Family-owned since 1972 and trusted across Central Florida. Get a fast, no-pressure estimate from a local roofer who treats your home like our own.
Tell us a little about your roof and we'll reach out the same day.
No obligation — we will reply the same day.
Winter Park is one of Central Florida's most distinguished addresses — brick streets, mature oak canopies, historic estates near Park Avenue, and homes where craftsmanship and curb appeal genuinely matter. Roofing here calls for premium materials, careful aesthetics, and a contractor who respects the home. Tip Top Roofing has served Orange County since 1972 and is the 2025 Central Florida's Favorite Roofer. See your price in about 60 seconds with our free instant estimate.
Discerning homeowners want quality they can count on, and roughly 95% of our business comes from referrals and repeat clients. You get a family-owned company led by Lee Wallace, GAF certification, a five-year workmanship warranty, and the kind of attention to detail a Winter Park home deserves — Lee's own standard is that "you're paying for the roof, but we still own it."
Estate homes and tile roofs reward experience: correct underlayment beneath tile, careful flashing on complex rooflines, and materials chosen to complement architecture and satisfy historic or HOA expectations. Winter Park's mature oaks also shade and shed onto roofs, so we install algae-resistant systems and proper ventilation to protect the investment.
Tile roofing suits many of Winter Park's Mediterranean and estate-style homes; premium architectural shingles and metal roofing are excellent choices as well. Our roof repair team handles precise fixes when a full replacement isn't needed.
What We Do
From a single leak to a full replacement — residential and commercial.
Full tear-off and replacement engineered for Florida sun, wind, and storms.
Learn More →Extend the life of an aging roof without a full replacement, where it fits.
Learn More →I have used Tip Top Roofing for over 30 years and they were always there when I needed them for repairs. As for roof replacements, they do excellent work and stand behind their install.
I had an excellent experience with Tip Top Roofing from start to finish. The entire team was professional, responsive, and incredibly knowledgeable throughout the process.
Tip Top Roofing did an excellent job replacing our roof. The crew was professional, friendly, and hardworking, and they did a thorough cleanup when the job was finished.
Great service — Rory was super friendly and handled the repair for us immediately!
Proof In Your Neighborhood
See real Tip Top roofs we've completed nearby.
Roofing FAQ
It varies with size, pitch, and material. The fastest way to a real number is our free instant estimate — no sales visit required.
Yes — we document the damage and guide you through the entire claim at no cost.
Fully — Florida license CCC013667, bonded and insured, GAF Master Elite certified.
Most homes are done in one to two days, weather permitting, with a thorough magnetic nail sweep before we leave.
Shingle, metal, tile, and flat/commercial systems — residential and commercial.
Often within a few days for estimates, faster for active leaks and storm emergencies. Call (407) 660-2212.
Get Your Free Estimate
A real, accurate roof estimate in minutes — no sales visit, no pressure.
.svg)