Pinnacle Roofing Group
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New architectural shingle roof on a single-story Florida home
★ 4.9 Google · 524 reviews · Serving Winter Park

Roof Replacement in Winter Park, FL

Winter Park is one of the few cities Pinnacle serves where the city itself may review your roof. Homes inside the local historic districts, College Quarter, Virginia Heights East and Interlachen Avenue, and individually designated homes on the Winter Park Register of Historic Places generally need a Certificate of Review from the Historic Preservation Board before a visible roof material or profile changes.

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FL License CCC1332542BBB Accredited, A+TAMKO Diamond contractorIn-house crew, family-owned
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 2020In-house crewOur own W-2 installersFree roof assessmentsWritten options, no pressure
0Google rating from homeowners like you
0five-star Google reviews
A+BBB Accredited, family-owned since 2020
0minutes from our DeBary office, give or take

The roof replacement problem in Winter Park

Winter Park replaces roofs in two very different worlds. In College Quarter, along Interlachen Avenue and in Virginia Heights, the 1920s Mediterranean Revival and Craftsman homes carry clay barrel tile and steep cottage gables over plank decking, with masonry chimneys, dormers and a century of additions that create dead valleys. East of Lakemont Avenue and west of Orlando Avenue, the 1950s and 1960s ranches of Winter Park Pines, Timberlane Shores, Lake Knowles Terrace and Killarney Estates are on their second or third shingle roof under oaks that predate the houses. In Windsong, the 2000s tile roofs are reaching the age where the underlayment, not the tile, fails. What goes wrong here is flashing at old masonry, soft eave decking under the canopy, and underlayment that outlived its rating.

What Winter Park roofs deal with

Winter Park is one of the few cities Pinnacle serves where the city itself may review your roof. Homes inside the local historic districts, College Quarter, Virginia Heights East and Interlachen Avenue, and individually designated homes on the Winter Park Register of Historic Places generally need a Certificate of Review from the Historic Preservation Board before a visible roof material or profile changes. Windsong adds a homeowners association with architectural review on top of that. Permits run through the City of Winter Park Building and Permitting Services division for addresses inside city limits, while Winter Park mailing addresses out along Aloma Avenue and Howell Branch Road in unincorporated Orange County permit through the county. Brick streets and protected oaks decide where a dump trailer can sit.

How Pinnacle handles roof replacement in Winter Park

Our crew reaches Winter Park from the DeBary office on I-4 to Fairbanks Avenue or Lee Road, or down US 17-92 through Maitland, about 25 road miles and 35 to 40 minutes, so Winter Park shares a crew day with Orlando and Apopka and materials arrive ahead of the crew. On a 1920s College Quarter home we photograph the decking from the attic before you see a number, because plank decking and chimney flashing decide the quote. On a Winter Park Pines ranch the tear-off usually reveals two layers and soft eaves. Every replacement gets sheathing renailed to current Florida Building Code, sealed underlayment, new drip edge and valley metal, flashings with kick-outs, corrected ventilation, and the TAMKO shingle you chose, installed by our own W-2 crew.

Neighborhoods, HOAs and permits in Winter Park

We treat the review step as the first inspection. For a designated home or a house inside College Quarter, Virginia Heights East or Interlachen Avenue, we prepare the product data sheet, color sample, photographs of the existing roof and a written scope that a preservation reviewer can read, and we tell you before the assessment ends whether your address appears to need one. For Windsong we prepare the association's architectural packet the same way and submit it before the permit. We never assume a historic or association rule applies because a home is near Park Avenue; we check the address. In the 1950s and 1960s neighborhoods east of Lakemont Avenue there is usually no association, and the city permit is the only approval.

The honest version

Most Winter Park homes do not need the most expensive roof on the block. A 1960s ranch in Winter Park Pines or Timberlane Shores needs sound decking, sealed underlayment, correct flashing at the valleys and real attic ventilation under the oaks, and TAMKO Heritage in our Essential package does that. A 1920s home with clay tile usually deserves to stay tile, and a Windsong tile roof often needs a tear-off and new underlayment with the tile relaid, not a new covering. We quote what the house needs first, and the full package ladder is on the roof replacement page.

Recent roof replacement work in Winter Park

Winter Park jobs from Pinnacle's completed-project record, 9 completed in Winter Park to date. Every project is documented with photos on the day it finished.

  • Winter Park, September 2026: Tile roof replacement, completed September 2026 View project ↗
  • Winter Park, January 2026: Modified Bitumen + Flat + Tile roof replacement, completed January 2026 View project ↗
  • Winter Park, November 2025: Tile roof replacement, completed November 2025 View project ↗

Related reading: Roof Replacement · Roofing in Winter Park · Planning guide · Pricing

How much does roof replacement cost in Winter Park?

Winter Park sits at the top of the sitewide $10,000 to $36,000 shingle band. Median household income is roughly $98,000 and home values are among the highest in Orange County, but the shingle market is split: the 1950s and 1960s ranch belt east of Lakemont Avenue and west of Orlando Avenue holds the floor near $14,000 because those roofs are modest in size and pitch, while the 1920s homes near Park Avenue and the Olde Winter Park rebuilds carry steep pitches, dormers, plank decking, chimney work, historic review time and brick-street staging that push the ceiling. Two-story share is moderate in the ranch belt and high in Olde Winter Park and Windsong. Tile share is high for an inland city, which pulls many of the largest homes out of the shingle band entirely and into the tile and metal pricing. Decking replacement under the oaks and review timelines are the variables that move a Winter Park quote most. The exact number comes from a written inspection of your roof. These are planning ranges, not a quote.

01

Roof Replacement in Winter Park

$10,500 to $28,000

Low end: single-story 1950s and 1960s ranches in Winter Park Pines, Brookshire Heights, Winter Park Estates and Killarney Estates, roughly 1,400 to 2,000 square feet of living area with low hips, TAMKO Heritage in the Essential package, sound decking after the two layers come off; small Hannibal Square cottages when the decking is good. Middle: 1950s and 1960s ranches in Timberlane Shores and Lake Knowles Terrace with additions, screen-enclosure tie-ins and soft eave decking, and 1920s Virginia Heights and Orwin Manor homes with chimney flashing rebuilds on Heritage or Titan XT. High end: large 1920s College Quarter and Interlachen Avenue homes with steep gables, dormers, plank decking replacement and a Certificate of Review, and big two-story homes in Olde Winter Park on Titan XT or impact-rated shingle with brick-street staging. Tile reroofs, lift-and-relay tile over new underlayment, and standing seam or stone-coated steel are priced separately on the tile and metal pages.

What is included in Pinnacle roof replacement ↗
02

Monthly, as example math

Example math only, not an offer: a $25,000 Winter Park roof replacement financed at an example 9.99 percent APR over 120 months is about $330 per month. Your real terms depend on the lender and your credit. Run your own numbers on the monthly payment planner at /roofpricing/ and read /guides/financing-a-new-roof-in-florida/ before you decide.

Estimate your monthly payment ↗
03

Compare proposals the right way

Same tear-off and decking assumptions, named products, flashing and ventilation listed, exclusions in writing, and who pulls the Winter Park permit.

Read the guide ↗

What roof replacement in Winter Park includes

The written scope is the plan. Every item below is stated in the proposal before work is scheduled. See how the process runs ↗

  • Free roof assessment by a Pinnacle inspector who walks and photographs your Winter Park roof, checks the attic side where there is access, then gives you written options to compare: repair, replace, or wait.
  • Historic and association review support where it applies: Certificate of Review packets for College Quarter, Virginia Heights East, Interlachen Avenue and designated homes, and the Windsong architectural submittal, with the TAMKO product data sheet, color sample, photographs and written scope prepared by us and submitted before the permit.
  • Reroof permit pulled with the right jurisdiction: the City of Winter Park Building and Permitting Services division for addresses inside city limits, or the Orange County Division of Building Safety for Winter Park addresses in unincorporated Orange County, with sheathing, dry-in and final inspections scheduled by us.
  • Full tear-off to the deck by our own W-2 crew, sheathing renailed to current Florida Building Code, plank or soft decking replaced and priced in writing from photographs, sealed underlayment, new drip edge, valley metal and flashings with kick-outs at every wall and chimney.
  • The TAMKO Heritage, Titan XT or impact-rated shingle you chose, with ridge ventilation corrected for a roof that sits under oak canopy, and brick-street staging planned with you so the dump trailer, material drop and landscaping netting respect the street and the trees.
  • Written workmanship warranty stated in the proposal and the manufacturer warranty for the TAMKO system installed; see the roof warranty guide for how to read both.
  • Final walkthrough with you after a magnet sweep of the yard, driveway and brick street, with the photographs from tear-off to finish delivered for your records and your insurer.
From a Central Florida homeowner

What homeowners say about Pinnacle roof replacement.

One of 4.9 stars on Google, 524 reviews. Read them all on the reviews page.

I recently had the pleasure of working with Pinnacle roofing group for a roofing project, and I am beyond impressed with their service. From the initial consultation to the completion of the job, the experience was seamless and professional. A special shoutout goes to Doug Guarino, who was incredibly helpful throughout the entire process. Doug's knowledge and expertise were evident from the start, and he took the time to explain every detail, ensuring that I fully understood the scope of the project. His recommendations were spot-on, and he went above and beyond to address all my concerns. Doug's dedication to customer satisfaction is truly commendable. He was always available to answer questions, provided timely updates, and made sure the work was completed to the highest standards. Thanks to Doug and the team at [Roofing Company Name], my new roof looks fantastic and has given me peace of mind. I highly recommend Pinnacle roofing group to anyone in need of roofing services, and I am especially grateful to Doug Guarino for his outstanding support and professionalism. Thank you, Doug, for making this such a positive experience!

Hayai · Google review, 2024
Winter Park questions, straight answers

Roof Replacement in Winter Park: what homeowners ask.

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

How much does a roof replacement cost in Winter Park?

Most shingle roof replacements Pinnacle installs in Winter Park run about $10,500 to $28,000. Single-story 1960s ranches in Winter Park Pines and Killarney Estates sit in the lower half; steep 1920s College Quarter homes and large Olde Winter Park houses push the top. Tile and metal are priced separately. You get an exact written price after a free assessment. That covers the typical 22 to 45 square roof here.

How long does a roof replacement take in Winter Park?

Most single-family shingle replacements in Winter Park are scheduled as a one- to two-day install once materials are on site, and the written scope states the plan for your roof. Steep 1920s College Quarter homes, plank decking replacement, tile lift-and-relay or a metal conversion take longer. Historic review, association approval and the permit come first and set the start date.

Does my Winter Park home need historic or HOA approval before a new roof?

It depends on the address, not the neighborhood name. Homes in College Quarter, Virginia Heights East, Interlachen Avenue or on the Winter Park Register of Historic Places generally need a Certificate of Review before the visible material or profile changes; like-for-like usually does not. Windsong requires association approval. We check your address at the assessment and prepare the packet.

Can I repair part of my Winter Park roof instead of replacing it?

Under Florida's 25 percent rule, a roof section built under the 2007 Florida Building Code or later can be repaired at any size, which covers Windsong's later phases and recent rebuilds. A 1960s Winter Park Pines ranch on its second shingle roof usually triggers replacement once more than a quarter of a section is involved. We tell you which applies.

Should I replace my Winter Park roof before or during hurricane season?

Before, when you can. We replace roofs year round, but June through November brings afternoon storms that shorten work windows and a backlog after any named storm. A documented, code-current roof before June 1 is also the best conversation to have with your insurer. If you are already in season, we dry in the deck the day we open it.

If a storm damages my Winter Park roof, do you handle the insurance claim?

You file the claim; we document and scope. Pinnacle does not act as a public adjuster, and we do not waive, rebate or absorb deductibles, which Florida law prohibits. We photograph the damage, write a scope your adjuster can read, and meet the adjuster on site if you ask. Read storm damage versus normal wear for what usually qualifies.

What happens if you find bad decking under my Winter Park roof?

We photograph it from the roof and the attic, show you the pictures, and price the replacement in writing before new material goes on. Plank decking on 1920s College Quarter homes and soft eaves on 1950s ranches under the oaks are the most common finds in Winter Park. The permit runs through the City of Winter Park or Orange County.

Keep exploring

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Service

Roof Replacement across Central Florida

How Pinnacle scopes, schedules and installs roof replacement, with the full package detail.

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Roofing in Winter Park

Everything Pinnacle does in Winter Park: repairs, replacement, metal, tile and inspections.

Keep reading ↗Guide

Plan the project

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