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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

While it may be less expensive initially to lay concrete vs. pavers, the long-term expenses that come with repairing concrete may prove to be less cost-friendly than simply replacing a few damaged pavers. On top of that, stamped concrete may only last for 25 years compared to pavers, which can last over 50 years.

Recycled asphalt is a durable choice for a driveway, but doesn’t have the same appearance and low maintenance as standard asphalt. For long driveways in rural communities, recycled asphalt can make a great choice. Recycled asphalt is 20% to 30% percent less expensive than standard asphalt and is better for the environment. 

Yes, with colored finishes and decorative stamping for a personalized touch.

Maintaining a driveway depends on its material. For concrete and asphalt, it's best to clean the surface thoroughly twice a year with a stiff broom and a pressure washer to remove accumulated dirt and debris. Sealing the driveway is crucial to protect it from water damage and freeze-thaw cycles. Before applying a sealant, pressure wash the surface to remove any loose sealant, dirt, or stains, as sealing over them will trap them. Any cracks or expansion joints should be filled with a flexible polyurethane caulk or asphalt sealer. In colder climates, use sand instead of salt for de-icing. Sand helps melt snow and ice without accelerating the freeze-thaw process, which can cause cracks.

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.

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.