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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
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
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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

Driveways should be sloped with a minimum 2% slope—anything lower will cause precipitation and runoff to collect. A 2% slope is the equivalent of a 2-foot rise over 100 feet. One quick way to check the integrity of your driveway’s slope: no more than four inches of water should collect on the surface longer than 15 minutes after rain.

Box fill refers to the maximum number of conductors that can be contained within a wiring enclosure box, as well as the total volume of the components. Determining the allowable number of conductors in a box requires adding up the number of conductors, clamps, support fittings, devices and equipment, and equipment grounding conductors to make sure you’re within the allowable volume.

If you notice minor cosmetic problems with your driveway, you should seal it. Look out for cracks and holes on the surface, faded asphalt or concrete, and stains from oil and other chemicals. Replacing your driveway may be necessary if you’re dealing with significant problems—¼-inch cracks, large potholes, and puddles from drainage issues. The cost to install an asphalt driveway typically ranges between $4,200 and $9,000, significantly more than resealing. Consider talking to a professional to discuss whether resurfacing your driveway—a midway project between resealing and replacing—is a better option for you.

If your new pavers look dull or unclean, it is likely due to efflorescence, a chalky, white powder that forms when lime in the pavers gets wet. This condition often resolves on its own, as rain will naturally wash it away within about a year. For faster results, you can use a pressure washer to clean the pavers. Alternatively, consider using cleaning products specifically designed to remove efflorescence or applying sulfuric acid crystals.

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.