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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
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"
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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!"
Additional Photos
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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

A 500-square-foot driveway can cost anywhere from $5,000 to $35,000, depending on the type of pavers you choose. Grass and concrete pavers are more affordable, while stone and cobblestone pavers are on the higher end of that price range. You’ll save some money by DIYing the installation, though we highly recommend sticking with a professional for this type of driveway installation.

Gravel is the cheapest way to extend a driveway. Gravel is an affordable, practical option that’s easy to install and perfect for DIY projects, helping you save on labor costs. It can be quickly spread and leveled to create extra driveway space without heavy preparation. While gravel doesn’t offer the same durability or finished look as concrete or asphalt, its low cost makes it ideal for budget-conscious homeowners who want a functional solution without overspending.

A pallet of pavers will cost about $300 to $700 per pallet. Each pallet covers about 56 square feet. The specific price you pay per pallet of pavers will depend on a few factors, including the type of paver you’re buying, the size and shape of the pavers, and how many pavers you need. In some cases, you’ll spend less per pallet if you’re buying in bulk for very large paver patios.

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.

Interlocking pavers offer a number of advantages over regular pavers. For instance, they’re more durable, more resistant to shifting, and easier to repair. There are also permeable options that allow for drainage. However, interlocking pavers are more often more expensive than regular pavers and are prone to growing weeds over time.

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.