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

$10,711,000

Trulia Estimate
  • 5 Beds
  • 5.5 Baths
  • 5,310 sqft (on 0.37 acres)

365 Windward Way, Naples, FL 34103

Moorings
Est. Refi. Payment $65,167/mo*
Refinance Your Home
Currently Off Market - Sold Nov 12, 2020 for $8,001,537

Home Value

Trulia Estimate
$10.7M
Since last month
Decreased$348K (-3.2%)
Since last year
Increased$542K (+5.4%)
Since last sale
Increased$3M (+32.7%)
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 +229% in the last 10 years
MonthEstimated value
2026
September 2026$10.62M
August 2026$10.97M
July 2026$10.94M
June 2026$11.07M
May 2026$10.61M
April 2026$10.06M
March 2026$10.09M
February 2026$10.45M
January 2026$9.98M
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
405 Putter Point DR, Naples, FL
0.07
Single-Family Home
$8,400,000
08/17/26
5
6
5,045
2805 Leeward LN, Naples, FL
0.11
Single-Family Home
$15,500,000
05/14/26
5
5.5
5,406
436 Putter Point CT, Naples, FL
0.17
Single-Family Home
$10,100,000
02/24/26
5
6
5,156
2825 Leeward LN, Naples, FL
0.13
Single-Family Home
$6,600,000
03/25/26
4
4.5
3,694
452 Putter Point DR, Naples, FL
0.11
Single-Family Home
$5,500,000
04/17/26
5
5.5
3,882
375 Bow Line DR, Naples, FL
0.19
Single-Family Home
$6,100,000
06/05/26
4
4.5
4,028
3011 Regatta RD, Naples, FL
0.36
Single-Family Home
$7,500,000
05/15/26
5
6
4,720
2990 Leeward LN, Naples, FL
0.29
Single-Family Home
$6,500,000
11/05/25
5
6
4,400
2550 Windward WAY, Naples, FL
0.12
Single-Family Home
$4,838,565
03/02/26
4
6.5
4,535
384 Mooring Line DR, Naples, FL
0.41
Single-Family Home
$5,200,000
01/05/26
5
5.5
5,512

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
405 Putter Point DR, Naples, FL 34103
0.07
$8,400,000
5
6
5,045
Recently Sold
445 Putter Point DR, Naples, FL 34103
0.07
$4,773,300
5
5.5
4,728
Off Market
2750 Leeward LN, Naples, FL 34103
0.09
-
-
-
-
Off Market
330 Putter Point DR, Naples, FL 34103
0.11
$2,250,000
4
2
1,600
Recently Sold
320 Putter Point DR, Naples, FL 34103
0.11
$2,254,000
3
2
2,267
Off Market
2550 Windward WAY, Naples, FL 34103
0.12
$4,838,565
4
6.5
4,535
Recently Sold
452 Putter Point DR, Naples, FL 34103
0.11
$5,500,000
5
5.5
3,882
Recently Sold
2790 Leeward LN, Naples, FL 34103
0.11
$4,899,700
4
4.5
3,604
Off Market
2805 Leeward LN, Naples, FL 34103
0.11
$15,500,000
5
5.5
5,406
Recently Sold
462 Putter Point DR, Naples, FL 34103
0.12
$2,449,400
4
2.5
2,097
Off Market
401 Wedge DR, Naples, FL 34103
0.13
$4,690,700
4
5
3,686
Off Market
2825 Leeward LN, Naples, FL 34103
0.13
$6,600,000
4
4.5
3,694
Recently Sold

Local Information

  • Map ViewExplore the area around 365 Windward Way.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2015
0.37 acre lot
5,310 sqft
$2,017/sqft
Garage

About this House

No bridges to the Gulf and wide western views of Moorings Bay, this recently constructed custom home is a coastal dream. Beachy shell stone flooring in the great room sets the tone for the light and bright finishes throughout. Double islands perfectly detailed with creamy Quartzite countertops enhance the gourmet kitchen with custom crafted cabinets by Ruffino and top of the line appliances. Bi-folding window walls separate the dining area to the covered lanai with outdoor kitchen making an easy setting to entertain family and friends. Well-equipped Butler's pantry with wine cooler and quick access to the pool bath finishes the space. Guests will be delighted by the spacious four en-suite bedrooms to retreat to after enjoying time in the resort like outdoor area which is paradise found; including a generous negative edge pool, integrated spa, terraced seating areas, boat dock with boat lift and submergible jet ski lift, all with unparalleled views of the Bay. Ideally situated in the quiet Moorings neighborhood, just a short distance to the Moorings beach park, shopping and dining in either north Naples or downtown and the Gulf of Mexico.
365 Windward Way, Naples, FL 34103 is a 5 bedroom, 6 bathroom, 5,310 sqft single-family home in Moorings, built in 2015. It last sold for $8,001,537 on Nov 12, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $10,711,000.

Home Details for 365 Windward Way

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Types of Rooms: Walk In Closet, OfficeWet Bar
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: Built Up, TileDeckExterior: StuccoPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2015Year Updated: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.37 acres

Price and Tax history

DateEventPrice
Nov 12, 2020
Source: N/A
Sold
$8,001,537
Sep 21, 2020
Source: Agent Provided
Pending
$8,450,000
Sep 2, 2020
Source: Agent Provided
PriceChange
$8,450,000
Price increased by 2%
Jun 18, 2020
Source: Agent Provided
Listed For Sale
$8,250,000
May 22, 2014
Source: N/A
Sold
$2,700,000

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 365 Windward Way

  • What is 365 Windward Way estimated to be worth?
    Trulia's estimated value for 365 Windward Way in Naples, FL is $10,711,000.
  • What is the price history for 365 Windward Way?
    365 Windward Way in Naples, FL last sold for $8,001,537 in November 2020.
  • 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 365 Windward Way have air conditioning?
    Yes, 365 Windward Way in Naples, FL has air conditioning.
  • Does 365 Windward Way have a pool?
    Yes, 365 Windward Way in Naples, FL has a pool.

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