2266 Windward Way
Description
- Listed by: Dana Renee Matthews • MVP Realty Associates LLC
Recent comparable sales
Median sold price
$2,500,000
Avg days on market
79
Sale-to-list ratio
84.8%
Naples, FL
9 comparable properties found
$3,603,970
Sold 12/23/24
- 3
- Bedrooms
- 2
- Bathrooms
- 2,064
- Square Feet
- 0.28
- Acres
$3,800,000
Sold 08/04/25
- 3
- Bedrooms
- 2
- Bathrooms
- 2,631
- Square Feet
- 0.37
- Acres
$2,360,000
Sold 11/06/24
- 3
- Bedrooms
- 2
- Bathrooms
- 2,039
- Square Feet
- 0.33
- Acres
$2,900,000
Sold 03/12/26
- 3
- Bedrooms
- 2
- Bathrooms
- 2,285
- Square Feet
- 0.33
- Acres
$3,000,000
Sold 09/10/25
- 3
- Bedrooms
- 2
- Bathrooms
- 2,326
- Square Feet
- 0.33
- Acres
$850,000
Sold 11/14/24
- 3
- Bedrooms
- 2
- Bathrooms
- 1,971
- Square Feet
- 0.23
- Acres
$1,195,000
Sold 01/27/25
- 3
- Bedrooms
- 2
- Bathrooms
- 1,900
- Square Feet
- 0.23
- Acres
$2,500,000
Sold 08/07/25
- 3
- Bedrooms
- 2
- Bathrooms
- 2,208
- Square Feet
- 0.49
- Acres
$2,300,000
Sold 08/22/25
- 3
- Bedrooms
- 2
- Bathrooms
- 2,267
- Square Feet
- 0.29
- Acres
Location
Sold By MVP Realty Associates LLC, Dana Renee Matthews; John R. Wood Properties, Barry Dunleavy
Payment Calculator
$22,847 per month
30 year fixed, 7.03% Interest
$22,155
$692
$0
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1Property Information for 2266 Windward Way
- Taxes: $8,308 / year
- MLS Type: Residential / Ranch
- County: Collier County
- Area: NA05 - Crayton Rd Area
- Development: MOORINGS
- Sub Condo Name: MOORINGS
- Waterfront: Yes
- Waterfront Desc: Bay, Navigable, Seawall
- Gulf Access Type: No Bridge(s)/Water Direct
- View: Bay
- Furnished Desc: Unfurnished
- Stories: 1
- Year Built: 1969
- Lot Size: 0.42 AC / 18,295 SF
- Amenities: Beach Access, Clubhouse, Park, Golf Course, Restaurant, Underground Utility
- Community Type: Clubhouse, Park, Golf Course, Restaurant
- Elementary School: LAKE PARK ELEMENTARY
- High School: NAPLES HIGH SCHOOL
- Middle School: GULFVIEW MIDDLE SCHOOL
- Pets: No Approval Needed
- Frontage Type: Bay/Harbor
- Road Responsibility: Public Maintained Road
- Carport Desc: Circular Driveway, Driveway Unpaved, Under Bldg Closed, Attached
- Carport Spaces: 0
- Attached Garage: Yes
- Garage Spaces: 2
- Carport: No
- Covered Spaces: 2
- Garage: Yes
- Total Parking: 2
- HOA Desc: No
- HOA Fee: $.00
- Condo Fee: $0
- Primary HOA Fee: $0
- Total Annual Recurring Fees: $.00
- Tax Annual Amount: $8,308.00
- Laundry Features: Laundry in Residence, Laundry Tub
- Approx Living Area: 2364.0
- Living Area Units: Square Feet
- Bedroom Desc: Split Bedrooms
- Bedrooms: 3 Bed
- Dining Description: Dining - Living,Eat-in Kitchen
- Elevator: None
- Appliances: Electric Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Freezer, Refrigerator/Icemaker, Washer
- Equipment: Auto Garage Door, Cooktop - Electric, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Freezer, Refrigerator/Icemaker, Security System, Smoke Detector, Washer
- Flooring: Carpet, Parquet, Tile
- Interior Features: Cathedral Ceiling, Custom Mirrors, Laundry Tub, Pantry, Smoke Detectors, Walk-In Closet
- Num Unit Floor: 1
- Private Pool Desc: Below Ground, Equipment Stays, Electric Heat, Screen Enclosure
- Private Pool: Yes
- Private Spa: No
- Room Count: 6
- Total Floors: 1
- Baths Full: 2
- Half Bathrooms: 0
- Bathrooms Total Decimal: 2.00
- Bathrooms: 2
- Bedrooms Total: 3
- Fireplace: No
- Foundation Details: Concrete Block
- View YN: Yes
- Floor Plan Type: Great Room, Split Bedrooms
- Kitchen Description: Built-In Desk, Island, Pantry
- Additional Rooms: Florida Room, Great Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Screened Lanai/Porch, Den - Study
- Gas: No
- Exterior Features: Boat Dock Private, Boat Slip, Dock Deeded, Dock Included, Wooden Dock, Screened Lanai/Porch, Patio
- Exterior Finish: Concrete Block, Metal Frame, Wood Frame, Stucco
- Roof: Tile
- Windows: Skylight(s)
- Storm Protection: None
- Cooling: Ceiling Fan(s), Central Electric
- Cooling YN: Yes
- Heat: Central Electric
- Heating YN: Yes
- Irrigation: Central
- Structure Type: House
- Room Length: 18.0
- Room Type: Kitchen
- Room Width: 10.0
- Room Length: 12.0
- Room Type: Bedroom
- Room Width: 11.0
- Room Length: 17.0
- Room Type: Living Room
- Room Width: 31.0
- Room Length: 19.0
- Room Type: Bedroom
- Room Width: 11.0
- Room Length: 17.0
- Room Type: Master Bedroom
- Room Width: 14.0
- Room Length: 30.0
- Room Type: Lanai
- Room Width: 40.0
- Lease Limits YN: No
- Horse: No
- Lease Term: Buyer Finance/Cash
- Transfer Fee: $.00
Property History for 2266 Windward Way
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Mar 11, 2021 | Sold Naples Area Board of REALTORS #220059252 | $4,150,000 | — |
| Mar 10, 2021 | Sold (Public Record) Public Record #692785518 | $4,150,000 | — |
| Mar 10, 2021 | Sold (Public Record) Public Record #1454350325 | $4,150,000 | — |
| Feb 11, 2021 | Pending Naples Area Board of REALTORS #220059252 | — | |
| Feb 11, 2021 | Pending With Contingencies Naples Area Board of REALTORS #220059252 | — | |
| Sep 18, 2020 | Listed (Active) Naples Area Board of REALTORS #220059252 | $4,300,000 | — |
| Jun 9, 2020 | Withdrawn Naples Area Board of REALTORS #220004164 | — | |
| Jan 20, 2020 | Listed (Active) Naples Area Board of REALTORS #220004164 | $4,200,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 03/11/2021 | Sold Naples Area Board of REALTORS #220059252 | $4,150,000 |
| 03/10/2021 | Sold (Public Record) Public Record #692785518 | $4,150,000 |
| 03/10/2021 | Sold (Public Record) Public Record #1454350325 | $4,150,000 |
| 02/11/2021 | Pending Naples Area Board of REALTORS #220059252 | — |
| 02/11/2021 | Pending With Contingencies Naples Area Board of REALTORS #220059252 | — |
| 09/18/2020 | Listed (Active) Naples Area Board of REALTORS #220059252 | $4,300,000 |
| 06/09/2020 | Withdrawn Naples Area Board of REALTORS #220004164 | — |
| 01/20/2020 | Listed (Active) Naples Area Board of REALTORS #220004164 | $4,200,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 2266 Windward Way
Schools near 2266 Windward Way
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Charter - | K to 12 |
Rating | School | Distance |
|---|---|---|
Lake Park Elementary School PublicPK to 5 | ||
Gulfview Middle School Public6 to 8 | ||
Naples High School Public9 to 12 | ||
Mason Classical Academy CharterK to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 2266 Windward Way, Naples, FL 34103 | $4,150,000 | 3 | 2 | 2,364 | 18,295 |
$7,175,000 | 4 | 6 | 5,960 | 20,473 | |
$3,337,500 | – | – | 3,972 | 14,810 | |
$2,100,000 | 3 | 3 | 2,346 | 20,473 | |
$5,100,000 | 3 | 5 | 3,978 | 18,730 | |
$6,500,000 | 4 | 5 | 5,057 | 17,424 | |
$750,000 | 3 | 2 | 1,666 | 16,988 | |
– | – | – | 2,542 | 16,117 | |
– | – | – | 2,736 | 16,117 | |
$2,600,000 | 4 | 3 | 2,981 | 18,730 | |
$3,395,000 | 4 | 4 | 3,313 | 0 | |
$5,850,000 | 4 | 3 | 2,244 | 17,859 | |
$1,525,000 | 3 | 2 | 2,011 | 12,632 | |
$4,245,000 | 5 | 4 | 2,640 | 14,374 | |
$5,750,000 | 4 | 4 | 3,388 | 17,859 | |
$6,500,000 | – | – | 2,692 | 17,860 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of MVP Realty Associates LLC, Dana Renee Matthews
The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.
