Residential Roofing, Doors, Windows, Siding, Gutters Commercial


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Over 25 Years Experience

Great Oak Roofing is a family-owned business, and our experts have the training, knowledge, and skill for your ideal roof, door, window, gutter, and siding replacement. Our team of roofers is fully licensed, insured and bonded. We are certified GAF installers for residential and roofing with over 25 years of experience. 

Roof Replacement

With our expertise spanning across a comprehensive range of services, we specialize in providing full roof replacement. Our commitment to excellence guarantees top-notch results for all your roofing needs.

Window Replacement

We offer top-quality window replacement services. We ensure a seamless installation process that will not only improve the energy efficiency of your home but also elevate its overall appearance.

Door Installation

Upgrade your home’s functionality and enhance its aesthetic appeal with energy-efficient doors.  With our expert door installation services, you can choose from a wide variety of entry doors, patio doors, and storm doors.

Siding Installation

Where many large roofing companies lack individualized service, we offer specialized one-on-one service. That means every project has its own dedicated project manager. We also specialize in standard and cedar siding.

Gutter Installation

Unparalleled commitment to using top-of-the-line materials, combined with skilled craftsmanship, ensures a superior outcome for your roofing needs. Trust us to deliver excellence that will leave you fully satisfied. We specialize in Bulldog Gutters.

Financing Available

We believe that every homeowner deserves the opportunity to enhance their home’s functionality and aesthetic appeal without financial constraints. With our financing options, you can confidently embark on your home improvement project knowing that we have got you covered.

Residential and Commercial Roofing Service

GAF Certified Company

Our team at Great Oak Roofing has undergone specialized training from GAF, a leading manufacturer of high-quality roofing materials. As a GAF certified company, we take pride in offering an extensive catalog of shingle options, including Timberline, Designer shingles, and metal roofing.

Standard Working Process

“Each roof, siding and gutter project we install or repair receives my personalized attention with the aim of your total satisfaction–and that is backed by my personal guarantee.” Ben Pascal, Owner-Operator

Designing Your New Roof

We will start the process with our project manager meeting who will review the roof options and build the contract for your ideal roof, while staying within your budget.

Pre-Construction Meeting

Once the contract is complete we will set up a pre-construction meeting. We will go over all the details in your meeting with your project manager and the owner. We will make sure there is a smooth process and answer any questions you have. Then you will set up your install dates.


Our certified crew and team of experts will arrive on your designated install day. We will review the contract and make sure all colors, materials, and tools are accurate for your job.

Drone Inspection

After installation we will have Drone image view to review your new roof. This will give use a chance to make sure your new roof is perfect.

roof top view house

What Are The Reasons Behind Choosing Us?

Great Oak Roofing, a family-owned and locally run company serving the Greater Severna Park, Annapolis region and has more than 40 years of demonstrated experience in providing high-quality roofing services.

“Each roof, siding and gutter project we install or repair receives my personalized attention with the aim of your total satisfaction–and that is backed by my personal guarantee.”

– Ben Pascal, Owner Great Oak Roofing LLC

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    Veteran Discounts

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    Senior Citizen Discounts

What Customers Saying About Great Oaks Roofing Service

Great people,fair pricing and work well done..I would definately recommend them and use them again!
Thanks Ben.

Adaly R.

Recent Customer

This company does outstanding work. They truly care about the quality of their work and making sure they make their customer happy. If you are looking for a roofer that will give you quality product, quality installation, and first class customer care, look no further – Great Oak is the best of the best!

Mary D.

Recent Customer

I highly recommend Ben and his crew! We used Great Oak Roofing to replace our gutters soffit and fascia. Ben was very knowledgeable, extremely helpful and professional. The workmanship was excellent and great quality! We are extremely happy with the results!

Larry S.

Recent Customer