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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
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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

The average cost of 1,500 square feet of asphalt ranges from about $10,500 to $22,500, depending on location, thickness, base material, and how accessible the job site is to crews and equipment. Keep in mind that your asphalt material cost may vary depending on its type, ranging from porous asphalt to heated blacktop. Standard asphalt costs $7 to $13 per square foot.

To ensure you hire a reliable and experienced paving company, you should start by finding companies in your area that have at least five to ten years of experience working in your neighborhood. Next, rule out companies with poor reviews online or a series of complaints filed with the Better Business Bureau. Since driveways affect your curb appeal, you should also ask each company for references and pictures of recent work to make sure the work the company does is professional and high quality. Finally, check that the company is licensed and insured.

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.

Three inches is a great thickness for a residential asphalt driveway that sees minimal to moderate traffic from cars, SUVs, and pickup trucks. However, a thicker driveway can better withstand the weight of a heavier vehicle, such as a trailer or a recreational vehicle. If you drive a heavy vehicle on a thin driveway, you risk cracking and damaging it.

A driveway's lifespan varies by material. Asphalt driveways typically last 15 to 30 years, while concrete driveways last longer, between 20 and 50 years. The longevity of any driveway is affected by factors like extreme temperatures, heavy traffic, and the quality of maintenance. Regular upkeep, such as filling cracks, resealing the surface, and ensuring proper drainage, can help extend its life. For gravel driveways, regrading to fill in uneven areas every year or two is recommended.

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.