Top-rated asphalt driveway pros.

Best asphalt driveway pros near 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

Top-Rated Asphalt driveway pros in Chestertown - Updated Nov 2026

Avatar for Robert & Son Paving
Robert & Son Paving
4.8(
93
)
Asphalt SealingGravel or Loose Fill Paving - Install, Spread or ScrapeAsphalt Paving - Install+2 more

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1955

Free estimates

Credit card accepted

"Robert was very nice. He gave me an estimate, which included cutting out parts and replacing sections of my driveway, revealing the entire driveway and was able to do it in the same week. His men did a wonderful job and he came to check on them several times during the process. Highly recommend!!"
Paved
Paved
Paved
Seal Coat
Seal Coat

+38

Response time9 hrs
2 neighbors recently requested a quote
Recommended by72%of homeowners
Avatar for Evans Paving
Evans Paving
4.2(
85
)
Asphalt Paving - Repair or PatchAsphalt Paving - InstallAsphalt Paving - Install- For Business+1 more

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

Response time2 days
2 neighbors recently requested a quote
Recommended by88%of homeowners
DDC Property Maintenance LLC
4.4(
11
)
Concrete Driveways - InstallConcrete Driveways & Floors - Install- For BusinessGravel or Loose Fill Paving - Install, Spread or Scrape+1 more

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 time2 days
7 neighbors recently requested a quote
Recommended by70%of homeowners
Avatar for JB Trakas Contractor, LLC
JB Trakas Contractor, LLC
4.6(
10
)
Concrete Driveways - Install

Serving Chestertown, MD and surrounding areas

Approved

In business since 2017

Free estimates

Small jobs welcome

"The professional of this company came out early in the morning and was finished by two in the afternoon. My house is about 2000 ft.² they installed a full 6 foot vinyl fence around the perimeter of my home. I would highly recommend them for additional projects."
Fencing project
Fencing project
Fencing project
Fencing project
Fencing project

+6

Response time2 days
Response rate100%
5 neighbors recently requested a quote
Avatar for Premier Paving
Premier Paving
5.0(
2
)
Asphalt Paving - InstallAsphalt Paving - Install- For BusinessAsphalt Paving - Repair or Patch+1 more

Serving Chestertown, MD and surrounding areas

Approved

We are a family owned Asphalt Paving company with over 30 years combined experience. \nWe specialize in detailed asphalt Driveway Paving and Sealcoating \nWe only use the finest materials and offer 100% customer satisfaction. \nWe also offer parking lot paving services, line stripping and parking Lot Sealcoating. \n

Response time3 days
1 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Boni Landscaping
Boni Landscaping
3.5(
12
)
Brick and Stone Driveways & Floors - InstallInterlocking Pavers for Driveways & Floors - Install

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

Response time2 days
Response rate100%
3 neighbors recently requested a quote
Avatar for Bayside excavation & Hauling
Bayside excavation & Hauling
5.0(
2
)
Gravel or Loose Fill Paving - Install, Spread or Scrape - For Business

Serving Chestertown, MD and surrounding areas

Approved

In business since 2023

Free estimates

Credit card accepted

We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

Response time5 hrs
7 neighbors recently requested a quote
Recommended by100%of homeowners
...
Showing 1-10 of 200
Asphalt Driveways FAQs, answered by experts

If you notice minor cosmetic problems with your driveway, you should seal it. Look out for cracks and holes on the surface, faded asphalt or concrete, and stains from oil and other chemicals. Replacing your driveway may be necessary if you’re dealing with significant problems—¼-inch cracks, large potholes, and puddles from drainage issues. The cost to install an asphalt driveway typically ranges between $4,200 and $9,000, significantly more than resealing. Consider talking to a professional to discuss whether resurfacing your driveway—a midway project between resealing and replacing—is a better option for you.

Chip seal layers gravel and a liquid bitumen one at a time on-site, while asphalt directly pours a pre-combined mixture. Asphalt must be sealed, but it will last up to four times as long as chip seal driveways. Aesthetically, chip seal has a natural, rustic look compared to the traditional asphalt slab.

At a depth of two inches, a ton of asphalt covers around 80 to 100 square feet. However, the thicker the asphalt, the less surface area it will cover. That’s why measuring correctly is essential when estimating asphalt needs and costs to ensure you get enough material to cover your entire driveway, patio, or other asphalt surface.

Since it has a smoother surface using a mixture of finer rock and sand, 41A tends to be the best asphalt grade for a driveway, especially for residential driveways. Other options are available, but more homeowners choose 41A for a smoother asphalt driveway. Talk with your asphalt driveway professional for recommendations of the best grade for your specific driveway.

Like all driveway materials, asphalt can crack in the wrong conditions and with age. Many things can cause asphalt to crack, including shifting soil or settling under the foundation. Other common causes are driving oversized vehicles on the asphalt, tree roots, and using rock salt during the snowy season. Proper installation and sealing the driveway every 10 years can help prevent cracks.

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.