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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

Box fill refers to the maximum number of conductors that can be contained within a wiring enclosure box, as well as the total volume of the components. Determining the allowable number of conductors in a box requires adding up the number of conductors, clamps, support fittings, devices and equipment, and equipment grounding conductors to make sure you’re within the allowable volume.

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.

Permeable paving is a good option for a lot of reasons. It can help prevent flooding, keeps harmful chemicals from polluting our water, and can divert water away from your home’s foundation. Plus, it can add a rustic aesthetic to your outdoor area, might prevent pests who breed in water, and may even qualify for tax rebates.

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.

Cobblestone driveways can take a major hit on anyone's bank account, begging the question of whether it's worth it to build a cobblestone driveway. Some homeowners might prefer more affordable driveway materials like concrete or pavers, which can give a similar appearance to cobblestone without the high price tag.

Paving your driveway costs between $2,500 and $6,600, to put that in perspective. But for others, there’s nothing quite like the timeless look of cobblestone 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.