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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

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.

While it may be less expensive initially to lay concrete vs. pavers, the long-term expenses that come with repairing concrete may prove to be less cost-friendly than simply replacing a few damaged pavers. On top of that, stamped concrete may only last for 25 years compared to pavers, which can last over 50 years.

Pavers will crack in a fire pit if they are made of the wrong materials. Be sure to use kiln-fired brick paver stones when building your backyard fire pit. You can also purchase a fire pit project kit, which will sometimes come with fire-safe pavers, to help you avoid the guessing game of buying pavers separately.

You’ll first need to install a base underneath your pavers for extra stability and drainage. Otherwise, the pavers can sink into the ground, and you’ll have to reinstall them. Use a base gravel layer of 4 to 6 inches for walkways and 10 to 12 inches for driveways. Compact your gravel layer every 2 to 4 inches so it’s nice and solid. After you install your gravel base, apply a 1-inch layer of sand on top.

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.

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.