Top-rated asphalt driveway pros.

Get matched with top asphalt driveway pros in Chestertown, MD

Enter your zip and get matched with up to 5 pros

Need a pro for your asphalt driveway service project in Chestertown, MD?

Select your specific project to find the pro for you.

TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.8
    Average homeowner rating
  • Verified reviews icon15
    Verified asphalt driveway services reviews

Verified Reviews for Asphalt Driveway Service pros in Chestertown, MD

*The Angi rating for Asphalt Driveway Service companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Asphalt Driveway Service needs.

*The HomeAdvisor rating for Asphalt Driveway Service companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Asphalt Driveway Service needs.

Last update on February 04, 2026

Find Asphalt driveway pros in Chestertown

Avatar for Robert & Son Paving
Robert & Son Paving
4.8(
91
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1955

Free estimates

Credit card accepted

"They did a great job, and they did it quickly. So many contractors take way too long. But they got right to it. Very happy with my new driveway. Drainage was a main concern; water runs right down the middle of the driveway."
Paved
Paved
Paved
Seal Coat
Seal Coat

+38

Response time8 hrs
4 neighbors recently requested a quote
Recommended by73%of homeowners
Request Quote
Avatar for Evans Paving
Evans Paving
4.2(
85
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 1974

Free estimates

Emergency services offered

"Mr. Evan's and his crew installed my circular driveway they made the whole process a wonderful experience they were prompt courtesy and professional I've recommended them to many friends and my family excellent service"
Tar n chip
Tar and chip driveway
Tar and chip
Parking lot
Parking lot

+17

2 neighbors recently requested a quote
Recommended by88%of homeowners
Request Quote
Avatar for Accurate Asphalt, LLC
Accurate Asphalt, LLC
4.9(
37
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2018

Free estimates

Warranties offered

"We had our driveway paved. They gave a great price and the job was completed with 3 days. I would recommend this company to anyone looking to have their driveway paved. Excellent job."
2017 Peterbilt 389
On the Job
Logo
2005 Peterbilt 379
On the Job

+70

Response time2 days
Recommended by100%of homeowners
Request Quote
Avatar for Always Waterproofing
Always Waterproofing
4.1(
416
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1995

Free estimates

Credit card accepted

"They provided a ball park estimate for replacing my driveway which is a few years away"
Updated concrete deck
Cozy front porch
471 neighbors recently requested a quote
Recommended by93%of homeowners
Request Quote
DDC Property Maintenance LLC
4.4(
11
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2018

Free estimates

Offers commercial services

"Wilson prepped the pad for our barndominium, installed our bioswale, helped with tree removal, Installed our septic, and did our driveway for our custom home build. He was great with dealing with the county for us and made things smooth and easy. All work exceeded our expectations. Great guy and it was great to support a small local family in our area."
Response time30 mins
3 neighbors recently requested a quote
Recommended by70%of homeowners
Request Quote
Avatar for JB Trakas Contractor, LLC
JB Trakas Contractor, LLC
4.6(
10
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2017

Free estimates

Small jobs welcome

"Jamie was very responsive, came to site and measured. We went over many options and agreed on a path forward. Fence looks great. Crew tidied up after. Very pleased! Highly recommended!! Doggie happy to have his area now."
Fencing project
Fencing project
Fencing project
Fencing project
Fencing project

+6

Request Quote
Avatar for Boni Landscaping
Boni Landscaping
3.5(
12
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2011

Free estimates

Customers say: True professional

"It went very well. Boni was recommended to us and he was so professional and helpful when we met that we did not ask for quotes from other companies. He did not disappoint. The only delays were due to delays with raw material suppliers. Once the work began, the crew worked incredibly hard and cleaned up after each day’s work was completed. Boni was responsive to all questions. We plan to continue hiring him as we decide on additional landscaping and yearly clean-up."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+7

1 neighbors recently requested a quote
Recommended by100%of homeowners
Request Quote
Avatar for Leading Edge Avelar Contractors LLC
Leading Edge Avelar Contractors LLC
4.2(
15
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2005

Free estimates

Credit card accepted

"This company was very professional, timely and responsive to install my 15x12 concrete pad. Oscar and Douglas provided knowledgeable and honest input as a few issues developed. I am very satisfied with the quality of work and would highly recommend them."
Concert porch
Adding a square of concrete
Side walk
Frame
Ready to pour concrete

+60

Response time1 day
8 neighbors recently requested a quote
Recommended by76%of homeowners
Request Quote
...
Showing 1-10 of 198
Asphalt Driveways questions, answered by experts

The cost to replace a driveway ranges from $8 to $15 per square foot, depending on factors that include material, size, and labor. If your driveway has deep cracks, potholes, or drainage issues (or if it’s simply past its prime), replacement might be the smarter investment over constant repairs. Resurfacing can be a cheaper alternative at $3 to $20 per square foot, but it won’t fix your driveway’s underlying problems.

In most cases, you don’t need a permit to repave your driveway, although some exceptions exist. If you’re widening your driveway and plan on widening the apron as well, you’ll usually need a permit from the Department of Transportation in your area. This permit costs between $50 and $300 in most cases. Most municipalities will also require a certified and insured contractor do the work relating to the apron and curb cut. You can contact your building department or ask your paving company if you need a permit. Your driveway professional will usually pull the permit for you.

Whether it's worth it to install a heated driveway depends on how often you'll use it, your lifestyle, and your budget. If you live in a mild climate with little snowfall, then installing a built-in heated driveway system may not be worth it. If you live in a region that experiences mild snowfall, then a portable mat could work better. However, if you live in a region with heavy snowfall, it makes sense to invest in a built-in heated driveway. 

While some areas may allow for a slope of up to 20%, this is often the maximum slope for driveways, with a few exceptions of up to 25%. Other regions may have a maximum of 12%, 15%, or 18%, so check with your local building department to ensure you’re laying a driveway that is up to code for your location.

Several materials are suitable for steep driveways. Gravel and crushed stone are affordable options that provide good traction. Permeable pavers—such as plastic, rubber, or concrete—filled with gravel or crushed stones are also excellent, as they allow water to drain without causing erosion and perform well in ice and snow. Another option is resin, which can be coated with an anti-slip finish and helps prevent puddles. For added stability, you can install a retaining wall to prevent pavers and gravel from shifting over time.

The Chestertown, MD homeowners’ guide to asphalt driveway services

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

See all articles