3940 Skyway DR #55, Naples, FL 34112
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Property image
PENDING
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$750,000

  • 2 Beds
  • 2 Baths
  • 1,713 sqft

3940 Skyway DR #55, Naples, FL 34112

Est. Mortgage $5,032/mo*
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Home Highlights

Condo
Built in 1974
$438/sqft
2 Car Garage
HOA $363/mo

Local Information

  • Map ViewExplore the area around 3940 Skyway DR #55.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

One or more photo(s) has been virtually staged, AI generated or rendered. Experience a lifestyle unlike any other in Southwest Florida at Wing South Airpark, Naples' private gated aviation community. Welcome all! Whether you're a pilot, aircraft owner, or just appreciate the unique fly-in lifestyle, this exceptional property offers a rare opportunity to live in one of only 59 homes with shared ownership of a private 4,400' x 100' lighted paved runway. This well-maintained residence features a two-car garage, convenient car/plane-port with direct access taxiway, and a private screened swimming pool that creates the perfect setting for relaxing and entertaining year-round. The spacious screened lanai provides seamless sun or shade, indoor-outdoor Florida living in a peaceful setting. Recent improvements include a brand-new metal roof, newer appliances include water heater, washer, dryer, range, and dishwasher. The home also features quality vinyl wood-look flooring, refreshed landscaping, a freshly painted exterior, and a newly painted pool deck. This home awaits your touches or updates. All furnishings and contents currently in the home may remain, offering a move-in-ready opportunity. Owners at Wing South Airpark enjoy access to a pilot lounge/clubhouse, aircraft tie-down facilities, and discounted on-site aviation fuel. Each homesite includes a 1/59th ownership interest in the community's private 4,400' x 100' lighted paved runway. Ideally located just minutes from downtown Naples, residents enjoy convenient access to world-class dining, shopping, entertainment, schools, churches, and the pristine Gulf beaches. The renowned Fifth Avenue South and Third Street South districts are only a short drive away. You do not need to own an aircraft or be a pilot to live here. This unique community appeals to aviation enthusiasts and non-pilots alike who appreciate the privacy, security, and distinctive character of a fly-in neighborhood. OWNER FINANCING may be considered. Agent see confidential remarks. Airpark Information FAA Identifier: FA37 Runway: 18/36 Runway Length: 4,400' x 100’ CTAF/UNICOM: 122.9Cypress VOR: 108.6 (4.6 NM) Coordinates: 26°06'09" N / 81°42'02" W Rarely available and exceptionally located, this is a unique opportunity to live, fly, swim, and relax in one of Naples' most distinctive communities. One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered.
Last check for updates: about 24 hours ago
Listing courtesy of Beverly Bragiel, (239) 450-0297
Premiere Plus Realty Company
Originating MLS: Naples
Source: SWFLMLS, MLS#226022994
Also Listed on SWFLMLS.

Home Details for 3940 Skyway DR #55

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Bedroom, Dining Room, Kitchen
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1713 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Dishwasher, Disposal, Dryer, Range, Refrigerator/Freezer, Safe, WasherDishwasherDisposalDryerLaundry: Washer/Dryer Hookup,Inside,Laundry TubWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Carpet, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Floors: Carpet, Vinyl
View
Has a ViewView: Lake, Landscaped Area
Security
Security: Gated Community

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Deck, Patio, Open Porch/Lanai, Screened Lanai/PorchFoundation: Concrete BlockHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Carport Spaces: 2Number of Covered Spaces: 4Has a CarportHas a GarageHas an Attached GarageParking Spaces: 4Parking: Attached,Attached Carport
Pool
Pool: In Ground, Concrete, Screen EnclosurePool
Frontage
Waterfront: NoneNot on Waterfront
Farm & Range
Not Allowed to Raise Horses

Days on Market

Days on Market: 32

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Ranch
Building
Building: DSL/Cable AvailableConstruction Materials: Block, StuccoNot a New Construction
Property Information
Parcel Number: 82942200009

Price & Status

Price
List Price: $750,000Price Per Sqft: $438

Active Status

MLS Status: Pending

Media

Location

Direction & Address
City: NAPLESCommunity: WING SOUTH AIRPARK

Agent Information

Listing Agent
Listing ID: 226022994

Building

Building Area
Building Area: 2519 Square Feet

Community

Community Features: Clubhouse, GatedNot Senior Community

HOA

Association for this Listing: NaplesNo HOAHOA Fee: $4,352/Annually

Lot Information

Lot Area: 0.36 acres

Rental Terms, Policies & Fees

Partially Furnished

Miscellaneous

Mls Number: 226022994Water ViewWater View: Lake

Additional Information

HOA Amenities: Clubhouse,Community Room,See Remarks,Underground UtilitySource Internet Entire Listing Display

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Naples

At least 1698 Trulia users voted on each feature.

  • 86 % Say it's dog friendly

  • 83 % Say car is needed

  • 78 % Say parking is easy

  • 75 % Say it's quiet

  • 69 % Say people would walk alone at night

  • 69 % Say there's holiday spirit

  • 67 % Say there are sidewalks

  • 62 % Say yards are well-kept

  • 61 % Say streets are well-lit

  • 60 % Say they plan to stay for at least 5 years

  • 53 % Say neighbors are friendly

  • 51 % Say there's wildlife

  • 48 % Say kids play outside

  • 47 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 39 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Mfontaine21
    "Many community events at our town center including food trucks, swim and dance parties and weekly bingo"
    0
    Flag
  • Jeff W
    "What an awesome community. From the beach, to the restaurants, the berm, the amenities, people … just love Pelican Bay. "
    1
    Flag
  • Trulia User
    "Safe neighborhoods but be wary of some of the complexes as you move east. Naples is amazing if you do your homework "
    1
    Flag
  • Swatson645
    "There is so much space to walk your dog on nice sidewalks."
    0
    Flag
  • Chad Roberson
    "Quiet, people leave you alone here. No hoa, can expand on your property. Weather is amazing 6-8 months out of the year. You’ll see amazing wildlife everywhere in this area. "
    0
    Flag
  • Jimandhelensimon
    "We have an excellent location to access numerous beaches and have an enormous amount of well landscaped green space. Our pool feels like a resort pool."
    0
    Flag
  • Jarek Przada
    "Bingo, pool gymnastics, potluck, every holiday is celebrated in the community. There are pool parties and grill dinners."
    0
    Flag
  • Jimandhelensimon
    "This is more of a senior community. There are not many families with children here. The greater community is very family oriented."
    0
    Flag
  • James
    "lots of green space in the area and there are dog parks that also can be visited by dog owners and the place is always well groomed"
    1
    Flag
  • Sandra Decain
    "Great friendly people - love the dining access to water amazing weather. Could not ask for more. "
    0
    Flag
  • Michael.mccann
    "Lovely and quiet. Great location with beach and shopping/dining nearby. Homes are well maintained "
    0
    Flag
  • Michelle SanFillipo
    "Great dog parks and open spaces for recreational activities. Safe and secure. Well lit at night. Wide sidewalks and others are respectful of dogs and clean up."
    1
    Flag
  • Cristiano Machado
    "Friendly and safe neighborhood Close to schools, lhospital and grocery stores plus great restaurants and pubs"
    0
    Flag
  • Lisa Ethier
    "Everyone would love living in my neighborhood it’s beautiful. It’s family oriented. Everyone gets along with everyone."
    0
    Flag
  • Brian.bird
    "Fun people and safe gated community with golf and tennis and good food. Homes are nice and the grounds are well kept"
    0
    Flag
  • waterman46
    "Pet friendly all dogs on leashes . We have never had a problem and 99% pick up after their dogs. Just a really nice pet friendly area."
    1
    Flag
  • Jimandhelensimon
    "It’s dog friendly but dogs must be on a leash. The dogs must be twenty pounds or less unless they are an emotional support dog."
    0
    Flag
  • DonnaT
    "Naples is a great place to retire. It is paradise. The cost of living is outrageous but it is worth every penny! "
    0
    Flag
  • Wheeler04
    "The Isles is surrounded by nature with 1/2 of its 2,400 acres dedicated to preserve and waterways. Such a friendly and active community! "
    0
    Flag
  • Airwavessystem
    "I great community to live close to everything shops supermarkets and the beach. 15 minutes to the mall and 5 minutes to the main highway 75 to tampa Orlando or to miami."
    0
    Flag
  • Scottjohnnewhouse
    "I’ve lived in Naples for 33 years. It is growing at an alarming rate but it is such a safe place to live…."
    0
    Flag
  • Trulia User
    "Everyone in Naples is very kind and friendly. The crime rate is very low. It’s a very family friendly city. "
    0
    Flag
  • Eric
    "There are a lot of young families with children out playing with each other. The community center is well equipped with gym equipment and a beautiful pool."
    0
    Flag
  • Oditth Ricardo
    "Peaceful and safe. No issues and no problems most of the time. Great schools. Great place to start a family and raise kids. "
    0
    Flag
  • Jimandhelensimon
    "Beautiful open spaces and amenities. Beaches and large variety of restaurants and entertainment. The shopping is awesome and the people are fun loving."
    0
    Flag
  • Laurel
    "This is a family friendly neighborhood. It is close to the beach, the Greenway, the zoo, parks, theater, shopping, and dining. It’s close to downtown Naples and just a few miles to The Mercato. "
    0
    Flag
  • Nmarranca
    "I am here on vacation and it is a wonderful community. We are in Beachwalk, which is very close to the beach and walking distance and we have a big pool."
    0
    Flag
  • Kldaniel29
    "Family neighborhood great place laid back great schools nice place to live but pretty hot. Only set back"
    0
    Flag
  • Twalkercillins
    "Mostly retirees. Not a lot of children. Would not recommend for families with young children. Not very walkable."
    0
    Flag
  • Mccartneyjosh
    "It is a standard city commute with lengthy traffic lights and moderate to heavy traffic, but generally it is a normal commute "
    0
    Flag
  • Amolter
    "Lake park is close to everything anyone would want. Mall, restaurants, parks, dog park, hospital, grocery store, zoo, move theatre,downtown, boat launch to the bay, and the beach!!"
    0
    Flag
  • Blondbasket
    "Great groups of people live in the area. Everything is relatively easy and close to the house. I know my neighbors and they are so far very helpful and all around happy people. "
    0
    Flag
  • Kim
    "Activities are organized by HOA director they always have lots of activities planned lots of fun "
    0
    Flag
  • Kim
    "Very well kept sidewalks and community areas, yards are well maintained it’s so easily accessible to markets and stores very easy to walk around , biking is also easy to do there are nice friendly people "
    0
    Flag
  • Swatson645
    "Very convenient to major roads and businesses but quiet neighborhoods. Love this area! Just beautiful!!!"
    0
    Flag
  • Juntig5
    "Naples is a lovely place, tends to get crowded in the season, nice beaches and the city is clean with lots of restaurants. Pleasant weather. "
    0
    Flag
  • Jkgc11
    "There are Lots of community parks and activities for children. Miles of bike paths. Near the beach. "
    0
    Flag
  • Trulia User
    "Close to the beaches restaurant downtown feel like you on vacation family friendly and pet friendly neighborhood. Very clean and safe. Beautiful area "
    0
    Flag
  • Trulia User
    "Super nice location ! Close to beaches, downtown, everything you might want. Friendly neighbors. Close to restaurants, groceries, cafes. Beautiful homes. Historic homes "
    0
    Flag
  • Trulia User
    "Easy commute. Beautiful area to live in. Lovely people, friendly, helpful, very neighborly and close to everything."
    1
    Flag

Market trends in Naples

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$550K
$18.33KMoM
Sale-to-List Price
95.0%
0.1%MoM
Price per sq ft
$323
$9MoM
Available listings
4452
376MoM

Home Value

Trulia Estimate
$695K
Since last month
Decreased$33K (-4.5%)
Since last year
Decreased$36K (-4.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value decreased by -5% in the last 10 years
MonthEstimated value
2026
September 2026$693K
August 2026$694K
July 2026$726K
June 2026$729K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6292 Shadowood CIR #1701, Naples, FL
0.40
Condo
$394,000
09/30/25
2
2
1,350
4150 Skyway DR, Naples, FL
0.21
Condo
$850,000
12/19/25
3
2.5
2,151
6312 Shadowood CIR #1801, Naples, FL
0.39
Condo
$350,000
02/05/26
3
2
1,350
6283 Shadowood Cir, Naples, FL
0.44
Condo
$370,000
01/12/26
3
2
1,350
4883 Hampshire CT #301, Naples, FL
0.63
Condo
$530,000
03/04/26
2
2
1,669
6222 Shadowood CIR, Naples, FL
0.47
Condo
$370,000
02/12/26
3
2
1,350
4883 Hampshire CT #105, Naples, FL
0.62
Condo
$425,000
04/17/26
2
2
1,487

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
3987 SKYWAY DR LOT#18, Naples, FL 34112
0.08
-
-
-
-
Off Market
3967 Skyway DR, Naples, FL 34112
0.07
$1,449,000
3
2.5
2,180
For Sale
4009 Skyway DR, Naples, FL 34112
0.11
-
-
-
-
Off Market
3995 SKYWAY DR LOT#19, Naples, FL 34112
0.08
-
-
-
-
Off Market
4017 Skyway DR, Naples, FL 34112
0.08
$425,000
-
-
-
For Sale
4065 E Skyway Dr, Naples, FL 34112
0.12
-
-
-
-
Off Market
4072 SKYWAY DR LOT#44, Naples, FL 34112
0.14
$799,000
-
-
-
For Sale
4060 SKYWAY DR #45, Naples, FL 34112
0.15
$1,975,000
4
4
4,154
For Sale
4085 SKYWAY DR LOT#33, Naples, FL 34112
0.17
$695,000
-
-
-
For Sale
4150 Skyway DR, Naples, FL 34112
0.21
$850,000
3
2.5
2,151
Recently Sold
6312 Shadowood CIR #1801, Naples, FL 34112
0.39
$350,000
3
2
1,350
Recently Sold
6292 Shadowood CIR #1701, Naples, FL 34112
0.40
$389,700
2
2
1,350
Off Market

Price and Tax history

DateEventPrice
Aug 15, 2026
Source: SWFLMLS #226022994
Pending
$750,000
Jun 24, 2026
Source: SWFLMLS #226022994
ListingRemoved
$750,000
Jun 17, 2026
Source: SWFLMLS #226022994
Listed For Sale
$750,000

LGBTQ Local Legal Protections

Beverly Bragiel, Premiere Plus Realty Company
Agent Phone: (239) 450-0297
The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS. Copyright 2026 Southwest Florida MLS. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.

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Frequently asked questions about 3940 Skyway DR #55

  • What is the estimated monthly payment for 3940 Skyway DR #55?
    Based on a $750,000 list price with 20% down at today's rates, the estimated monthly payment for 3940 Skyway DR #55 in Naples, FL is approximately $4,751 (about $4,070 principal & interest, $606 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 3940 Skyway DR #55 compare to homes in Naples?
    3940 Skyway DR #55 in Naples, FL is listed at $750,000, about 36% above the $550K median sale price in Naples.
  • What do residents say about Naples?
    Residents describe Naples, FL as dog-friendly, easy to park in, and quiet. Most residents say you need a car. See homes for sale in Naples, FL.
  • What are the closest schools to 3940 Skyway DR #55?
    The closest schools to 3940 Skyway DR #55 in Naples, FL are East Naples Middle School (rated 8/10), Lely Elementary School (Pre-K, rated 7/10), Lely High School (rated 5/10).
  • Does 3940 Skyway DR #55 have air conditioning?
    Yes, 3940 Skyway DR #55 in Naples, FL has air conditioning.
  • Does 3940 Skyway DR #55 have a pool?
    Yes, 3940 Skyway DR #55 in Naples, FL has a pool.
3940 Skyway DR #55, Naples, FL 34112 is a 2 bedroom, 2 bathroom, 1,713 sqft condo built in 1974. This property is currently available for sale and was listed by SWFLMLS on Aug 15, 2026. The MLS # for this home is MLS# 226022994.