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

$8,670,400

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

2266 Windward Way, Naples, FL 34103

Moorings
Est. Refi. Payment $52,767/mo*
Refinance Your Home
Currently Off Market - Sold Mar 11, 2021 for $4,150,000

Home Value

Trulia Estimate
$8.67M
Since last month
Increased$211K (+2.5%)
Since last year
Increased$1M (+16.1%)
Since last sale
Increased$5M (+111.8%)
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 +176% in the last 10 years
MonthEstimated value
2026
September 2026$8.79M
August 2026$8.58M
July 2026$8.14M
June 2026$8.26M
May 2026$7.83M
April 2026$7.64M
March 2026$7.81M
February 2026$7.81M
January 2026$7.78M
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
300 Mooring Line DR, Naples, FL
0.15
Single-Family Home
$4,000,000
04/30/26
3
3
3,106
320 Bow Line DR, Naples, FL
0.07
Single-Family Home
$5,800,000
04/13/26
3
3
2,590
2570 Crayton RD, Naples, FL
0.34
Single-Family Home
$2,900,000
03/12/26
3
2
2,285
455 Bow Line DR, Naples, FL
0.20
Single-Family Home
$4,275,000
03/26/26
3
3.5
3,512
350 Windward Way, Naples, FL
0.23
Single-Family Home
$2,600,000
03/26/26
3
2.5
2,670
330 Putter Point DR, Naples, FL
0.16
Single-Family Home
$2,250,000
08/28/26
4
2
1,600
441 Mooring Line Dr, Naples, FL
0.24
Single-Family Home
$13,250,000
08/05/26
3
2
2,241
2363 Crayton RD, Naples, FL
0.28
Single-Family Home
$2,750,000
10/29/25
4
3
3,000
375 Bow Line DR, Naples, FL
0.11
Single-Family Home
$6,100,000
06/05/26
4
4.5
4,028
2050 Crayton RD, Naples, FL
0.44
Single-Family Home
$2,650,000
12/18/25
4
3
2,500

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
320 Bow Line DR, Naples, FL 34103
0.07
$5,800,000
3
3
2,590
Recently Sold
350 Bow Line BEND, Naples, FL 34103
0.11
$7,995,000
6
5
5,659
For Sale
375 Bow Line DR, Naples, FL 34103
0.11
$6,100,000
4
4.5
4,028
Recently Sold
300 Mooring Line DR, Naples, FL 34102
0.15
$4,000,000
3
3
3,106
Recently Sold
2170 Gulf Shore BLVD N #44E, Naples, FL 34102
0.12
$837,500
2
2
974
Recently Sold
2170 Gulf Shore BLVD N #23W, Naples, FL 34102
0.13
$872,500
2
2
1,155
Recently Sold
2170 Gulf Shore BLVD N #64E, Naples, FL 34102
0.13
$940,400
2
2
974
Off Market
387 Bow Line DR, Naples, FL 34103
0.13
$5,676,600
5
5
4,836
Off Market
2170 Gulf Shore BLVD N #24W, Naples, FL 34102
0.14
$735,000
1
1.5
1,020
For Sale
380 Wedge DR, Naples, FL 34103
0.13
$2,284,200
3
2
1,537
Off Market
383 Mooring Line DR, Naples, FL 34102
0.18
$15,875,600
6
7
6,950
Off Market
2246 Gulf Shore BLVD N #L2, Naples, FL 34102
0.14
$1,600,000
2
2
1,491
Recently Sold

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

Single-Family Home
Built in 1969
0.42 acre lot
2,364 sqft
$3,668/sqft
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $8,670,400.

Home Details for 2266 Windward Way

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

Interior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 0.42 acres

Price and Tax history

DateEventPrice
Mar 11, 2024
Source: SWFLMLS #220059252
ListingRemoved
Aug 16, 2022
Source: SWFLMLS #220059252
ListingRemoved
$4,300,000
Mar 11, 2021
Source: NABOR FL #220059252
Sold
$4,150,000
Feb 11, 2021
Source: SWFLMLS #220059252
Pending
$4,300,000
Sep 18, 2020
Source: Agent Provided
Listed For Sale
$4,300,000

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 2266 Windward Way

  • What is 2266 Windward Way estimated to be worth?
    Trulia's estimated value for 2266 Windward Way in Naples, FL is $8,670,400.
  • What is the price history for 2266 Windward Way?
    2266 Windward Way in Naples, FL last sold for $4,150,000 in March 2021.
  • 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 2266 Windward Way have air conditioning?
    Yes, 2266 Windward Way in Naples, FL has air conditioning.
  • Does 2266 Windward Way have a pool?
    Yes, 2266 Windward Way in Naples, FL has a pool.

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