Poised along the shimmering waterways of Vanderbilt Beach, 231 Trade Winds Avenue presents a rare opportunity to create an architectural statement on one of Conners’ most coveted Gulf-access parcels. Perfectly positioned at the end of a serene cul-de-sac, the property is surrounded by exceptionally wide waterways—over 400 feet of open water to the west and more than 200 feet to the north—offering a commanding backdrop of panoramic vistas, tranquil reflections, and unobstructed sunsets. A brand-new seawall will be built and is included in the price, providing added value and peace of mind for future development. Spanning more than 200 feet of direct waterfrontage, this expansive lot invites a custom estate crafted to embrace the grandeur of its setting. Envision an infinity-edge pool that visually merges with the intersecting waterways, vast terraces designed for year-round coastal living, and a yacht-ready dock offering effortless, bridgeless access to the Gulf of Mexico. The site’s exceptional width, depth, and orientation allow for a dramatic floor plan with seamless indoor-outdoor flow, a chef’s kitchen opening to waterside entertaining areas, and a sophisticated primary suite positioned to capture the serene water views from sunrise to sunset. Located within the sought-after Conners enclave, this premier address places you moments from the white-sand beaches of Vanderbilt, the refinement of Waterside Shops, the vibrant dining and boutique scene at Mercato, and the best of North Naples’ coastal lifestyle. A truly extraordinary canvas, 231 Trade Winds Avenue offers the rare freedom to bring your vision of elevated waterfront living to life—set against some of the widest and most breathtaking water views in all of Conners.
Lot/land
$4,295,000
231 Trade Winds AVE, NAPLES, FL 34108
--beds
--baths
0.37Acres
Unimproved Land
Built in ----
0.37 Acres Lot
$-- Zestimate®
$--/sqft
$-- HOA
What's special
Tranquil reflectionsUnobstructed sunsets
- 15 days |
- 116 |
- 4 |
Zillow last checked: 8 hours ago
Listing updated: November 28, 2025 at 08:23am
Listed by:
Chris Resop 239-231-6164,
The Agency Naples,
Kara Resop 239-280-8955,
The Agency Naples
Source: SWFLMLS,MLS#: 225080905
Originating MLS: Naples
Facts & features
Interior
Features
- Has fireplace: No
Property
Features
- Exterior features: Dock, Boat Lift, Elec Avail at dock
- Has view: Yes
- View description: Bay
- Has water view: Yes
- Water view: Bay
- Waterfront features: Bay, Navigable Water
- Frontage type: Bay/Harbor
Lot
- Size: 0.37 Acres
- Features: Corner Lot, Cul-De-Sac, Dead End, Oversize
- Residential vegetation: Grassed, Cleared
Details
- Parcel number: 27585560006
Utilities & green energy
- Water: Central
- Utilities for property: Cable Connected, Electricity Connected, Phone Connected, Water Connected
Community & HOA
Community
- Features: Boating, Non-Gated
- Subdivision: CONNERS
HOA
- Has HOA: No
- Amenities included: None
Location
- Region: Naples
Financial & listing details
- Tax assessed value: $3,608,460
- Annual tax amount: $32,417
- Date on market: 11/28/2025
- Lease term: Buyer Finance/Cash
- Electric utility on property: Yes
- Road surface type: Paved
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/28/2025 | Listed for sale | $4,295,000+22.7% |
Source: | ||
| 5/15/2025 | Sold | $3,500,000-7.9% |
Source: | ||
| 4/3/2025 | Pending sale | $3,799,000 |
Source: | ||
| 3/29/2025 | Listed for sale | $3,799,000 |
Source: | ||
| 3/28/2025 | Pending sale | $3,799,000 |
Source: | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $32,418 -12.8% | $2,754,444 +13.7% |
| 2023 | $37,155 +18.8% | $2,422,264 +5.5% |
| 2022 | $31,263 +27.7% | $2,296,867 +10% |
Find assessor info on the county website
BuyAbility℠ payment
Estimated monthly payment
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Neighborhood: 34108
Nearby schools
GreatSchools rating
- 6/10Naples Park Elementary SchoolGrades: PK-5Distance: 1.1 mi
- 9/10Pine Ridge Middle SchoolGrades: 6-8Distance: 3.9 mi
- NAHospital/HomeboundGrades: K-12Distance: 4.8 mi
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