390 Windward Way, Naples, FL 34103
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OFF MARKET

390 Windward Way
Naples, FL 34103

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

$4,948,200

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $29,724/mo*

$4,948,200

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $29,724/mo*
4 Beds
5 Baths
4,513 sqft
(on 0.29 acres)

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

Property Type
Single-Family Home
Year Built
2017
Lot Size
0.29 acres
Living Area
4,513 sqft
Price/Sqft
$1,096
Parking
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). It is currently off market. The Trulia Estimate is $4,948,200, with a rent estimate of $3,713/month.
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Home Details for 390 Windward Way

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: OtherHeating Fuel: Other

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: Single Family Home

Exterior Features

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

Lot Information

Lot Area: 0.29 acres

Price History for 390 Windward Way

DatePriceEventSource
06/01/2026$5,495,000ListingRemovedSWFLMLS #225064219
03/20/2026$5,495,000PriceChange
SWFLMLS #225064219
11/03/2025$5,895,000Listed For SaleSWFLMLS #225064219
07/21/2025$5,895,000ListingRemovedSWFLMLS #225016511
03/12/2025$5,895,000PriceChange
SWFLMLS #225016511
02/19/2025$6,189,000Listed For SaleSWFLMLS #225016511
10/09/2015$1,287,500Sold
N/A
05/09/2015$1,395,000Listed For SaleAgent Provided
04/16/2015$1,065,000Sold
N/A
02/14/2015$1,150,000Listed For SaleAgent Provided
06/19/2003$560,000Sold
N/A

Market trends in Moorings

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.44M
$186K
MoM
Sale-to-List Price
—
Price per sq ft
$843
$33
MoM
Available listings
160
34
MoM
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Property Tax and Assessment

Year2025
Tax$25,724
Assessment$3,955,934
Home facts updated by county records

Comparable Sales for 390 Windward Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.15
Single-Family Home
$3,500,000
01/05/26
4
5
3,928
0.12
Single-Family Home
$4,838,565
03/02/26
4
6.5
4,535
0.07
Single-Family Home
$5,500,000
04/17/26
5
5.5
3,882
0.04
Single-Family Home
$2,600,000
03/26/26
3
2.5
2,670
0.18
Single-Family Home
$6,100,000
06/05/26
4
4.5
4,028
0.15
Single-Family Home
$6,600,000
03/25/26
4
4.5
3,694
0.33
Single-Family Home
$6,750,000
05/08/26
4
4.5
3,598
0.18
Single-Family Home
$4,275,000
03/26/26
3
3.5
3,512
0.11
Single-Family Home
$2,300,000
08/22/25
3
2
2,267
0.34
Single-Family Home
$3,900,000
04/16/26
4
5
4,084

Nearby homes

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Assigned Schools

These are the assigned schools for 390 Windward Way.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

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."
  • 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 !"
  • 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. "
  • Sally W.
    "Have visited neighborhood several times & it make a significant impression. Love the layout & amenities. Not far to Moorings Beach."
  • 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."
  • Marc D.
    "Great beach community. There is a neighborhood beach park and a large public beach park. Community has two large hotels too..."
  • 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"
  • 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"
  • 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."
  • 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."
  • 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"
  • zadehkhali
    "Visit Naples 2-3 times per year and each visit is more spectacular that the previous one.. Highly Recommended."

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Homes for sale near 390 Windward Way

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Off Market Homes Near 390 Windward Way

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