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A collage of images showing O'lyn has been in business for 40 years, O'lyn team members at an event, and an O'lyn Roofing crew.


Three story yellow house with a white wrap around porch.

Chestnut Hill Roofing Projects

O’LYN Roofing has done many jobs of replacing shingles, roof cleanings, guttering, and various other types of roof service projects in the Chestnut Hill, MA area.

An O'lyn Roofing crew working on a home in Belmont, MA.

Roofing Contractor Services in Belmont, MA

O’LYN Roofing’s various roofing projects in Belmont include roof replacement, gutters, skylights, attic insulation, and roof cleaning, among others.

An O'lyn Roofing crew installing new gutters on a home in West Roxbury

West Roxbury Roofing Projects

West Roxbury projects include roof replacement, gutters, skylights, attic insulation, and roof cleaning, among others.

An O'lyn Roofing crew installing a new roof replacement in Hyde Park

Major Hyde Park Roof Replacement

When our inspector saw this roof, he knew it was time to replace it. After reviewing the estimate, the homeowner agreed. Our crew stripped & re-shingled the roof, replaced rotted roof boards, stripped & installed rubber roofing areas, replaced soffits and fascia as necessary, and installed 6” seamless gutters.

An O'lyn Roofing crew hard at work installing new shingles on a home.

O’LYN Work Images

Photos showing the O’LYN Team hard at work doing what we do best.

An antique home with wood gutters installed by O'lyn Roofing.

Wood and PVC Gutters

Many Antique homes try to stay true to the original construction. While this may allow it to remain historically accurate, there may be problems with outdated materials. This home still had old-fashioned wood gutters. These simply do not last and also allow for the spread of wood rot and water damage. We were able to replace the wood gutters with PVC gutters. These will not rot like wood and also do not detract from the historic appearance of the home.

A new roof installation in North Easton

North Easton Roof Replacement and Upgrade

We did a complete roof replacement for a home in North Easton, installed two skylights, a solar attic fan, and replaced gutters. If you need a complete remodel of your roof and gutter system, call O’LYN Roofing for a free estimate today!

A new roof replacement in Mansfield, MA.

New Roof Replacement in Mansfield, MA

For the first time ever, we created a sweepstakes for a new roof replacement for one lucky customer. Here is our winner’s house in Mansfield from Beginning to completion.

Our winner chose Owens Corning TruDefinition Duration shingles in the color Driftwood. Both the homeowner and our team agree that the shingles beautifully bring out the blue trim and make the house look brand new!

A beautiful cedar shingle roof installed in Falmouth.

Cedar Shingle Roof Installed in Falmouth

This home needed a roof replaced, and the owners wanted to have a natural look to it. Our inspector presented the owner with an estimate, and they decided to use cedar shingles on the roof. Our crew expertly installed the roof, and the homeowner couldn’t be happier.

Two people on a golf course.  One of them is putting on the green.

2017 Tom Olen Memorial Golf Outing

Our 5th annual Tom Olen Memorial Golf Outing took place on Thursday, June 15th, 2017. All of the proceeds from the golf tournament are used to support cancer research organizations and financially assist families struggling with cancer and persons in need of organ transplants. The tournament is held in honor of the long-time employee and resident of the Neponset Valley community, Tom Olen, who passed away from cancer in 2010.

The O'lyn Roofing team at the 2014 Tom Olen Memorial Golf Outing.

2014 Tom Olen Memorial Golf Outing

A second hugely successful golf outing raised funds for people fighting cancer and in need of organ transplants.

A white two story home with a new roof installed by Mike Riley.

Mike Riley’s Roofing Projects

Images of projects Mike Riley has worked on in the past.

A snow covered home with a roof ice melt system installed by O'lyn Roofing.

O’LYN Roof Ice Melt Systems At Work

O’LYN Ice Melt Systems really got put to the test during the Winter of 2015’s all-time record-setting snowfall. The systems that some homeowners were fortunate enough to install before it set in saw them doing a great job at keeping ice off their roof edge and doing the extensive damage that many other homeowners suffered.

A two story home with icicles hanging off the roof.

Roof Ice Dams & Ice Melt Systems

We wanted to share images of the effects of heavy snow loads on roofs and the resulting ice dams. Also included are images of O’LYN ice melt systems installed and working.

A Massachusetts home with copper roofing.

Massachusetts Slate, Copper, and Wood Roofing Materials

Many different materials go into installing a new roof. There are also many types of roofing options to choose from. Contact O’LYN Roofing today for an estimate, and our inspector will go over all the options available to you!

A Massachusetts home getting new skylights installed.

Skylight and Rubber Roofing Installations

Certain types of roofs require a little more skill than others. Flat roofs have a higher potential for holding water. That means there is a greater risk of leaking. We have the know-how to install professional rubber roofs on homes and commercial locations. Call for an estimate today!

A Victorian home being worked on by O'lyn Roofing.

O’LYN Loves Working on Victorian Homes

O’LYN Roofing crews are always happy to do quality work on the beautiful Victorian Homes in the area. If you have a historic home, you shouldn’t trust your contracting to just anyone. O’LYN Roofing has the experience and skill needed to tackle these jobs. Call for an inspection and estimate today!

A new asphalt shingle roof.

Asphalt Shingle Roofing Installations

O’LYN Roofing can provide your home with quality asphalt shingle roofing. Call for your estimate today!

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