Tree Service in Winter Park, FL
Tree removal, pruning and stump grinding for Winter Park homes, from oak-lined brick streets to lakefront lots on the Chain of Lakes, with ISA Certified Arborist oversight.
Tree down on the house or across the drive? Our phones are answered 24/7. Crews are dispatched as availability, weather and safety allow. Emergency tree removal
- 4.8 ★Over 1,000 Google reviews
- ISA Certified ArboristProfessional oversight
- Fully insuredGeneral liability + workers’ comp
- Since 1987Serving Central Florida
Recent Tree Work in the Winter Park Area
Completed jobs from our own records, November 2025–July 2026, listed by ZIP code. We never publish customer names or street addresses.
- Hollow laurel oak by the driveway
A laurel oak beside the drive had a hollow cavity at the base. We took it down from the lift, then pruned and separated two front oaks to lift limbs 6–8 ft off the garage roof and take weight off a limb growing into the house.
RemovalPruningLift - Uprooted oak on a neighbor’s house
A laurel oak came out of the ground, roots and all, and fell across the neighbor’s backyard onto their house. We removed it in sections and hauled away all the debris. With the root ball out of the ground, there was no stump to grind.
Storm damageRemoval - Five pines and a 36-inch laurel oak
Five pines around the house and circle drive, plus a 36-inch laurel oak behind the home, came down with crane assistance and lift access. All stumps ground and grindings hauled, and a live oak pruned for clearance on the same job.
Crane-assistedStump grindingPruning - Overgrown fence line beside power lines
Volunteer trees, a dead citrus and a 12-inch tree growing beside overhead power lines had taken over the back fence. We cleared the fence line, ground stumps where it was safe for nearby oak roots, and lift-pruned two oaks and a camphor for about 8 ft of clearance.
RemovalPower linesPruning - Bamboo and fence-line trees removed
A strip of bamboo along the side property line came out and the clumps were ground, working around marked gas and water lines. A camphor, a queen palm and a cherry laurel growing into the back fence were removed and their stumps ground.
RemovalStump grindingArborist letter - Broken limb resting in the tree
A large limb had snapped and was hanging on the tree’s lowest limb in a back corner of the yard. We brought it down safely and hauled away everything on the ground.
Hazard limb
Our crews at work
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General photos of KTS crews and equipment, not photos of the specific jobs above. See more of our work
Tree services in Winter Park
Tree Removal
Dead, decaying and storm-broken trees taken down in sections, by climber, lift or our grapple-saw truck, planned around houses, pools, fences and the neighbor’s yard.
Tree removal in Winter Park →Tree Trimming & Pruning
Roof, driveway and street clearance, deadwood removal, lakefront view pruning and structural pruning for oaks, pines and palms, following ANSI A300 pruning standards.
Tree trimming in Winter Park →Crane Services
Our grapple-saw crane for tight or hazardous removals. When a tree is too big or too far from the street, we hire a larger crane and tell you before the job is booked.
Crane services →Storm Prep & Emergency Response
Pruning before hurricane season, phones answered 24/7, and cleanup of fallen trees and broken limbs. Dispatch depends on crew availability, weather and safety.
Emergency tree service →Also available: Stump grinding · Palm trimming · Arborist assessments & letters · Grapple truck debris hauling
What we see on Winter Park properties
Winter Park is known for its canopy. Big live oaks shade the older streets, and many yards have laurel oaks and pines that are older than the houses beside them. On smaller, older lots that usually means limbs over the roof, a driveway squeezed between two trees, and little room to bring equipment in. On lakefront lots, owners often want low limbs and moss lifted for the view without anything driving across the backyard.
Laurel oaks are our most common removal here. They’re shorter-lived than live oaks and often show a hollow or decay at the base, so our ISA Certified Arborist checks them before we recommend taking one down. We also remove a lot of dead Norfolk Island and Cook pines, which turn brittle quickly once they die.
Our crews prune to ANSI A300 standards: no topping, no lion-tailing and no stripping out the interior of the canopy. Winter Park is part of our regular routes, from 32789 near Park Avenue to the 32792 neighborhoods to the east.
Neighborhoods we work in
- Park Avenue & Downtown
- Hannibal Square
- Windsong
- Timberlane Shores & Lake Sue
- Lakemont
- Interlachen & Lake Osceola
- Along the Chain of Lakes
ZIP codes 32789 and 32792. Many homes with a Winter Park mailing address, especially in 32792, are in unincorporated Orange County. We work there too.
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.
ISA Certified Arborist Oversight
Our ISA Certified Arborist reviews hazard trees, keep-or-remove decisions and pruning plans. Estimates for ordinary tree work are free. A formal arborist assessment or letter, for example to document a dangerous tree, is a separate paid service.
Equipment that fits the yard
We own the equipment most Winter Park jobs need, so we plan the right setup for your property instead of waiting on rentals.
- Fassi 390 grapple-saw crane. Grips a section, cuts it and sets it down where we choose, so less climbing in dead or damaged trees and less rigging over fences.
- CMC 72HD spider lift. A tracked lift that fits through many backyard gates to reach oaks over pools, lanais and roofs.
- Chippers, loader and stump grinders. Brush is chipped on site, logs carried out without dragging them across the lawn, and stumps ground below grade.
For trees too large or too far from the street for our crane, we hire a larger crane and include it in your quote. On lakefront lots where equipment can’t go in, a climber does the work and limbs are lowered on ropes.
What tree work costs
Every job gets a free written quote with one fixed price. What moves the price most is the tree’s size and condition, what’s underneath it (roof, pool, power lines), how we get equipment to it, and whether stump grinding is included.
Typical price ranges from our job records: Tree removal cost guide · Tree trimming cost guide · Financing for jobs over $500
How an estimate works
- VisitWe look at the tree, access and what’s underneath it.
- Written quoteOne fixed price for the job, with any options laid out.
- Job dayMats down, controlled lowering, crane or lift if needed.
- Walk-throughWood hauled, site raked, you check the finish.
What customers say
Request a free estimate
Tell us about the tree and add a few photos. It only takes a couple of minutes.
Request a Free EstimatePrefer to talk?
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 service questions
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.
Are estimates free?
Yes. Estimates for ordinary tree work like removal, trimming and stump grinding are free, and you get one fixed price in writing. Formal arborist assessments and letters are a separate paid service.
What if a tree falls at night or on a weekend?
Call us. Phones are answered 24/7, and we dispatch a crew as availability, weather and safety allow. If anyone is hurt or a tree is on a power line, call 911 and the power company first.
Can you work on a lakefront lot without driving across the yard?
Yes. When equipment can’t go in the backyard, a climber does the pruning or removal and limbs are lowered on ropes and carried out. We plan access and protection with you at the estimate.
How often should oaks in Winter Park be trimmed?
Mature live oaks often do well on a 2–3 year pruning cycle. Laurel oaks, which are shorter-lived and more prone to decay, and any tree hanging over a roof may need a look more often.
What’s included in your cleanup?
Brush is chipped and hauled away, wood is removed, and hard surfaces are raked and blown. When stump grinding is part of the job, grindings are hauled away unless you ask us to leave them for your beds.
Are you insured?
Yes. Kevin’s Tree Service carries general liability and workers’ compensation insurance. Certificates of insurance are available upon request.
Nearby areas
Maitland Orlando Casselberry Winter Springs Oviedo Longwood All service areas
