Top-rated roofing installation & roof repairers.

Get matched with top roofing installation & roof repairers in Winter Park, FL

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Roofing installation & roof repairers in Winter Park

David Lundberg Building & Roofing
4.9(
242
)

Serving Winter Park, FL and surrounding areas

In business since 1994

Free estimates

Emergency services offered

"Everything was perfect! We had storm damage on a Saturday & David came over immediately to put a tarp on our roof. We were under a time constraint for repairs & they were done ASAP & done well. We cannot say enough positives about this company! Everyone is professional & helpful as well as knowledgeable . The very best!"
Recommended by96%of homeowners
Avatar for Winter Park Roofing Inc
Winter Park Roofing Inc
4.9(
200
)

Serving Winter Park, FL and surrounding areas

In business since 2003

Free estimates

Emergency services offered

"We had Winter Park Roofing out before to do some minor repairs and once they came out and told us our roof was fine--no charge! Based on those good experiences, we decided to hire them to reroof our house. Communication was excellent, the proposal was submitted in a timely manner, and the job started about two weeks after we signed a contract. The work was all done in a day and a half and they careful to clean up debris and nails. We couldn't be happier with the entire process. Special shout-out to Corey and his team for doing a great job."
Recommended by97%of homeowners
Avatar for RenewPro Roofing, LLC
RenewPro Roofing, LLC
4.9(
36
)

Serving Winter Park, FL and surrounding areas

In business since 2013

Free estimates

Emergency services offered

"Our overall experience with RenewPro Roofing was very positive and I would have no hesitation to recommend them to others for roof replacement projects. Our salesman Brian Douek was knowledgeable and took time to explain our need for replacing our roof and the whole process including billing through insurance. The actual replacement was super efficiently done and the crew did the tear down and replacement all in one day - my house is a single floor single family home. Brian also was very good in working with me to settle the billing and payment through Insurance."
Recommended by97%of homeowners
Avatar for Robert Kettelle Roofing LLC
Robert Kettelle Roofing LLC
4.8(
105
)

Serving Winter Park, FL and surrounding areas

In business since 2005

Free estimates

Emergency services offered

"If you are looking for a responsible, competent, and professional roofing company, look no further than Robert Kettelle. I had several leaks during the rainy season which needed immediate attention. Although Robert Kettelle Roofing had a lead time of 4 weeks, because of the serious nature of my problems, they started my job within a few days of estimate. They arrived on time with a crew of 5 workers. They worked as a team for several days and hardly took any breaks. They value hard work and were proud to complete the job to my satisfaction. They were very respectful of my property and cleaned up every day with a final clean up at the end. Roof repair and/or new roofs are an extremely important decision for all homeowners. Make sure you get more than one quote and include Kettelle Roofing in your search. Some roofers didn't even go into my attic for their analysis, and missed several problems that couldn't be seen from the outside. Some diagnosed my leaks incorrectly and as a result would have worked on areas that weren't leaking, and missed some that were. Robert's crew does all aspects of the job themselves, whereas other companies may bring in subs, requiring you to get additional quotes. Make sure you understand the details of all your quotes. Robert is an honest owner of a company that has a great reputation for a long period of time. Call him!"
Recommended by92%of homeowners
Avatar for FloridaRoof Werks INC
FloridaRoof Werks INC
5.0(
59
)

Serving Winter Park, FL and surrounding areas

In business since 2004

Free estimates

Warranties offered

"David is an honest person. while other were either refusing or asking several thousands for a new home roof roof repair, I fortunately found him on my local magazine. He did an excellent job and great work. Love to hire him again. Thanks David"
Recommended by100%of homeowners
Avatar for Sheegog Contracting
Sheegog Contracting
5.0(
17
)

Serving Winter Park, FL and surrounding areas

In business since 2010

Free estimates

Warranties offered

"I hired Sheegog Contracting to replace my roof and other damage after finding I had squirrels in my attic. A leak was found near my chimney and there was damage to some of the trusses near the leak. My insulation needed to be removed and my attic cleaned and sanitized and new insulation installed. When the shingles I needed for replacement were available, my roof was installed quickly and efficiently. Robert Bonesteel was avaiable to answer any questions I had and guided me through the whole process. All work was done quickly and efficiently and all the repairs were made making my home safe from Florida weather and looking brand new. I would highly recommend Sheegog Contracting to any home owners needing their services."
Recommended by100%of homeowners
Avatar for Castle Roofing Group LLC
Castle Roofing Group LLC
5.0(
30
)

Serving Winter Park, FL and surrounding areas

In business since 2004

Free estimates

Warranties offered

"Please remember that your home is the single largest investment that your will make in your lifetime and if done correctly each project that you do will add value to your home. After spending 40 plus years doing major upgrades in manufacturing facilities, I have come to expect a high level of professional service from contractors industry and also working on my home. Castle Roofing is one of those contractors I strongly recommend. They took the time to understand what the total project included and made recommended products exceeded my standards. We found some water damage on one of the eves and around the chimney. The owner of the company came over and took care of it right away and at a reasonable price. They did a excellent job at a very reasonable price and did a great job cleaning up."
Recommended by100%of homeowners
Avatar for Property Renovations & Construction
Property Renovations & Construction
4.7(
162
)

Serving Winter Park, FL and surrounding areas

In business since 2011

Free estimates

Emergency services offered

"We had a couple false starts due to hurricane Irma followed by a death in the family. We had to postpone two installation dates, but once things settled down we were guickly rescheduled. The two-man crew arrived at the scheduled and proceeded with the job. There were some significant issues with the French door, but they were handled professionally and cheerfully without extra charge. A large amount of stucco around the door had to be repaired and that was done quickly by another crew while we were out of town. Lorne and Kurt did an excellent job on the doors and windows. Lorne returned a few days later by himself to install the garage door and did a beautiful job of installing trim around the inside on what was a very challenging surface. One panel of the French door had the inside frame installed upside down, making it impossible to operate to blinds. It took too long, about two weeks, for the door vendor to come to remedy the situation. Once they got here the repair was quickly made. The project manager, Andy, was initially a little slow to respond to calls. That could be an effect of the hurricane. Once things got underway Andy was very responsive to both calls and texts and was easy to work. Everyone bent over backward to make sure the job went well. We are very pleased with the job and highly recommend PRC to anyone in need of new windows or doors."
Recommended by90%of homeowners
...
Showing 1-10 of 675
FAQs for roofing installation & roof repair projects in Winter Park, FL

An average Cape Cod roof-raising project requires approximately two to three months from start to finish. The timeline depends on several variables, including weather conditions, contractor availability, material delivery schedules, and the specific complexity of your home's structure. The process involves multiple phases, including demolition, framing, roofing, window installation, and interior finishing. Working with an experienced contractor who provides a detailed timeline can help set realistic expectations for the project duration.

While most Cape Cod homes can accommodate roof-raising modifications, each house requires individual structural assessment. Older homes may need foundation reinforcement or wall strengthening before supporting additional weight. Factors like the existing roof framing system, load-bearing wall placement, and overall structural integrity all influence feasibility. A qualified structural engineer should evaluate your specific property before proceeding with design plans. Additionally, local zoning ordinances may restrict maximum building height or architectural modifications in certain neighborhoods.

Temporary relocation is highly recommended during a Cape Cod roof raising project. The construction process involves removing portions of your existing roof, exposing interior spaces to potential weather damage, and creating significant noise and dust. Most homeowners find temporary accommodations for the two to three-month construction period, with relocation costs ranging from $2,000 to $6,000, depending on your housing choices. If staying with family or friends isn't possible, budget for short-term rental or extended-stay hotel expenses as part of your overall project cost.

Consider roof raising when you experience severely limited headroom throughout the second floor, find yourself constantly stooping under sloped ceilings, or have minimal usable floor space due to low ceiling heights. Other indicators include inadequate natural light, poor ventilation, and difficulty accommodating standard furniture in upstairs rooms. Simple renovations can improve an attic's appearance, but cannot create additional headroom without structural modifications. A complete roof-raising project makes more sense than cosmetic renovations if you're seeking genuine second-floor living space rather than just storage improvements.

Begin your search by seeking contractors with specific experience in Cape Cod structural modifications and dormer additions. Request detailed portfolios showing similar completed projects and ask for references from previous clients with comparable work. Verify that potential contractors hold appropriate licenses and insurance coverage and understand local building codes relevant to roof raising. Interview multiple candidates, comparing price quotes and their communication style, project approach, and proposed timeline. The ideal contractor should demonstrate a thorough understanding of Cape Cod architectural characteristics and structural requirements.

The Winter Park, FL homeowners’ guide to roofing installation & roof repairs

From average costs to expert advice, get all the answers you need to get your job done.