2266 Windward Way, Naples, FL 34103
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Property image
OFF MARKET

2266 Windward Way
Naples, FL 34103

Moorings
  • 3 Beds
  • 2 Baths
  • 2,364 sqft (on 0.42 acres)

$8,142,800

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $48,865/mo*

$8,142,800

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $48,865/mo*
3 Beds
2 Baths
2,364 sqft
(on 0.42 acres)

Local Information

  • Map ViewExplore the area around 2266 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
1969
Lot Size
0.42 acres
Living Area
2,364 sqft
Price/Sqft
$3,445
Parking
Garage

About this House

This charming midcentury modern home designed by Florida Architect Richard W. Morris is nestled along a quiet cul-de-sac with sweeping views of Bowline Bay and immediate, no bridge access to the Gulf of Mexico. The home is situated on over a third of an acre with nearly eighty feet of waterfront and a large dock. The existing home is perfect for updating with a split bedroom layout and light filled great room with cathedral ceilings and a Florida room. The property offers the flexibility to renovate or build your own Naples dream home! Residents will appreciate breathtaking sunsets with access to the Moorings Private Beach just a few minutes away. This property is located in an exclusive neighborhood within the heart of Naples, close to award winning restaurants, shops, and all the amenities the Gulf Coast has to offer!
2266 Windward Way, Naples, FL 34103 is a 3 bedroom, 2 bathroom, 2,364 sqft single-family home in Moorings, built in 1969. It last sold for $4,150,000 on Mar 11, 2021. It is currently off market. The Trulia Estimate is $8,142,800, with a rent estimate of $6,011/month.

Home Details for 2266 Windward Way

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Interior Details
Number of Rooms: 5Types of Rooms: Walk In ClosetCeiling Fan
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Tile, Carpet
Security
Security System

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoPatioPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1969Year Updated: 1969
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.42 acres

Price History for 2266 Windward Way

DatePriceEventSource
03/11/2024ListingRemovedSWFLMLS #220059252
08/16/2022$4,300,000ListingRemovedSWFLMLS #220059252
03/11/2021$4,150,000Sold
NABOR FL #220059252
02/11/2021$4,300,000PendingSWFLMLS #220059252
09/18/2020$4,300,000Listed For SaleAgent Provided
06/09/2020$4,200,000ListingRemovedAgent Provided
01/20/2020$4,200,000Listed For SaleAgent Provided
06/22/1995$565,000Sold
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$88,372
Assessment$10,901,094
Home facts updated by county records

Comparable Sales for 2266 Windward Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.15
Single-Family Home
$4,000,000
04/30/26
3
3
3,106
0.07
Single-Family Home
$5,800,000
04/13/26
3
3
2,590
0.15
Single-Family Home
$2,300,000
08/22/25
3
2
2,267
0.34
Single-Family Home
$2,900,000
03/12/26
3
2
2,285
0.20
Single-Family Home
$4,275,000
03/26/26
3
3.5
3,512
0.23
Single-Family Home
$2,600,000
03/26/26
3
2.5
2,670
0.46
Single-Family Home
$2,500,000
08/07/25
3
2
2,208
0.28
Single-Family Home
$2,750,000
10/29/25
4
3
3,000
0.40
Single-Family Home
$4,000,000
09/08/25
3
4
3,845
0.11
Single-Family Home
$6,100,000
06/05/26
4
4.5
4,028

Nearby homes

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Assigned Schools

These are the assigned schools for 2266 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 2266 Windward Way

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Off Market Homes Near 2266 Windward Way

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