14733 Windward Ln, Naples, FL 34114
Property image
Property image
OFF MARKET

14733 Windward Ln
Naples, FL 34114

  • 3 Beds
  • 4 Baths
  • 3,182 sqft

$1,249,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $7,464/mo*
Refinance Your Home

$1,249,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $7,464/mo*
Refinance Your Home
3 Beds
4 Baths
3,182 sqft

Local Information

  • Map ViewExplore the area around 14733 Windward Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2018
Living Area
3,182 sqft
Price/Sqft
$393

About this House

WELCOME TO THIS MAGNIFICENT POOL HOME IN THE AMENITY RICH COMMUNITY OF NAPLES RESERVE...THE IMPROVEMENTS & UPDATES ARE TOO MANY TO LIST!! IT'S SPECTACULAR LANAI WILL BE HOST TO ENDLESS ENTERTAINING!!...NEWLY RENOVATED & OVERSIZED SALTWATER POOL, CUSTOM BUILT SUMMER KITCHEN, EXTENDED COVERED AREA WITH LOTS OF SEATING AREAS, POOL BATH & STORM SMART STORM PROTECTION!! INSIDE THIS BREATHTAKING HOME YOU WILL FIND 3BR+DEN, 3 FULL BATHS & 2) 1/2 BATHS...A BEAUTIFUL CUSTOM BUILT BUNK ROOM...PLANK FLOORING...UPDATES IN CLOSETS INCLUDING THE SUPER ORGANIZED WALK-IN PANTRY...THE 3-CAR GARAGE HAS EPOXY FLOORS...LOTS OF OVER-HEAD STORAGE & YES AN A/C UNIT:)...THIS ENTIRE HOME SHOWS LIKE A MODEL & THE OUTDOOR LIVING/LANAI AREA WILL BLOW YOU AWAY..EXACTLY WHAT THE OUTDOOR FLORIDA LIFESTYLE IS ALL ABOUT!!...THE AWARD WINNING NAPLES RESERVE IS EQUAL DISTANCE TO THE BEAUTIFUL MARCO ISLAND & DOWNTOWN NAPLES FOR DELICIOUS DINING, AMAZING SHOPPING & ENDLESS WHITE SAND BEACHES...THIS DR. HORTON WHEATON IS A MUST SEE!!!
14733 Windward Ln, Naples, FL 34114 is a 3 bedroom, 5 bathroom, 3,182 sqft single-family home built in 2018. It last sold for $1,615,000 on May 31, 2022. It is currently off market. The Trulia Estimate is $1,249,900, with a rent estimate of $7,741/month.

Home Details for 14733 Windward Ln

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Concrete
Interior Details
Types of Rooms: Pantry
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileDeck
Pool
Pool
Parking & Garage
Parking Spaces: 3

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 8276 sqft

Building

Fitness & Sports
Tennis Court

Price History for 14733 Windward Ln

DatePriceEventSource
10/24/2022ListingRemovedBHHS broker feed
06/01/2022$1,599,900PendingBHHS broker feed #222017043
05/31/2022$1,615,000Sold
Marco Multi List #2220628
03/19/2022$1,599,900PendingSWFLMLS #222017043
03/15/2022$1,599,900Listed For SaleSWFLMLS #222017043
04/28/2018$0ListingRemovedAgent Provided
04/10/2018$0Listed For SaleAgent Provided
04/03/2018$585,275Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$11,584
Assessment$900,360
Home facts updated by county records

Comparable Sales for 14733 Windward Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14752 Windward Ln, Naples, FL
0.07
Single-Family Home
$1,349,000
12/18/25
3
3.5
3,144
14776 Spinnaker Way, Naples, FL
0.21
Single-Family Home
$1,400,000
06/03/26
3
3.5
2,896
14844 Dockside LN, Naples, FL
0.24
Single-Family Home
$1,425,000
12/12/25
4
4
3,516
14748 Windward LN, Naples, FL
0.06
Single-Family Home
$1,065,000
05/27/26
4
5
3,164
14792 Spinnaker Way, Naples, FL
0.27
Single-Family Home
$1,400,000
06/18/26
4
3.5
2,704
14785 Dockside LN, Naples, FL
0.32
Single-Family Home
$1,875,000
04/22/26
4
3.5
3,097
14878 Windward LN, Naples, FL
0.22
Single-Family Home
$920,000
06/09/26
3
2.5
2,344
14591 Regatta LN, Naples, FL
0.36
Single-Family Home
$2,050,000
07/31/26
4
3.5
2,704
14785 Leeward Dr, Naples, FL
0.29
Single-Family Home
$1,395,000
03/10/26
4
5
3,447
14741 Leeward Dr, Naples, FL
0.15
Single-Family Home
$775,000
11/04/25
3
2
2,066

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 14733 Windward Ln.
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. "
    0
    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 "
    0
    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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

380 pet-friendly rentals in Naples, FL

Explore by feature - Garage

873 rentals with a garage in Naples, FL

Explore by feature - Air Conditioning

1299 rentals with air conditioning in Naples, FL

Explore by feature - Pool

3252 rentals with a pool in Naples, FL

Explore by feature - Washer/dryer

1357 rentals with a washer/dryer in Naples, FL

Explore by feature - Outdoor Space

200 rentals with an outdoor space in Naples, FL

Homes for sale near 14733 Windward Ln

Skip to last item
Skip to first item

Off Market Homes Near 14733 Windward Ln

Skip to last item
Skip to first item