
Orange County, Florida
Roofing Contractor in Winter Park, FL
Brick streets, old oaks and a chain of lakes make Winter Park one of the most photographed towns in Central Florida. They also make its roofs harder to work on, and easier to neglect.
- Our home city
- Oak canopy care
- Free inspection
Winter Park
A town that grew up before the code did
Winter Park was platted in 1881 by Loring Chase and Oliver Chapman and chartered in 1887, and Rollins College opened in 1885. The census puts the median home at a 1976 build year, and 56 percent of the housing units predate 1980. That is a lot of roof decks nailed to rules that no longer exist.
The town's trees are the other half of the story. A canopy keeps a slope shaded and damp, so algae shows up early and leaves settle in valleys and behind chimneys. We look at those spots first, because they tell us what the rest of the roof has been doing.
Our office is based here, which means a Winter Park estimate is rarely more than a short drive. We look, we photograph, and we write down what the roof needs and what it does not.

Local advantage
Why Winter Park homeowners call us
Oak-shaded slopes
We check valleys, north-facing planes and gutters for debris and algae before we talk about replacement.
Mixed ages on one street
A 1930s cottage beside a 1990s infill home means two different decks. Each gets its own plan.
Two state licenses
CCC1337306 and CBC1266379: one for the roofing, one for the structure under it.
What we do here
What we do in Winter Park, FL
Shingle, tile, metal and flat roofs, handled by one state-certified company under licenses CCC1337306 and CBC1266379.

Roof Replacement for Winter Park homes
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Roof Installation for Winter Park homes
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Roof Repair for Winter Park homes
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Tile Roofing for Winter Park homes
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Metal Roofing for Winter Park homes
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Shingle Roofing for Winter Park homes
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Roof Maintenance for Winter Park homes
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Flat Roofing for Winter Park homes
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Gutters for Winter Park homes
Read moreWhat Winter Park roofs deal with
The postcard version of the town is canopy, brick and water. On the roof, that adds up to moisture, debris and a lot of older construction.
Homes that are locally designated as historic can carry extra review before exterior work. We ask the question at the start of the estimate instead of after the contract.
- Moss and algae on slopes that rarely get full sun
- Valleys, gutters and chimney crickets packed with oak leaves
- Spanish-style tile roofs with aging underlayment beneath
- Original 1920s to 1950s decks that need re-nailing at a re-roof
- Limbs rubbing the roof edge in a storm
- Possible design review on historic properties

Permits and the city
A re-roof in Winter Park goes through the city's Building and Permitting Services, and the city publishes a roofing product approval cover sheet with its permit paperwork.
We prepare that package, file it for the job and book the inspections as the work moves along.
- Permit filed by the contractor of record
- Product approval documents for the chosen roofing material
- Inspection of the deck and final inspection at the end
- A walk through the finished roof with you

Around town
Neighborhoods and corners of Winter Park
- Hannibal Square
- Interlachen
- Isle of Sicily
- Winter Park Pines
- Orwin Manor
- Virginia Heights
Other towns on our route

Pay for the roof over time
Do not let the budget decide the date
A leak or an insurer's letter sets the schedule, and the money should not hold up the work. Our financing starts a new roof with nothing down.
- No credit check required
- $0 down with 100% financing
- Secured and unsecured financing
- 10, 20 and 30 year terms
- No pre-payment penalty
Terms vary with approved credit and project size. Ask us for the exact numbers on your roof.
The monthly payment for a 15-year home improvement installment loan of $10,000 with an APR of 10.99% would be $113. No down payment required. Not all loan products will be available to all partners or all consumers.
Questions
Winter Park roofing questions, answered
Can you handle a tile roof in Winter Park?
Yes. Many Mediterranean and Spanish-style homes here have clay or concrete tile. We inspect from the deck, since the underlayment beneath the tile is what actually keeps the water out.
My house is old. Does that change the roof?
Often. A deck laid decades ago may be skip sheathing or thin boards, which can need replacing or re-nailing before a new roof goes on. We say what we find in writing.
Does a historic home need special approval?
It can, when the property is locally designated. The city's preservation rules decide, so we check your address before the work is scheduled and build any required review into the timeline.
Do you also cover the area around Winter Park?
Yes. Maitland, Eatonville, Edgewood and Belle Isle, along with the towns a few miles to the north, each have a page on this site, and we confirm coverage of any other address by phone.
Reviews
Homeowners nearby on Google
5.0 out of 5 across 7 Google reviewsas of
Latest reviews pulled from our Google listing.
Service area map
Where Winter Park sits on the map
The two counties we work in, with every town that has a page here. Winter Park is marked on the drawing.
- County has a page
- City has a page
- Where you are
- Its county
Select a county by hovering, tapping or tabbing onto it.
Reset to all countiesCounties and cities listed as links
Service area
Working in Orange County and past it
Orange and Seminole counties are our territory, from Winter Park and Maitland north to Casselberry, Longwood and Oviedo. Pick a town to read about its roofs, or ring the office and ask whether your street is covered.
Free estimate
Free roof estimate in Winter Park, FL
Free visit, written roof report and an estimate on paper for any property in Winter Park. Financing choices are there too if you want them.
- Call or text(407) 768-4791
- Service areaWinter Park, FL and nearby
- State licensesCCC1337306 · CBC1266379
Ask for a free estimate
The form accepts requests day and night.

