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

$1,023,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,595 sqft (on 0.27 acres)

155 Windward Cay, Naples, FL 34114

Est. Refi. Payment $6,344/mo*
Refinance Your Home
Currently Off Market - Sold Nov 2, 2022 for $990,000

Home Value

Trulia Estimate
$1.02M
Since last month
Decreased$25K (-2.4%)
Since last year
Increased$96K (+10.4%)
Since last sale
Increased$32K (+3.2%)
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 +104% in the last 10 years
MonthEstimated value
2026
September 2026$1.02M
August 2026$1.05M
July 2026$1.03M
June 2026$1.03M
May 2026$1.03M
April 2026$950K
March 2026$957K
February 2026$960K
January 2026$942K
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
0.18
Single-Family Home
$945,000
12/16/25
3
2
2,250
171 Cays DR, Naples, FL
0.09
Single-Family Home
$750,000
11/03/25
3
2
1,913
171 Sunset Cay, Naples, FL
0.28
Single-Family Home
$1,175,000
01/21/26
3
2
1,929
110 Morning Star Cay, Naples, FL
0.30
Single-Family Home
$900,000
02/05/26
3
2.5
2,124
101 Morning Star Cay, Naples, FL
0.24
Single-Family Home
$1,426,000
04/24/26
3
2
2,661
127 Newport DR, Naples, FL
0.34
Single-Family Home
$775,000
04/30/26
3
2
1,841
144 Wilderness CAY, Naples, FL
0.07
Single-Family Home
$1,600,000
02/24/26
4
3.5
2,595
121 Newport Dr, Naples, FL
0.33
Single-Family Home
$885,000
09/15/26
4
2
2,129
200 Cays Dr, Naples, FL
0.21
Single-Family Home
$466,000
07/15/26
3
2
1,487
191 Eveningstar Cay, Naples, FL
0.36
Single-Family Home
$630,000
10/23/25
3
2
1,997

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
161 Cays Dr, Naples, FL 34114
0.01
$1,478,400
3
2.5
2,487
Off Market
144 Wilderness CAY, Naples, FL 34114
0.07
$1,600,000
4
3.5
2,595
Recently Sold
141 Wilderness Cay, Naples, FL 34114
0.06
$1,888,000
3
3
2,223
For Sale
171 Cays DR, Naples, FL 34114
0.09
$744,600
3
2
1,913
Off Market
140 Wilderness Cay, Naples, FL 34114
0.08
-
-
-
-
Off Market
133 Wilderness Cay, Naples, FL 34114
0.10
$1,738,300
3
3
2,678
Off Market
132 Wilderness Cay, Naples, FL 34114
0.10
$1,405,100
3
2.5
2,146
Off Market
176 Venus Cay, Naples, FL 34114
0.13
$900,000
3
2
1,773
For Sale
172 Venus Cay, Naples, FL 34114
0.13
$790,000
4
2
2,320
Off Market
157 Venus Cay, Naples, FL 34114
0.15
$600,000
-
-
-
For Sale
191 Cays DR, Naples, FL 34114
0.17
$1,068,500
3
2.5
2,410
Off Market
120 Wilderness Cay, Naples, FL 34114
0.16
$1,747,300
4
3.5
3,040
Off Market

Local Information

  • Map ViewExplore the area around 155 Windward Cay.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1997
0.27 acre lot
2,595 sqft
$394/sqft
Garage

About this House

For sale by owner, priced to sell! Located in the beautiful Port of the Islands with access to the gulf through the Ten Thousand Islands. This waterfront home offers three bedrooms, two full baths, large living room, dining room, office/den, an oversized two car garage with plenty of built in storage, and a large lanai with tropical plantings and in ground spa. The roof is a top of the line standing seam aluminum roof installed in 2021, and the air conditioning is new in 2022. This could be your piece of paradise!
155 Windward Cay, Naples, FL 34114 is a 3 bedroom, 2 bathroom, 2,595 sqft single-family home built in 1997. It last sold for $990,000 on Nov 2, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,023,500, with a rent estimate of $8,247/month.

Home Details for 155 Windward Cay

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Interior Details
Number of Rooms: 9Types of Rooms: Walk In Closet, Dining Room, Laundry Room, Master Bath, Office
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Laminate

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: Stucco
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1997Year Updated: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.27 acres

Price and Tax history

DateEventPrice
Sep 8, 2024
Source: Marco Multi List #2221664
ListingRemoved
$1,149,000
Nov 2, 2022
Source: N/A
Sold
$990,000
Sep 23, 2022
Source: N/A
Pending
$995,000
Sep 22, 2022
Source: N/A
Listed For Sale
$995,000
Sep 20, 2022
Source: Marco Multi List #2221664
ListingRemoved

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 155 Windward Cay

  • What is 155 Windward Cay estimated to be worth?
    Trulia's estimated value for 155 Windward Cay in Naples, FL is $1,023,500.
  • What is the price history for 155 Windward Cay?
    155 Windward Cay in Naples, FL last sold for $990,000 in November 2022.
  • 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 155 Windward Cay have air conditioning?
    Yes, 155 Windward Cay in Naples, FL has air conditioning.
  • Does 155 Windward Cay have laundry facilities?
    Yes, 155 Windward Cay in Naples, FL has in-unit laundry.

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Off Market Homes Near 155 Windward Cay

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