Tree Service in Windermere, FL
Tree removal, pruning and stump grinding for Windermere homes, from the oak-canopied streets of the town to lakefront lots on the Butler Chain, 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 Windermere Area
Completed jobs from our own records, August 2025–September 2026, listed by ZIP code. We never publish customer names or street addresses.
- Buddhist pine and palm removed, stumps ground
A Buddhist pine in the back corner needed a climber to remove it, and a palm in the other corner was also coming out. We removed both, ground their stumps plus an old stump in the middle of the yard, hauled everything away and trimmed two front palms.
RemovalClimberStump grinding - Laurel oak by the shed, climber pruning over the roof
A laurel oak stood at the corner of the detached shed, and other limbs hung over the roof, a chicken coop and the putting green by the lanai. We removed the oak by lift and ground the stump. A climber cut back the limbs over the roof and coop, and from the lift we raised branches over the circle drive.
RemovalClimberPruning - Bougainvillea removed, oak and magnolias raised
Three large bougainvillea had taken over the back wall, and the front trees crowded the driveway and the house. We cut the bougainvillea out and hauled them away, tipped back the front oak’s low limbs over the driveway, cut a magnolia back off the house and raised two more for clearance.
RemovalPruning - Four palms trimmed and a tree raised
Four palms were carrying seed pods and old fronds, and a tree in the yard had limbs growing downward. We trimmed the palms and, from the lift, raised and thinned the tree.
PalmsPruning
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 Windermere
Tree Removal
Dead, decaying and storm-broken trees taken down in sections, by climber, lift or crane, planned around houses, pool enclosures, driveways and lakefront lawns.
Tree removal in Windermere →Tree Trimming & Pruning
Roof, driveway and pool-enclosure clearance, deadwood removal and structural pruning for live oaks, pines and palms, following ANSI A300 pruning standards.
Tree trimming in Windermere →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 Windermere properties
Windermere is known for its tree canopy. The town’s streets run under big live oaks, and many lakefront lots on the Butler Chain of Lakes have oaks, cypress and pines that are older than the homes beside them.
Large trees close to houses, pool enclosures, driveways and roads mean access and clearance get planned before the work starts. Our ISA Certified Arborist checks a tree before we recommend taking it down, and many oaks here only need a good prune.
Our crews prune to ANSI A300 standards: no topping, no lion-tailing and no stripping out the interior of the canopy. Windermere is part of our regular routes between Winter Garden, Gotha and Dr. Phillips.
Neighborhoods we work in
- Town of Windermere
- Butler Chain of Lakes
- Keene’s Pointe
- Lake Down area
- Windermere Downs
- Lake Butler area
ZIP code 34786. Most homes with a Windermere mailing address are in unincorporated Orange County rather than the Town of Windermere. We work in both.
Permits
Tree rules differ between the Town of Windermere, 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 Windermere 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.
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.
Windermere tree service questions
Do I need a permit to remove a tree in Windermere?
It depends on where your property is and on the tree. Tree rules differ between the Town of Windermere, 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?
Yes. On soft lakefront ground we lay mats, use our tracked spider lift or have a climber do the work and carry the wood out, so the lawn and shoreline aren’t torn up.
How often should oaks in Windermere 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
Winter Garden Gotha Dr. Phillips Bay Hill Ocoee Orlando All service areas
