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Find Roofing installation & roof repairers in Chestertown

Avatar for Remodeling Wizards of Maryland
Remodeling Wizards of Maryland
5.0(
167
)

Serving Chestertown, MD and surrounding areas

In business since 2001

Free estimates

Credit card accepted

"I am very pleased with Remodeling Wizards of Maryland. I was super happy with the deck work that has been completed. I have used this company for many different projects over 2 homes and about 10 years. Thanks!"
Beautiful and functional bathroom
Washer and Dryer
Beautiful and functional bathroom
Functional toilet and vanity
Shower seat for relaxing bath

+75

Recommended by98%of homeowners
Avatar for Ned Stevens Gutter Cleaning
Ned Stevens Gutter Cleaning
4.7(
2,691
)

Serving Chestertown, MD and surrounding areas

In business since 2005

Free estimates

Credit card accepted

"I used this company for a number of years and the overall service is no longer the same. I had them over to clean my gutters and I witnessed ladders slamming against the side of my house and they tore one of the edges from the corner of my roof with their step ladder. I will not use them going forward."
Atlanta's Best Gutter Cleaners
Gutter Cleaning in Atlanta
Atlanta Gutter Cover Installation
Recommended by93%of homeowners
Avatar for The Gutter Guys
The Gutter Guys
4.8(
448
)

Serving Chestertown, MD and surrounding areas

In business since 1988

Free estimates

Credit card accepted

"Don’t hire The Gutter Guys. This is the second time they came to my house. The first time they did a great job. The second time they ruined the screens on my gutters. I called them to provide feedback. I was not looking for a discount. The customer service was horrible. They said (1) I inspected the work, (2) the screens were old, and (3) they were probably like that for some time. I hung Christmas lights, which I took down in January, and the screens were fine. And, if someone damages your property, you would think they would tell you, instead of driving off. Avoid them!"
Recommended by96%of homeowners
Avatar for Homecraft Inc
Homecraft Inc
4.9(
218
)

Serving Chestertown, MD and surrounding areas

In business since 1981

Free estimates

Emergency services offered

"I had been a customer many years ago and needed a part for a storm door that I couldn’t find. I called and spoke with Mike who easily could have put me off due to the age and nature of the issue but he took great interest in helping me to resolve an issue that I had been unable to resolve myself. You know in this day and age it can seem rare to find someone that goes up and above the norm to treat you with exceptional respect and friendship. It goes a long way in their business. I highly recommend HomeCraft to anyone needing what they have to offer. And thanks again to Mike for his professionalism, his patience, and his kindness."
GAF Preferred Contractor Badge
GAF High Definition Roof
Recommended by96%of homeowners
Avatar for D & T Home Improvements
D & T Home Improvements
4.9(
45
)

Serving Chestertown, MD and surrounding areas

In business since 2014

Free estimates

Emergency services offered

"These guys spent 5 days crawling under my deck in mud and cold weather replacing rotten supports causing my sunroom and deck to sink. I have no doubt, the work they did will remain sturdy long after I decide to move (no plans at this time). Great job!"
Additional Photos
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+83

Recommended by95%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

"Jesse was very responsive and performed a quick repair after a windstorm to prevent further damage while we were preparing for a full roof replacement. His proposal was very competitive and thorough. Jess kept us up to date on the schedule and when the team would be available to complete the work. They arrived around 7:30am, brought extra people and worked late to complete the full roof replacement in one day due to rain that was forecasted for overnight. This included ripping off all of the old shingles and tar paper, repairing some damaged sheathing, replacing all of the drip edge, tar paper, ice guard, and new architectual shingles. During the installation, the team accidentally dented one piece of the fascia and Jesse replaced it at no cost immediately. I would highly recommend Jesse and his team if you are considering a roof repair or full replacement. Very professional, responsive, and competitive on their pricing."
Before
After
Half & Half
Additional Photos
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+2

Recommended by96%of homeowners
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

Credit card accepted

"The customer service was good as Spartan responded to all of my phone calls within a short period of time. The actual work was completed in 2 days which was extremely acceptable to me. After the work was done my house and surrounding property was cleaned thoroughly."
After
After
After
After
After

+67

Recommended by100%of homeowners
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Showing 1-10 of 183
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.