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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

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.

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.

Professionals restore the surface to a fresh, attractive finish by applying a new, even sealant layer.

Yes, a paved or repaved driveway can boost your home's value by increasing its curb appeal and the functionality of your outdoor space. A new driveway can add anywhere from $5,000 to $20,000 to a property's value. An old, crumbling driveway can be a red flag for potential buyers and inspectors.

The amount of value added depends on the materials used, the design, and local market conditions. Concrete is often cited as adding the most value due to its long lifespan, though asphalt may be more desirable in colder climates. The return on investment is greatest when replacing a driveway that is in poor condition; repaving a driveway that is already in good shape will not yield as significant an increase in value.

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.

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.