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

$4,916,700

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 4,513 sqft (on 0.29 acres)

390 Windward Way, Naples, FL 34103

Moorings
Est. Refi. Payment $30,191/mo*
Refinance Your Home
Currently Off Market - Sold Oct 9, 2015 for $1,287,500

Home Value

Trulia Estimate
$4.92M
Since last month
Increased$7K (+0.1%)
Since last year
Decreased$304K (-5.8%)
Since last sale
Increased$4M (+282%)
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 +265% in the last 10 years
MonthEstimated value
2026
September 2026$4.92M
August 2026$4.91M
July 2026$4.95M
June 2026$4.93M
May 2026$4.95M
April 2026$4.92M
March 2026$4.93M
February 2026$5.27M
January 2026$5.29M
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
2550 Windward WAY, Naples, FL
0.12
Single-Family Home
$4,838,565
03/02/26
4
6.5
4,535
452 Putter Point DR, Naples, FL
0.07
Single-Family Home
$5,500,000
04/17/26
5
5.5
3,882
350 Windward Way, Naples, FL
0.04
Single-Family Home
$2,600,000
03/26/26
3
2.5
2,670
375 Bow Line DR, Naples, FL
0.18
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
405 Putter Point DR, Naples, FL
0.05
Single-Family Home
$8,400,000
08/17/26
5
6
5,045
660 Wedge DR, Naples, FL
0.33
Single-Family Home
$6,750,000
05/08/26
4
4.5
3,598
455 Bow Line DR, Naples, FL
0.18
Single-Family Home
$4,275,000
03/26/26
3
3.5
3,512
875 Wedge DR, Naples, FL
0.42
Single-Family Home
$4,600,000
08/14/26
4
5
4,517

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
0.07
$5,500,000
5
5.5
3,882
Recently Sold
2750 Leeward LN, Naples, FL 34103
0.09
-
-
-
-
Off Market
462 Putter Point DR, Naples, FL 34103
0.08
$2,449,400
4
2.5
2,097
Off Market
405 Putter Point DR, Naples, FL 34103
0.05
$8,400,000
5
6
5,045
Recently Sold
2790 Leeward LN, Naples, FL 34103
0.12
$4,899,700
4
4.5
3,604
Off Market
2570 Crayton RD, Naples, FL 34103
0.13
$2,900,000
3
2
2,285
Recently Sold
330 Putter Point DR, Naples, FL 34103
0.10
$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
0.14
$15,500,000
5
5.5
5,406
Recently Sold
401 Wedge DR, Naples, FL 34103
0.11
$4,690,700
4
5
3,686
Off Market
320 Putter Point DR, Naples, FL 34103
0.11
$2,254,000
3
2
2,267
Off Market

Local Information

  • Map ViewExplore the area around 390 Windward Way.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2017
0.29 acre lot
4,513 sqft
$1,089/sqft
Attached Garage

About this House

The interior of the home has remained completely unaffected by hurricanes or flooding, with no water intrusion to the interior during any storm event. Designed, built, and decorated by a renowned interior designer, this stunning four bedroom, five bathroom estate blends timeless Southern charm with modern luxury. Boasting two master suites, one on the main level and another upstairs, both feature spa-like ensuite baths with heated floors for ultimate comfort.
Step inside to an awe-inspiring great room with soaring ceilings, seamlessly flowing out to a screened in lanai that overlooks an oversized resort style pool, complete with a sun shelf and spa. Custom wide plank oak flooring by Legno Bastone enhances the warmth and elegance of every space.
At the heart of the home, the chef designed kitchen is a culinary dream, outfitted with a gas Wolf range, SubZero refrigeration, two beverage drawers, a warming drawer, two dishwashers, and a built-in microwave drawer. A banquette, oversized island, and formal dining area provide multiple dining options, while a nearby wet bar with a wine fridge adds convenience.
Outdoor living is equally impressive, featuring a fully equipped summer kitchen, pool deck dining under the stars, and a screened in dining area, all protected by forty two SWAT Mosquito sprayers. Upstairs, discover two additional spacious ensuite bedrooms and a versatile family room that doubles as a sleeping porch for family sleepovers.
This home also includes two oversized garages, a custom laundry room with a second refrigerator, sink, and standalone Scotsman ice maker, a Kinetico water filtration system, a Sonos sound system, Lutron smart lighting, and WiFi controlled heating and cooling. Built with solid concrete walls, steel beams, and a poured concrete second floor, this residence offers exceptional durability and safety. Thoughtfully designed to create a sanctuary of comfort, style, and security, this home is truly one of Naples finest residences.
390 Windward Way, Naples, FL 34103 is a 4 bedroom, 5 bathroom, 4,513 sqft single-family home in Moorings, built in 2017. It last sold for $1,287,500 on Oct 9, 2015 (78% below the $5,895,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,916,700.
Contact this Building
Property Website

Home Details for 390 Windward Way

Property Information

Year Built
Year Built: 2017
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

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Jun 1, 2026
Source: SWFLMLS #225064219
ListingRemoved
$5,495,000
Mar 20, 2026
Source: SWFLMLS #225064219
PriceChange
$5,495,000
Price decreased by 7%
Nov 3, 2025
Source: SWFLMLS #225064219
Listed For Sale
$5,895,000
Jul 21, 2025
Source: SWFLMLS #225016511
ListingRemoved
$5,895,000
Mar 12, 2025
Source: SWFLMLS #225016511
PriceChange
$5,895,000
Price decreased by 5%

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 390 Windward Way

  • What is 390 Windward Way estimated to be worth?
    Trulia's estimated value for 390 Windward Way in Naples, FL is $4,916,700.
  • What is the price history for 390 Windward Way?
    390 Windward Way in Naples, FL last sold for $1,287,500 in October 2015.
  • 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 390 Windward Way have a pool?
    Yes, 390 Windward Way in Naples, FL has a pool.
  • How big is the lot at 390 Windward Way?
    The lot at 390 Windward Way in Naples, FL is about 0.29 acres (12,632 sq ft).

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