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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
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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"
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+10

Response time2 days
Response rate100%
3 neighbors recently requested a quote
RCM Paving
4.0(
8
)
Asphalt Paving - InstallAsphalt Paving - Install- For Business

Serving Chestertown, MD and surrounding areas

Approved

Emergency services offered

Credit card accepted

Customers say: True professional

"Richard and his crew were awesome! They did an excellent job on my walkway/patio combination as well as the new asphalt driveway! They were very professional and accommodating. Richard’s pricing was far better than any other company I had received for the job. He made suggestions I hadn’t even thought of which really made it easy to work with. He was very knowledgeable and his crew knew exactly what to do. He treated us with respect and as he would with anyone. Great customer service! We highly recommend his company and will definitely use them in the future when the need arises, Thank you Rich and crew for a beautiful job! We love you guys!"
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+32

Response time8 hrs
Response rate100%
2 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

Compared to a 10x20 concrete driveway costing between $800 and $3,000, a resin bound driveway of the same size costing $3,900 to $4,000 is the more expensive option. However, the cost still makes resin a cheaper option compared to a 10x20 paver driveway costing an average of $12,000.

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.

While paving a driveway is possible to do as a DIY project, we don’t recommend it. Hiring a driveway professional to pave it will ensure that your driveway looks neat and clean and lasts for years to come, and it will also prevent a weak driveway and, potentially, damage to your foundation. Paving a driveway requires heavy machinery, and while you can rent the equipment needed, operating it close to your garage slab or around your home’s foundation can crack it and lead to structural issues. 

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.

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.

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.