Pinnacle Roofing Group
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Gray tile roof on a two-story stucco home, photographed from above
★ 4.9 Google · 524 reviews · Serving Winter Springs

Roof Replacement in Winter Springs, FL

The city-true fact in Winter Springs is Tuscawilla's double oversight. About a third of the city lives there; the Tuscawilla Homeowners Association and its village sub-associations review exterior color and material, and the Tuscawilla Lighting and Beautification District, a city assessment district created in 1999, sets the streetscape standard a job site is held to.

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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 Springs

Winter Springs is a late 1970s to early 2000s city, and the roofs show it. Tuscawilla's 17 neighborhoods, more than 3,000 homes around the Tuscawilla Country Club built out from the late 1970s through the early 2000s, hold most of the city's replacement candidates: Oak Forest went up from 1979 to 1994, and the original ranch sections are on a second or third shingle roof. The Highlands dates to 1978, and the North Orlando Ranches blocks along State Road 434 go back to the 1960s. These are hip roofs under live oaks, so what fails is valley metal rusted under leaf litter, soft decking at the eaves where gutters overflowed, step flashing at Tuscawilla two-story walls, and granule loss on the open south slopes of the golf-course lots.

What Winter Springs roofs deal with

The city-true fact in Winter Springs is Tuscawilla's double oversight. About a third of the city lives there; the Tuscawilla Homeowners Association and its village sub-associations review exterior color and material, and the Tuscawilla Lighting and Beautification District, a city assessment district created in 1999, sets the streetscape standard a job site is held to. The second fact is the age line in Florida's revised 25 percent rule (SB 4-D, 2022): a roof section permitted under the 2007 Florida Building Code, effective March 1, 2009, repairs by section, while the late 1970s to 2004 roofs in Tuscawilla, the Highlands and Parkstone still trip full replacement once more than a quarter of a section is involved. Winter Springs Village and Tuskawilla Crossings sit on the newer side of that line.

How Pinnacle handles roof replacement in Winter Springs

Our crew reaches Winter Springs in roughly 25 to 30 minutes from the DeBary office: I-4 east to State Road 434, or US 17-92 south to State Road 419, with Tuskawilla Road carrying us into Tuscawilla. On a 1980s Oak Forest two-story we photograph every valley, wall transition and eave edge before you see a number, because oak litter and overflowing gutters decide how much decking is coming off. Every tear-off gets sheathing renailed to current Florida Building Code, a sealed underlayment, new drip edge, valley metal and flashings, and the TAMKO Heritage, Titan XT or impact-rated shingle you choose from the Essential, Peace of Mind or Complete Protection packages. On the open fairway lots along Northern Way, Titan XT's wind rating is the upgrade we talk about first.

Neighborhoods, HOAs and permits in Winter Springs

In Tuscawilla the association comes before the permit. The Tuscawilla Homeowners Association and village sub-associations such as Oak Forest and the Reserve at Tuscawilla review roof color and material, and Parkstone, Avery Park, Winter Springs Village and Tuskawilla Crossings each run their own architectural review. The Highlands has an association as well, and in its townhome sections the association, not the owner, may control the roof. We prepare the product data sheet, color sample and written scope for the submittal. The reroof permit goes to the City of Winter Springs Community Development Department through its Civic Access Portal, with the roof permit application and the city's Product Approval Form, and we schedule the inspections the city requires. North Orlando Ranches homes have no association, just the permit.

The honest version

Most Winter Springs homes do not need the top of the ladder. A single-story 1978 Highlands ranch or a North Orlando Ranches block home with sound decking needs TAMKO Heritage installed correctly, new flashings and real attic ventilation, and that is the Essential package. The money is worth spending in two places: on the open golf-course lots in Tuscawilla, where a wind-rated Titan XT and heavier underlayment earn their keep, and on the deep-shade streets of Oak Forest, where a sealed underlayment and new valley metal matter more than the shingle brand. The minority of Tuscawilla tile roofs are a different conversation, priced on the tile roofing page. If your roof is a repair candidate, we say so in writing and point you to the repair page.

Recent roof replacement work in Winter Springs

Winter Springs jobs from Pinnacle's completed-project record, 5 completed in Winter Springs to date. Every project is documented with photos on the day it finished.

  • Winter Springs, September 2026: Shingle roof replacement, completed September 2026 View project ↗
  • Winter Springs, December 2025: Shingle roof replacement, completed December 2025 View project ↗
  • Winter Springs, September 2025: Shingle roof replacement, completed September 2025 View project ↗

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

How much does roof replacement cost in Winter Springs?

Winter Springs sits a step inside the top of the sitewide $10,000 to $36,000 shingle band, below Lake Mary and above the Volusia volume cities. The median household income near $86,000 (2019 to 2023 ACS) and roughly 74 percent owner-occupancy describe a city of owners replacing roofs they intend to keep, not flipping them. Tuscawilla's larger two-stories, cut-up rooflines and open fairway lots push the top, and the oak canopy drives more eave decking replacement than an average inland city. The floor is held by the Highlands single-stories and townhome-adjacent ranches and the 434 corridor block homes, which keep an Essential-package job reachable. Two-story share is moderate, tile share is small and mostly inside Tuscawilla, and the top is capped at $33,000 because Winter Springs lacks the Heathrow- and Timacuan-scale estates that pull Lake Mary to $36,000. The exact number comes from a written inspection of your roof. These are planning ranges, not a quote.

01

Roof Replacement in Winter Springs

$9,500 to $24,000

Low end: single-story 1978 to 1980s Highlands ranches and the 1960s to 1970s North Orlando Ranches block homes along State Road 434, roughly 1,200 to 1,800 square feet of living area with simple hips, TAMKO Heritage in the Essential package, sound decking. Middle: 1979 to 1994 Oak Forest and original Tuscawilla ranches and early two-stories with several valleys, step flashing and some eave decking replaced under the oaks, and 2000 to 2004 Parkstone and Avery Park two-stories on their first replacement, on Heritage or Titan XT with association submittal time. High end: large Tuscawilla golf-course and Reserve two-stories with long hips, many valleys, Titan XT or impact-rated shingle, decking replacement under the eaves and HOA review. Tile reroofs, tile-to-shingle conversions and standing seam or stone-coated steel are priced separately on the tile and metal roofing pages and can run above this band.

What is included in Pinnacle roof replacement ↗
02

Monthly, as example math

Example math only, not an offer: a $20,000 Winter Springs roof replacement financed at an example 9.99 percent APR over 120 months is about $264 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 Springs permit.

Read the guide ↗

What roof replacement in Winter Springs 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 Springs roof, checks the attic side where there is access, then gives you written options to compare: repair, replace, or wait.
  • Association submittal support where it applies: the Tuscawilla Homeowners Association and village sub-associations such as Oak Forest and the Reserve at Tuscawilla, plus Parkstone, Avery Park, Winter Springs Village, Tuskawilla Crossings and the Highlands, with the product data sheet, color sample and scope prepared by us.
  • Reroof permit pulled with the City of Winter Springs Community Development Department at 1126 East State Road 434 through the Civic Access Portal, including the city's Product Approval Form, with every required inspection scheduled by us.
  • Full tear-off to the deck by our own W-2 crew, sheathing renailed to current Florida Building Code, and any soft or rotted decking, most often at the eaves under the oak canopy, photographed and priced in writing before it is replaced.
  • Sealed underlayment, new drip edge, valley metal, step, wall and pipe flashings with kick-outs at two-story walls, attic ventilation corrected, and the TAMKO Heritage, Titan XT or impact-rated shingle system you chose from the Essential, Peace of Mind or Complete Protection package, with netting over landscaping and our own dump trailers on site.
  • Written workmanship warranty stated in your proposal, plus the manufacturer warranty for the TAMKO system installed; see /roof-warranty-guide/ for how to read both.
  • Final walkthrough with you, a magnet sweep of the yard, driveway and pool deck for nails, and the permit closed out before we call the job done.
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.

Had 2 other roofing companies come out and give me estimates. One of them conned me into signing a contract with them, which I didn’t realize I was signing a contract. I had to jump through hoops to get them to release me from the contract. Right after I signed the contract with them, the girl quit her job . I called pinnacle roofing because I was referred to by a friend and John came out. Instantly, I knew they were the ones that I wanted to go with. They didn’t force me to sign anything. they were easy to work with on price. They were a couple thousand dollars higher than I expected, but when I explained that to him, he negotiated with me and we came to an agreement. They watched the weather and didn’t rip the roof off my house because there were possible possible storms in the area. They made sure the weather was good before tearing my roof off so we didn’t unexpected surprises. All the workers were very polite and worked very hard to replace my roof. They came by after the roof was complete two times to do a walk-through and make sure me and my wife are completely satisfied before asking for the final payment . I would recommend pinnacle roofing every time. They will be my only roofing company if I ever need another roofing company again. They treated me and my family like we were their family. If you’re putting a roof on your house, that’s a big deal and you should use somebody that treats you like family and that’s why I recommend pinnacle roofing. They use all the best materials and they tell you every step of the way what’s going on and why they are doing what they are doing. Do not use some fly-by-night “Roofer“ because your family has to live with the decisions that you make. John treated us like we were his family and he only one of the best for us. Thank you pinnacle roofing

joe · Google review, 2024
Winter Springs questions, straight answers

Roof Replacement in Winter Springs: 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 Springs?

Most shingle roof replacements Pinnacle installs in Winter Springs run about $9,500 to $24,000. Single-story Highlands ranches and North Orlando Ranches block homes along 434 sit in the lower half; large cut-up Tuscawilla two-stories on the golf course push the top. Tile and metal are priced separately. You get an exact written price after a free assessment. That covers the typical 20 to 38 square roof here.

How long does a roof replacement take in Winter Springs?

Most single-family shingle replacements in Winter Springs are scheduled as a one- to two-day install once materials are on site, and the written scope states the plan for your roof. Large Tuscawilla two-stories, tile removal or a metal conversion take longer. Association approval and the City of Winter Springs permit come first and set the real start date.

Do I need HOA approval to replace my roof in Winter Springs?

In Tuscawilla, almost always: the Tuscawilla Homeowners Association and village sub-associations such as Oak Forest and the Reserve review roof color and material, and Parkstone, Avery Park, Winter Springs Village and Tuskawilla Crossings have their own review. We prepare the product sheet, color sample and scope. North Orlando Ranches homes off 434 have no association to satisfy.

Can I repair part of my Winter Springs roof instead of replacing it under Florida's 25 percent rule?

It depends on when the roof was permitted. Since Florida's 2022 revision, a roof built under the 2007 Florida Building Code or later, which covers Winter Springs Village, Tuskawilla Crossings and any roof replaced since 2009, repairs by section. Pre-2009 roofs, most of Tuscawilla, the Highlands and the 434 corridor, still require full replacement past 25 percent of a section.

Should I schedule a Winter Springs roof replacement during hurricane season?

Yes, if the roof needs it. Hurricane season runs June 1 to November 30, and Winter Springs took more than 15 inches of rain and downed oaks from Hurricane Ian in September 2022. A sealed, code-nailed roof going on in July beats a worn one waiting for December. Every opened section is dried in before the crew leaves.

Will Pinnacle handle my insurance claim for storm damage in Winter Springs?

The claim is yours to file with your carrier. Pinnacle inspects, photographs and documents the roof and writes the scope your adjuster needs, the documentation homeowners needed after Hurricane Ian in 2022 and Hurricane Milton in 2024. We do not act as a public adjuster, and we do not waive or rebate deductibles, which Florida law prohibits.

Who pulls the permit for a Winter Springs roof replacement, and what if you find bad decking?

We pull it through the City of Winter Springs Community Development Department on East State Road 434, using the city's Civic Access Portal and Product Approval Form, and schedule the inspections. If we find soft decking under the oaks, common at Oak Forest and Highlands eaves, we photograph it and price the fix in writing before shingles go on.

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