Tree Removal in Winter Park, FL
Dead, decaying and storm-broken trees taken down in controlled sections, planned around your roof, pool, fences and the neighbor’s yard, with ISA Certified Arborist oversight and full cleanup.
Tree on the house right now? Phones are answered 24/7. Emergency tree removal
- 4.8 ★Over 1,000 Google reviews
- ISA Certified ArboristProfessional oversight
- Fully insuredGeneral liability + workers’ comp
- Since 1987Serving Central Florida
Most removals we do in Winter Park happen on lots with very little room. The tree is beside the house or the pool, on the property line with a fence on both sides, or in a backyard you can only reach through a neighbor’s yard. Often it’s a laurel oak with a hollow at the base or a pine that has died. Each one gets a plan for how the wood comes down, where it lands and how equipment gets to it before anyone starts a saw.
You get a written quote with one fixed price. Only need clearance? See tree trimming in Winter Park, or go back to our Winter Park tree service page.
When removal is the right call
- The tree is dead or dying. Dead pines and oaks get brittle quickly and shouldn’t be climbed, so we use our grapple-saw truck, a crane or a lift where we can.
- Decay at the base or a split trunk. Hollows, fungus at the root flare, cracks in the trunk or a co-dominant split that’s opening up.
- Storm damage that can’t be pruned out. A tree uprooted or leaning after a storm, a trunk broken in half, or a top that has failed.
- The wrong tree in the wrong place. Camphors, bamboo and other fast growers pushing into the roof, the fence or a better tree.
Not sure? Our ISA Certified Arborist can tell you if pruning will do instead of removal. Many oaks just need a good prune.
Recent Winter Park removals
From our own job records, April–October 2026. Listed by ZIP code only. We never publish customer names or addresses.
- Front-yard laurel oak, crane-assisted
A 26-inch laurel oak, about 50 ft tall, stood in the middle of the front yard. It came down with crane assistance, the stump was ground and roots chased inside the bed border, and landscape rock and a small shrub were moved out of the way first.
- Two big laurel oaks beside the house
Two laurel oaks of about 24 and 20 inches, with 50–60 ft spreads, stood along the side of the home. Both were removed with crane assistance and our grapple truck, and the stumps were ground and the grindings hauled.
- Dead two-stem Norfolk pine behind the home
The crane was set up out front and a climber rigged both stems so the sections could be lifted out over the house. Trunks were left 2–3 ft tall at the owner’s request, with a light grind in the bed around a crape myrtle’s roots.
- Laurel oak in a fenced side yard
An 18-inch laurel oak grew inside a fenced side yard right on the neighbor’s line. Our grapple-saw crane cut and lifted each section out from above, so nobody had to rig over the fences. All debris hauled away.
- Dead pine reached through the neighbor’s yard
The only way to a dead Norfolk pine beside the house was through the neighbor’s front yard. With their permission, we removed it with crane assistance and lift access, then ground its stump and an old one in the front bed.
- Dead pine and an overgrown back corner
A dead Cook pine in the back corner came down from the lift and its stump was ground. Small camphors and a plumeria crowding the wall were removed, the other corner was cleared of underbrush, and everything was hauled away.
What happens on removal day
- Walk-throughWe reconfirm the plan with you: which trees, where the wood comes down, and how equipment gets in.
- ProtectionGround mats at entries, spotters at pools and service lines, a fence panel taken down and put back if access needs it.
- Controlled removalSections lowered on ropes, lifted out with our grapple-saw crane, or cut from our lift, depending on the tree.
- CleanupBrush chipped, wood hauled, beds raked and hard surfaces blown off. Stumps ground if they’re on your quote.
Climber, lift or crane?
We pick the method for each tree, not one method for every job.
- Climbing and rigging: for trees we can’t reach with equipment, like on a lakefront lot or along a back property line where nearby oak roots need protecting.
- Our CMC 72HD spider lift: for backyard trees over pools and lanais. It’s tracked and fits through many gates a truck can’t.
- Our Fassi 390 grapple-saw crane: for dead or hazardous trees reachable from the street or driveway. It holds each piece while it’s cut.
- A hired larger crane: for very large trees or long reaches over a house. We arrange it and include it in your quote before the job is booked.
Stumps and cleanup
Stump grinding can go on the same quote. We grind roughly 4–12 inches below grade, depending on roots and site conditions, and can chase surface roots in beds. Choose whether the grindings are hauled away (best before new sod) or left for your beds.
Sometimes we recommend not grinding, for example when a stump shares roots with an oak you’re keeping. We’ll explain that at the estimate. More about stump grinding
Permits
Tree rules differ between the City of Winter Park, unincorporated Orange County and HOAs, so we’ll help you check what applies to your property. Kevin’s Tree Service can assist with tree removal permit applications when required.
Arborist letters
Certain trees on eligible single-family residential properties may qualify for an exemption under Florida Statute 163.045. Not every tree qualifies, and HOA requirements are separate.
Our ISA Certified Arborist can assess the tree and, when it qualifies, provide a letter documenting the risk. This assessment is a paid service, separate from your free removal estimate. About our ISA Certified Arborist
What affects the price
We price by the job, not by the hour. The biggest factors are the tree’s size and condition, what’s under it, how we get equipment to it, and whether a hired crane or stump grinding is needed. You get one fixed price in writing before anything is scheduled.
Insured crews
Kevin’s Tree Service carries general liability and workers’ compensation insurance. Certificates of insurance are available upon request. Insurance details
What customers say
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Our phones are answered 24 hours a day, 7 days a week.
| Office | Monday–Friday, 8 am–4 pm |
| Weekends | Office closed; phones still answered |
| Holidays | Office closed on major holidays |
Emergency dispatch depends on crew availability, weather and safety.
Winter Park tree removal FAQs
Do I need a permit to remove a tree in Winter Park?
It depends on where your property is and on the tree. Tree rules differ between the City of Winter Park, unincorporated Orange County and HOAs, so we’ll help you check what applies to your property. Kevin’s Tree Service can assist with tree removal permit applications when required. Certain trees on eligible single-family residential properties may qualify for an exemption under Florida Statute 163.045. Not every tree qualifies, and HOA requirements are separate. Professional arborist assessments and letters are separate paid services.
Can you remove a tree beside my house or over the pool?
Yes. That’s most of our Winter Park removal work. We take the tree down in sections and lower or lift the wood with ropes, our spider lift or our grapple-saw crane, depending on the tree and access.
What if the only access is through a neighbor’s yard?
We’ll plan it with you. Sometimes a neighbor agrees to let equipment through, and we protect their yard the same way we protect yours. Otherwise a climber, our spider lift or a crane working from the street can often do the job.
Do you grind the stump too?
If you want. Stump grinding can go on the same quote, and you choose whether the grindings are hauled away or left for your beds. When a stump shares roots with a tree you’re keeping, we may recommend leaving it.
Are you insured?
Yes. Kevin’s Tree Service carries general liability and workers’ compensation insurance. Certificates of insurance are available upon request.
