Two-story house with a fresh charcoal roof on a red brick lane beneath moss-draped live oaks, lake water glinting between the trunks

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
State certifiedCCC1337306 · CBC1266379
Winter Park crewsOrange and Seminole counties
$0 down financingThe 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.Credit check not required
Free inspectionEstimate on paper, no strings
5.0 on GoogleReviews from real customers

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.

Two workers kneeling on bare plywood and unrolling gray synthetic underlayment, shingle bundles stacked at the ridge and a lake beyond

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 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
Cream stucco villa with terracotta barrel tiles, an arched loggia and a calm lake with a boat dock behind palms

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
Georgian brick house with white shutters, a steep slate-look roof, azaleas and a magnolia out front

Around town

Neighborhoods and corners of Winter Park

  • Hannibal Square
  • Interlachen
  • Isle of Sicily
  • Winter Park Pines
  • Orwin Manor
  • Virginia Heights
Wooden kitchen table with a roof sketch, a tablet, a mug and reading glasses while hands rest on the pages
$0to get started

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

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 reviews

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.

Skip the map and go to the list of areas
Map of the two Central Florida counties USA Roofing Winter Park servesShapes show the counties we cover. Dots mark the cities that have a page of their own.Altamonte SpringsLongwoodCasselberryWinter SpringsOviedoMaitlandEatonvilleWinter ParkEdgewoodBelle Isle
  • County has a page
  • City has a page
  • Where you are
  • Its county

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.

Ask for a free estimate

The form accepts requests day and night.

Optional. The more you share, the sharper the estimate.

Call the officeEstimate