2266 Windward Way
Naples, FL 34103
Moorings- 3 Beds
- 2 Baths
- 2,364 sqft (on 0.42 acres)
3 Beds
2 Baths
2,364 sqft
(on 0.42 acres)
Local Information
-- mins to
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!
Home Details for 2266 Windward Way
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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 |
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Exterior Home Features Roof: TileDeckExterior: StuccoPatioPorch |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 1969Year Updated: 1969 |
Property Type / Style Property Type: Single Family Home |
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Units in Building: 1 |
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Lot Area: 0.42 acres |
Price History for 2266 Windward Way
| Date | Price | Event | Source |
|---|---|---|---|
| 03/11/2024 | ListingRemoved | SWFLMLS #220059252 | |
| 08/16/2022 | $4,300,000 | ListingRemoved | SWFLMLS #220059252 |
| 03/11/2021 | $4,150,000 | Sold | NABOR FL #220059252 |
| 02/11/2021 | $4,300,000 | Pending | SWFLMLS #220059252 |
| 09/18/2020 | $4,300,000 | Listed For Sale | Agent Provided |
| 06/09/2020 | $4,200,000 | ListingRemoved | Agent Provided |
| 01/20/2020 | $4,200,000 | Listed For Sale | Agent Provided |
| 06/22/1995 | $565,000 | Sold | N/A |
Market trends in Moorings
Last updated June 2026
Avg. sale price
$1.44M
$186KMoM
Sale-to-List Price
—
Price per sq ft
$843
$33MoM
Available listings
160
34MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 2266 Windward Way.
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.
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