14865 Windward Ln, Naples, FL 34114
OFF MARKET

$1,090,800

Trulia Estimate
  • 3 Beds
  • 4 Baths
  • 3,165 sqft

14865 Windward Ln, Naples, FL 34114

Est. Refi. Payment $6,704/mo*
Refinance Your Home
Currently Off Market - Sold Apr 2, 2019 for $581,490

Home Value

Trulia Estimate
$1.09M
Since last month
Decreased$2K (-0.1%)
Since last year
Increased$14K (+1.3%)
Since last sale
Increased$508K (+87.3%)
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 +80% in the last 10 years
MonthEstimated value
2026
September 2026$1.09M
August 2026$1.09M
July 2026$1.09M
June 2026$1.08M
May 2026$1.06M
April 2026$1.12M
March 2026$1.11M
February 2026$1.12M
January 2026$1.08M
2025
2024
2023
2022
2021
2020

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
14878 Windward LN, Naples, FL
0.05
Single-Family Home
$920,000
06/09/26
3
2.5
2,344
14741 Leeward Dr, Naples, FL
0.09
Single-Family Home
$775,000
11/04/25
3
2
2,066
14776 Spinnaker Way, Naples, FL
0.22
Single-Family Home
$1,400,000
06/03/26
3
3.5
2,896
14852 Dockside Ln, Naples, FL
0.13
Single-Family Home
$1,385,000
09/17/26
3
2.5
2,832
14844 Dockside LN, Naples, FL
0.17
Single-Family Home
$1,425,000
12/12/25
4
4
3,516
14503 Manchester DR, Naples, FL
0.24
Single-Family Home
$570,000
08/20/26
4
2.5
2,248
14752 Windward Ln, Naples, FL
0.24
Single-Family Home
$1,349,000
12/18/25
3
3.5
3,144
14785 Leeward Dr, Naples, FL
0.11
Single-Family Home
$1,395,000
03/10/26
4
5
3,447
14748 Windward LN, Naples, FL
0.24
Single-Family Home
$1,065,000
05/27/26
4
5
3,164
14730 Sonoma Blvd, Naples, FL
0.26
Single-Family Home
$545,000
09/16/26
3
2
2,151

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
14849 Windward LN, Naples, FL 34114
0.04
$971,100
3
2.5
2,344
Off Market
14731 Nautilus PL, Naples, FL 34114
0.07
$1,180,000
3
4
2,585
For Sale
14837 Windward LN, Naples, FL 34114
0.07
$744,400
4
2
2,046
Off Market
14870 Windward LN, Naples, FL 34114
0.04
$883,900
4
3.5
2,433
Off Market
14821 Windward LN, Naples, FL 34114
0.09
$1,197,100
4
5
3,164
Off Market
14805 Windward LN, Naples, FL 34114
0.11
$1,103,700
3
4
2,585
Off Market
14878 Windward LN, Naples, FL 34114
0.05
$920,000
3
2.5
2,344
Recently Sold
14733 Leeward DR, Naples, FL 34114
0.09
$972,500
3
2.5
2,344
Off Market
14741 Leeward Dr, Naples, FL 34114
0.09
$784,400
3
2
2,066
Off Market
14796 Windward LN, Naples, FL 34114
0.15
$799,999
4
3
2,133
For Sale
14856 Dockside LN, Naples, FL 34114
0.12
$1,175,500
4
4.5
2,802
Off Market
14785 Leeward Dr, Naples, FL 34114
0.11
$1,395,000
4
5
3,447
Recently Sold

Local Information

  • Map ViewExplore the area around 14865 Windward Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2019
3,165 sqft
$345/sqft
Garage

About this House

Beautiful home with high quality custom upgrades to kitchen that include glass subway tile, glass upper cabinets to ceiling (Cornerstone), built in coffee maker, and finished with viking appliances, butler pantry with library ladder, cabinets, quartz counters, and display pedestal cabinets; tile statement walls, whole house Generac generator, high impact windows, beautiful pool/spa, fabulous custom designer outdoor kitchen with ceiling accents, storm smart screens for the outdoor kitchen/lanai area, exceptional designer interior and exterior lighting (from Lighting First), beautiful walk-in custom closets, garage storage system and work area, laundry room updates to include full custom cabinets. Beautiful shutter up plantation shutters in bedrooms and office, aquarium window in dining area. Panoramic view pool cage. Lanai backs up to lake. Too many upgrades to fully capture. A one of a kind coastal contemporary home. Close to all that Naples and Marci Island offer in a community with exceptional amenities.
14865 Windward Ln, Naples, FL 34114 is a 3 bedroom, 5 bathroom, 3,165 sqft single-family home built in 2019. It last sold for $581,490 on Apr 2, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,090,800, with a rent estimate of $8,567/month.

Home Details for 14865 Windward Ln

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Additional StorageStorage
Fireplace & Spa
Hot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoLawnSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 5Parking: Garage Attached

Property Information

Year Built
Year Built: 2019
Property Type / Style
Property Type: Single Family HomeArchitecture: Modern

Lot Information

Lot Area: 8712 sqft

Building

Fitness & Sports
Basketball CourtTennis Court
Community rooms
Fitness Center

Additional Information

Assisted Living CommunitySport Court

Price and Tax history

DateEventPrice
Apr 2, 2019
Source: N/A
Sold
$581,490

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
    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 14865 Windward Ln

  • What is 14865 Windward Ln estimated to be worth?
    Trulia's estimated value for 14865 Windward Ln in Naples, FL is $1,090,800.
  • What is the price history for 14865 Windward Ln?
    14865 Windward Ln in Naples, FL last sold for $581,490 in April 2019.
  • 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 14865 Windward Ln have a pool?
    Yes, 14865 Windward Ln in Naples, FL has a pool.
  • How big is the lot at 14865 Windward Ln?
    The lot at 14865 Windward Ln in Naples, FL is about 0.20 acres (8,712 sq ft).

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