Older Winter Park home with a new roof under live oaks

Roof replacement · Winter Park · Orange County

Roof replacementin Winter Park, FL.

Metal, tile, shingle and flat roof replacement for Winter Park homes, from 1920s cottages near Park Avenue to new builds on the Chain of Lakes.

  • Licensed & insured
  • Free inspection & estimate
  • Financing available
5.0 on Google · Over 300 five-star reviews

New roofs in Winter Park

Replacing a roof
in Winter Park.

Winter Park roofs are rarely simple. Older homes combine steep main roofs with low-slope porches and additions, some have barrel tile or flat sections hidden behind parapets, and many have original board decking under several generations of repairs. A replacement is the chance to fix all of it at once, down to the deck.

Homes inside city limits are permitted through the City of Winter Park, and designated historic properties may need a Certificate of Review before exterior changes. We document the existing roof and recommend materials and profiles that suit the house.

Under one of the region’s heaviest tree canopies, ventilation and drainage matter as much as the shingle or panel on top. We plan valleys, flashing and attic ventilation as part of every replacement. Hi Low is a Florida certified roofing contractor (CCC1332547) and certified general contractor (CGC1529815).

Our work

Recent work
in Winter Park.

A standing-seam metal roof Hi Low installed on a Winter Park home, with the pool enclosure and every hip and valley tied in.

Materials

Which roof fits
a Winter Park home?

The right roof depends on the house, the lot and the community rules. These are the systems we install most often in Winter Park, and where each one fits.

Standing-seam metal

Lakefront homes, mid-century and modern rebuilds

Long-lasting, light and strong in wind, with concealed fasteners and clean lines. It suits many mid-century and contemporary homes and comes in a wide range of colors.

Architectural shingle

Cottages, ranches and two-story homes

Cost-effective and familiar on Winter Park’s older streets. We match ridge and hip details and flash every place a porch or addition ties in, instead of relying on sealant.

Barrel and flat tile

Mediterranean Revival homes

Tile suits the 1920s Mediterranean houses in Olde Winter Park. We replace the underlayment, rebuild hips and ridges and match the profile as closely as possible.

Low-slope systems

Porches, carports, parapet roofs

Flat sections need a real low-slope system such as modified bitumen or TPO, never shingles. Drainage and the edge details at parapets decide how long they last.

Compare all four roof systems

Reroofing in Winter Park

What’s different
about this job here.

Historic review

Plan before you schedule

If your home is a designated historic property or in a local historic district such as the College Quarter or Virginia Heights East, ask the city whether the new roof needs a Certificate of Review. We provide product data and photos of the existing roof.

Permits

City or county

The City of Winter Park permits homes inside city limits; some Winter Park mailing addresses are in unincorporated Orange County, which has its own building division.

Tree canopy

Ventilation and drainage

Shade, moss and debris keep roofs damp. Balanced intake and exhaust ventilation and open valleys help a new roof dry out and last longer.

Solar later?

Plan it now

If you may add solar with Winter Park Electric, the new roof is the time to plan panel areas and attachment points. The city asks historic homes to keep panels off street-facing roofs where possible.

How it goes

From inspection
to final sign-off.

Most of the work happens before the crew arrives. See the full replacement process

  1. 01

    Free inspection

    We inspect the roof and attic, measure, and show you photos of what we find in Winter Park.

  2. 02

    Estimate & approvals

    A written estimate, samples in hand, the HOA submittal if your community needs one, and financing if you want it.

  3. 03

    Permit & install

    We pull the permit, tear off to the deck, replace damaged boards and install the new roof, flashing and ventilation.

  4. 04

    Inspection & records

    The final inspection, cleanup, and your warranty information and project records for your insurer.

More in Winter Park

Not sure it’s time
for a new roof?

Many roofs have years left after the right repair. Our Winter Park page covers repairs, storm damage, commercial roofs and solar, with local details on neighborhoods and permits.

Roofing in Winter Park

Roof replacement in Winter Park

Before you
reroof.

What Winter Park homeowners ask us most about replacing a roof.

Call 407-287-6171 7 questions answered
Does my historic Winter Park home need approval for a new roof?

It may. Designated historic properties can need a Certificate of Review from the City of Winter Park before exterior changes such as a new roof material. Check with the city early; we provide the product information and photos you need.

Can I put a metal roof on an older Winter Park home?

Often, yes. Standing-seam metal works on many older and mid-century homes. For designated historic properties, confirm with the city first.

My house has flat sections behind a parapet. Can you replace those too?

Yes. We replace flat and low-slope sections with modified bitumen or TPO and rebuild the parapet flashing and drainage as part of the job.

Who issues the permit?

The City of Winter Park for addresses inside city limits and Orange County for unincorporated addresses. Hi Low pulls the permit for your address.

Will the crew protect my landscaping and brick drive?

Yes. Landscaping, pools and driveways are protected throughout the tear-off and installation, and we clean up the site when the job is complete.

Will a new roof help with insurance?

It can. A wind mitigation inspection after the reroof documents features that Florida insurers use for premium credits. Results depend on your home and your insurer.

Is the inspection free?

Yes. The inspection and written estimate are free, with no obligation.

Roof replacement · Winter Park

Your new roof starts
with an inspection.

We’ll inspect your current roof, talk through materials and colors that suit your home and your HOA, and give you a free written estimate. If a repair would do the job, we’ll tell you that too.

Schedule my free inspection

Prefer to talk? 407-287-6171
13330 W Colonial Dr, Suite 110
Winter Garden, FL 34787