14744 Windward Ln, Naples, FL 34114
Property image
Property image
OFF MARKET

$961,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,256 sqft

14744 Windward Ln, Naples, FL 34114

Est. Refi. Payment $5,917/mo*
Refinance Your Home
Currently Off Market - Sold Dec 26, 2024 for $1,095,000

Home Value

Trulia Estimate
$961K
Since last month
Decreased$22K (-2.3%)
Since last year
Decreased$65K (-6.3%)
Since last sale
Decreased$132K (-12.1%)
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 +235% in the last 10 years
MonthEstimated value
2026
September 2026$963K
August 2026$985K
July 2026$1M
June 2026$1.02M
May 2026$1.01M
April 2026$1.01M
March 2026$1.02M
February 2026$1.03M
January 2026$1.02M
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
14741 Leeward Dr, Naples, FL
0.20
Single-Family Home
$775,000
11/04/25
3
2
2,066
14571 Topsail DR, Naples, FL
0.15
Single-Family Home
$690,000
02/26/26
3
2
1,709
14878 Windward LN, Naples, FL
0.27
Single-Family Home
$920,000
06/09/26
3
2.5
2,344
14559 Topsail Dr, Naples, FL
0.18
Single-Family Home
$807,500
08/18/26
4
2
2,046
14658 Topsail DR, Naples, FL
0.16
Single-Family Home
$682,000
03/31/26
2
2
1,830
14752 Windward Ln, Naples, FL
0.03
Single-Family Home
$1,349,000
12/18/25
3
3.5
3,144
14730 Sonoma Blvd, Naples, FL
0.24
Single-Family Home
$545,000
09/16/26
3
2
2,151
14523 Topsail Dr, Naples, FL
0.27
Single-Family Home
$765,000
08/21/26
4
2
2,046
14604 Catamaran Pl, Naples, FL
0.28
Single-Family Home
$675,000
04/23/26
3
2
1,679
14748 Windward LN, Naples, FL
0.01
Single-Family Home
$1,065,000
05/27/26
4
5
3,164

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
14748 Windward LN, Naples, FL 34114
0.01
$1,065,000
4
5
3,164
Recently Sold
14752 Windward Ln, Naples, FL 34114
0.03
$1,349,000
3
3.5
3,144
Recently Sold
14631 Topsail DR, Naples, FL 34114
0.09
$777,900
3
2
2,021
Off Market
14584 Topsail Dr, Naples, FL 34114
0.12
$882,500
3
2
2,046
Off Market
14666 Catamaran PL, Naples, FL 34114
0.13
$799,900
4
2
2,046
For Sale
14572 Topsail DR, Naples, FL 34114
0.15
$717,600
4
3
2,143
Off Market
14796 Windward LN, Naples, FL 34114
0.15
$799,999
4
3
2,133
For Sale
14571 Topsail DR, Naples, FL 34114
0.15
$690,000
3
2
1,709
Recently Sold
14658 Catamaran Pl, Naples, FL 34114
0.15
$927,700
3
2.5
2,587
Off Market
14658 Topsail DR, Naples, FL 34114
0.16
$682,000
2
2
1,830
Recently Sold
14731 Nautilus PL, Naples, FL 34114
0.16
$1,180,000
3
4
2,585
For Sale
14567 Topsail Dr, Naples, FL 34114
0.16
$649,000
3
2
1,709
For Sale

Local Information

  • Map ViewExplore the area around 14744 Windward Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2018
2,256 sqft
$426/sqft
Attached Garage

About this House

This immaculate and rarely available KADEN floorplan home is loaded with Designer Upgrades and Special Features that will take your breath away as soon as you open the front door. The foyer with floating bookshelves and designer lighting, welcomes you to the home of your dreams. Your eyes will be drawn to the 2 sets of sliding doors leading to the expansive lanai which stretches across the back of the home. Start your day by the pool with your morning coffee as you watch the coveted Florida sunrise and reflect on your sparkling lake view. With the wide layout of this home, opening the sliders all the way, brings the outside in making the home seem even larger. Electric Storm Smart Shutters protect the home and furniture from inclement weather and offer peace of mind if you are away. The Chef in the home will love cooking and entertaining with the environmentally friendly induction cook-top and modern and sophisticated quartz countertop and back splash. Friends and family can gather around the kitchen island or built-in bar as they make new lasting memories. The dining room flows from the kitchen with views of the pool and lake. The gracious living room is exquisite with designer wallpaper and beautiful ceiling detail with crown molding trim. Attention to detail and impeccable taste is seen throughout the home including the custom-built tri-level wooden clothes rods and shelving in the primary bedroom closet making lots of extra room. Naples Reserve is an active, fun and social community with a resort-style pool and lap pool, restaurant and outside Tiki bar. Amenities include water bikes, kayaks, pedal boats, pickleball, tennis, bocce, fitness center and more. Close to downtown Naples and Marco Island's restaurants, shopping, and beaches with many new delights on the way!
14744 Windward Ln, Naples, FL 34114 is a 3 bedroom, 2 bathroom, 2,256 sqft single-family home built in 2018. It last sold for $1,095,000 on Dec 26, 2024 (9% below the $1,199,000 asking price). More recently, it was listed as a rental in October 2018 with an asking price of $3,500 per month. That rental listing was removed on December 14, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $961,300, with a rent estimate of $8,523/month.
Contact this Building
Property Website

Home Details for 14744 Windward Ln

Property Information

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

Interior Features

Heating & Cooling
Air Conditioning

Exterior Features

Pool
Pool
Parking & Garage
GarageParking: Garage Attached, Garage Attached

Media

Lot Information

Lot Area: 8276.4 sqft

Price and Tax history

DateEventPrice
Dec 26, 2024
Source: N/A
Sold
$1,095,000
Sep 29, 2024
Source: SWFLMLS #224031860
Pending
$1,199,000
Apr 10, 2024
Source: SWFLMLS #224031860
Listed For Sale
$1,199,000
Mar 31, 2024
Source: SWFLMLS #223085595
ListingRemoved
Feb 17, 2024
Source: SWFLMLS #223085595
Listed For Sale
$1,249,000

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

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
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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!!"
    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 14744 Windward Ln

  • What is 14744 Windward Ln estimated to be worth?
    Trulia's estimated value for 14744 Windward Ln in Naples, FL is $961,300.
  • What is the price history for 14744 Windward Ln?
    14744 Windward Ln in Naples, FL last sold for $1,095,000 in December 2024.
  • 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 14744 Windward Ln have a pool?
    Yes, 14744 Windward Ln in Naples, FL has a pool.
  • How big is the lot at 14744 Windward Ln?
    The lot at 14744 Windward Ln in Naples, FL is about 0.19 acres (8,276 sq ft).

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Off Market Homes Near 14744 Windward Ln

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