Top 1 cedar roofing contractor in Freeland, MD

"Four Seasons Roofing replaced my roof in August 2025, and I couldn’t be happier with the experience. Everyone I worked with was respectful, knowledgeable, and genuinely helpful. Both the roofing and gutter crews did a fantastic job, and Chris went above and beyond in answering all of my questions. I highly recommend Four Seasons Roofing to anyone looking for quality work and great customer service!"

"We are very pleased with our new Duradek roof installed by Four Seasons Roofing. The entire team of Shawn, Vasille, Debbie, Julio, Miguel, Adrien, and Fernando provided us quality service from start to finish addressing all of our questions throughout the process. Attached is a before and after picture."

"Four Seasons replaced the Duradek rooftop deck at my townhouse about 1 year ago. The quoted price was much better than another competitor's estimate, the work was performed quickly, and the results were very high quality. The vinyl and trim has held up very nicely over the past year through many rainstorms, and we have not had any issues. I will definitely be calling on Four Seasons again for my future roofing repairs."

"I recently had the pleasure of working with Four Seasons Roofing for a skylight repair, and I couldn’t be more pleased with the experience. From start to finish, the team was professional, knowledgeable, and incredibly courteous. A special thank you to Debbie, who was absolutely wonderful to work with. She was responsive, kind, and made sure every detail was handled smoothly. Her communication kept us well-informed throughout the process, and she truly went above and beyond to ensure everything was taken care of. The repair itself was done efficiently and with great care. The crew was respectful of our home and completed the job with a high level of craftsmanship. The skylights look fantastic and no more leaks — we’re thrilled with the results! I highly recommend Four Seasons Roofing for anyone in need of roofing services. Thank you again to the entire team, and especially to Debbie, for such a positive experience!"

"Four Season roofing did a phenomenal job on my roof and I would recommend them to anyone! My experience began with excellent customer service from Debbie in the main office; Debbie expeditiously set my appointment and then Shawn came out to my home, did an estimate of my roof, and went over all the specs while telling a few jokes. Once I decided to go with them I immediately knew that I made the right choice. Four seasons communicated each step of the way and made me feel confident with my choice. The crew was set to arrive at 7 am, however when I went outside at 6:30 to walk the dog, they were already parked and ready to go. The crew chief was amazing and super imformative about the entire process checking in with me throughout the day. The men were fast, hard-working, and they were meticulous with every detail; I felt like they paid attention to every detail as if it was their own home. The clean up and attention to every piece of scrap, nail, dust, etc. being removed from my yard was top-tier. Four Season left my yard cleaner than when they came. Their work was so impressive that two of my neighbors raved about the level of craftsmanship and one called for an estimate for their roof. If you have to get your roof done (no one wants to) then give them a call."