398 Windward Way, Naples, FL 34103
Property image
Property image
OFF MARKET

$3,610,200

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 4,309 sqft (on 0.32 acres)

398 Windward Way, Naples, FL 34103

Moorings
Est. Refi. Payment $22,014/mo*
Refinance Your Home
Currently Off Market - Sold Jan 13, 2017 for $2,250,000

Home Value

Trulia Estimate
$3.61M
Since last month
Decreased$75K (-2.1%)
Since last year
Decreased$174K (-4.6%)
Since last sale
Increased$1M (+59.1%)
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 +57% in the last 10 years
MonthEstimated value
2026
September 2026$3.58M
August 2026$3.65M
July 2026$3.65M
June 2026$3.71M
May 2026$3.65M
April 2026$3.75M
March 2026$3.74M
February 2026$3.87M
January 2026$3.7M
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
491 Wedge DR, Naples, FL
0.15
Single-Family Home
$3,500,000
01/05/26
4
5
3,928
452 Putter Point DR, Naples, FL
0.06
Single-Family Home
$5,500,000
04/17/26
5
5.5
3,882
350 Windward Way, Naples, FL
0.06
Single-Family Home
$2,600,000
03/26/26
3
2.5
2,670
2550 Windward WAY, Naples, FL
0.14
Single-Family Home
$4,838,565
03/02/26
4
6.5
4,535
375 Bow Line DR, Naples, FL
0.19
Single-Family Home
$6,100,000
06/05/26
4
4.5
4,028
2825 Leeward LN, Naples, FL
0.15
Single-Family Home
$6,600,000
03/25/26
4
4.5
3,694
455 Bow Line DR, Naples, FL
0.19
Single-Family Home
$4,275,000
03/26/26
3
3.5
3,512
405 Putter Point DR, Naples, FL
0.06
Single-Family Home
$8,400,000
08/17/26
5
6
5,045
2363 Crayton RD, Naples, FL
0.28
Single-Family Home
$2,750,000
10/29/25
4
3
3,000
330 Putter Point DR, Naples, FL
0.12
Single-Family Home
$2,250,000
08/28/26
4
2
1,600

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
445 Putter Point DR, Naples, FL 34103
0.03
$4,773,300
5
5.5
4,728
Off Market
452 Putter Point DR, Naples, FL 34103
0.06
$5,500,000
5
5.5
3,882
Recently Sold
2750 Leeward LN, Naples, FL 34103
0.07
-
-
-
-
Off Market
462 Putter Point DR, Naples, FL 34103
0.07
$2,449,400
4
2.5
2,097
Off Market
405 Putter Point DR, Naples, FL 34103
0.06
$8,400,000
5
6
5,045
Recently Sold
2790 Leeward LN, Naples, FL 34103
0.10
$4,899,700
4
4.5
3,604
Off Market
2570 Crayton RD, Naples, FL 34103
0.11
$2,900,000
3
2
2,285
Recently Sold
330 Putter Point DR, Naples, FL 34103
0.12
$2,250,000
4
2
1,600
Recently Sold
436 Putter Point CT, Naples, FL 34103
0.12
$10,100,000
5
6
5,156
Recently Sold
2805 Leeward LN, Naples, FL 34103
0.13
$15,500,000
5
5.5
5,406
Recently Sold
401 Wedge DR, Naples, FL 34103
0.13
$4,690,700
4
5
3,686
Off Market
320 Putter Point DR, Naples, FL 34103
0.13
$2,254,000
3
2
2,267
Off Market

Local Information

  • Map ViewExplore the area around 398 Windward Way.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2001
0.32 acre lot
4,309 sqft
$838/sqft
Garage

About this House

Welcome home to this gracefully remastered and southerly exposed Moorings custom home situated in an exceptional west of Crayton location on Windward Way. The owners have recently completed a tasteful and comprehensive update including an all new custom gourmet kitchen with Calcutta gold counter tops and Sub Zero/Jenn-Air appliances, rich wide plank wood flooring through the first level, stunning marble filled master bath, designer lighting, pool features and lanai decking, custom built ins, and much more. Residence is filled with light and offers a generous and open layout including the master, den, and 2 additional bedrooms on the main living level complemented by an upper level lounge and guest suite. Home also offers a convenient side load 3 car garage, impeccable landscaping, and an abundance of storage. This superb location provides easy access to Naples finest amenities and is within walking distance to multiple beach access points including the highly coveted Moorings private beach.
398 Windward Way, Naples, FL 34103 is a 4 bedroom, 6 bathroom, 4,309 sqft single-family home in Moorings, built in 2001. It last sold for $2,250,000 on Jan 13, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,610,200.

Home Details for 398 Windward Way

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Office
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigeratorWasher
Security
Security System

Exterior Features

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

Property Information

Year Built
Year Built: 2001Year Updated: 2001
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price and Tax history

DateEventPrice
Jan 13, 2017
Source: N/A
Sold
$2,250,000
Oct 24, 2016
Source: Agent Provided
PriceChange
$2,450,000
Price decreased by 2%
Sep 14, 2016
Source: Agent Provided
PriceChange
$2,495,000
Price decreased by 7%
Mar 22, 2016
Source: Agent Provided
PriceChange
$2,695,000
Price decreased by 4%
Feb 26, 2016
Source: Agent Provided
Listed For Sale
$2,795,000

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

Neighborhood Overview

Moorings
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Moorings

At least 45 Trulia users voted on each feature.

  • 88 % Say it's dog friendly

  • 84 % Say it's quiet

  • 80 % Say car is needed

  • 80 % Say parking is easy

  • 78 % Say people would walk alone at night

  • 77 % Say it's walkable to restaurants

  • 76 % Say they plan to stay for at least 5 years

  • 73 % Say streets are well-lit

  • 71 % Say there's holiday spirit

  • 68 % Say it's walkable to grocery stores

  • 67 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 51 % Say there are community events

  • 45 % Say yards are well-kept

  • 36 % Say kids play outside

  • 21 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Marc d'Acunzo
    "Baker park has a great dog park area. One for small dogs and the other for medium and larger dogs. Plenty of areas to walk dogs."
    0
    Flag
  • Trulia User
    "Safe and a great place to live . Dog friendly and easy walk to the beach and shopping. Sunsets you never get tired of !"
    0
    Flag
  • Trulia User
    "This neighborhood is beautiful and safe. Great beach town with upscale dining and classy people. The farmers market downtown is excellent and the beaches are clean. "
    0
    Flag
  • Sally W.
    "Have visited neighborhood several times & it make a significant impression. Love the layout & amenities. Not far to Moorings Beach."
    1
    Flag
  • Marc D.
    "There is no dog beach. Condos/coops usually do not allow for dogs. Private homeowners are likely the only way to keep a dog in the moorings."
    6
    Flag
  • Marc D.
    "Great beach community. There is a neighborhood beach park and a large public beach park. Community has two large hotels too..."
    2
    Flag
  • Axlroze2001
    "Its in Napple which is very very nice no one here in the summer. Very very busy in the winter. Garbage pick up is great. Legal marijuana delivery is easy from Bonita Springs No crime even with me living here"
    5
    Flag
  • Kersh8899
    "It’s great we spent our first winter in the Mooring s loved everything about it Looking forward to our return to our many new friends and easy lifestyle"
    0
    Flag
  • Xactimate
    "I've lived in the neighborhood for quite a few years and it is a good neighborhood. I especially enjoy the golf course and all of the wildlife that surrounds the area."
    3
    Flag
  • Di K. T.
    "I lived in Naples for many years & this is one of the reasons I am looking at retiring back to this area. It is most refreshing, delightful & so refined & relaxing! The lifestyle is elegant, laid back & reminiscent of Old Florida Ways, in that it is very friendly & most hospitable."
    4
    Flag
  • shalet
    "love the moorings area of Naples. short walk to the gulf of mexico and powder sand beaches. your price point is way off. too low"
    0
    Flag
  • zadehkhali
    "Visit Naples 2-3 times per year and each visit is more spectacular that the previous one.. Highly Recommended."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 398 Windward Way

  • What is 398 Windward Way estimated to be worth?
    Trulia's estimated value for 398 Windward Way in Naples, FL is $3,610,200.
  • What is the price history for 398 Windward Way?
    398 Windward Way in Naples, FL last sold for $2,250,000 in January 2017.
  • 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 398 Windward Way have air conditioning?
    Yes, 398 Windward Way in Naples, FL has air conditioning.
  • Does 398 Windward Way have a pool?
    Yes, 398 Windward Way in Naples, FL has a pool.

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