Pinnacle Roofing Group
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Gray shingle roof on a brick home photographed from above
★ 4.9 Google · 524 reviews · Serving Longwood

Longwood roofing, done right the first time.

Block by block, Longwood roofs shift in age and style, from Historic District cottages to Wekiva-side ranches and Sweetwater estates. Pinnacle Roofing Group's dated example here was a shingle replacement in February 2026.

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FL License CCC1332542BBB Accredited, A+TAMKO Diamond contractorFamily-owned since 2020
4.9 star Google customer rating4.9 on Google524 homeowner reviewsBBB Accredited Business, A+ ratingBBB AccreditedA+ rating · accredited since 2021FL licensed contractorCCC1332542 · verify anytimeTAMKO Diamond contractorTAMKO DiamondContractorRoofing Strong Alliance by TAMKORoofing Strong AllianceTAMKO contractor programLocally owned and operated, DeBary, Florida, since 2020Locally ownedDeBary, Florida · since 2020Free roof assessmentsWritten options, no pressure
4.9Google rating from homeowners like you
524Google reviews
A+BBB Accredited, family-owned since 2020
25+roofs completed in Longwood, estimated from logged jobs
Local roof radar

What Longwood weather does to a roof.

Lakes and the Wekiva River shape the exposure in Longwood: Irma's 2017 flooding closed Wekiva Island, and during Ian in 2022 flooding was reported on Penelope Drive near E. E. Williamson Road, so wind-driven rain, not salt, is what a roof here has to shed.

Shade, dew and algae

Big oaks and lake humidity keep roofs damp longer. Dark streaks and moss hold moisture against the shingle and shorten its life.

Afternoon thunderstorms, almost daily

Summer storms bring gusty wind, heavy rain and the occasional hail. Valleys, flashing and pipe boots take the beating first.

Hurricane season, June 1 to November 30

A documented roof condition before the season starts is the best conversation you can have with your insurer. It is also the cheapest.

Services

Everything we do in Longwood.

Shingle, metal, tile and low-slope. Repair when a repair is honest, replacement when it is not. Every job starts with a look at the roof and a written scope.

Gray shingle roof on a brick home photographed from above

Roof replacement

Written options, our crews, and a yard that looks like we were never there.

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New architectural shingle roof on a single-story Florida home

Roof repair

Find the source first. Then fix it once.

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Metal roof on a home beneath a sunset sky

Metal roofing

Standing seam and stone-coated steel, detailed for Florida wind.

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New standing-seam metal roof photographed from above

Commercial roofing

Occupied buildings, planned around the business under the roof.

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From Stum's Corner to Wekiva Island: reroofing Longwood

Tile and shingle came off the same Longwood house in December 2025, when Pinnacle replaced both on one reroof. The other dated jobs in the city were shingle replacements in March 2025, April 2025 and February 2026, part of five Longwood jobs in all. Downtown cottages, Wekiva-side ranches and Sweetwater estates change from one block to the next here, so every visit begins with a free assessment, photographs and a written scope for that particular roof.

National Register status covers the Longwood Historic District, the area bounded by West Pine Avenue, South Milwee Street, Palmetto Avenue and CR 427. Of its 37 historic buildings, most are residences, while several former homes have been turned to commercial use. The Queen Anne style Bradlee-McIntyre House is among them, though it did not start out here: it was moved from Altamonte Springs in 1973 to escape demolition.

Inside the city limits, Longwood issues its own reroof permits: the Building Division of the Community Development Department takes building construction applications. The city's online public portal carries both applications and inspections. Pinnacle submits the application for its own reroofs and schedules each inspection. A city notice explains a change from 2023: homeowners in association subdivisions stopped having to show HOA sign-off before the permit is issued. Deed restrictions still bind those houses, so the association's color and material rules are worth reading before you choose between shingle, standing seam metal and stone-coated steel.

Longwood's storm history is written in floodwater rather than salt. In 2017, Hurricane Irma's flooding damaged Wekiva Island, a riverside spot in Longwood, and forced it to close. During Hurricane Ian in 2022, flooding was reported on Penelope Drive near E. E. Williamson Road off I-4. Heavy rain pushes water at valleys, wall flashing and pipe boots long before a ceiling stains, which is why those details get checked first on a Longwood roof.

Incorporated as a city in 1923, Longwood counted 15,087 residents in the 2020 census. Roof ages vary across it, from the streets around Stum's Corner, where Church Avenue and Rangeline meet, out to the Wekiva-side lots. On a house that pairs tile with shingle, as the December 2025 job did, ask first how the seam between the two materials will be flashed.

Check the current permit guidance. Confirm the property jurisdiction and requirements for the actual scope before work begins.

Recent Pinnacle work in Longwood

Selected dated jobs from the archived project record in Longwood, not a complete job history.

More regional roofing guides

These service guides provide additional planning information. Your roof's size, condition, material and written scope determine its price, not the price of a neighboring city's project.

How it works

From first call to final walkthrough in Longwood.

Most homeowners have never bought a roof before. We keep it simple and keep you informed at every step. See the full process ↗

1

Tell us what is happening

Call, or send the request. Someone from the DeBary office follows up to book a time that works for you.

2

We look, photograph, explain

An inspector walks your roof and shows you what is actually there. No pressure, no scare tactics.

3

You get written options

Repair, replace, or wait. Each option in writing with the scope and price so you can compare.

4

We build, clean up, walk through

Netting over landscaping, our own dump trailers, a cleanup that includes the yard and driveway, then a final walkthrough with you.

Real jobs

Recent Pinnacle roofs across Central Florida.

Shingle, tile and metal from our own project gallery. Select a photo to enlarge it, or browse the full gallery.

Photos are from Pinnacle’s Central Florida project gallery, not necessarily this community.

4.9
524 Google reviews
Google rating

Homeowners in Longwood and across Central Florida rate Pinnacle 4.9 out of 5.

Read them before you call. Ask us anything you read there, and we will answer it straight.

Read the reviews Free assessment
Justin Coltharp, founder and owner of Pinnacle Roofing Group
Choosing a roofer is a big decision. My goal is to make it easier to understand what is happening on your roof, what your options are, and why we are recommending a particular approach.
Justin Coltharp Founder and owner, Pinnacle Roofing Group · DeBary, FL Meet Justin →
The details behind the decision

Follow the water. Understand the repair.

A stain tells you where water became visible. It does not, by itself, identify where water entered the roof. A useful repair assessment traces the likely entry point, looks at surrounding materials, and explains whether a localized repair can address the cause.

From Pinnacle’s project gallery · Select to enlarge

Read the supporting guidance: IBHS: roof flashing · IBHS: roof weathering and maintenance

01A leak near a wall or chimney

The transition between roofing and a vertical surface needs its own water-shedding details. Ask the roofer to show the flashing condition and explain how the repair will connect to the surrounding roof. A bead of sealant and a rebuilt flashing detail are different scopes of work.

02A stain that returns after a patch

Bring the earlier invoice and photos. They help distinguish a repeated problem in the same area from a new leak nearby. Ask what the next repair changes and which parts of the previous work can remain. Make the limits of a localized repair clear before authorizing it.

03Visible damage in one area

A missing shingle, damaged vent or cracked tile deserves inspection of the surrounding assembly. The relevant question is whether adjacent materials can accept a durable repair. Color matching, access and discontinued products can affect the finished result even when the repair area is small.

Explore roof repair Repair or replace?
Questions we get from Longwood

Asked every week. Answered straight.

If yours is not here, call (386) 631-5566. A real person at the DeBary office picks up.

Will a roof replacement in Longwood need a permit?

Yes. Building construction permit applications in Longwood go to the Building Division of the Community Development Department, and the city runs an online public portal for applications and inspections. For a Pinnacle reroof, that submission and every inspection booking come from our office rather than from the homeowner.

Is HOA sign-off still part of getting a Longwood roof permit?

Not since 2023. A city notice reports that an ordinance that year dropped HOA approval as a condition of the building permit. Deed restrictions did not go away with that change, so your association can still hold the new roof to its color and material rules.

Are houses in the downtown Historic District reroofed differently?

The district between West Pine Avenue, South Milwee Street, Palmetto Avenue and CR 427 is on the National Register, and most of its 37 historic buildings are still homes. The city sources we work from describe no separate historic review step for a reroof there, so for a house inside those streets, confirm the address with the Building Division before settling on a material.

Which Longwood reroof combined tile and shingle?

The December 2025 job. That house carried both materials, and Pinnacle replaced both. The other dated Longwood jobs, in March 2025, April 2025 and February 2026, were shingle replacements.

Free assessment, financing, repair or replace?

The answers are the same in every city, so they live in one place: the free assessment, the monthly payment planner and the repair-or-replace guide.

Keep your next step simple

Prepare for a roofing visit in Longwood

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Also nearby

Neighbors of Longwood we also serve.

Altamonte SpringsLake MaryCasselberryAll of Seminole CountyEvery service area →
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