Trusted Local Roofers Serving Orlando, Winter Park, Lake Mary, Windermere, and the Greater Orlando Area
Bigfoot Roofing & Construction has been working on Florida roofs since 2011. Our Oviedo office is the home base for the work we do across the Orlando market — inspections, repairs, replacements, gutters, and James Hardie siding for homes and businesses throughout Central Florida.
Kyle Maxwell, a third-generation contractor, founded the company on a clear standard: name the products, document the work in writing, and give every homeowner an honest assessment of what the roof actually needs. That is the same standard our Orlando crews bring to every project.
If you are looking for a roofing contractor in Orlando who will tell you what your roof needs — and what it does not need — you are in the right place. Call our Oviedo office to schedule a free on-site estimate with written documentation.
TRUSTED SINCE 2011
THREE GENERATIONS OF ROOFING EXPERTISE
GAF-CERTIFIED CONTRACTOR · JAMES HARDIE AUTHORIZED INSTALLER · IMPROVIFY & GREENSKY FINANCING PARTNER · OWENS CORNING PRODUCTS · GOOGLE REVIEWS — [5 ★ rating] · BBB ACCREDITED
A Local Roofing Company Serving the Greater Orlando Area
Bigfoot Roofing is a Florida-based roofing company with four offices across the state and a dedicated Oviedo location for Orlando-area projects. We are not a franchise. We are not a national operation with a satellite office in Florida. We are a family-owned business that has been investing in Florida communities since 2011.
Kyle Maxwell was born and raised in Jacksonville. The company’s growth from a single Jacksonville office into a four-office Florida operation — including the Oviedo office serving the Orlando market — reflects what happens when a family-owned roofing company builds long-term relationships in the communities it serves.
Call our Oviedo office to schedule a free estimate with a contractor that is in this for the long term.
What We Do for Orlando Homeowners
We handle roofing and exterior work for both residential and commercial property owners across the Orlando market. From a single missing shingle to a full roof replacement, our crews work to the same standard on every project — specific materials, written estimates, and honest recommendations.
Below is a breakdown of the core roofing services we provide for Orlando homeowners and business owners. Each one starts with the same step: a free on-site assessment that comes with photos and a written report you can reference later.
Need help deciding which service fits your situation? Schedule a free inspection with our Oviedo office and we will walk you through what we find.
Roof Inspections
A roof inspection from Bigfoot Roofing is a documented assessment, not a sales pitch. We climb the roof, check the components that matter, and put what we find in a written report — photos included.
Roof Repairs
Our roof repairs cover leaks, damaged or missing shingles, flashing issues, and other fixes that extend the life of your existing roof. You will get a written roof repair estimate before any work begins.
Roof Replacements
When a roof has reached the end of its service life, the right move is a residential roof replacement — done correctly, with the right materials, the first time. Get your written estimate today.
Storm Damage Repairs
Storm damage can be a few missing shingles or significant structural issues that need urgent attention. We handle storm damage roof repairs including targeted fixes and full replacements.
Emergency Services
A roof emergency does not wait for business hours. If your Orlando home has an active leak, exposed decking, or major damage, our roofing team can respond with emergency roof repair work to stabilize the situation as soon as possible.
Gutters
Gutters do more than catch rain — they protect the foundation, the siding, and the landscaping from water that would otherwise sit where it should not. We install seamless gutters sized to handle the demands placed on Orlando-area homes.
Siding
We handle both new fiber cement siding installations and siding repairs across Orlando. We are an authorized James Hardie installer one of the many reasons customers choose Bigfoot for their siding solutions.
Insurance Support
We document storm damage with photos and detailed scope reports to give your adjuster exactly what the claim requires.
Roofing Contractors Come and Go. We Have Been in Florida Since 2011.
Transient operators flood the Florida roofing market and disappear before the warranty matters.
Bigfoot Roofing has been a four-office Florida company for over a decade.
Same team. Same standard. Same Oviedo office to call when something needs follow-up — five, ten, twenty years from now.
Why Orlando Homeowners Call Bigfoot Roofing
Choosing a roofing contractor is a high-stakes decision — the right contractor protects an investment most homeowners do not want to revisit for decades. Bigfoot Roofing earns that call by leading with verifiable credentials, not generic claims.
Here is what Orlando homeowners point to when they tell us why they chose Bigfoot:
- Founded in 2011 — 14+ years of Florida roofing work
- GAF-certified contractor used on 90% of our residential projects
- James Hardie authorized siding installer
- GreenSky financing partner for qualified homeowners
- Free on-site estimates with written documentation
- Honest repair-versus-replace guidance
- Four offices across Florida, including Oviedo for the Orlando market
Call our Oviedo office to schedule your free estimate.
A Roof Replacement Is a Long-Term Investment
A roof on a $500,000-plus Orlando home is not a maintenance expense. It is asset management — a system that, done correctly, protects the value of everything underneath it for the next 25 to 30 years. Cutting corners up front costs more on the back end, not less. Homeowners thinking in decades, not quarters, look at it that way.
That is why we lead with GAF-certified installation and the warranty terms that come with it. When the work is documented, the products are named, and the install is done to manufacturer specification, the roof becomes the last one most homeowners will need to replace. That is the standard worth investing in.
One Team for the Roof, the Gutters, and the Siding.
Most exterior projects involve coordinating two or three different contractors — and the seams between them are usually where problems start. Bigfoot Roofing handles roof replacement, seamless gutter installation, and James Hardie siding as one integrated project. One crew. One timeline. One point of accountability when it matters years from now.
What Roofing Materials We Use
The material on the roof matters as much as the crew installing it. Bigfoot Roofing installs systems from manufacturers with the engineering and warranty backing that long-term homeowners look for.
We work with the following roofing materials on Orlando-area projects:
- GAF asphalt shingles — used on roughly 90% of our residential roof replacement projects
- Owens Corning shingle systems — available as an alternative when the project calls for it
- Tile roofing — installation, repair, and replacement on tile-roofed Orlando homes
- Metal roofing — a long-life option for homeowners thinking in decades
- James Hardie fiber cement siding — installed to manufacturer specification by an authorized installer
Ask our team which material is the right fit for your home.
Financing for Greater Orlando
A roof replacement on a high-value Orlando home is a meaningful investment — and one that, done correctly, protects the rest of the asset for decades. Some homeowners prefer to spread that investment over time rather than draw it from savings in a single quarter.
Bigfoot Roofing offers roof financing options for qualified homeowners across the greater Orlando area. The application is straightforward, and our team can walk you through the available roof financing options before you commit to anything.
Roof financing is one of the most common questions we get from Orlando homeowners, and we will give you a clear answer in writing.
Ask about our financing when you schedule your free estimate.
The Greater Orlando Area and Communities We Protect
Our Oviedo office is the home base for the work Bigfoot Roofing does across the greater Orlando market. These are homes built to a standard — established neighborhoods like Winter Park and Maitland with mature architecture, master-planned communities like Lake Mary and Heathrow, and high-investment areas like Windermere and Dr. Phillips where the roof is part of how the property presents.
Our crews work on homes of every size and architectural style across Central Florida.
Orlando-area communities we serve include:
- Winter Park
- Lake Mary
- Heathrow
- Windermere
- Dr. Phillips
- Baldwin Park
- Maitland
- Altamonte Springs
- Winter Garden
- Longwood
- Oviedo
- Sanford
- Apopka
- Casselberry
- Lake Nona
- College Park
If your community is not listed, call our Oviedo office — chances are we are already working in your area.
What to Expect From a Free Estimate
A free estimate from Bigfoot Roofing is a documented assessment of your roof, not a high-pressure sales call. We walk you through the process up front so there are no surprises.
Here is what happens when you schedule a free estimate:
- We arrive at your Orlando home at the scheduled time
- We inspect the roof — and the gutters or siding if those are part of the conversation
- We document the condition with photos
- We provide a written report and a written estimate
- You decide what makes sense for your home
Schedule your free estimate. We document what we find and give you a written report. No follow-up pressure. No artificial deadlines. No “today only” pricing.
Want to Talk Through Your Project Before Scheduling an Inspection?
Some Orlando homeowners prefer to ask questions before booking an on-site visit; about materials, GAF warranty options, Improvify or GreenSky financing, or how one of our Orlando projects typically runs. Our Ovideo team will walk you through it on a quick call No pressure. No inspection commitment until you are ready.
What Orlando Homeowners Are Saying
Reviews from real Orlando-area homeowners say more about a roofing contractor than any marketing copy can. Below are recent reviews left by customers across the greater Orlando market — neighbors of yours in Winter Park, Lake Mary, Windermere, and Dr. Phillips.
These guys were recommended to us when a tree fell on our garage. They were amazing! They handled all of the construction from the roof, to painting, and to fixing the garage door. They were extremely responsive, quick and always showed up on time! A pleasure to work with!! Highly recommend.
Bigfoot Roofing created a new roof for our home that far exceeded our hopes. The workmanship was excellent and timely. The crew were very experienced and completed our roof in two days. They cleaned up all the materials and the grounds surrounding our home. We highly recommend this company.
Can’t say enough good things about Bigfoot Roofing & Construction. They worked through the August heat and finished in a timely manner, the workmanship was top notch and clean up was excellent.
I just had a small repair that needed attention, and I was very impressed with the fact that they treated this job with the same importance as a big job. I will definitely use them for any future work I might need.
We are very pleased with the workmanship of the crew who replaced the roof and the excellent customer service from the sales rep. He was very professional, straightforward and informative. Handled all questions and concerns we had. We recommend Bigfoot Roofing!
Callahan Roofing FAQs
How often should I have my roof inspected?
Annual professional roof inspections help identify developing issues while they’re still inexpensive to address. In addition, we recommend having your roof inspected after any severe storm event with high winds or hail. Regular inspections support maintenance planning and help you budget for eventual replacement before it becomes an emergency.
How long does a roof replacement take?
- Most residential roof replacements are completed in 1-3 days, depending on home size, roof pitch, and complexity, and material type.
- Commercial projects vary based on building size, roof system, and whether we need to work around business operations.
Weather delays can affect any timeline. We provide project-specific schedules with every estimate.
Do you offer free estimates?
Yes, we provide free estimates for all roofing services in Callahan. Our process includes a property visit, roof assessment, discussion of your concerns and priorities, and a detailed written proposal. No charge, no obligation.
Which roofing materials are available for installation?
For residential properties, we install asphalt shingles (primarily GAF and Owens Corning brands), metal roofing systems, and tile where appropriate. For commercial buildings, we work with various systems including modified bitumen, TPO, EPDM, and other commercial roofing materials. We recommend materials based on your building type, environmental factors, performance requirements, and budget.
Do you provide assistance with storm damage insurance claims?
Yes, we provide comprehensive damage documentation, including photos and measurements, prepare detailed estimates in insurance-standard formats, and can communicate directly with adjusters when helpful. Our extensive storm damage experience supports appropriate claim evaluation and settlement.
Schedule Your Roofing Service With Bigfoot Roofing Today
Ready to schedule your roof inspection, repair, replacement, or any other service for your Orlando-area home? We have made it easy to reach our Oviedo team. Whether you prefer to call, fill out a request form, or schedule directly through our calendar, the path to a free written estimate is straightforward.
Florida Strong. Legendary Results. The contractor you call when it matters.
