138 Windward Cay, Naples, FL 34114
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Property image
OFF MARKET

138 Windward Cay
Naples, FL 34114

  • 2,228 sqft (on 0.29 acres)

$796,600

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $4,705/mo*
Refinance Your Home

$796,600

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $4,705/mo*
Refinance Your Home
2,228 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 138 Windward Cay.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Lot/Land
Year Built
2019
Lot Size
0.29 acres
Living Area
2,228 sqft
Price/Sqft
$358

About this House

Port of the Islands Phase II key lot with south exposure. 151 feet on the water for your dock with your boat. Direct access to excellent fishing (Tarpon, Snook, Redfish, Grouper, Stone Crab, Flounder, Pompano, Snapper, Sea Trout, Sheepshead) and boating in The Ten Thousand Islands and the Gulf of Mexico. Build your dream retirement home in one of the nature wonderlands of the world. Port of the Islands has its own Collier County fire station with fully trained EMS firemen. And its own water (new reverse osmosis treatment plant 2014) and sewage treatment plant. Located inthe edge of the Everglades yet only 20 miles from Naples and 14 miles from Marco Islands restaurants, attractions and shopping. 50 miles to the SW Florida Airport in Fort Myers. 90 miles to Miami. Three hours to the Florida Keys.
138 Windward Cay, Naples, FL 34114 is a 2,228 sqft lot/land built in 2019. It last sold for $126,500 on Mar 12, 2019. It is currently off market. The Trulia Estimate is $796,600, with a rent estimate of $3,914/month.

Home Details for 138 Windward Cay

Exterior Features

Exterior Home Features
Roof: OtherDeck
Pool
Pool

Property Information

Year Built
Year Built: 2019
Property Type / Style
Property Type: Lot LandArchitecture: Other

Lot Information

Lot Area: 0.29 acres

Price History for 138 Windward Cay

DatePriceEventSource
03/12/2019$126,500Sold
N/A
03/04/2019$155,000PendingAgent Provided
11/03/2018$155,000Listed For SaleAgent Provided
09/08/2018$165,000ListingRemovedAgent Provided
01/25/2018$165,000PriceChange
Agent Provided
12/07/2017$175,500PriceChange
Agent Provided
01/03/2017$195,500PriceChange
Agent Provided
01/10/2015$225,000Listed For SaleAgent Provided
02/08/2011$125,000Sold
N/A
01/05/2011$125,000Listed For SaleAgent Provided
12/28/2010$74,900Sold
N/A
04/19/2005$575,000Sold
N/A

Market trends in Naples

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$568K
$19KMoM
Sale-to-List Price
95.2%
0.1%MoM
Price per sq ft
$330
$0MoM
Available listings
5204
766MoM
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Property Tax and Assessment

Year2025
Tax$6,350
Assessment$945,857
Home facts updated by county records

Comparable Sales for 138 Windward Cay

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
525 Newport Dr, Naples, FL
0.40
Lot/Land
$62,000
02/27/26
-
-

Nearby homes

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Assigned Schools

These are the assigned schools for 138 Windward Cay.
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 1696 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.
  • Swatson645
    "There is so much space to walk your dog on nice sidewalks."
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  • 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. "
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  • 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."
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  • Jarek Przada
    "Bingo, pool gymnastics, potluck, every holiday is celebrated in the community. There are pool parties and grill dinners."
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  • Jimandhelensimon
    "This is more of a senior community. There are not many families with children here. The greater community is very family oriented."
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  • 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
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  • Michael.mccann
    "Lovely and quiet. Great location with beach and shopping/dining nearby. Homes are well maintained "
    0
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  • 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
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  • Lisa Ethier
    "Everyone would love living in my neighborhood it’s beautiful. It’s family oriented. Everyone gets along with everyone."
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  • Brian.bird
    "Fun people and safe gated community with golf and tennis and good food. Homes are nice and the grounds are well kept"
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  • 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
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  • DonnaT
    "Naples is a great place to retire. It is paradise. The cost of living is outrageous but it is worth every penny! "
    0
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  • 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
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  • 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
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  • 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
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  • Trulia User
    "Everyone in Naples is very kind and friendly. The crime rate is very low. It’s a very family friendly city. "
    0
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  • 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
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  • 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
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  • Jimandhelensimon
    "Beautiful open spaces and amenities. Beaches and large variety of restaurants and entertainment. The shopping is awesome and the people are fun loving."
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  • 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
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  • 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
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  • Kldaniel29
    "Family neighborhood great place laid back great schools nice place to live but pretty hot. Only set back"
    0
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  • Twalkercillins
    "Mostly retirees. Not a lot of children. Would not recommend for families with young children. Not very walkable."
    0
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  • Mccartneyjosh
    "It is a standard city commute with lengthy traffic lights and moderate to heavy traffic, but generally it is a normal commute "
    0
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  • Jt276297
    "It’s one of the cleanest towns in the United States and has a vast number of culture with in it’s population "
    0
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  • 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!!"
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  • 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. "
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  • Kim
    "Activities are organized by HOA director they always have lots of activities planned lots of fun "
    0
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  • 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 "
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  • Swatson645
    "Very convenient to major roads and businesses but quiet neighborhoods. Love this area! Just beautiful!!!"
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  • H5hnmg992c
    "none. i like that it isn’t gated. its a friendly neighborhood and people are kind. it’s becoming more accessible to food and restaurants"
    2
    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
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  • Jkgc11
    "There are Lots of community parks and activities for children. Miles of bike paths. Near the beach. "
    0
    Flag
  • Naplesjan29
    "The school’s are excellent and close by! It’s a very safe and convenient area!!The school bus picks up here daily."
    0
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  • 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
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  • 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

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Homes for sale near 138 Windward Cay

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Off Market Homes Near 138 Windward Cay

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