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4 Beds
4 Baths
3,447 sqft

$5,400,000

371 Bayside AVE, Naples FL, 34108

Price per sqft$1,566.58
Built in1998
Property size3,447 sqft
Property typeResidential

Overview

Active

Listed Sep 30, 2025

Updated 10 days ago

A Rare Investment Opportunity in one of Naples’ Most Sought After Waterfront Communities. Where the beauty of Vanderbilt Bay meets boundless possibility, discover a property unlike any other in Conners. Spanning over .58 acres on a rare corner tip lot with more than 300 feet of pristine bay frontage, this extraordinary offering presents the chance to create something truly remarkable. Here, western exposure sunsets melt into the water, boats drift by in the golden light, and every view feels like a postcard. But beyond its beauty lies extraordinary investment potential—the opportunity to design a grand 11,000+ sq/ft waterfront estate, divide the parcel for dual residences, or reimagine the current home while planning your next masterpiece. A new seawall and dock (2019), along with a rare covered boathouse and sun deck, ensure this property is ready to enjoy today while holding immense value for tomorrow. Just two miles to the Gulf of Mexico via Wiggins Pass, the location offers seamless access for boaters and unbeatable proximity to Vanderbilt Beach, the Ritz-Carlton Resorts, LaPlaya, Mercato, and Naples’ finest dining and shopping. For the visionary investor or homeowner who understands that opportunity and beauty seldom converge—this is your moment. Endless views. Endless potential. Endless Naples waterfront lifestyle.

$35,926/mo

Est. mortgage payment based on a $5,400,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
225072095

Interior Features

Bedrooms
4
Bathrooms
4
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.58 Acres

Other Property Details

Taxes
$24,468
Tax Frequency
Annually
Secondary Association Fee
Not Listed
Garage
Yes
View
Yes
Pets Allowed
Yes
Pool
Yes
Waterfront
Yes
55+/Senior Community
No

Listed by Debbie Pappas-Burback, PA, Compass Florida LLC

Listing Contact: 239-404-4900 

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Aston Rose Sports and Entertainment shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

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Data last updated 4:19 AM UTC, 9/30/2026

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