Roofing Contractors Serving Lake Bluff since 1952

For more than 68 years, L.R. Gregory & Son has been a family business providing the entire community the best service and products. Having the top and most experienced technicians, allows us to solve all of your roofing problems, no matter how big or small the problem is. Our experience in the industry and improving our services year by year, has allowed us to offer the best service that our clients can receive.

Call Today for Immediate Assistance

Request a Free Roof, Gutter, and Chimney Inspection

Ensure your roof, chimney, and gutters are ready for Fall and Winter weather. Our trusted team will give you the true condition of your home. Request a free inspection today.

Roof and Gutters

Licensed Residential and Commercial Roofing Contractors

Our roofing services include from initial inspections, preventative maintenance and repairs, up to a full-scale roof replacement of your house. We work with Asphalt, Cedar, Slate, Tile, Aluminum, and Cooper roofs. In addition to our roofing services, we provide installation and the maintenance of gutters and flashing. There is no project too big for us, we do both commercial, and residential roofing.

Bay Roof Before 

Bay Window

​​ Copper bay Roof After

bay window

Professional Roofing Services

Our roofing services include initial inspections, preventative maintenance, and repairs, up to a full-scale roof replacement of your house. We work with Asphalt, Cedar, Slate, Tile, Aluminum, and Cooper roofs. In addition to our roofing services, we provide installation and maintenance of gutters and flashing. There is no project too big for us, we do both commercial, and residential roofing.

  • Roof Repair
  • Roof Inspection
  • Roof Replacement
  • Roof Maintenance
  • New Construction
house with tree in front

Ice Dam Prevention and Removal

Ice dams, which can be caused by long winters, can be destructive to your roof´s structure.Not only are ice dams unsightly, but they can cause significant damage to your home or business. All these alarming facts, leads everyone to the question of: how do ice dams form? And we bring you the answer to that.

The process of how the ice dams form is simple. As warm air leaks into your attic or your space under your roof, the snow on top of your roof melts, re-freezes into ice that can also infiltrate your shingles, and melts again to eventually leak water into your structure.

If you notice ice building up on the edges of your roof , and over your gutters, you have ice dams. Act quickly to prevent any hard damages! We are here to help you solve your roofing problems.

small icicles on roof
ice on roof

Call us today and let us work with you to select, optimize, or maintain the best-heated air solution for you.

Chimney Repair

With over 60 years of experience, we are experts when it comes to chimney problems. If you have chimney leaks, we can determine if it´s flashing or masonry problems.

We provide stainless steel and copper rain caps with screens to protect your flues if you have any animal intrusion.

Utilize chimney crowns to inhibit masonry deterioration or install a flue liner to stop condensation moisture from damaging the chimney.

men working on roof

Gutters Installation and Repair

man installing gutter
hand cleaning gutter

No one wants to get their hands dirty cleaning, repairing, or replacing the gutters of your house.

It’s a difficult job that should be left to the experts, and that’s when we come in. L.R. Gregory & Son takes care of your gutters, whichever problem you need to fix.

​It is essential to keep the house’s sanitary system working correctly, which means repairing and replacing gutters on time. L.R. Gregory & Son is happy to assist and serve you in gutter repair and replacement! Avoid having problems in your home because of your gutters and contact us!

Call us for a free quote and find out more about our services!

Call us today and let us work with you to select, optimize, or maintain the best-heated air solution for you.

How Does Our Roofing Installation Process Work?

Schedule Appointment

We create a plan personalized for you, creating an action plan to meet all of your needs and not the least, stay inside of your budget.

In most cases we follow this process:

  • Free in-home consultation
  • Receive and Approve quote
  • Schedule Installation Date
  • Complete Work
  • Verify Quality of Work

Do you need a new roof a simple repair? We can Help!
Request a Service Call today.

Service Area

For nearly 70 years, graciously serving Chicago’s North Shore communities.

Call us today and join our growing family of happy customers who deserve nothing less than excellence in both workmanship and service.

Our service area includes:

  • Lake Forest
  • Lake Bluff
  • Highland Park
  • Libertyville
  • Glencoe
  • Winthrop Harbor
  • Waukegan
  • Highwood
  • Glenview
  • Winnetka
  • Kenilworth
  • Wilmette
  • Gurnee
  • Lindenhurst
  • Deerfield
  • Northfield
  • Northbrook
  • Evanston
  • North Chicago

What Customers Are Saying

Google Review

Mr Gregory came to individually inspect my home. He offered a fair deal on pricing on a new furnace and home A/C unit. His men were quick and thorough in the installation, and answered all my questions regarding new unit operation, as well and parts and service warranties. This is a great family business to work with!

Eric L.
5 Star Review on Google

Angie's List Logo

Absolutely love them, they are fabulous! They are awesome. They have been awesome. They have done our air conditioning, our heating, and they replaced our roof as well because they do roofing as well. They are number one. We go to them now for anything that we need.

They have been servicing our furnace they have installed a new central air conditioning unit for us. We have them out usually twice a year for furnace inspection and the air conditioner inspection to keep everything running well. The last time they had to do a major install, thank goodness, was a couple years ago. It always goes out on like either the coldest day of the year or the hottest day of the year, you know, and that is what happened. And they were awesome with the quick turn around and, you know, making sure I think we were only out of a air conditioning unit for two days, maybe three, but that was also because we had called other people in the meantime, so, you know, just to get estimates, but they were awesome. They need to come out and do the regular service and to just check up on the air conditioner.

Phyllis (Sue) L.
5 Star Review on Angie’s List

Why choose LR Gregory & Son as your roofing contractor?

As Lake Bluff’s top roofing contractor, our mission is to set the standard of excellence in workmanship and quality, one job at a time. In addition to our nearly 70 years of experience, quality work requires quality tools and equipment. No matter if you need to repair a roofing leak, install a new roof, or replace an old roof; we want to do a great job for you! We can also help keep your space comfortable with our heating and air conditioning services.

Why Choose LR Gregory?
  • We are fully licensed and insured.
  • Provide 24/7 emergency service, no matter the time we are always one call away.
  • Our highly professional service and work are 100% guaranteed.
  • We offer a wide variety of services from Plumbing to Heating/Cooling to Plumbing, if it’s broken or needs attention, chances are we can help.

Do you need a new heating system, maintenance, or repair?
Request a Service Call today.

© 2020 LR Gregory & Son. All Rights Reserved.