Roof concerns in Winter Park? Start with a free inspection. FLORIDA ROOFING LICENSE · CCC1332547
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Home with a new roof in Winter Park, Florida

Winter Park · Orange County

Roofing contractorin Winter Park, FL.

Roof repairs, replacements and solar for Winter Park’s historic homes and lakefront properties, from Park Avenue to the Chain of Lakes.

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  • Licensed & insured
  • Free roof inspections
  • Financing available
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Your local roofer

Winter Park roofs,
old and new.

Winter Park was planned in 1881 and incorporated in 1887, and much of its character comes from what has been kept: brick streets, live oaks and camphor trees draped in Spanish moss, Park Avenue, Rollins College and the canals that link the Winter Park Chain of Lakes. Homes range from early-20th-century cottages and 1920s Mediterranean Revival houses to mid-century ranches and new construction.

That variety makes roofing here more than a material choice. Older homes can have steep, complex roofs, original board decking and low-slope sections over porches. Some properties sit in local historic districts, and the City of Winter Park runs its own electric utility, which matters if you are considering solar.

Hi Low is a Florida certified roofing contractor (CCC1332547) and certified general contractor (CGC1529815). We pull permits through the City of Winter Park or Orange County and install shingle, tile, metal and flat roofing, plus solar and batteries.

Services in Winter Park

One team for every
roofing need.

Neighborhoods we work in

Roofing across
Winter Park.

Some of the Winter Park neighborhoods where our crews inspect, repair and replace roofs, and what we usually find on the homes there.

  • Olde Winter Park

    Historic homes on brick streets around Park Avenue and the lakes.

  • College Quarter

    A local historic district near Rollins College.

  • Virginia Heights

    Home of the Virginia Heights East local historic district.

  • Hannibal Square & West Winter Park

    A historic neighborhood west of the railroad with older and new homes.

  • Windsong

    Larger homes in a lake-lined neighborhood on the north side of the city.

  • Kiwi Circle area

    Quiet lakeside streets with a mix of older and rebuilt homes.

  • Homes near Baldwin Park

    Neighborhoods on Winter Park’s south side toward Orlando.

Map of the 22 Greater Orlando communities Hi Low Roofing & Solar serves, with our Winter Garden headquarters SEMINOLE COUNTY ORANGE COUNTY LAKE COUNTY OSCEOLA COUNTY POLK COUNTY VOLUSIA COUNTY Lake Apopka Lake Toho East Lake Toho Lake Jesup Lake Monroe Lake Conway 4 4 429 417 TPK To Tampa Bay 0510 mi N Orlando Ocoee Windermere Apopka Winter Park Maitland Horizon West Dr. Phillips Lake Nona Altamonte Springs Longwood Casselberry Winter Springs Oviedo Lake Mary Sanford Kissimmee St. Cloud Clermont Davenport Deltona Winter Garden · HQ
Our office (Winter Garden)Cities we serveCounties we serveInterstates & toll roads

Around Winter Park

Local knowledge,
roof by roof.

Winter Park is about 35 minutes from our office via SR 408 and I-4, or along Fairbanks Avenue.

Park Avenue and Rollins College

Downtown Winter Park, Central Park and Rollins College anchor the city. Many nearby homes are decades old, with roofs that have been repaired many times. We start with an honest assessment of what can be repaired and what should be replaced.

The Chain of Lakes and the canopy

Lakes Osceola, Virginia, Maitland and their canals, plus one of the region’s heaviest tree canopies, mean shade, debris and moisture on many roofs. Clean valleys and gutters and good attic ventilation make the biggest difference.

Historic preservation

Winter Park has local historic districts, including the College Quarter and Virginia Heights East, and its own Historic Preservation Board. If your home is a designated historic property, check whether exterior changes need a Certificate of Review before work starts.

ZIP codes we serve in Winter Park: 32789, 32792

Homes & roofs

Every Winter Park roof
has a story.

Historic cottages and Mediterranean Revival homes

Olde Winter Park, College Quarter, Virginia Heights

Steep and low-slope sections meet in tricky places, and many of these homes have barrel tile or flat roofs hidden behind parapets. We match details carefully and replace damaged decking.

Mid-century ranches

West Winter Park and the north side

Low-pitched roofs and flat carports are common. We focus on drainage, flashing and ventilation.

Lakefront and new construction

Windsong and lakeside streets

Larger homes with complex roofs and premium materials. Design, flashing and fastening details matter more than ever.

Roofing in Winter Park

What’s different
about roofs here.

Storm season

Hurricanes reach inland

Central Florida is inland, but hurricanes still get here. Ian in 2022 and Milton in 2024 both brought damaging wind and flooding rain to the area. Have your roof checked before June 1 and again after any major storm, and keep your inspection photos for your insurer.

Permits

City of Winter Park

Homes inside city limits are permitted through the City of Winter Park; some Winter Park addresses are in unincorporated Orange County. Designated historic properties may also need preservation review.

Historic homes

Plan the details

For homes in a historic district or on the local register, we document the existing roof and recommend materials and profiles that respect the house. Ask the city whether your project needs a Certificate of Review.

Solar

Winter Park Electric

The City of Winter Park operates its own electric utility, with its own rules for crediting solar exports and a separate meter for system output. The city also asks historic homes to avoid street-facing panels where possible. We design around both.

Aerial view of a dark gray standing-seam metal roof on a Winter Park home

Nearby

Also serving
your neighbors.

Hi Low works across Greater Orlando from our Winter Garden headquarters.

All service areas

Winter Park roofing questions

Local questions.
Straight answers.

What Winter Park homeowners and property managers ask us most.

Call 407-287-6171 8 questions answered
Do you work on historic homes in Winter Park?

Yes. We repair and replace roofs on older homes across Winter Park, including Olde Winter Park, the College Quarter and Virginia Heights. We document the existing roof and recommend materials that suit the house.

Does my historic home need approval for a new roof?

It may. Winter Park’s Historic Preservation Division reviews alterations to designated historic properties through a Certificate of Review. Check with the city before work starts; we provide the product information you need.

Who issues roof permits in Winter Park?

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

How does solar work with Winter Park’s electric utility?

The City of Winter Park runs its own utility and credits excess solar generation under its own program, which requires an additional meter. We size the system using the city’s current terms.

Do you repair flat roofs and roofs behind parapets?

Yes. Many older Winter Park homes have flat or low-slope sections. We repair and replace them with modified bitumen, TPO or coatings, depending on the roof.

Is the inspection free?

Yes. Inspections and written estimates are free, with no obligation.

Do the trees affect my roof?

Heavy canopy brings shade, moss and debris. Keeping valleys and gutters clear and trimming branches back extends a roof’s life.

Do you serve Windsong and the lakefront homes?

Yes. We work across the city, including Windsong and homes on the Chain of Lakes.

Serving Winter Park

Get a free roof
inspection in Winter Park.

Tell us what you’re seeing. We’ll inspect the roof, show you photos and give you a written estimate, with no pressure to sign.

Book my free inspection

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