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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
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

"Tom C. ⭐️⭐️⭐️⭐️⭐️ Excellent Service from Evans Paving, LLC I couldn’t be more impressed with the outstanding work Evans Paving did on our challenging driveway. They professionally paved over 1,500 feet of driveway, including two large parking pads, pitched driveway for water runoff and completely transformed our property. Their team didn’t just pave — they went the extra mile by removing and cutting away invasive tree roots that had destroyed the old driveway. The attention to detail was clear from start to finish, and they sealed the entire project beautifully, leaving us with a clean, smooth driveway. Every step of the project was handled with professionalism, quality and attention to detail at a very reasonable price. If you’re looking for quality work, a reliable crew, and a reasonable price, Evans Paving is the team to call. We already recommended them to our family and friends."
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
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
Additional Photos
Additional Photos
Additional Photos
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

After removing existing moss, consider using paver blocking sand to fill the joints. This specialty material hardens once placed and serves as an effective barrier against moss and weeds. From there on, regularly clean your pavers and try to keep them dry. You can also seal your paver as a semi-permanent solution — just make sure you reseal every 3 to 5 years.

If your driveway is cracked, you can repave it with a process called asphalt overlay. Overlay is more cost-effective than a full replacement but is better suited for minor cracks and issues. If you have major cracks or other problems like water pooling, asphalt overlay isn’t your best bet. Plus, paving over a cracked driveway only extends the lifetime by about 10 years, whereas replacing it would start the clock over completely to give you up to 30 years.

In most cases, driveway repair is worth the investment. Your driveway is one of the first things people see when they look at your home, so repairing cracks, chips, and potholes can improve your home’s curb appeal and overall value. Repairing your driveway is also almost always more affordable than replacing it entirely—an average of $1,765 compared to the cost of replacing a driveway, which typically costs around $5,000.

The most obvious disadvantage of permeable paving is that the cost is typically higher compared to non-permeable concrete, pavers, or asphalt methods. Also, the porous material can get clogged with dirt and debris, requiring cleaning and power washing more frequently than standard paving materials and methods. Although permeable paving is not ideal for highways, airports, and other surfaces supporting heavy traffic and machinery, it is suitable for regular residential driveways.

Driveway pavers are often worth the cost. Paver types like cobblestone, brick, and concrete are highly durable, and permeable paver options can be tremendously eco-friendly. While you may pay more for a paver driveway, you’ll see great returns from the increased curb appeal and low maintenance compared to other types of driveways.

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.