About Chesapeake Tree Service

Chesapeake Tree Service is a licensed and insured tree service built around Annapolis and the surrounding Anne Arundel County communities. We're a service-area business: rather than a storefront, we bring the crew, the equipment, and the expertise directly to your property — from the historic lots of West Annapolis and Eastport to the larger wooded parcels in Arnold and along the Annapolis Neck. That model keeps our overhead low and our response fast, which matters most when a tree is leaning over your roof or a storm has already brought one down.

Maryland Licensed Tree Experts

Every job we take is performed under a Maryland Licensed Tree Expert (LTE) credential, Maryland LTE-0000. Maryland is one of the few states that legally regulates tree care, and for good reason — removing or pruning a mature tree near a home or power line is genuinely dangerous work. Our LTE training covers safe rigging, hazard-tree assessment, proper pruning cuts, and the state and local rules that govern when and how trees can be removed. We carry full liability and workers' compensation insurance, and we're glad to show you our certificate before any work begins.

We know the Chesapeake Critical Area

What sets an Annapolis tree company apart isn't just horsepower — it's understanding where you can and can't cut. A large share of Annapolis sits within the Chesapeake Bay Critical Area, the regulated buffer that extends 1,000 feet inland from tidal waters. Removals in that zone often require a permit and a replanting plan, and the Historic District adds its own layer of review. We've worked these neighborhoods long enough to flag those requirements before they become a problem, helping you stay compliant while protecting the Severn, Spa Creek, and the Bay that make this area special.

Local trees, local knowledge

Annapolis canopies are a mix of loblolly pine, red and willow oak, tulip poplar, sweetgum, and crepe myrtle — each with its own habits and hazards. Salt-laden wind stresses waterfront pines, tight historic lots leave little room to drop a limb, and nor'easters and the occasional derecho test every weak crotch and dead leader. We bring the right approach and equipment for each situation, whether that's a careful crane-assisted takedown on a narrow Eastport street or routine structural pruning to keep a street tree healthy.

Straightforward service, every time

We believe in clear pricing, clean job sites, and honest advice — including telling you when a tree can be saved instead of removed. Estimates are always free, and we respond around the clock for emergencies. When the work is done, we haul away the debris and leave your property better than we found it.

Ready to talk about your trees? Call (540) 422-2198 or request a free estimate and we'll be in touch quickly.