Roof Replacement in Winter Park, FL
From the historic, oak-canopied streets near Park Avenue to estates on the Winter Park Chain of Lakes, TruTop Roof delivers premium roof replacements with honest, all-inclusive pricing.
Rated 5.0 on Google
Roofing That Respects Winter Park's Character
Winter Park is known for its brick streets, towering live oaks and a housing stock that ranges from 1920s Mediterranean Revival homes to stately estates around the Winter Park Chain of Lakes. Many of these homes carry tile or architectural roofs that demand careful, detail-oriented work.
That famous tree canopy is beautiful, but it also drops debris, casts shade that encourages moss and algae, and sends limbs onto roofs during storms. We install premium tile, metal and architectural shingle systems with the flashing and detailing these distinctive homes deserve, protecting your investment while keeping the look your neighborhood is known for. Every Winter Park project comes with one honest, all-inclusive price.
Roofing Work In and Around Winter Park
A look at real roofs we have installed in the Winter Park area.



A Review From Winter Park
“Best roofing company in Florida! My roof looks amazing.”
Roofing Services Across Winter Park
As a Central Florida roofing contractor specializing in roof replacements and reroofs, we work throughout Winter Park, including neighborhoods and communities like Olde Winter Park, Windsong, Orwin Manor, the Park Avenue district and Kewannee. Explore the systems we install:
Also serving nearby: Orlando, Casselberry, Altamonte Springs, Oviedo and Windermere.
Why Winter Park Homeowners Choose Us
Licensed & Insured
Florida State License CCC1337085, fully insured for your protection.
One Honest Price
All-inclusive pricing with no hidden fees. The price we agree on is the price you pay.
Great Warranty
Materials warrantied for the life of the materials, plus 5 years of covered workmanship.
Local Family Team
A family-owned, women-owned business based nearby in Winter Garden, not a far-off corporation.
Common Questions From Winter Park Homeowners
Can you re-roof a historic or tile home in Winter Park?
Absolutely. We install and replace tile, metal and architectural shingle roofs, and we handle the underlayment, flashing and detailing that older and upscale Winter Park homes require.
Do I need a permit to replace my roof in Winter Park?
Yes. The City of Winter Park requires a permit and inspection for roof replacement. We manage all permitting and the final inspection for you.
Do you offer financing for a new roof in Winter Park?
Yes. We offer $0 down financing options, and checking your options will not impact your credit score. Just ask during your free Winter Park roof inspection.
How much does a new roof cost in Winter Park?
It depends on your roof size, pitch and material. We give one honest, all-inclusive price after a free inspection, with no hidden fees, so you know your full cost up front.
Need a New Roof in Winter Park?
Get a free, no-obligation inspection and an honest, all-inclusive quote. Ask about $0 down financing with no impact to your credit to check.