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

Windermere · Orange County

Roofing contractorin Windermere, FL.

Roof repairs, replacements and solar for Windermere’s lakeside homes, from the Town on the Butler Chain to the gated communities around it.

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  • Licensed & insured
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Your local roofer

Windermere roofs,
handled with care.

The Town of Windermere sits on a strip of land between Lake Butler and Lake Down, part of the Butler Chain of Lakes. It was incorporated in 1925 and still feels like a small town: about 3,000 residents, a Town Hall on Main Street and many unpaved streets lined with oaks. Around it, the Windermere area includes some of Central Florida’s best-known lakefront communities, many of them outside town limits in unincorporated Orange County.

Larger homes, complex rooflines and premium materials are common here, from concrete and clay tile to standing-seam metal. These roofs reward careful work: proper underlayment under tile, clean valleys under heavy tree cover, and flashing that holds up to wind off the open water.

Hi Low is a Florida certified roofing contractor (CCC1332547) and certified general contractor (CGC1529815). We pull permits through the Town of Windermere’s building department or Orange County, depending on the address, and coordinate with HOAs and gated-community access.

Services in Windermere

One team for every
roofing need.

Neighborhoods we work in

Roofing across
Windermere.

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

  • Town of Windermere

    Historic lakeside town between Lake Butler and Lake Down, with oak-lined dirt roads.

  • Isleworth

    A gated lakefront golf community in unincorporated Orange County.

  • Keene’s Pointe

    A gated community on the Butler Chain with large tile-roofed homes.

  • Lake Butler Sound

    Lakefront estates on Lake Butler.

  • Lake Down area

    Established homes on large wooded lots along Lake Down.

  • Communities along Winter Garden-Vineland & Conroy-Windermere Roads

    Newer subdivisions between Windermere and Dr. Phillips.

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 Windermere

Local knowledge,
roof by roof.

Windermere is about 15 minutes from our office via Winter Garden-Vineland Road, Ficquette Road or SR 429 and Conroy-Windermere Road.

The Butler Chain of Lakes

Lake Butler, Lake Down and the rest of the chain give Windermere its character. Homes on open water see more wind than homes on inland streets, so we check ridge caps, hip tiles and edge details closely and install new roofs to the wind requirements of the site.

Oaks, moss and dirt roads

Heavy oak canopy keeps homes cool but drops leaves, twigs and moss into valleys and gutters. On tile roofs, debris trapped behind tiles holds moisture against the underlayment, so we clean and inspect these areas on every visit.

Gated communities

Many Windermere-area homes are behind gates with HOA architectural review. We schedule access in advance and prepare the submittals your association asks for.

ZIP codes we serve in Windermere: 34786

Homes & roofs

Every Windermere roof
has a story.

Large tile-roofed homes

Keene’s Pointe, Isleworth, Lake Butler Sound

On many tile roofs the underlayment wears out before the tiles do. We repair or replace underlayment, reset slipped tiles and use matching profiles where possible.

Lake houses on the chain

Lake Butler and Lake Down shorelines

More exposure to wind and sun means more wear on edges and ridges. We focus on fastening, flashing and attic ventilation.

Older homes in town

Town of Windermere

Older homes on wooded lots can have aging decking and roofs that were patched many times. A careful tear-off gives you a fresh, documented start.

Roofing in Windermere

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

Town or county

Homes inside the Town of Windermere go through the Town’s building department; many Windermere addresses, including several gated communities, are in unincorporated Orange County. We handle either.

Tile roofs

The underlayment matters

Tile can last for decades, but the underlayment beneath it usually doesn’t last as long. If you have leaks under intact tiles, the underlayment is often the cause.

Solar

Design for the roofline

Complex roofs need careful layout so panels look right and stay serviceable. We plan solar around tile type, shading from the oaks and your HOA’s rules.

Aerial view of a clay tile roof Hi Low completed on a Windermere home with a pool

Nearby

Also serving
your neighbors.

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

All service areas

Windermere roofing questions

Local questions.
Straight answers.

What Windermere homeowners and property managers ask us most.

Call 407-287-6171 8 questions answered
Do you work inside the Town of Windermere and in the gated communities?

Yes. We work in the town and across the Windermere area, including Isleworth, Keene’s Pointe and Lake Butler Sound. We arrange gate access ahead of time.

Who issues roof permits in Windermere?

Homes inside town limits are permitted through the Town of Windermere’s building department. Homes in unincorporated Orange County, including several gated communities, go through the county. Hi Low pulls the permit for your address.

Do you repair tile roofs?

Yes. We replace broken tiles, reset slipped ones, repair underlayment and rebuild hips and ridges on concrete and clay tile roofs.

My tiles look fine but I have a leak. Why?

On many older tile roofs the underlayment fails before the tiles. We lift tiles in the leak area, check the underlayment and recommend a repair or a tile reset with new underlayment.

Can you help with HOA approval?

Yes. We provide product specifications, color samples and documents for architectural review.

Do you install metal roofs in Windermere?

Yes. We install standing-seam and other metal roofing systems with Florida product approvals.

Is the inspection free?

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

Can solar work on a tile roof?

Yes, with the right mounting and flashing for your tile type. We plan the layout around shading and your HOA’s rules.

Serving Windermere

Get a free roof
inspection in Windermere.

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