Longwood's trusted roofing contractor — quality work, fair prices, and people who actually pick up the phone.
Everything you need from one trusted local team — done right the first time.
Full tear-off and replacement with premium architectural shingles built for Florida weather.
Leaks, missing shingles, flashing, and storm damage fixed fast and fixed right.
Free inspections and insurance-claim help after wind, hail, and hurricane damage.
Honest, no-pressure roof assessments with photos and a clear plan.
Seamless gutters and guards that protect your roof, siding, and foundation.
Fast response to stop the water and protect your home today.
No runaround. No pressure. Just honest work and clear communication.
Call or request a free quote. Tell us what you need — we listen first.
We assess the job and give you a clear, written price. No pressure, ever.
Our crew gets it done right, on schedule, and leaves your property clean.
Winter Springs Roofing & Repair has earned its name across Longwood the right way — one happy customer at a time. Call and you get straight answers, fair pricing, and work that holds up.
A look at the kind of quality you can expect.
"Such a pleasure to work with! Our 20 year old roof was falling apart and needed major repairs. Bill and his crew got it done in about 4 days and it looks fantastic. You've made a customer for life. Thank you!"
— Riddlebx3 · a year ago"Bill & his team are amazing. From the very first time I spoke with Bill, I could tell he knew what he was talking about. He was very confident & very good at doing it. Our re-roof work was completed in a great manner. The workers were respectful & friendly. Everyday they cleaned up after themselves & left the property in a manner…"
— Tina Williams · 5 years ago"Extremely professional from estimate to permit approval. I have worked with a lot of contractors over the years and the customer service that Winter Springs Roofing provided was better than all. The main things were that they were there each day at 7:00 sharp and went right to work. Their equipment was in tip top shape. They were fast…"
— Anthony Perrone · 7 years ago"After putting it off for a few years I called Bill Sumner and requested a quote. He came out to the house and gave me the quote, told me the timeline, and then did exactly what they said they were going to do. I was so pleased and proud to see the new roof, I appreciate the hard work, the extra care to detail, and the professional way…"
— Christine Furru · 5 years ago"From my initial phone conversation and estimate, it was great speaking with the owner of the company and not a salesperson. Bill explained everything in detail, understood my timeline and got the roof installed quickly. Could not have asked for a smoother experience. Thank you Bill and crew for your excellent service."
— Hakeem Edward · 3 years agoFrom Longwood to the surrounding towns, Winter Springs Roofing & Repair is just a phone call away.
Yes. Winter Springs Roofing & Repair is fully licensed and insured, so you're protected from the first call to the final walkthrough.
Absolutely. We provide free, no-obligation quotes throughout Longwood and the surrounding area.
Most homes are completed in one to two days, weather permitting. We protect your property and clean up thoroughly when we're done.
Often within days. Call and we'll get you on the schedule as quickly as possible.
Tell Winter Springs Roofing & Repair what you need — we'll get right back to you. No pressure, no obligation.
📞 Call (321) 316-4774We’re so confident in what we do that we put the risk where it belongs — on us, not you. If we can’t attribute 2× what you invest within 90 days, we give you the difference back in cash, cancel your service, and hand you the website — code and all. You genuinely own it. Best of luck.
We built this whole website for Winter Springs Roofing & Repair — free. The AI assistant in the corner answers every call and web chat and books jobs straight onto your calendar, 24/7. Add a free CRM so no customer ever slips through the cracks.
We've reserved this website for Winter Springs Roofing & Repair through August 31. When this round fills it goes to $397 — and unclaimed sites come down.