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TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.8
    Average homeowner rating
  • Verified reviews icon21
    Verified paving services reviews

Top-Rated Paving pros in Chestertown - Updated Nov 2026

Avatar for Robert & Son Paving
Robert & Son Paving
4.8(
93
)
Gravel or Loose Fill Paving - Install, Spread or ScrapeAsphalt Paving - InstallAsphalt Paving - Install- For Business

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1955

Free estimates

Credit card accepted

"Everything was perfect from start to finish. The price was competitive. The attention to detail was beyond my expectations and the job looked beautiful when it was done. Recommend this company highly for any paving needs to have."
Paved
Paved
Paved
Seal Coat
Seal Coat

+38

Response time10 hrs
2 neighbors recently requested a quote
Recommended by72%of homeowners
Zweemers Paving and Sealcoating
4.4(
34
)
Asphalt Paving - InstallAsphalt Paving - Install- For BusinessAsphalt Paving - Repair or Patch+1 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 1995

Free estimates

Emergency services offered

"Jimmy and his crew were on time, worked well together and completed our driveway in a professional and orderly fashion. I would strongly recommend Zweemer paving Mason E"
Additional Photos
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Additional Photos

+10

Response time2 days
Response rate100%
3 neighbors recently requested a quote
DDC Property Maintenance LLC
4.4(
11
)
Gravel or Loose Fill Paving - Install, Spread or Scrape

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
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Paving Services FAQs, answered by experts

A driveway approach is the part of a driveway where the public road meets the private driveway. This section contains several key elements, including the driveway apron, the curb cut, and the end slope. Depending on the slope of the driveway, this area may also contain the trench drain.

A driveway's lifespan varies by material. Asphalt driveways typically last 15 to 30 years, while concrete driveways last longer, between 20 and 50 years. The longevity of any driveway is affected by factors like extreme temperatures, heavy traffic, and the quality of maintenance. Regular upkeep, such as filling cracks, resealing the surface, and ensuring proper drainage, can help extend its life. For gravel driveways, regrading to fill in uneven areas every year or two is recommended.

The stones do not work well on uneven ground. If the stones are not buried into the ground and made level upon installation, they almost certainly will shift or crack on uneven ground. Additionally, rainwater or water from sprinklers can run under the edge of an uneven paver, causing erosion. In a freeze and thaw cycle, trapped water under the paver can cause the problem to worsen by shifting the stepping stones around. Use a bubble level to make sure the ground under each paver is as even as possible, even if the nearby ground is uneven.

Paver driveways are durable and aesthetically pleasing, but they do have a few cons. For instance, paver driveways are often more expensive than asphalt and concrete driveways. They also make it easier for weeds to grow where the separate pavers meet up. They may also be more likely to settle over time.

While water-related pressure caused by poor drainage is one common cause of paver cracking, other factors can include ground movement beneath pavers, heavy loads and wear and tear over the pavers, and climates with constant freeze-thaw cycles. In general, pavers should be resealed every three to five years to prevent cracking.

The Chestertown, MD homeowners’ guide to paving services

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