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TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.8
    Average homeowner rating
  • Verified reviews icon15
    Verified asphalt driveway services reviews

Verified Reviews for Asphalt Driveway Service pros in Chestertown, MD

*The Angi rating for Asphalt Driveway Service companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Asphalt Driveway Service needs.

*The HomeAdvisor rating for Asphalt Driveway Service companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Asphalt Driveway Service needs.

Last update on February 04, 2026

Find Asphalt driveway pros in Chestertown

Avatar for Robert & Son Paving
Robert & Son Paving
4.8(
91
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1955

Free estimates

Credit card accepted

"Robert was very nice. He gave me an estimate, which included cutting out parts and replacing sections of my driveway, revealing the entire driveway and was able to do it in the same week. His men did a wonderful job and he came to check on them several times during the process. Highly recommend!!"
Paved
Paved
Paved
Seal Coat
Seal Coat

+38

Response time10 hrs
4 neighbors recently requested a quote
Recommended by73%of homeowners
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Avatar for Evans Paving
Evans Paving
4.2(
85
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 1974

Free estimates

Emergency services offered

"Mr. Evan's and his crew installed my circular driveway they made the whole process a wonderful experience they were prompt courtesy and professional I've recommended them to many friends and my family excellent service"
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
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Avatar for Always Waterproofing
Always Waterproofing
4.1(
416
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1995

Free estimates

Credit card accepted

"They provided a ball park estimate for replacing my driveway which is a few years away"
Updated concrete deck
Cozy front porch
Response time10 hrs
473 neighbors recently requested a quote
Recommended by93%of homeowners
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DDC Property Maintenance LLC
4.4(
11
)

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
3 neighbors recently requested a quote
Recommended by70%of homeowners
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Avatar for JB Trakas Contractor, LLC
JB Trakas Contractor, LLC
4.6(
10
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2017

Free estimates

Small jobs welcome

"Jamie was very responsive, came to site and measured. We went over many options and agreed on a path forward. Fence looks great. Crew tidied up after. Very pleased! Highly recommended!! Doggie happy to have his area now."
Fencing project
Fencing project
Fencing project
Fencing project
Fencing project

+6

Response time2 days
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Avatar for Boni Landscaping
Boni Landscaping
3.5(
12
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2011

Free estimates

Customers say: True professional

"It went very well. Boni was recommended to us and he was so professional and helpful when we met that we did not ask for quotes from other companies. He did not disappoint. The only delays were due to delays with raw material suppliers. Once the work began, the crew worked incredibly hard and cleaned up after each day’s work was completed. Boni was responsive to all questions. We plan to continue hiring him as we decide on additional landscaping and yearly clean-up."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+7

Response time2 days
1 neighbors recently requested a quote
Recommended by100%of homeowners
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Avatar for Leading Edge Avelar Contractors LLC
Leading Edge Avelar Contractors LLC
4.2(
15
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2005

Free estimates

Credit card accepted

"This company was very professional, timely and responsive to install my 15x12 concrete pad. Oscar and Douglas provided knowledgeable and honest input as a few issues developed. I am very satisfied with the quality of work and would highly recommend them."
Concert porch
Adding a square of concrete
Side walk
Frame
Ready to pour concrete

+60

Response time1 day
8 neighbors recently requested a quote
Recommended by76%of homeowners
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Asphalt Driveways questions, answered by experts

Many asphalt companies have experience with tar and chip paving, but not all. The process is unique enough—and not incredibly common enough—that you may have to look around for a tar and chip specialist. However, speaking with a driveway company is a great place to start, especially if they have experience with multiple materials.

Cobblestone is just one of many driveway materials. Other, more economical, albeit less elaborate options include concrete, asphalt, and gravel. 

If you want a material that most closely resembles cobblestone, your best option is bricks or pavers. Both cost anywhere from $10 to $50 per square foot and can be laid in all kinds of patterns. Depending on the type of paver you choose, you can also get a good bang for your buck by investing in durable natural stone.

Yes, with colored finishes and decorative stamping for a personalized touch.

The material that’s best for your private road depends on your property, the climate in your area, and your personal preferences. Gravel is an affordable option, but some homeowners don’t like how it looks. It can be a pain to remove snow from, and it requires more ongoing maintenance than asphalt or concrete. However, while these other options require less maintenance and make snow removal a breeze, they’re more expensive and will need repairs from time to time. Ultimately, you’ll have to choose the road material that suits you and your property best.

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

The Chestertown, MD homeowners’ guide to asphalt driveway services

From average costs to expert advice, get all the answers you need to get your job done.

See all articles