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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 time9 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
6 neighbors recently requested a quote
Recommended by70%of homeowners
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Paving Services FAQs, answered by experts

The material that’s best for your private road depends on your property, the climate in your area, and your personal preferences. Gravel is an affordable option, but some homeowners don’t like how it looks. It can be a pain to remove snow from, and it requires more ongoing maintenance than asphalt or concrete. However, while these other options require less maintenance and make snow removal a breeze, they’re more expensive and will need repairs from time to time. Ultimately, you’ll have to choose the road material that suits you and your property best.

The dimensions of a driveway apron vary based on local building codes, the width of your driveway, and the distance between the driveway and the road. On average, aprons range from 12 to 24 feet wide and 8 to 18 feet long. Typically, the end of the apron connected to the driveway matches its width—such as 10 to 12 feet for a single-car driveway—while the end at the street flares out to allow cars to turn in and out more easily. In some areas, you may not be responsible for the portion of the apron that extends beyond the sidewalk, but this depends on local laws.

If you miss the perfect time frame to trowel finish concrete, you likely won’t get the smooth, flawless result you’re looking for. In this case, you should contact a concrete professional or look to methods like sanding, grinding, or patching once the concrete dries. These methods will ensure the best final result for the lowest cost.

Costs range from $3 to $7 per square foot, depending on the area size and project scope.

Yes, it is possible to pave over an existing driveway, but whether it's the right choice depends on several factors. If the underlying structure of your current driveway is still strong, concrete or asphalt resurfacing can be a cost-effective way to prolong its life. However, if your driveway has significant issues like potholes, deep cracks, or other inconsistencies, it is best to remove the old driveway and start from scratch. Key factors to consider include the current driveway's condition, the compatibility of the new material, the added thickness and height, and the necessary surface preparation.

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.