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Find Roofing installation & roof repairers in Chestertown

Avatar for Spartan Shield Roofing and Home Improvement Inc.
Spartan Shield Roofing and Home Improvement Inc.
4.9(
26
)

Serving Chestertown, MD and surrounding areas

In business since 2019

Free estimates

Warranties offered

"We had our new roof installed in Mid August. The job took about a day and a half. The crew was very professional and did a fantastic job. All the old shingles and nails were picked up every day throughout the day and they even blew out our gutters. The evening of the first day there was a threat of rain. Two crew members came back around 9:30 that evening and placed more tarps to make sure that if it did rain our roof would be protected. We are very pleased with their work."
Recommended by100%of homeowners
Avatar for Antietam Roofing LLC
Antietam Roofing LLC
4.9(
93
)

Serving Chestertown, MD and surrounding areas

In business since 2009

Free estimates

Emergency services offered

"Recent high winds had loosened the vinyl wrap on the fascia board on the front of our house. The poorly-installed wrap was evidently the only thing holding the soffit vents in place, and 3 of them dropped to the ground below. I contacted Jessie at Antietam Roofing and got an estimate on the repair cost. Because of inclement weather, he said it would probably be 3 days before they could do the work. When I called him near the estimated day, he said they would be there as promised and that the crew would call when they were on their way. I got a call the morning of the repair to let me know they were on their way. Tony (head guy) and Michael (his assistant) arrived right on time. Tony described what caused the problem and what he suggested doing to keep it from happening again (i.e., nail the wrap to the sill and do it with more than 2 nails!). We agreed on the plan, and they immediately started to work. They were finished in about an hour. The repair looks great."
Recommended by96%of homeowners
JC Services
5.0(
63
)

Serving Chestertown, MD and surrounding areas

In business since 1997

Free estimates

Emergency services offered

"I don’t usually write recommendations, but rarely do you come across an individual or company that takes this much pride in his workmanship and instills these same qualities into his employees, and it shows. Joe Call is a local contractor who was recommended to my wife and I and we are very happy with our roof and gutters that JC Services installed. Joe and his team were prompt, professional and extremely courteous throughout the entire job. They worked diligently and quickly while taking every precaution to ensure all the debris was disposed of properly. The job was meticulously maintained. The entire experience was positive and hassle free. If you are looking for a professional and experienced local roofer, gutter, and siding expert, JC Services is without a doubt the best choice for the job. JOSEPHCALL@CALLJCSERVICES.COM"
Recommended by95%of homeowners
Avatar for Politz Enterprises Roofing Inc.
Politz Enterprises Roofing Inc.
4.6(
28
)

Serving Chestertown, MD and surrounding areas

In business since 1963

Free estimates

Emergency services offered

"Oh my goodness! There are truly no words to convey how happy we are with our new shingles. Rob came out and met with us after we got estimates from three other companies. His knowledge, professionalism, and personality immediately helped us make up our minds to hire Politz Enterprises to replace our shingles on our home and detached garage. Rob was very attentive to helping us meet our timeline and explained the materials he would use and also explained their outstanding warranty. The crew he sent did an outstanding job at removing the old shingles, applying the new under-layment, installing the new drip edge, and finally applying the shingles. Despite how chilly it was in November, the men worked efficiently and did an outstanding job. They also did an excellent job at cleaning up once the job was complete. Rob came by once the job was complete to make sure we were completely satisfied. In our opinion, we are blessed to have the best roofing contractor in Maryland replace our roof. Thank you Rob and the entire crew who made our home look great again with the new roof you installed! Mike & Kathy D. - Middletown"
Recommended by89%of homeowners
Avatar for Complete Home Remodeling Services, LLC.
Complete Home Remodeling Services, LLC.
5.0(
24
)

Serving Chestertown, MD and surrounding areas

In business since 1996

Free estimates

Emergency services offered

"Home Remodeling Services did exceptional work on the project. Top of the line customer service experience. They are efficient, timely and go above and beyond to meet expectations. Definitely a must hire..."
Recommended by100%of homeowners
Avatar for Alternative Roofing Inc
Alternative Roofing Inc
4.5(
54
)

Serving Chestertown, MD and surrounding areas

In business since 2004

Free estimates

Warranties offered

"This company replaced Monarch Roofing at 5511 Maggie St, Baltimore, MD. 21225. It went great and the guys were so nice. I previously used this company in 2010 to add aluminum siding on my front porch. I called again but found they had new owners and no longer did siding. I had projects for two homes, both required gutter covers and aluminum coating on the porch roof. One house also needed window shutters replaced and one needed a downspout replaced and porch siding caulked. The old downspout was underground and clogged causing water to backup to the gutter and overflow when it rained. They gave me the cost to dig underground to replace piping or recommended bringing it above ground. I also called Homeserve to see if my insurance covered it and BGE Home to see if they offered a different price with my plumbing Smart plan. No, and no. I went with the above ground downspout replacement. Monarch also removed the cast iron device that held the old downspout in place and covered the hole in cement."
Recommended by83%of homeowners
Avatar for Advance Roofing Windows Siding & Doors
Advance Roofing Windows Siding & Doors
4.6(
255
)

Serving Chestertown, MD and surrounding areas

In business since 1989

Free estimates

Emergency services offered

"My install was completed flawlessly and I couldn't be happier! Both my siding and windows were installed by Jose's crew and done very professionally. I will hire Advance in a heartbeat for other work that I may need done in the future."
Recommended by86%of homeowners
Avatar for Exterior Home Solutions LLC
Exterior Home Solutions LLC
5.0(
7
)

Serving Chestertown, MD and surrounding areas

In business since 2012

Free estimates

Warranties offered

"My property in Gambrills needed a new roof. I did my research and found Exterior Home Solutions LLC had great reviews. They completed the job quickly and no issues. I recommend them to everyone!"
Recommended by100%of homeowners
Avatar for D A Improvements LLC
D A Improvements LLC
5.0(
10
)

Serving Chestertown, MD and surrounding areas

In business since 2019

Free estimates

Emergency services offered

"DA Improvements is a CertainTeed ShingleMaster Credentialed roofing contractor. Danny and his crew did an excellent job replacing our residential roof. Provided timely quote along with thorough explanation of the CertainTeed Integrity Roof System, designed for optimum roof performance with industry leading warranty coverage. Installed beautiful Landmark Pro architectural shingles with high attention to detail throughout the project. Very professional from start to finish. I highly recommend."
Recommended by100%of homeowners
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FAQs for roofing installation & roof repair projects in Chestertown, MD

An average Cape Cod roof-raising project requires approximately two to three months from start to finish. The timeline depends on several variables, including weather conditions, contractor availability, material delivery schedules, and the specific complexity of your home's structure. The process involves multiple phases, including demolition, framing, roofing, window installation, and interior finishing. Working with an experienced contractor who provides a detailed timeline can help set realistic expectations for the project duration.

While most Cape Cod homes can accommodate roof-raising modifications, each house requires individual structural assessment. Older homes may need foundation reinforcement or wall strengthening before supporting additional weight. Factors like the existing roof framing system, load-bearing wall placement, and overall structural integrity all influence feasibility. A qualified structural engineer should evaluate your specific property before proceeding with design plans. Additionally, local zoning ordinances may restrict maximum building height or architectural modifications in certain neighborhoods.

Temporary relocation is highly recommended during a Cape Cod roof raising project. The construction process involves removing portions of your existing roof, exposing interior spaces to potential weather damage, and creating significant noise and dust. Most homeowners find temporary accommodations for the two to three-month construction period, with relocation costs ranging from $2,000 to $6,000, depending on your housing choices. If staying with family or friends isn't possible, budget for short-term rental or extended-stay hotel expenses as part of your overall project cost.

Consider roof raising when you experience severely limited headroom throughout the second floor, find yourself constantly stooping under sloped ceilings, or have minimal usable floor space due to low ceiling heights. Other indicators include inadequate natural light, poor ventilation, and difficulty accommodating standard furniture in upstairs rooms. Simple renovations can improve an attic's appearance, but cannot create additional headroom without structural modifications. A complete roof-raising project makes more sense than cosmetic renovations if you're seeking genuine second-floor living space rather than just storage improvements.

Begin your search by seeking contractors with specific experience in Cape Cod structural modifications and dormer additions. Request detailed portfolios showing similar completed projects and ask for references from previous clients with comparable work. Verify that potential contractors hold appropriate licenses and insurance coverage and understand local building codes relevant to roof raising. Interview multiple candidates, comparing price quotes and their communication style, project approach, and proposed timeline. The ideal contractor should demonstrate a thorough understanding of Cape Cod architectural characteristics and structural requirements.

The Chestertown, MD homeowners’ guide to roofing installation & roof repairs

From average costs to expert advice, get all the answers you need to get your job done.