Roofing Central Mass and Beyond Since 1988

“When The Roof Is Leaking, The Forecast Is Always Rain”

Call Today! 508-829-9675

Roofing Central Mass and Beyond Since 1988

“When The Roof Is Leaking, The Forecast Is Always Rain”

Mission Statement

At O’Brien Home Services, we take great pride in our professional approach, efficient work ethic, and high quality results. We strive not just to provide outstanding results, but to do so with an accommodating and courteous approach with every client. We have an A+ rating with the Better Business Bureau (BBB) and work with only with the highest quality products and materials like CertainTeed.

Highly Competitive Pricing

We work with your budget to develop a plan to get the job done without breaking the bank or sacrificing quality materials.

Owner Present For All Jobs

Our owner, Ken, is present of every job to ensure everything goes smoothly and professionally.

Over 30 Years Of Experience

With over 30 years of industry experience, we are one of the oldest roofing contractors in Central MA!


Residential Roofing

Replacing, repairing, or installing a roof on your home can be an intensive and often obtrusive process. Our team aims to be as efficient as possible to have everything wrapped up quickly to not disrupt your daily life.

Commercial Roofing

Whether you need a simple repair or full replacement our crew can help! We have experience working with various different types of commercial roofing materials. Such as ballasted, TPO membranes, metal, and asphalt.

Asphalt Shingles

Asphalt shingle roofs are a popular choice of material due to its durability and affordable price point. They are also one of the few materials that come in various colors for accenting your home!

Rubber Roofs

Rubber roofing can be an excellent choice for cost-effective, weather-resistant roofing. We have experience installing different types of rubber roofing membranes with different adhering processes, so we can help recommend the best choice for your home or project.

Installs & Repairs

If you’re having issues with an old or damaged roof, it could be dealing debilitating damage to the structure of your house and even put you and your family in danger. At O’Brien, we can make crucial repairs or install a brand new, reliable roof to give you peace of mind and improve your home’s exterior in the process.

Vinyl Siding

Damaged or aging siding can be harmful to the value of your house as well as its appearance, but the team at O’Brien has a history of producing beautiful home siding that can transform your home. We work with quality materials and recommend options that best suit your home.

Gutter Installation

There’s nothing more irritating to a home owner than a leaky gutter during a rainy night. Malfunctioning gutters can produce all types of headaches and even cause lasting damage to your home. We install secure gutter systems and make customizations to best suit your home.

Chimney Flashing

Reworking or replacing the chimney flashing on your roof is an important adjustment to make to your home. Faulty flashing is one of the most common causes of chimney leaking. Luckily, our skilled, experienced team will flash your chimney properly to save you money and headaches over time.

General Contracting

At O’Brien, we offer a wide range of services to help our customers with their home projects. From repairs and installations to custom work, we apply the same standard of quality to every job we take on. Contact us today to find out more and to get an estimate on your home project.

Ask about gutter discounts with roof replacements!

Discounts for gutter installation or replacement may be available with your roof replacement.

Only takes a few seconds!

Only takes a few seconds!

Our Home Owners Say

“Ken O’Brien came in advance with materials and came with a full crew two days later. They stripped, installed new boots, cut in bath vents that were just vented into the attic, cleaned up as they went, magnetically raked all nails when all were finished, all done in the same day. Ken has all his crew rope themselves off for safety (and homeowner peace of mind). Couldn’t be any better or more efficient. Ken is also a most likable nice guy. I needed a power washer for a day and Ken loaned me his. I found him through a friend who was also happy with his work.”


“Great contractor. Ken was on time with all his appointments, worked efficiently and neatly, cleaned up the work area multiple times during the day and overall a true professional. Ken was on the job with his crew the entire time work was being done, working very hard always. I had never done any business with him prior to this, but i would highly recommend him to anyone who needs a quality roofer with years of experience. Truly my pleasure.”


“Ken O’Brien did a spectacular job on my roof. VERY prompt, neat as can be. He has a hard working crew. His price was very fair. He and his crew start early in the morning and work right until dark. He doesn’t cut corners. I recommend Ken O’Brien unconditionally. You can’t go wrong.”


Contact Us

Customer satisfaction is our top priority. If you have any questions regarding any of our services please fill out the form below and we will respond to you as soon as possible! Or call today at 508-829-9675 !

Contact Us


Contact Information

Main Office:

391 Salisbury St.
Holden, MA 01520

Serving: All of MA, RI, NH & CT

Office Phone: 508-829-9675

Field Phone: 508-373-4653

Email: [email protected]

Availability: 24/7 Availability