14740 Windward Ln, Naples, FL 34114
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Property image
OFF MARKET

14740 Windward Ln
Naples, FL 34114

  • 3 Beds
  • 4 Baths
  • 2,565 sqft

$995,600

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $5,962/mo*
Refinance Your Home

$995,600

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $5,962/mo*
Refinance Your Home
3 Beds
4 Baths
2,565 sqft

Local Information

  • Map ViewExplore the area around 14740 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
2,565 sqft
Price/Sqft
$388
Parking
Garage

About this House

This "like new" Wheaton floor plan home has all the upgrades you want. The open floor plan and huge outdoor lanai with the saltwater pool and spa, designer summer kitchen and pool bath are perfect for your Naples lifestyle. Overlooking a serene lake and lots of Mother Nature with plenty of room for family and friends in the three bedrooms plus office/den, three full baths plus two half baths. The master suite is open, bright and offers a large walk-in shower, private toilet, and huge walk-in closets. One guest suite with en-suite bath and other guest suite has easy access to the full bath. The kitchen is a dream for the chef, a large eat-in counter and separate dining room give plenty of room for entertaining. The contemporary coastal feel of this home is inviting and relaxing. All the many upgrades are on a separate list. Naples Reserve has an award-winning clubhouse, resort pool, fitness center, water sports center, walking trails, biking, kayaking and so much more to explore.
14740 Windward Ln, Naples, FL 34114 is a 3 bedroom, 5 bathroom, 2,565 sqft single-family home built in 2018. It last sold for $699,000 on Nov 3, 2020. It is currently off market. The Trulia Estimate is $995,600, with a rent estimate of $7,027/month.

Home Details for 14740 Windward Ln

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Types of Rooms: Walk In ClosetCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Hot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoPatioPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

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

Lot Information

Lot Area: 8276 sqft

Building

Fitness & Sports
Basketball CourtTennis Court

Price History for 14740 Windward Ln

DatePriceEventSource
11/03/2020$699,000Sold
Marco Multi List #2201908
09/22/2020$699,000PendingAgent Provided
09/17/2020$699,000PriceChange
Agent Provided
08/31/2020$710,000Listed For SaleAgent Provided
11/28/2018$638,313Sold
N/A
04/28/2018$0ListingRemovedAgent Provided
04/10/2018$0Listed For SaleAgent Provided

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$2,125
Assessment$895,590
Home facts updated by county records

Comparable Sales for 14740 Windward Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14752 Windward Ln, Naples, FL
0.04
Single-Family Home
$1,349,000
12/18/25
3
3.5
3,144
14601 Tropical DR, Naples, FL
0.31
Single-Family Home
$650,000
08/11/25
4
3.5
2,438
14653 Tropical DR, Naples, FL
0.25
Single-Family Home
$639,900
09/08/25
3
2.5
2,039
14878 Windward LN, Naples, FL
0.26
Single-Family Home
$920,000
06/09/26
3
2.5
2,344
14748 Windward LN, Naples, FL
0.03
Single-Family Home
$1,065,000
05/27/26
4
5
3,164
14741 Leeward Dr, Naples, FL
0.19
Single-Family Home
$775,000
11/04/25
3
2
2,066
14776 Spinnaker Way, Naples, FL
0.23
Single-Family Home
$1,400,000
06/03/26
3
3.5
2,896
14571 Topsail DR, Naples, FL
0.16
Single-Family Home
$690,000
02/26/26
3
2
1,709
14536 Topsail Dr, Naples, FL
0.24
Single-Family Home
$840,000
03/13/26
4
3
2,307
14658 Topsail DR, Naples, FL
0.15
Single-Family Home
$682,000
03/31/26
2
2
1,830

Nearby homes

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Assigned Schools

These are the assigned schools for 14740 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

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Homes for sale near 14740 Windward Ln

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Off Market Homes Near 14740 Windward Ln

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