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  • Average homeowner rating star icon4
    Average homeowner rating
  • Verified reviews icon25
    Verified tree services reviews

Top-Rated Tree service pros in Princess Anne - Updated Nov 2026

William Dagenhart Tree Service
4.6(
180
)
Tree RemovalTree TrimmingTree Removal - For Business+3 more

Serving Princess Anne, MD and surrounding areas

Approved

In business since 1991

Free estimates

Customers say: True professional

"The Dagenhart did a very nice job at my house. They were very personable and professional. The trees I needed trimed were extremely tall and they had no trouble completing the job. They were able to give me the estimate the same day they came to look and that was exactly what they charged. I listened to their suggestions and appreciated their knowledge. I’m very happy with the outcome. when they were done they cleaned up all the limbs and branches that they took down. I highly recommend them for their 40 years of experience and professional workmanship."
3 neighbors recently requested a quote
Recommended by95%of homeowners
Olbin Construction Services
4.6(
50
)
Tree RemovalTree Trimming

Serving Princess Anne, MD and surrounding areas

Approved

In business since 2004

Free estimates

Offers commercial services

Olbin Construction Services is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers interests and make their concerns the basis of our business.

3 neighbors recently requested a quote
Recommended by80%of homeowners
Avatar for Turf Dog Landscaping LLC
Turf Dog Landscaping LLC
5.0(
4
)
Tree Stump - RemoveTree Stump - Remove - For Business

Serving Princess Anne, MD and surrounding areas

Approved

Free estimates

Emergency services offered

Small jobs welcome

"Derrick brought in the mulch I needed within days. He and his crew are talented and dedicated, my beds were covered with 22 cubic yards. Derrick and one of his crew are also skilled at concrete and masonry, so I hired the pair to raise custom shaped and installed flag stones. I never thought I would find artisans with the skill to re-install them with the slope and fit required. They pulled it off"
Front view flower bed with stone edging
Patio make over
Patio make over
Patio make over
Patio make over

+1

6 neighbors recently requested a quote
Avatar for William R Dagenhart Tree Service
William R Dagenhart Tree Service
4.6(
162
)
Tree RemovalTree Trimming

Serving Princess Anne, MD and surrounding areas

In business since 2011

Free estimates

Credit card accepted

"Mr Dagenhart is extraordinary - knows what he is doing, does it efficiently and well, cleans up, great guy to talk with and work with - and the most reasonable prices. I strongly recommend Daganhart Tree Service"
Take Down
take down before and after
Response time1 day
Response rate96%
Recommended by97%of homeowners
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Tree Service FAQs, answered by experts

Generally, you’ll want to avoid pruning more than 25% of the tree’s canopy at one time. While pruning your tree is important, it’s possible to do it too often or to go too far. Again, this is why hiring a tree trimming pro to do the work is wise. However, if you do decide to DIY, going slow and trimming gradually is the name of the game.

It depends on the type of tree. Typically, late spring on the cusp of winter is ideal for trees about to emerge from dormancy and produce new buds. That said, late fall is ideal for certain deciduous trees prone to bleeding sap. Avoid trimming trees in early spring, when they’re prone to disease.

Leaving a dead tree can expose your other trees to potential diseases, pests, and fungi, and it can also be a hazard. If your tree is dead, then you should hire a tree maintenance service to remove it. Cutting down trees is extremely dangerous, and a professional can ensure no one gets hurt and there is no damage to your property. Tree removal costs between $200 and $2,000 and will prevent future issues and keep you and your property safe.

There are a few general rules to follow that will help you prune your trees correctly. One of the most important rules is to prune during the correct season for the type of tree you have. Typically, pruning should be during late winter. For younger trees, you should not remove more than a ⅓ of the tree's crown when pruning. Also, remember to remove dead and diseased branches first, then proceed with pruning the rest of the tree.

If the roots are still alive, the dead tree will usually try to put out new shoots. That doesn’t mean the tree will survive or that the dead parts of a tree will come back to life. If parts of the tree have died and turned gray or rotten, nothing will bring them back to life and they need to be safely removed.

The Princess Anne, MD homeowners’ guide to tree services

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