements typically run $7–$13 per square foot and pavers $10–$30, as estimates.
Roots and old bases
Mature oaks are part of what makes Winter Park, and their roots lift and crack driveways. We remove the damaged surface, cut out root-filled soil where it is safe for the tree, rebuild the base and repave. Where roots are the long-term issue, pavers can be the better choice because sections can be lifted and reset.
Fitting the street
Brick and paver driveways suit many Winter Park streets and older homes. We match colors and patterns to the house, and lay borders that tie into walkways and garden beds.
Small-site logistics
Tight lots and narrow streets mean planning where the trucks park and how material comes in. We schedule around neighbors and keep the street clean.
Paver aprons on city right-of-way
The strip between the sidewalk and the street belongs to the City of Winter Park. Building the apron there in brick or pavers instead of standard concrete means signing the city's non-standard apron agreement, which lets the city ask you to remove it later at your own cost. The contractor normally pulls the right-of-way permit. We explain the trade-off before you pick a material for that last few feet.
Estimates only. The paving cost guide has the full price list.
Last reviewed October 8, 2026.