top of page

I lived at 3940 Skyway Drive, Naples, FL from 2020-2026.

3940 Skyway Dr, Naples FL 34112

I created this page so a potential buyer understands what they're walking into.
Everything stated herein is
100% factual.

Let's talk about the house.

This property is not “charming.” It is worn out and was maintained to the absolute minimum. The listing photos do not represent the issues with the property. It likely needs around $100,000 to bring it to a basic modern standard. I had previously considered buying it myself, so I did the math. This house was a rental unit for at least the past 6 years, and I think since 2013 (as that's when the current owner bought it, and he's never lived in it). In the 6 years I lived there, the owner never visited once. The owner's pattern has been to extract as much money as he can out of this house and put the least into it.

The listing states “newer appliances include water heater, washer, dryer, dishwasher.” The reality: the water heater is 5 years old and fails regularly. The washer has a recurring mold problem and does not dispense soap properly. The dishwasher is at least 6 years old.

 

The owner just put a new roof on the home—as the roof was over 50 years old—but that's where the good news starts and ends. There was a major leak in the laundry room for over a year (water damage in the attic, and floor, was never repaired). The east side of the plane port roof leaked for over two years and the owner refused to repair it.

Unless the owner replaced it with the re-roof (I suspect not), all ductwork is original (from 1972). An HVAC contractor told me the blown-in attic insulation is essentially gone from age. You are paying to cool and heat the outdoors.

All windows are original, and paper thin—you hear everything. Every cold start from neighbors’ Corvettes, Shelby Cobras, and Cadillac V-series cars cuts straight through the glass and into your sleep. Early-morning engine noise is routine (Cadillac guy is an airline pilot and sometimes leaves for the airport at 4am. Every time he starts that Cadillac, you'll hear and feel it in bed.)

The pool patio sliding doors are 50+ years old and not all fully close. All of the exterior doors are/were missing proper weatherstripping.

The house may require a full repipe. I heard drips inside the walls (especially behind the kitchen sink/living room wall after using hot water). Copper residue from the pipes clogged multiple shut-off valves and spigots during the years I lived there.

The HVAC system (air handler and condenser) is 15 years old and worked very hard in the south Florida heat. When the current HVAC system was installed, the air handler was relocated from the attic into the kitchen panty. The consequences of this were: halved panty space, permanently blocked off ceiling air return vents (but they lazily left dummy vents in the ceiling), and a condensate pump that you regularly hear running as it pumps the condensation from the coils up into the attic and out the side of the house. Check for mold in the air handler. The owner didn’t like paying for replacement UV lamps.

The standby generator and gas components (including regulator) are over 20 years old. It is much louder than any of the neighbors' generators and unlikely to produce even 9kW at full load despite being rated for 12kW. It does not power the A/C or hot water heater—only minimal circuits like lights and refrigerator. If you want meaningful backup power, you will need all new wiring because the current wiring cannot support more than 12kW.

The front driveway is two different colors from a recent patchwork repair. It is over 50 years old, heavily pitted with dozens of dark permanent stains, and could use a full replacement.

The rear driveway (plane parking area) has serious drainage issues and many foundation cracks. It floods in heavy rain and sometimes leaves hundreds of earthworms stuck to the surface that must be scraped off one by one (leaf blower, nor a broom, won't cut it). The epoxy coating on the rear driveway is failing and needs replacement (~$6K based on quotes).

The house originally had two driveway lights. The owner removed one entirely rather than spend $80 to replace a corroded lamp post. (Removing the light was cheaper than fixing it, which is a common modus operandi for the individual who has owned this house since 2012.) Unfortunately, good luck finding wherever the wiring for the removed lamp post is now.

The lawn usually looks great June/July/Aug, but spotty and weed-filled for about 9 months out of the year (I think due to problematic drainage — could never figure it out, as was always diligent with watering).

The carpeting throughout the home is builder-grade (lowest quality) and needs constant re-stretching or it bubbles (I had it re-stretched three times).

Some DIY electrical work is deeply concerning. The pool light is a 120V lethal shock hazard with no ground (I was forced to indefinitely turn off the circuit breaker after I discovered the issue and the owner refused to fix it.). Multiple exterior wall outlets do not function. One was arcing so bad it almost caused a fire (I have photos).

An HOA contractor repaired a severed underground power line using only electrical tape—an NEC violation and fire risk. I sent photos to the owner of this improper repair and recommended a proper waterproof burial kit. The owner stated, in writing, that he was satisfied with the tape repair. This is all but guaranteed to fail the remaining driveway light in time, and will be costly to dig up the yard to find the splice. That repair philosophy tells you everything about how this property has been maintained.

Breaker labeling was nonexistent and impossible to tell what circuit actually controls what. The breaker panel is located in the master bedroom closet (so if it ever catches fire, pray you'll wake up quick).

An electrician told me the pool cage is ungrounded, possibly causing electrolysis. Portions of the base of the pool cage have literally eroded into dust, leaving gaps. Paint has been flaking off of the pool cage for years, creating an endless recurring mess. I believe the owner put a new coat of paint on after I left, simply covering up the mess that is sure to recur.

The pool likely has a small but persistent leak. A professional leak detection company could not locate it. Maintaining water level is a constant chore.

The irrigation system frequently fails (likely due to the HOA's landscaper) and I poured $1,000 of my own money into it in the time I lived here (owner disclaimed responsibility, again trying to save every dollar).

 

The lawn is so mixed with so many varieties of weeds and incompatible grasses that a professional company said that a full resodding of the entire property would be required to ever have a nice looking lawn again.

Let's talk insects and wildlife.

The mosquitos are relentless. Don't even try going outside near sunset or sunrise. I had to put on pants if I wanted to go outside even for a minute during those hours. Wasps are worse—an abnormal number of mud daubers build mud nests across the exterior of this house every season. It must be their favorite house to build on—I removed at least 20 each season. One summer there were hundreds of frogs; you could not walk on the driveway without stepping on them. It was so bad that I made a post on Reddit seeking help with the "frog war" I expected the following season. I ended up paying $200 every two months to have a pest control company fog the entire yard. Frogs leave large droppings that must be cleaned regularly—it's a constant chore. Rabbits chewed through my landscape lighting wires three separate times. Extra large flying American cockroaches appear indoors regularly—at least two every couple of weeks. Worst of all are the anole lizards inside the house because they've proved impossible to eliminate. Peppermint sprays, sealing entry points, deterrent decoys—nothing worked. They likely inhabit the attic and reproduce faster than removal. And because the wall half way up and all the way around in the living room is directly open to the attic, there is no way to prevent pests in the attic from coming into the house. Living here simply means cohabitating with the lizards and seeing them on the walls and living room ceiling regularly. I'm told anoles primarily eat spiders and if you eliminate the anoles, then you might have a serious spider problem. And this all was not for lack of pest control. I invested more into pest control than almost any homeowner does and spared no expense ($100+ every month).

Let's talk neighbors.

Directly across the street is a former cop who patrols the neighborhood in his golf cart and monitors activity. If you're doing something he doesn't like, he's going to let you know about it. If you have a service van parked on the street in front of the house for more than a minute, he's going to tell them to move. (However, he doesn't follow this rule himself.) His house overlooks yours like a bird's nest. Privacy is limited. The immediate west neighbor (extremely loud Corvette) is the HOA president and is prone to shouting expletives from time to time when anything from his tiny dogs not obeying his orders, to tools not cooperating with him, sends him instantly crashing out. Worst of all, for your audible sanity, is the neighbor just 99 feet away to the northwest who has operated loud power tools on his driveway for years. Instead of sawing, grinding, and sanding inside of his garage, he rolls all of his power tools out onto his driveway so you can listen to every cut and every grind. Hundreds of cuts per week for years. I know the sound his tools make so well now that I hear them in my sleep. 

Let's (briefly) talk HOA.

One meeting was enough to see the dysfunction. It was a circus, to say the least. Board member turnover is frequent. The Wing South HOA, in my opinion with what I observed and from what other residents I've talked to have said, is as inefficient and frustrating as any HOA can possibly be. Lucky you if you get to live directly next to the president in charge of it.

Let's talk noise.

The noise here is never-ending—and it is not primarily from airplanes. This is unexpected because at first glance this appears like a quiet and peaceful location. But in this case, looks are very deceiving. 

MLS # 226022994

MLS #226022994

MLS# 226022994

MLS # 226022994

01

CONSTRUCTION.

An 80-acre master-planned development is being built 275 feet north. Construction likely continues through 2028. Work begins at 7am, Monday–Friday. Months of dynamite blasting shook the house enough to shift artwork.​​

02

LAWN MAINTENANCE.

HOA-controlled landscaping occurs up to four days per week in summer. You cannot opt out. Want to cut your own lawn? You can’t. Want to hire your own landscaper to cut the grass? Not allowed. The HOA’s landscaper is the epitome of incompetent. Their schedule is erratic and disorganized—often mowing the same lawn two consecutive days in a row. Often they’ll blow first, then edge (the opposite of how it’s supposed to be done). They routinely miss cutting large sections of the lawn. Equipment is extremely loud. Once they reach the bedroom windows, sleep is over. I tried putting sound blankets over the windows and using multiple noise machines—nothing can defeat the noise.

03

NEIGHBORS CUTTING/GRINDING/SANDING.

Across the street: three- to six-hour cutting sessions many Saturdays and Sundays and some week days too, often starting early. The table saw is rolled onto the driveway. Every cut is audible inside the home. If you don’t go batshit from the lawnmower, you will from the saw. And if the saw doesn’t do it, the 100 decibels cars will… 

04

NEIGHBORS CARS.

Three of four adjacent homes have extremely loud vehicles. West neighbor’s Corvette Z06 exceeds 110 dB on startup (and close to 100 dB at idle). Across the street: an AC Cobra rattles the home's window glass just when it’s idling. The neighbor with the saw drives a loud Cadillac and sometimes departs before sunrise for his airliner job.

05

GENERATORS.

Nearly every home at Wing South has a standby generator. Weekly 10–15 minute self-tests from multiple units create recurring noise. During outages, they all activate simultaneously (sleeping on power outage nights requires earplugs). The immediate neighbor installed their generator 15 feet away from the master bedroom window!

06

SHOOTING.

Somewhere west of the property is someone's private outdoor shooting range. Weekend afternoons can involve sustained gunfire for hours and thousands of rounds fired. Impossible to enjoy a peaceful evening on the lanai.

07

AIRPLANES.

Expected in an airpark—but additive. The two neighbors to the immediate west (including the HOA president) perform full-throttle static runs directly in front of the house rather than taxing to the nearby ramp.

The cumulative effect of noise is overwhelming. It resembles dense urban noise—but spread across mechanical, construction, and industrial sources instead of sirens. I rarely ever got good sleep, despite my best attempts to soundproof the bedroom.

 

If you are seeking peace and quiet, or low maintenance, this property will not provide it.

This house is the most problematic I ever lived in. If you decide to make an offer, my best advice is:

 

Hire a really good home inspector so you rightfully negotiate six figures off the price! The current owner paid just $120K for the house back in 2013, buying it off a dying friend who sold it to him well under market.

Here are some helpful notes for your home inspector...

PRE-SALE DISCLOSURE MEMO

3940 SKYWAY DRIVE, NAPLES FL 34112

 

Executive Summary 

 

This property presents substantial deferred maintenance, infrastructure risk, chronic environmental noise, and neighborhood-related quality-of-life concerns. Estimated baseline remediation exceeds $100,000 before elective upgrades.

I. Structural & Major Systems

Windows • Original 50+ year-old windows (paper thin)

HVAC & Insulation • Original ductwork (50+ years) • Attic insulation largely deteriorated • 15-year-old air handler and condenser

Plumbing • Audible in-wall drip leaks • Copper residue clogging shut-offs and spigots • Possible full repipe needed

Electrical • Pool light: 120V, ungrounded (shock hazard) • Multiple non-functional exterior outlets • Underground line previously repaired with electrical tape only (NEC violation) • Breaker panel poorly labeled; located in master closet • Pool cage reportedly ungrounded; evidence of electrolysis damage

Generator • 20-year-old unit • Rated 12kW; likely produces <9kW under load • Does not power A/C or hot water heater • Upgrade requires new wiring

Kitchen • Original (50+ years) and overdue for reno

Ceilings • Mismatch throughout house; some rooms have had the 1970s heavy popcorn removed and some remain with it

II. Exterior & Grounds

Driveways • Front: 50+ years old, pitted, mismatched patch repairs • Rear: flooding issues; epoxy failure (~$6K to refinish)

Pool • Suspected leak; professional detection inconclusive

Gutters • Missing gutters over plane port; gutters leak over pool

Irrigation & Lawn • Chronic failures despite >$1K in repairs • Lawn requires full resodding per professional opinion

Lighting • One driveway lamp removed rather than repaired ($80 fix avoided)

III. Environmental & Wildlife Factors

• Heavy mosquito activity • High mud dauber wasp presence (20+ nests per season) • Seasonal frog surges (hundreds at a time) • Rabbits damaging wiring • Frequent large American cockroaches indoors • Persistent anole lizards inside home despite heavy mitigation attempts

IV. Neighborhood & HOA Considerations

HOA • High turnover and dysfunction reported • Landscaping vendor mandated; cannot opt out

Privacy • Single story home surrounded by two-story homes; direct line-of-sight oversight from neighboring properties

V. Chronic Noise Exposure

Construction • 80-acre development 275 ft north • Ongoing through ~2028 • 7am weekday start times • Months of dynamite blasting historically

Landscaping • Up to 4 days/week in summer • Loud commercial equipment • Erratic scheduling

Neighbor Tool Use • Weekend wood cutting 6+ hours/day • Power tools operated on driveway

Vehicles • Multiple high-decibel performance cars • Early-morning departures (~4am)

Generators • Weekly multi-home test cycles • Simultaneous activation during outages

Shooting • Nearby private range activity on weekends

Aircraft • Expected airpark operations • Neighbors perform static full-throttle runs directly in front of house

VI. Also Check

  • Check for the water damaged floor in the laundry room from a roof leak.

  • Check the lanai slider doors in the dining room for a large gap where insects can come through.

  • Check the epoxy floor in the plane port. They appear to have concealed it in the listing photos, but the epoxy was installed poorly and will need to be redone.

  • Check in the living room half way up the wall above the ledge that goes around the perimeter. It’s directly open to the attic in many locations, and I had constant problems with lizards and cockroaches coming inside the home (plus cooling difficulties). 

  • Check the sliding door in the master bedroom. It scrapes and tears paint off the backside of the door. 

  • Look for the countless excavator-caused gashes on the north end of the driveway (looks like a t-rex chewed it up). The front driveway is mismatched due to a late 2025 project in which the entire front yard was dug up and the driveway cut through. 

  • Note there’s a hard start kit on the AC condenser outside.

  • Note the gutters only go half way around the house, which contributes to significant flooding in the plane port and run-out of the plant beds (dissolves the mulch and leaves bare dirt).

  • Look for multiple panels of the pool cage screening with holes/tears.

  • Note that several of the kitchen cabinets don’t close all the way and sit ajar. 

  • Note that not all of the kitchen cabinet faces match. 

  • Note the owner put a new coat of paint on the house before listing it, covering up multiple areas that aggressively rust.

Conclusion 

This property carries significant financial exposure, ongoing maintenance burden, and persistent noise intrusion. It is unsuitable for buyers seeking quiet enjoyment, low maintenance, or modern infrastructure reliability.

bottom of page