143 Windward Cay, Naples, FL 34114
OFF MARKET

$1,084,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,688 sqft (on 0.31 acres)

143 Windward Cay, Naples, FL 34114

Est. Refi. Payment $6,720/mo*
Refinance Your Home
Currently Off Market - Sold Mar 3, 2011 for $500,000

Home Value

Trulia Estimate
$1.08M
Since last month
Decreased$11K (-1%)
Since last year
Increased$23K (+2.1%)
Since last sale
Increased$587K (+117.4%)
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 increased by +64% in the last 10 years
MonthEstimated value
2026
September 2026$1.09M
August 2026$1.1M
July 2026$1.09M
June 2026$1.11M
May 2026$1.09M
April 2026$1.1M
March 2026$1.11M
February 2026$1.11M
January 2026$1.09M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
161 Venus Cay, Naples, FL
0.12
Single-Family Home
$945,000
12/16/25
3
2
2,250
171 Cays DR, Naples, FL
0.12
Single-Family Home
$750,000
11/03/25
3
2
1,913
200 Cays Dr, Naples, FL
0.22
Single-Family Home
$466,000
07/15/26
3
2
1,487
101 Morning Star Cay, Naples, FL
0.13
Single-Family Home
$1,426,000
04/24/26
3
2
2,661
127 Newport DR, Naples, FL
0.23
Single-Family Home
$775,000
04/30/26
3
2
1,841
171 Sunset Cay, Naples, FL
0.21
Single-Family Home
$1,175,000
01/21/26
3
2
1,929
110 Morning Star Cay, Naples, FL
0.20
Single-Family Home
$900,000
02/05/26
3
2.5
2,124
121 Newport Dr, Naples, FL
0.24
Single-Family Home
$885,000
09/15/26
4
2
2,129
191 Eveningstar Cay, Naples, FL
0.25
Single-Family Home
$630,000
10/23/25
3
2
1,997
158 Eveningstar Cay, Naples, FL
0.18
Single-Family Home
$650,000
01/07/26
3
2
1,342

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
157 Venus Cay, Naples, FL 34114
0.11
$600,000
-
-
-
For Sale
172 Venus Cay, Naples, FL 34114
0.11
$790,000
4
2
2,320
Off Market
161 Venus Cay, Naples, FL 34114
0.12
$945,000
3
2
2,250
Recently Sold
149 Venus Cay, Naples, FL 34114
0.12
-
-
-
-
Off Market
171 Cays DR, Naples, FL 34114
0.12
$744,600
3
2
1,913
Off Market
176 Venus Cay, Naples, FL 34114
0.13
$900,000
3
2
1,773
For Sale
133 Wilderness Cay, Naples, FL 34114
0.08
$1,738,300
3
3
2,678
Off Market
141 Wilderness Cay, Naples, FL 34114
0.10
$1,888,000
3
3
2,223
For Sale
161 Cays Dr, Naples, FL 34114
0.11
$1,478,400
3
2.5
2,487
Off Market
101 Morning Star Cay, Naples, FL 34114
0.13
$1,426,000
3
2
2,661
Recently Sold
191 Cays DR, Naples, FL 34114
0.17
$1,068,500
3
2.5
2,410
Off Market
132 Wilderness Cay, Naples, FL 34114
0.11
$1,405,100
3
2.5
2,146
Off Market

Local Information

  • Map ViewExplore the area around 143 Windward Cay.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
0.31 acre lot
2,688 sqft
$404/sqft

About this House

Executive retreat. Very Nice. You'll like it. Newer pool. Dock/Lift...both 3 years old. Large Hot Tub Too. Doorway to the 10,000 Islands, the Fisherman's Paradise. Elec. Storm Shutters. Larger Rooms with Neutral Tile. Furnished Turnkey & Boat Negotiable. Port of the Islands is a direct access to the Gulf of Mexico and 10,000 Islands boating and fishing community in Naples Florida, at the edge of the Everglades just 20 miles south of cosmopolitan downtown 5th Avenue and Naples white sandy beaches. Some of the best fishing in Southwest Florida is just steps from your door. Fish for tarpon, snook, redfish, snapper, pompano, trout, catfish...or head across the street where the fresh water river boasts bass fishing! Watch the manatees play, gators cruise, even the dolphins make their way up the channel. Nature is all around the Port of the Islands community. You'll see eagles soar, egrets, and pelicans.
143 Windward Cay, Naples, FL 34114 is a 3 bedroom, 2 bathroom, 2,688 sqft single-family home built in 1999. It last sold for $500,000 on Mar 3, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,084,800, with a rent estimate of $8,201/month.

Home Details for 143 Windward Cay

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Property Information

Year Built
Year Built: 1999Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Exterior Features

Exterior Home Features
Deck
Pool
Pool

Community

Units in Building: 1

Lot Information

Lot Area: 0.31 acres

Price and Tax history

DateEventPrice
Mar 3, 2011
Source: N/A
Sold
$500,000
Jan 31, 2011
Source: Agent Provided
Pending
$575,000
Jan 27, 2011
Source: Agent Provided
Listed For Sale
$575,000
Jul 24, 2010
Source: Agent Provided
ListingRemoved
$685,000
Feb 16, 2010
Source: Agent Provided
PriceChange
$685,000
Price decreased by 12%

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

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.
  • Silvia Polgati
    "Is a quiet neighborhood we really enjoy "
    0
    Flag
  • 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
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 143 Windward Cay

  • What is 143 Windward Cay estimated to be worth?
    Trulia's estimated value for 143 Windward Cay in Naples, FL is $1,084,800.
  • What is the price history for 143 Windward Cay?
    143 Windward Cay in Naples, FL last sold for $500,000 in March 2011.
  • Is Naples a buyer's or seller's market?
    Naples is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Naples?
    The median sale price in Naples is $550K. That is down $18.33K from the prior month.
  • Does 143 Windward Cay have a pool?
    Yes, 143 Windward Cay in Naples, FL has a pool.
  • How big is the lot at 143 Windward Cay?
    The lot at 143 Windward Cay in Naples, FL is about 0.31 acres (13,503 sq ft).

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Off Market Homes Near 143 Windward Cay

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