Illustrative view of a lakeside home and roof

Winter Park, FL

Roof Replacement, Re-Roofs & Roof Repair in Winter Park, FL | Assure-U Roofing

Detail-driven roofing for Winter Park's historic and luxury homes, with materials chosen to match architectural character.

Get Your Free Estimate

Most requests get a response the same business day.

Prefer to talk now? Call (407) 794-2820

3,500+

Roofs Completed

4.9★

Google Rating (54 reviews)

20+

Years Serving Central Florida

Lic. CCC1326792

Licensed & Insured

Roofing in Winter Park, FL you can actually trust

Winter Park homes set a high bar. Between the historic districts near Park Avenue, the estates along the Chain of Lakes, and newer luxury builds, roofing here is as much about appearance and detailing as it is about protection. Assure-U Roofing works on Winter Park properties where a sloppy ridge line or a mismatched color simply is not acceptable.

We help Winter Park owners select designer and architectural shingles, standing seam metal, and specialty profiles that suit the home's period and neighborhood context, then install them with the flashing, valley, and termination detail those roofs demand. As an Owens Corning Preferred Vendor with A+ BBB accreditation, our material options come with strong documented warranties.

Our crews are in-house, respectful of the property, and supervised by our owner. Winter Park clients — including realtors preparing listings and luxury property managers — value that we work on schedule, communicate clearly, price transparently, and provide free wind mitigation reports and free annual inspections afterward.

Illustrative roofing materials and installation details

Why Choose Us

Why Winter Park property owners call us first

  • Licensed & insured Florida roofing contractor (License # CCC1326792)
  • Fair, transparent pricing — no high-pressure sales tactics, ever
  • Premium materials as an Owens Corning Preferred Vendor
  • In-house crews only — we never subcontract your roof
  • On time and on budget, with the owner on every job site
  • Clear communication from first inspection to final walkthrough

Service Examples

Roofing service examples for Winter Park, FL

Representative examples of roofing materials and installation methods.

Gutter cleaning along a roof edge

Seamless Gutter System Installation

Gutter Installation · Service area: Winter Park, FL

Discuss seamless gutter sizing and downspout placement, or ask about cleaning to keep roof runoff moving.

Worker fastening metal roofing with a drill

Standing Seam Metal Roof Replacement

Roof Replacements · Service area: Windermere, FL

Compare standing seam and metal panel options, with underlayment, flashing, and edge details included in your replacement scope.

Architectural shingles being laid on a roof

Architectural Shingle Roof Replacement

Roof Replacements · Service area: Orlando, FL

Explore architectural shingle profiles and colors alongside underlayment, ventilation, and flashing options.

Gloved hands positioning flat-roof membrane material

Commercial Flat Roof Replacement

Roof Replacements · Service area: Lake Mary, FL

Discuss flat-roof membrane options, drainage, and details around roof penetrations for your commercial property.

Service Area Map

Serving Winter Park, FL and nearby communities

Answers

Winter Park, FL Roofing FAQs

Do you pull roofing permits for Winter Park, FL projects?

Yes. We handle permitting for every Winter Park roofing project and build to current Florida Building Code. Municipal and county review typically takes a few business days, and we schedule your install around approval so nothing sits open.

Do Winter Park historic district homes have special roofing requirements?

They can. Historic and architectural review guidelines may limit materials, colors, and profiles. We prepare the submittals and samples needed for approval before ordering material.

Can you match the roof style on a luxury Winter Park home?

Yes. We work with designer shingle lines, standing seam metal, and specialty profiles, and we mock up color and profile choices against your existing exterior before committing.

Get a free roofing estimate in Winter Park, FL

Free inspection, free estimate, and a free wind mitigation report on replacements. No pressure, ever.

Free Estimate

Request your free Winter Park roof inspection

Call us and you will reach our team, not a call center. Or send the form and we will follow up during business hours.

(407) 794-2820

nicole@assureuroofing.com · 3236 Scallion Court, Orlando, FL 32825

Hours: 8:00 AM – 6:00 PM, Monday – Friday

Licensed & Insured · License # CCC1326792

Get Your Free Estimate

Tell us about your roof and we'll respond during business hours.

Prefer to talk now? Call (407) 794-2820

Google Reviews

What Central Florida says about us

4.954 Google reviews · Assure-U Roofing

Google rating checked Oct 29, 2026

R

Robert Maynard

a month ago

Assure-U Roofing was a really great choice. I did a lot of research into the few companies I wanted to get quotes from for a full shingle roof replacement, and Nick came out for the quote and was so refreshingly honest and nice.

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R

Ryan Winters

3 months ago

Nick and his team did a great job with our roof! Great communication through the whole process and pricing was very reasonable. Definitely would go with Assure-U again in the future on the next roof replacement.

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K

Katie McPherson

2 months ago

Nick and his crew were great to work with from start to finish! We liked that he was honest and up front. We would definitely recommend Assure-U Roofing to other people!

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M

Michael Bruschi

3 months ago

Lots of roofers out there. Multiple people recommended Assure-U, so I went with them for a roof certificate and they were great — beyond fair and reasonable. Recommend you give them a chance.

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D

Dell Miller Foundation

7 months ago

Have used Assure-U on several houses, both personal and rentals. Both the office staff and roofing crews are professional and thorough and do excellent work. They do not cut any corners and actually go above to ensure no leaks.

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Call (407) 794-2820