OFF MARKET

Off market mar 2021 for $4.1M

$5,581,037

Est. refi paymentEst. refi $28,078/mo

•

2,364

sq ft

2266 Windward Way, Naples, FL 34103

About this home

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!

Single-familyProperty Type

1969Year Built

0.42 acresLot Size

$2,361Est. Price/Sq.Ft.

2 spacesParking

Listed by Dana Matthews • MVP Realty Associates LLC

Bought with Dana Matthews • MVP Realty Associates LLC

Redfin checked: a minute ago

•Source:NAPLESMLS #220059252

Redfin Estimate

$5,581,037

$1.4M since sold in March 2021$581K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 73.7% higher than the average sale price ($3.21M) of 6 comparable homes.

SOLD JUN 1, 2026
$3,000,000
A
3 beds3 baths2,310 sq ft
1949 Alamanda Dr, Naples, FL 34102
SOLD APR 13, 2026
$5,800,000
B
3 beds3 baths2,590 sq ft
320 Bow Line Dr, Naples, FL 34103
SOLD APR 30, 2026
$4,000,000
C
3 beds3 baths3,106 sq ft
300 Mooring Line Dr, Naples, FL 34102
SOLD AUG 28, 2026
$2,250,000
D
4 beds2 baths1,600 sq ft
330 Putter Point Dr, Naples, FL 34103
SOLD OCT 9, 2026
$1,900,000
E
3 beds2 baths2,058 sq ft
717 Park Shore Dr, Naples, FL 34103
SOLD OCT 30, 2026
$2,325,000
F
2 beds2 baths1,809 sq ft
635 Wedge Dr, Naples, FL 34103

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Sell

$2,309,601

Est. take-home

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Refinance

Est. cash available

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Rent

$6,983/mo

Redfin rental estimate

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Market trends in 34103, FL

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

92.9%

+0.2% MoM

Median sale price

$1.4M

$324K MoM

Avg. days on market

132d

13 days MoM

Recently sold homes

8 MoM

New listings for sale

NEW 14 HRS AGO
$3,450,000
3 beds3 baths2,327 sq ft
4551 Gulf Shore Blvd N #902, Naples, FL 34103
NEW 15 HRS AGO
$6,900,000
3 beds3.5 baths4,276 sq ft
4201 Gulf Shore Blvd N #1602, Naples, FL 34103
NEW 21 HRS AGO
$1,795,000
3 beds2 baths1,346 sq ft
50 Seagate Dr Unit 904B, Naples, FL 34103
3D & VIDEO TOUR
$3,325,000
3 beds3.5 baths2,287 sq ft
4000 Gulf Shore Blvd N #400, Naples, FL 34103
$7,950,000
3 beds3.5 baths3,755 sq ft
255 Bay Pt, Naples, FL 34103
3D WALKTHROUGH
$1,900,000
2 beds2.5 baths2,669 sq ft
4951 Gulf Shore Blvd N #104, Naples, FL 34103
3D WALKTHROUGH
$668,000
2 beds2 baths1,311 sq ft
3410 Gulf Shore Blvd N #304, Naples, FL 34103
$1,995,000
3 beds3 baths1,950 sq ft
250 Park Shore Dr #101, Naples, FL 34103
$14,995,000
4 beds5.5 baths5,929 sq ft
323 Neptunes Bight, Naples, FL 34103
OPEN SAT, 9:30AM TO 12PM
$1,100,000
2 beds2 baths1,320 sq ft
3500 Gulf Shore Blvd N #206, Naples, FL 34103
See all

Provided by Redfin

Sale history for 2266 Windward Way

Tax history for 2266 Windward Way

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning
Permits

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.42 Acres

Year renovated

2023

Sq. Ft.

4,401

Year built

2023

Style

Single Family Residential

County

Collier County

APN

12786640002

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 19, 2026.

Property details

Parking

Parking Information
Parking: 2+ Spaces, Circle Drive, Driveway Unpaved, Under Building Closed
# of Garage Spaces: 2
Garage Description: Attached

Interior

Bedroom Information
# of Bedrooms: 3
Bedroom Description: Split Bedrooms

Bathroom Information
# of Bathrooms (Full): 2
Master Bath Description: Combo Tub And Shower, Dual Sinks, Separate Tub And Shower

Interior Features
# of Rooms: 6
Approximate Living Area: 2364
Interior Features: Cathedral Ceiling, Custom Mirrors, Laundry Tub, Pantry, Smoke Detectors, Walk-In Closet
Kitchen Description: Built-In Desk, Island, Pantry
Dining Description: Dining (Living), Eat-in Kitchen
Additional Rooms: Florida Room, Great Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Screened Lanai/Porch, Den (Study)
Equipment: Auto Garage Door, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Icemaker, Security System, Smoke Detector, Washer
Furnished Description: Unfurnished
Flooring: Carpet, Parquet, Tile
Floor Plan Type: Great Room, Split Bedrooms

Exterior

Exterior Features
Exterior Features: Fruit Trees, Patio, Sprinkler (Auto)
Roof: Tile
Windows: Bay, Double Hung, Skylight, Sliding
Has Private Pool
Private Pool Description: Below Ground, Equipment Stays, Heated Electric, Screened
Exterior Finish: Stucco
Security: Alarm Unmonitored

Property Information
Property Type: Residential
Construction: Concrete Block, Metal Frame, Wood Frame
Year Built: 1969
Development: MOORINGS
Development Name: MOORINGS
Building Design: Single Family
1 Story/Ranch, Florida
Rear Exposure: SE

Lot Information
Lot Unit: 32
Lot Description: Cul-De-Sac, Irregular Shape
Lot Frontage: 140
Lot Right: 180
Lot Left: 197
Lot Back: 79
Total Area: 2967
Section: 28
Road: City Maintained, Cul-De-Sac, Paved Road, Public Road
Property Appraiser Office
Restrictions: No Commercial, No RV, No Truck

Land Information
Acres: 0.4200
Has Waterfront
Waterfront Description: Bay, Navigable, Seawall
Range: 25
View: Bay
Irrigation: Central

Marina/Dock Information
Boat Access: Boat Dock Private, Boat Lift, Boat Slip, Dock Deeded, Dock Included, Electricty Available at Dock, Water Available at Dock, Wooden Dock
No Bridge(s)
Gulf Access

Financial

Tax Information
Taxes: $8,308
Tax Year: 2019
Not Applicable
Homestead

Utilities

Utility Information
Water: Central
Sewer: Central
Heat: Central Electric
Cooling: Ceiling Fans, Central Electric
Cable Available

Location

Multi-Unit Information
# of Units/Floor: 1
# of Units in Complex: 1
# of Units in Building: 1
# of Floors: 1

Homeowners Association Information
Maintenance: None
Amenities: Beach Access, Clubhouse, Community Park, Golf Course, Restaurant, Underground Utility
Community Type: See Remarks, Non-Gated

School Information
Elementary School: LAKE PARK ELEMENTARY
Middle School: GULFVIEW MIDDLE SCHOOL
High School: NAPLES HIGH SCHOOL

Location Details
Sub Condo Name: MOORINGS

Public facts

Beds: —
Baths: —
Sq. Ft.: 4,401
Stories: —
Lot Size: 0.42 acres
Style: Single Family Residential
Year Built: 2023
Year Renovated: 2023
County: Collier County
APN: 12786640002

Home facts updated by county records on Oct 19, 2026

Other

Listing Information
Possession: At Closing

Around this home

Schools

K - 12
Preschool & daycare

Lake Park Elementary School

Public PreK-5 • Assigned • 1.2mi

10/10

Gulfview Middle School

Public 6-8 • Assigned • 2.2mi

9/10

Naples High School

Public PreK-12 • Assigned • 0.8mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

10/10 Heat Factor

7 days above 111° expected this year, 26 days in 30 years

10/10 Wind Factor

99% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Naples, FL • 34103

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.6 hours in June and 6.9 hours in December, placing it above the U.S. average for solar exposure.

9.6 hrs

6.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$5.30M – $6.42M

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New listings for sale in 34103

NEW 14 HRS AGO

$3,450,000

3 beds3 baths2,327 sq ft

4551 Gulf Shore Blvd N #902, Naples, FL 34103

Direct gulf views • Laundry room • Ample counter space

NEW 15 HRS AGO

$6,900,000

3 beds3.5 baths4,276 sq ft

4201 Gulf Shore Blvd N #1602, Naples, FL 34103

Beachfront addresses • Boutique building • Private lobby

NEW 21 HRS AGO

$1,795,000

3 beds2 baths1,346 sq ft

50 Seagate Dr Unit 904B, Naples, FL 34103

Flowering gardens • Winding paths • $2,250 HOA

3D & VIDEO TOUR

$3,325,000

3 beds3.5 baths2,287 sq ft

4000 Gulf Shore Blvd N #400, Naples, FL 34103

Private elevator • Deeded beach access • Leased boat slips

$7,950,000

3 beds3.5 baths3,755 sq ft

255 Bay Pt, Naples, FL 34103

Bayfront residence • Remodeled in 2025 • Expansive kitchen

3D WALKTHROUGH

$1,900,000

2 beds2.5 baths2,669 sq ft

4951 Gulf Shore Blvd N #104, Naples, FL 34103

Gulf views • Direct beach access • $1,983 HOA

3D WALKTHROUGH

$668,000

2 beds2 baths1,311 sq ft

3410 Gulf Shore Blvd N #304, Naples, FL 34103

Waterfront location • Open layout • Natural light

$1,995,000

3 beds3 baths1,950 sq ft

250 Park Shore Dr #101, Naples, FL 34103

Venetian bay views • Waterfront living • Electric shades

$14,995,000

4 beds5.5 baths5,929 sq ft

323 Neptunes Bight, Naples, FL 34103

Water views • Water frontage • Dock for boat

Home values near 2266 Windward Way

Data from public records.

Address	Redfin Estimate
2350 Windward Way, Naples, FL 4 Beds \| 4.5 Baths \| 5057 Sq. Ft.	$6,555,008
2351 Windward Way, Naples, FL 4 Beds \| 5.5 Baths \| 6729 Sq. Ft.	$14,831,346
2222 Windward Way, Naples, FL 4 Beds \| 6 Baths \| 5960 Sq. Ft.	$13,465,926
2200 Windward Way, Naples, FL - Beds \| - Baths \| 3804 Sq. Ft.	$6,693,618
375 Bow Line Dr, Naples, FL 4 Beds \| 4.5 Baths \| 4028 Sq. Ft.	$6,829,319
313 Bow Line Dr, Naples, FL - Beds \| - Baths \| 2736 Sq. Ft.	$2,975,845
328 Bow Line Bnd, Naples, FL - Beds \| - Baths \| 5146 Sq. Ft.	$9,661,784

Address	Redfin Estimate
2393 Windward Way, Naples, FL - Beds \| - Baths \| 4343 Sq. Ft.	$9,511,530
2331 Windward Way, Naples, FL - Beds \| - Baths \| 2615 Sq. Ft.	$6,002,001
2244 Windward Way, Naples, FL 4 Beds \| 4 Baths \| 5100 Sq. Ft.	$11,044,840
2300 Windward Way, Naples, FL 3 Beds \| 3 Baths \| 2346 Sq. Ft.	$6,129,927
305 Bow Line Dr, Naples, FL - Beds \| - Baths \| 2542 Sq. Ft.	$2,763,508
340 Wedge Dr, Naples, FL 3 Beds \| 2 Baths \| 2011 Sq. Ft.	$2,761,309
320 Bow Line Bnd, Naples, FL 3 Beds \| 3 Baths \| 2590 Sq. Ft.	$5,771,730

Address	Redfin Estimate
2400 Windward Way, Naples, FL 4 Beds \| 4.5 Baths \| 5245 Sq. Ft.	$6,495,237
2323 Windward Way, Naples, FL 3 Beds \| 2 Baths \| 1775 Sq. Ft.	—
2341 Windward Way, Naples, FL 3 Beds \| 4 Baths \| 3978 Sq. Ft.	$9,413,373
2226 Gulf Shore Blvd N Apartment P4, Naples, FL - Beds \| - Baths \| 1265 Sq. Ft.	$1,365,217
363 Bow Line Dr, Naples, FL 4 Beds \| 5 Baths \| 5900 Sq. Ft.	$8,695,669
370 Wedge Dr, Naples, FL 3 Beds \| 2.5 Baths \| 2182 Sq. Ft.	$2,361,075
300 Bow Line Bnd, Naples, FL - Beds \| - Baths \| 3972 Sq. Ft.	$7,407,252

Property information provided by NAPLESMLS when last listed in 2020. This data may not match . Learn more.

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