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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

The answer to whether or not you need to get a permit before you start your driveway can vary widely based on local ordinances and the scope of your driveway ideas. In most urban and suburban areas, a permit is needed before building a new driveway to ensure that a homeowner is using safe materials and proper drainage practices while designing and constructing a new driveway. In some rural areas, a homeowner may not be required to apply for a permit. When building a new driveway on your own, always check with your local building department to see if you need to request a permit. When hiring a driveway contractor, verify that the right permits are being used before driveway construction begins.

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.

You can pour concrete over asphalt if it’s in good condition, thick, stable, and well-compacted. Concrete is more durable than asphalt and can extend the lifetime of your driveway without having to pay frequent asphalt driveway repair costs or replace it completely. 

But this is best reserved as a temporary solution based on budget restraints, as asphalt requires more frequent repairs and assessments than concrete. Once that concrete top is poured, it’ll be harder to accurately understand what’s happening beneath that layer, which could lead to more issues.

Pavers are a type of permeable hardscape that can be used for driveways, patios, walkways, and other landscaping features. Unlike poured concrete or asphalt, pavers typically have a layer of gravel underneath to prevent water runoff from damaging your property—though you can also lay pavers on grass. Because pavers are installed piece by piece, you can customize a one-of-a-kind hardscape that best suits your aesthetics, boosting your curb appeal along the way.

You can expect your asphalt pavement to last anywhere from 20 to 30 years, or 25 years on average. The life expectancy of your asphalt driveway depends on the climate, the amount of traffic, and how well you maintain it. While you can’t necessarily control some of these factors, you can control the amount of maintenance effort you put into your driveway. 

To prevent your asphalt from deteriorating prematurely, you should follow a good maintenance routine involving regular cleaning, reparation work, and resealing.

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.