$5,900,000

371 Bayside AVE, Naples, FL 34108

4 beds |
4 baths |
3,447 sqft

Single-Family Home
Built in 1998
0.58acre lot
4 car garage
$1,712/sqft
Listed 4 months ago

Property Description

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.

Listing Status:: Active
Date Added:: September 30, 2025
Data Last Updated:: February 13, 2026 at 2:08AM
Listing Office:: Compass Florida LLC : 239-268-8976
MLS ID:: 225072095

General: Built-In CabinetsPull Down StairsSmoke DetectorsVaulted Ceiling(s)Volume CeilingWalk-In Closet(s)Wet BarWindow CoveringsZero/Corner Door Sliders
Kitchen: IslandPantry
Appliances: Electric CooktopDishwasherDisposalMicrowaveRefrigerator/FreezerSelf Cleaning OvenWasher
Dining: Breakfast BarDining - FamilyEat-in KitchenFormal
Laundry: Laundry in Residence
Flooring: ConcreteTileWood
A/C: Ceiling Fan(s)Central Electric
Heating: Central Electric

General: Boat Canopy/CoverBoat Dock PrivateBoat LiftBoat SlipComposite DockDock IncludedElec Avail at dockHoist/DavitWater Avail at DockWooden DockBalconyScreened BalconyScreened Lanai/PorchOutdoor ShowerBoat HouseBelow GroundEquipment StaysHeated ElectricJetted Tub
Style: Multi-Story HomeSingle Family
Pool: Below GroundConcreteEquipment StaysElectric Heat
Parking: Circular DrivewayAttachedParking spaces: 4

Roofing: Metal
Windows: Window Coverings
General: Concrete BlockPoured ConcreteWood FrameStuccoVinyl Siding2Concrete BlockPoured Concrete

HOA Amenities: Fish Cleaning StationFishing PierInternet AccessStreetlightUnderground Utility0.0
Originating MLS: Naples
County: Collier

Zoning: 27583080009
View: BayGulf and BayPartial GulfView
Restrictions: Deeded

Water: Central

Source: Naples

This listing courtesy of Compass Florida LLC

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Naples Park Elementary School

685 111th Ave N, Naples, FL, 34108

Grades PK-5

1.13 miles away

Pine Ridge Middle School

1515 Pine Ridge Rd, Naples, FL, 34109

Grades 6-8

3.72 miles away

Aubrey Rogers High School

, Naples, FL, 34110

Grades 9-12

3.56 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.