GutterHawk Roofing & Gutter Specialists
Crawfordville is the seat of Wakulla County, and it is one of only two county seats in Florida that is not an incorporated city. It sits about 18 miles south of Tallahassee along U.S. 319, which runs through town as Crawfordville Highway, and it has been growing fast: the census counted 3,702 residents in 2010 and 4,853 in 2020. That mix of long-standing homes and newer houses on the roads off 319 means we see every stage of roof wear here, from first-generation shingles reaching the end of their life to roofs that were patched one too many times.
GutterHawk handles roof replacement in Crawfordville, FL from our two Tallahassee offices, on North Monroe Street and on Shamrock Street North. The drive down 319 is short, so an estimate visit, a tear-off and a final walkthrough are all routine trips for our crews rather than a special journey.
This page explains what a replacement actually includes, which materials make sense on a Crawfordville house, how the Wakulla County permit fits in, and what moves the price.
In Crawfordville, GutterHawk also handles seamless gutters and gutter guards. Closer to town? See our roof replacement in Tallahassee page.
A replacement starts by taking every layer off the house. Shingles, old felt and worn flashing come off until the wooden deck is bare, and nothing new goes on over the old material. Stacking a second layer on top hides problems you are still paying for, so we do not do it.
With the deck open, we walk each sheet of plywood or plank and press on it. Boards that flex, show water stains or have started to separate in layers are cut out and replaced with new sheathing. This is the step a homeowner never sees from the yard, and it is the reason we give a final price only after we have been on the roof.
Once the deck is sound, new underlayment goes down across the whole surface. Valleys, the area around plumbing vents and any spot where the roof meets a wall get self-adhering ice and water membrane, because those are the places where water concentrates in a hard rain. New drip edge goes along the eaves and rakes, new step and counter flashing goes in where walls and chimneys meet the roof, and then the finished roofing material is installed to the manufacturer’s instructions.
Attic ventilation gets checked during the same visit. A roof that cannot breathe cooks its own shingles from underneath in a Florida summer, so if the intake at the soffits or the exhaust at the ridge is blocked or missing, we tell you and correct it as part of the job.
Throughout the tear-off, debris goes straight from the roof into a container instead of piling up on the lawn, and we cover shrubs and beds along the drip line. At the end the crew runs magnets over the yard and driveway for stray nails and walks the finished roof with you.


Most of the roofs we replace in Wakulla County go back on as architectural shingles. They are thicker than the old flat 3-tab style, they carry a wind rating, and they last longer, which is why they are the default recommendation for most houses. Our crews install them as a GAF certified contractor.
3-tab shingles are still available and cost less. They make sense for a rental, a workshop or a homeowner who needs a sound roof on a tight budget and does not plan to stay for decades.
Metal roofing costs more at the start, but it lasts far longer than shingle and stands up well to wind. If you expect to keep your home for many years, and most people who ask us about roof replacement in Crawfordville, FL plan to, the math often works out in its favor. Switching from shingles to metal is a common request, and it is handled as a full replacement, with the old roof removed down to the deck first.
We lay out the trade-offs of each option during the estimate. The choice is yours, and we put the price of each material in writing so you can compare them side by side.

Crawfordville is unincorporated, so building permits here come from Wakulla County rather than a city hall. The county building department is on Crawfordville Highway, right in town. We pull the permit for your roof replacement in Crawfordville, FL and schedule the inspections the county requires, so you do not have to fill out the paperwork or wait in line.
The work itself is done to the Florida Building Code, which sets the standard for how a roof covering, its underlayment and its fastening are installed across the state. Florida roofs are expected to hold up in strong wind, and a correctly installed, wind-rated roof is part of what the inspector looks for.
GutterHawk holds Florida roofing license CCC 1330917 and building contractor license CBC 1255295, and we are licensed and insured for the work. The building license matters on older homes, because when the tear-off turns up a damaged rafter or soft framing, we can repair the structure ourselves instead of bringing in another contractor.

Crawfordville sits only about 16 feet above sea level, and much of the land around it is flat. On flat ground, the water that comes off your roof has to be carried away from the house on purpose, because the yard will not do it for you. That makes the roof edge and the gutters part of the same conversation.
GutterHawk started as a gutter company. Jared Reinstein, who owns the company, started installing seamless gutters in 1993, and we added roofing in 2017. When we replace a roof, we look at the gutters hanging on the fascia at the same visit. If they are sound, we protect them during the tear-off and leave them in place. If they are undersized, pulling away or leaking at old joints, we can quote new seamless gutters formed on site from our trailer-mounted machine, sized to the new roof.
New drip edge sends water cleanly into the gutter instead of letting it run behind onto the fascia. Doing the roof and the gutters together means one crew is responsible for how water leaves your roof, from the ridge to the end of the downspout.

Four things decide most of the cost of a roof replacement in Crawfordville, FL. The first is size: more roof means more material and more labor. The second is pitch, since a steep roof takes more time and more safety setup than a low one. The third is complexity. A simple gable roof costs less than a roof of the same size with hips, valleys, dormers and a chimney, because every one of those joints needs its own flashing. The fourth is the material you choose.
The one thing nobody can price from the ground is the deck. We count replaced sheathing honestly and show you what we found, and our written estimate explains how decking is handled so there are no surprises.
Disposal of the old roof and cleanup are included in the job, not added afterward. You also get a written workmanship warranty on every replacement. Should any part of our work fail, our crew returns to repair it. With more than 400 customer reviews behind us, we would rather earn your next referral than rush your roof.
If your roof has started leaking, losing shingles or needing repairs every season, an on-roof inspection will tell you where it really stands. Call GutterHawk at (850) 779-1081, or our Shamrock office at (850) 842-7818, to set up a free estimate for roof replacement in Crawfordville, FL. We will give you a straight answer on repair versus replacement and a written price before any work begins.
Do you work in Crawfordville, or only in Tallahassee?
We work in Crawfordville and across Wakulla County. Our crews come down U.S. 319 from our two Tallahassee offices for estimates and installs.
Who issues the permit for a Crawfordville re-roof?
Wakulla County does, because Crawfordville is unincorporated. We pull the permit and book the inspections as part of the job.
Can I switch from shingles to a metal roof?
Yes. We remove the old shingles down to the deck, repair any bad sheathing, and install the metal roof over new underlayment.
Will my gutters survive the tear-off?
Sound gutters are protected and stay in place. If yours are failing, we can quote new seamless gutters at the same visit so both jobs are done together.
What should I do before the crew arrives?
Move cars out of the driveway, take fragile items off shelves in the attic and on walls near the roof, and expect noise overhead while the work is underway.
How many days will my roof job take?
A typical house is finished in one to three days. Roof size and weather set the exact length, and your estimate includes a schedule.
Can you help after storm damage?
We inspect the roof, document what we find, and give you a written report for your insurance claim. We are not a public adjuster.
Q.2 How much does roof replacement cost in Havana?
It depends on your roof’s size, pitch, and the materials you choose. Smaller, simpler roofs typically run a few thousand dollars, while larger roofs with steep pitches or premium materials can run well into five figures. We provide a written estimate after inspecting the roof in person.
Q.3 How long does a roof replacement take?
Most residential roof replacements take one to three days, depending on the size of the roof and the weather. We’ll give you a specific timeline during your estimate.
Q.4 Will you handle the permit for my roof replacement?
Yes, we pull any required permits as part of the job, so you don’t have to deal with the paperwork yourself.
Q.5 What happens to my old roof once it’s removed?
We remove and dispose of the old roofing material as part of the job. Cleanup is included, not billed as an add-on.
Q.6 Can you help with an insurance claim for storm damage?
We can inspect the roof, document the damage, and provide a written report you can submit with your claim. We’re not a public adjuster, but we’ll give you what you need to support the claim.
Q.7 Is there a best time of year to replace a roof in Havana?
Late fall through early spring tends to have the most predictable weather, which makes scheduling easier, but we replace roofs year-round. If your roof is failing, we won’t tell you to wait for a better season.
Getting the process started is easy! Simply fill out our quick form or call us at (850) 779-1081. One of our friendly staff members will get in touch to finalize the details.
One of our expert estimators will get to to work analyzing your job and crafting a proposal. Of course, we’re here to answer any questions you may have.
Have questions about your roof? Do you need information on gutter maintenance plans? No matter the question, GutterHawk is here to help!


