Gray tile roof on a two-story stucco home, photographed from above
★ 4.9 Google · 524 reviews · Serving Maitland

Maitland roofing, done right the first time.

Around Lake Lily and Lake Catherine, homes in Maitland's historical corridor are still standing and still lived in, while Winfield at Maitland Park and The Hamlet at Maitland add newer rooflines off Fennell Street and Monroe Avenue. Pinnacle Roofing Group, a family-owned roofer from DeBary, repairs and replaces roofs in both parts of the city.

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
Freeroof assessments with written options, no pressure
Local roof radar

What Maitland weather does to a roof.

Shade from Maitland's tree-lined streets slows drying after afternoon storms and invites algae, and a local news report described a storm uprooting a large tree outside a Maitland home and crushing two cars, so overhanging limbs deserve a look at every roof here.

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.

From the 1838 fort on Lake Maitland to The Hamlet off Monroe Avenue

In 1838, during the Second Seminole War, the U.S. Army established Fort Maitland on the west shore of Lake Maitland, and the fort lent the city its name. Incorporation came after rail service helped local citrus growers ship fruit: the Town of Lake Maitland formed in 1885, and a 1959 charter trimmed the name to plain Maitland. The 2020 census counted 19,543 residents. Until the later twentieth century this was farmland between Orlando and Sanford, and Central Florida's growth then built much of it up, so the city holds homes from widely separated eras. Any roof conversation here begins with that question of age.

Older homes still stand and are still lived in around Lake Lily and Lake Catherine, part of a historical corridor the city recognizes through central Maitland. The city's historic home list starts with the Robert L. Wagner House of 1881, adds the Arthur O'Heir House and the James Arch House from 1885 and Chadburne Hall, also known as High Oaks, from 1890, and closes with the Hill-Stone House of 1908. A construction date on a list says nothing about the roof covering those rafters today. That is why the free assessment Pinnacle runs before any job comes with photographs and a written scope: the owner of a century-old house sees the roof's real condition before choosing among TAMKO architectural shingles, standing seam metal or stone-coated steel.

Newer named neighborhoods raise other questions. Winfield at Maitland Park lies off Fennell Street, and The Hamlet at Maitland lies off Monroe Avenue. For homes there, the useful facts are how old the current roof is, what shape it is in, and whether a homeowners association sets rules on material or color before work begins.

Re-roofs inside city limits go through the City of Maitland Building Division, whose permit page lists a Roof Permit Checklist and a Re-roof Affidavit among its forms. Inspection requests are made on the city's online permitting site or by email to [email protected]. On its own reroofs, Pinnacle files the application and books those inspections, so the homeowner is not left handling city paperwork.

Trees are the other half of the Maitland picture. Its tree-lined streets put many roofs in shade, and shaded shingles dry slowly after afternoon storms, which invites algae. Limbs bring a bigger risk: a local news report described a storm uprooting a large tree outside a Maitland home and crushing two cars. Homeowners with branches over the roofline can point them out during the free assessment, and trimming them before installation protects the new roof.

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

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 Maitland.

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.

4.9
524 Google reviews
Google rating

Homeowners in Maitland 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.

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.

Questions we get from Maitland

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 Maitland need a permit?

Yes. The City of Maitland Building Division handles re-roofs inside city limits, and its permit page lists a Roof Permit Checklist and a Re-roof Affidavit among the forms. Inspections are requested on the city's online permitting site or by emailing [email protected]. On its own reroofs, Pinnacle files the application and schedules each inspection with the city.

Our home is in the corridor around Lake Lily and Lake Catherine. What changes for an older house?

Mostly the order of decisions. The city's historic home list reaches back to 1881, and while a house's build year is on record, the roof over it today has to be looked at in person. Pinnacle's free assessment documents that condition with photographs and a written scope before any material is picked. If your house is on the city's historic list, ask the city whether anything beyond the standard roof permit applies before you settle on a material.

Should overhanging limbs be cut back before our new Maitland roof goes on?

In most cases, yes. A local news report described a storm uprooting a large tree outside a Maitland home and crushing two cars, and limbs over a roof also keep shade and debris on the shingles. An arborist can trim them before installation, and the photographs from Pinnacle's free assessment help show which branches hang over the roofline.

What matters for a roof in Winfield at Maitland Park or The Hamlet at Maitland?

These newer named neighborhoods, off Fennell Street and Monroe Avenue, raise different questions than the historical corridor near Lake Lily. The focus is the current roof's age and condition, and if an association governs your street, its approval of material and color should be in hand before the permit is filed.

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

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Roof questions in Maitland?(386) 631-5566Free assessment

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