Highland Roofing Company

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Licensed and Insured Roofing Contractor

Licensed & Insured

preferred contractor

Owens Corning Preferred Contractor

5 Star Rated

5 Star Rated Local Company

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Free Inspections & Estimates

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Family Owned and Operated

Highland packs about 24,000 people into roughly seven square miles, which makes it the most tightly built town we serve. Houses sit close, driveways are short, and a tear-off has to be planned around the neighbors as much as the roof. Pursuit Exteriors is the family owned, Owens Corning Preferred Contractor that Highland homeowners call for roof replacement, repair, and storm damage.

What Highland Roofs Deal With

Density is the first thing that shapes a Highland job. With around 24,000 residents on about seven square miles of land, houses here sit closer together than anywhere else in our area. That changes the work before anyone gets on the roof: where the truck parks, where the dumpster sits, and how we protect the siding and landscaping on both sides. It also changes how water behaves, because a downspout that discharges wrong ends up in a neighbor's yard or against a shared foundation line.

The median Highland home was built in 1976, so the town's main construction wave is now about fifty years old. Most of those houses are on their second or third roof. Highland also has an older, long-settled population, with better than one in five residents over 65. Plenty of those homes have not had a roof touched in twenty years, and nobody has been up there to look.

The weather is the usual Lake County mix. Hail most summers, a 2026 storm season among the region's worst, and freeze and thaw winters that work at flashing and seals. Wind is the one people miss, because it breaks the adhesive strip under a shingle without moving it, and the leak turns up the following spring.

If you do not know how old your roof is, we will find out for free.

Common Roofing Problems We See in Highland Homes

  • Second and third generation roofs on 1970s homes coming due again
  • Tight lot lines that complicate staging, dumpster placement, and cleanup
  • Gutter and downspout runs that discharge toward a neighbor's property
  • Long-owned homes where nobody has inspected the roof in twenty years
  • Wind-broken shingle seals that leak the following season
  • Hail bruising and flashing wear from freeze and thaw winters

WHY CHOOSE PURSUIT EXTERIORS FOR YOUR NEW ROOF IN Highland, INDIANA?

We provide complete roofing solutions

No home is too steep, too small or too difficult for us to tackle. Our team has over 30 years of experience in all situations of roofing and siding repair.


  • Experienced and skilled professionals
  • Premium materials from top manufacturers
  • Comprehensive warranties for your peace of mind
  • Exceptional customer service and clear communication
  • Fully licensed, bonded, and insured

Let's work together to find a solution to your home's needs. Reach out for a  Free Estimate today.

Pursuit Exteriors Giving a Customer a Free Quote for a New Roof in Crown Point, Indiana
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15 Point Roof and Attic Inspection

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100% Customer Service Guarantee

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Dedicated to a Safe Work Environment

WE WORK WITH QUALITY MATERIALS

Owens Corning Preferred Contractor
LP SmartSide
JamesHardie Siding

Our Roof Installation Services for Highland, Indiana Homeowners

When you need a new roof, our skilled team will assist you every step of the way, from choosing materials to finishing the project.


We focus on installing a wide range of roofing materials, including:

  • Asphalt shingles
  • Metal roofing
  • Flat roofing
  • Slate and Shakes


We start our installation process with a detailed inspection of your roof to evaluate its condition and uncover any hidden problems.We will collaborate with you to choose the perfect materials that match your home's style and fit your budget. This way, your new roof will not only enhance your home's appearance but also offer long-lasting protection.

How Your Roof Replacement Works

No surprises. Here is exactly what happens from first call to final walkthrough.

1. Inspection

We get on the roof and into the attic, document everything and tell you straight whether you need a repair or a full replacement.

2. Estimate

You receive a detailed, written estimate with no hidden costs. It’s free and comes with no pressure to commit.

3. Material Selection

As an Owens Corning Preferred Contractor, we help you choose shingles, colors, and warranty coverage that fit your house and your budget.

4. Installation

Our reliable crew arrives on time, removes the old roof, and installs the new one, keeping you informed about the timeline.

5. Cleanup

Magnetic sweep for nails, full haul-away of the old materials, and your property left the way we found it.

6. Final Walkthrough

We walk the finished job with you, answer every question, and hand over your warranty paperwork.

Reach out to us for a quote today!
Roof Installation Valparaiso, Indiana
Damaged asphalt roof shingles with cracks, lifting tabs, and patches of wear

Roof Repair or Roof Replacement? Here's How We Decide.

A roof with life left in it does not need replacing, and we will say so out loud. One damaged area is a repair. Widespread wear, or a roof that has simply aged out, is a replacement, because patching an old roof buys a season at a time and never gets cheaper.

In Highland the practical side matters as much as the shingles. On a tight lot we plan the tear-off around where the truck and dumpster can actually sit, and we protect the properties on both sides before anything comes off. On the roof itself, a 1970s home carrying an unknown number of layers usually needs a full tear-off rather than another layer on top. If your roof went on within the last fifteen years and a storm took one slope, that is a repair or an insurance claim. We inspect first and tell you which one you actually need.

Signs Your Highland Roof May Be Ready for Replacement

Shingles are Curling, Cracked or Missing.

  • Asphalt shingles are designed to protect your home, but over time they can break down from UV rays, ice dams, and high winds. If you see granule loss, curling edges, or bare spots, your roof may be at risk. Give us a call today for a free inspection! 

Your Roof is Over 20 Years Old

  • Most roofing materials have a lifespan of 20–25 years. If your home in Highlandwas built in the early 2000s or earlier, it may be time to consider a full replacement — especially if repairs are becoming more frequent. Give us a call today for a free inspection! 

Interior Leaks and Water Stains

  • Moisture coming through your ceiling, attic, or around roof penetrations (like chimneys or vents) is a clear sign the roof system has failed. Don’t wait until the damage spreads even small leaks can lead to mold and insulation issues.

Moss, Algae or Black Streaks

  • These signs of excess moisture are common in shaded areas of Highland homes. They’re not just unsightly — they can trap water and deteriorate your shingles faster than you might expect.


Roofing Homes Throughout Highland and surrounding areas

We've worked on homes throughout Highland, from established neighborhoods including: Homes throughout Highland, from the older blocks near Ridge Road and Kennedy Avenue to the neighborhoods around Wicker Memorial Park and along the Erie Lackawanna Trail

Also serving nearby:

Griffith Munster Hammond

Frequently Asked Questions about Roof Installation

We find many of our clients have similar questions when it comes to roof installation so we have put together a list of commonly asked questions as a reference.

How do I know if I need a new roof on my home?

Look for curling or missing shingles, granules collecting in gutters, stains on interior ceilings, or a roof past 20 years old. The only way to know for sure is an inspection, and ours are free.

How much does a new roof cost?

It depends on the size of your roof, the material you choose, and the condition of the decking underneath. That is why we give written, itemized estimates instead of ballpark numbers. The estimate is free and comes with no pressure.

Will my homeowner's insurance cover roof replacement?

If the damage came from a storm, wind, or hail, often yes. Our inspection documents what the adjuster needs to see, and we can meet the adjuster at your home. Age and normal wear are not covered.

How long will my new roof last?

Modern architectural shingles installed correctly are rated for 30 to 50 years depending on the product line. Ventilation and installation quality matter as much as the shingle, which is why manufacturer certification counts.

Our lot is tight and the houses on both sides are close. Can you still do a full tear-off?

Yes, and it is most of what we do in Highland. We look at access before we quote: where the truck sits, where the dumpster goes, and how we protect the neighbors' siding, landscaping, and driveways. Tarps go up before anything comes off, and we clean the full work area when the job is done. If access is unusually tight, we tell you at the estimate rather than on the morning the crew shows up.

We have owned our Highland house since the 1990s and never touched the roof. Is that a problem?

It is worth checking. A roof installed in the 1990s carried a 20 to 25 year rating, so it is at or past the end of that window. Roofs that age often look acceptable from the driveway while the shingles have gone brittle and the seals have let go. That is the condition where one hail storm turns into a ceiling repair. The inspection takes under an hour and costs nothing.

Have more questions?

New Siding Northwest Indiana

More Than Roofing for Your Highland Home

Siding Installation & Replacement

Your roof is only one part of your home's exterior. Pursuit Exteriors also provides siding installation and replacement in Highland, helping homeowners protect their homes while improving curb appeal and energy efficiency.


We offer high quality siding materials, including LP Smart Siding and James Hardie Siding, and back our work with a strong guarantee. Our skilled team of installers is committed to providing expert advice and exceptional service.

Gutter Services

On lots as tight as Highland's, where the downspout empties matters as much as the gutter itself. A downspout that dumps toward a neighbor's yard or a shared foundation line is a problem waiting to happen. We place downspouts and extensions to move water away from both houses, and form seamless gutters on site to fit rooflines that sit close to the property line.

Learn more about Gutter Installation

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