A True Lakeland Roofing Horror Story: What One Crew Found
31 October, 2025
I’ve been replacing roofs in Lakeland for near twenty-seven years now, and I thought I’d seen everything. Thought I knew every creak, every leak, every way water finds its way through layers of tar paper and shingle. Thought I understood how a roof ages, how it dies. But the house on Pinecrest Lane taught me different.
It was mid-October when Mrs. Pemberton called. Her voice had that thread of worry you hear sometimes-not panic, just the quiet knowledge that something’s wrong and getting worse. She’d noticed dark stains spreading across her bedroom ceiling, she said. Granules piling up in the gutters. A soft spot near the bathroom vent that gave a little when you stepped on it in the attic.
“How old’s your roof?” I asked, pulling up my schedule.
“We bought the place in 2003,” she said. “Original roof. Never been touched.”
Twenty-two years. Right at that point where Florida weather finishes what it started. I told her I’d come by Thursday morning, take a look, let her know what made sense.
The house sat at the end of Pinecrest, where the newer Lakeland developments give way to older neighborhoods with oak trees that arch across the street. Nice place. Two-story colonial with faded blue siding and white trim that needed paint. The roof looked tired from the ground-shingles curled at the edges, a few missing altogether, dark streaks where algae had taken hold in the shade.
I set up my ladder against the east side and climbed up with my clipboard and camera. The shingles felt brittle under my boots, granules coming loose with each step. Not unusual for a roof that age. What was unusual was the cold.
It was eighty-six degrees that morning, humidity thick enough to chew. But up on that roof, the air felt different. Cooler. Not pleasant-cool, but wrong-cool, the way a meat locker feels when you first walk in. I figured it was just shade from the oaks, maybe a weird breeze coming off the pond behind the property. I’ve learned not to overthink things on a job.
I started my inspection on the south slope, working methodical like I always do. Checked the flashing around the chimney-rusted through in two places. Looked at the ridge caps-half of them cracked or missing. Lifted a few shingles to check the underlayment, and that’s when I found the first one.
A handprint.
Pressed into the tar paper beneath the shingles, clear as day. Small hand, like a child’s. The print was old, the tar darkened around it, but distinct enough that I could see each finger. I took a picture, marked it in my notes. Sometimes workers leave prints when they’re installing, though it’s sloppy work. Nothing to worry about.
I found three more as I moved across the roof. All small hands. All in places that didn’t make sense-one near the peak where no installer would need to put their hand, another tucked under the eave where you couldn’t reach unless you were trying. The fourth one was different. It wasn’t pressed into the tar. It was scraped through it, fingernails dragging through the paper in four parallel lines, like something had been trying to claw its way out.
The cold got worse as I worked. My hands started going numb. I could see my breath, just for a second, when I exhaled over a section near the bathroom vent. The soft spot Mrs. Pemberton mentioned wasn’t just soft-it was rotted clean through, the plywood underneath black with water damage and something else. Something that looked like rust but smelled wrong. Sweet and metallic, like old pennies left in the rain.
I should’ve climbed down right then. Should’ve told Mrs. Pemberton she needed a roof replacement, given her a quote, scheduled the work. That’s what twenty-seven years of experience tells you to do. But I kept looking, because something about that smell made my skin crawl, and I needed to know why.
The attic access was through a hatch in the garage. Mrs. Pemberton had already pulled down the ladder for me. “I don’t go up there much,” she said, standing in the doorway with her arms crossed. “Not since we moved in. Always felt wrong, you know?”
I knew.
The attic was worse than the roof. Hot as hell despite the cold I’d felt outside, and dark even with my flashlight. The insulation had been pulled back in places, shoved aside like something had been digging through it. The soft spot I’d found was directly above me, a hole the size of a dinner plate in the plywood, edges black and crumbling. Water had been getting in for months, maybe years. But water doesn’t explain what I saw in the rafters.
Scratches. Hundreds of them. Carved into the wood beams, clustered thick around the area near the bathroom vent. Not random-deliberate. Patterns. The same four lines, over and over, like tally marks. Like something had been counting. Counting days, maybe. Or counting something else.
And in the corner, tucked behind a roof truss where the slope met the exterior wall, I found the box.
It was small, made of cedar, the kind you might keep jewelry in. It sat on a piece of old underlayment, positioned careful-like, almost ceremonial. The wood was dry despite all the water damage around it, and when I picked it up, it was cold. That same wrong-cold from the roof.
I should’ve left it alone. God knows I should’ve.
Inside were photographs. Old ones, the kind with scalloped edges from the forties or fifties. They showed a family-mother, father, two young girls-standing in front of a house I didn’t recognize at first. Then I saw the oak trees in the background, the angle of the roofline, and I realized it was this house. Pinecrest Lane, seventy years ago, before the additions and the siding and the neighborhood that grew up around it.
The family looked happy in the first few pictures. Normal. But the photos were arranged in sequence, and as I flipped through them, things changed. The mother’s smile got tight. The father stopped appearing. The two girls-maybe seven and nine years old-started looking thin. Hollow. In the last photograph, only one girl remained, standing alone in front of the house, and she was looking up. Not at the camera. Up, at the roof, with an expression I’ve seen on the faces of people who know they’re going to die and can’t do anything about it.
Tucked beneath the photographs was a piece of paper, folded small. The handwriting was childish, the letters uneven: She’s still up here. She won’t let me leave. The roof keeps her close. Under the shingles where it’s dark.
My hands were shaking when I climbed back down that ladder. Mrs. Pemberton was waiting in the garage, and she must’ve seen something in my face because she took a step back.
“What did you find?”
I didn’t know how to answer. Didn’t know what I’d found, really, except that this roof was older than 2003, older than the records showed, and something had happened here long before the Pembertons bought the place. Something that left marks. Not just in the wood and tar paper, but deeper.
“You need a full roof replacement,” I said, keeping my voice steady. “The system’s compromised. Water damage, rot, structural issues. It’s been failing for a while.”
She nodded slowly. “Can you do it?”
I wanted to say no. Wanted to hand her a card for another company and drive away. But I’ve been in this business too long to walk away from work that needs doing. And something about those photographs, about that box tucked in the corner-something about the way the scratches clustered around that one spot-made me think maybe replacing the roof was the right thing to do. The only thing to do.
“We’ll start next week,” I said. “Strip everything down to the deck, replace what’s rotted, install new materials. High-quality shingles and underlayment that’ll hold up to Florida weather. Get you something that’ll last.”
The crew showed up Monday morning. Six good men I’ve worked with for years. We set up, tarped the property, started tearing off the old shingles. The work went smooth at first. The material came up easy, brittle and sun-damaged like I expected. But when we got to that section near the bathroom vent, when we pulled back the layers where the rot had set in deepest, we found it.
A space. Between the rafters and the roof deck, someone had carved out a hollow, maybe three feet wide and four feet long. Just big enough for a child. The wood inside was scratched to hell, marked with those same four-line patterns I’d seen in the attic. And tucked in one corner, barely visible, was a piece of fabric. Small. Pink. The kind of thing a little girl might’ve worn.
Nobody said anything. We just looked at it for a long moment, the six of us standing on that roof in the October heat, and then Carlos-my foreman, worked with me fifteen years-crossed himself and said, “We’re tearing all of it off. Every shingle. Every piece of underlayment. Down to bare wood.”
We did. Spent two days stripping that roof clean, hauling away decades of material. The cold stayed with us the whole time. Even in direct sun, even with the temperature pushing ninety, that section near the vent stayed cold enough that our tools felt like ice.
When we finally got down to the deck and started replacing the rotted plywood, the feeling changed. The cold lifted. The air felt normal again, just hot and humid like October in Lakeland should be. Whatever had been up there, whatever had left those marks and that box and that space between the rafters-it was gone.
We installed new decking, new ice and water shield, new TAMKO shingles rated for high wind. Sealed every penetration, replaced all the flashing, made sure every edge was tight. The kind of roof that’ll handle Florida weather for the next twenty years easy. When we finished, the house looked different. Lighter, somehow. Like a weight had been lifted.
Mrs. Pemberton paid us, thanked us, said the bedroom felt warmer now, more comfortable. She didn’t ask what we’d found under the old shingles, and I didn’t tell her. Some things don’t need saying.
But I kept that box. Kept the photographs and the note. And sometimes, late at night when I’m going over estimates for the next day’s work, I take them out and look at that last picture. The girl standing alone, looking up at the roof. I think about how long she was up there. How many years she counted in those scratches. How many Lakeland summers and storm seasons passed while she stayed trapped under those shingles, in that dark space, unable to leave.
I think about all the other roofs I’ve replaced over the years. All the houses from the early 2000s and before, the ones with original systems that have been sitting there for decades, wearing down slow. And I wonder what else might be waiting under those old layers. What other marks and spaces and cold spots we might find when we tear them down to bare wood.
Time for a New Roof?
If your Lakeland roof is getting close to that fifteen- to twenty-year mark, or you’re noticing cracked shingles, small leaks, or soft spots, it might be time to think about a full roof replacement. Florida weather is tough on roofs. Long months of sun, heavy summer rain, and high winds can wear them down faster than you’d expect.
Charlie’s Roofing has been helping Lakeland homeowners replace aging roofs with durable, high-quality systems that are built to last. We’ve been doing this work across West Florida for nearly thirty years. Our team is licensed, insured, and certified to install TAMKO materials-products known for their strength and long life. Because we’re a local roofing company, we know how Lakeland weather wears on different materials, and we plan every job with that in mind.
We take a simple, straightforward approach: inspect the roof, show you what we find, and explain what makes sense for your home. If replacement is the right call, we handle the entire process-from removing the old shingles to installing new materials that meet state codes and local requirements. We use high-quality shingles and underlayment that hold up to sun and rain, and our crew takes care to do it right the first time.
A new roof isn’t just about looks. It’s about having a system that can actually handle Florida weather. That means better energy efficiency, stronger wind protection, and fewer worries every storm season. Most of our new customers come from word of mouth, neighbors who liked how we handled their project and sent us to the next street over. That’s how we’ve stayed in business this long.
We show up when we say we will, explain things clearly, and stand behind our work