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371 Bayside Ave., Naples, FL 34108
$3,600,000 For Sale
- Beds
- 4
- Baths
- 4
- Sq Ft
- 3,447
- Built
- 1998
MLS# 225072095 405 days on market
Fees & taxes
- Seller’s 2025 taxes
- $68,538
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Ask about this home or arrange a tour.
Listing description
Luxury Live Auction! Bidding to start from $3,600,000.00!
An Extraordinary Naples Waterfront Opportunity.
Rarely does a waterfront property of this size, location, and potential become available in one of Naples' most desirable boating communities. Situated on an exceptional .58+ acre corner tip lot in Conners at Vanderbilt Beach, this remarkable property offers more than 300 feet of bay frontage, sweeping water views, and spectacular western sunsets.
The possibilities are as impressive as the setting. Envision building a magnificent 11,000+ square-foot waterfront estate, exploring the potential to subdivide for two luxury residences, or enjoying and enhancing the existing home. Whether you're seeking an exceptional personal retreat or a compelling investment opportunity, this property offers the flexibility to bring your vision to life.
A seawall and dock completed in 2019, along with a rare covered boathouse and expansive sun deck, add to the property's appeal. Boating enthusiasts will appreciate convenient Gulf access through Wiggins Pass, approximately two miles away. Just minutes from Vanderbilt Beach, the Ritz-Carlton Resorts, LaPlaya, Mercato, and Naples' finest dining and shopping, the location delivers the very best of the Naples waterfront lifestyle.
Now offered through auction, this is a unique opportunity to acquire one of the area's most distinctive waterfront properties. Exceptional frontage, an irreplaceable setting, and remarkable possibilities make this an offering worthy of serious consideration.
Your vision. Your opportunity. An extraordinary Naples waterfront address.
Property details
Building & ownership
- Ownership
- Single Family
- Furnishings
- Unfurnished
- Building style
- Multi-Story Home, Single Family
- Floor plan
- Split Bedrooms, 2 Story
- Construction
- Concrete Block, Poured Concrete, Wood Frame, Stucco, Vinyl Siding
- Roof
- Metal
- Lot size
- 0.58 acres
- Lot description
- Cul-De-Sac, Oversize
Interior
- Features
- Built-In Cabinets, Pull Down Stairs, Smoke Detectors, Vaulted Ceiling(s), Volume Ceiling, Walk-In Closet(s), Wet Bar, Window Coverings, Zero/Corner Door Sliders
- Flooring
- Concrete, Tile, Wood
- Cooling
- Ceiling Fan(s), Central Electric
- Additional rooms
- Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Screened Balcony, Screened Lanai/Porch, Workshop
Kitchen & dining
- Kitchen
- Island, Pantry
- Appliances
- Electric Cooktop, Dishwasher, Disposal, Microwave, Refrigerator/Freezer, Self Cleaning Oven, Washer
- Dining
- Breakfast Bar, Dining - Family, Eat-in Kitchen, Formal
Outdoor & view
- View
- Bay, Gulf and Bay, Partial Gulf
- Rear exposure
- West
- Exterior
- Boat Canopy/Cover, Boat Dock Private, Boat Lift, Boat Slip, Composite Dock, Dock Included, Elec Avail at dock, Hoist/Davit, Water Avail at Dock, Wooden Dock, Balcony, Screened Balcony, Screened Lanai/Porch, Outdoor Shower
- Storm protection
- Shutters Electric, Shutters - Manual
Parking
- Garage
- Yes
- Car port
- No
- Spots
- 4
- Description
- Circular Driveway, Attached
Pool & spa
- Private pool
- Yes
- Private spa
- Yes
- Pool description
- Below Ground, Concrete, Equipment Stays, Electric Heat
- Spa description
- Below Ground, Equipment Stays, Heated Electric, Jetted Tub
Waterfront
- Waterfront
- Yes
- Description
- Bay, Canal Front, Intersecting Canal, Navigable, Seawall
- Gulf access
- Yes
- Gulf access type
- Bridge(s)/Water Indirect
- Canal
- Canal Width 200+
- Boat / dock
- Boat Canopy/Cover, Boat Dock Private, Boat House, Boat Lift, Boat Slip, Composite Dock, Dock Included, Elec Avail at dock, Hoist/Davit, Water Avail at Dock, Wooden Dock
Community amenities
- Amenities
- Fish Cleaning Station, Fishing Pier, Internet Access, Streetlight, Underground Utility
- Elevator
- Private
- Security
- Smoke Detector(s)
What the fees cover
- Maintenance
- None
Pets & leasing
- Pets allowed
- Yes
- Restrictions
- Deeded
Schools
- Elementary
- Naples Park Elementary School
- Middle
- Pine Ridge Middle School
- High
- Barron Collier High School
Additional details
- Parcel number
- 27583080009
- Potential short sale
- No
- Auction
- Yes
Listing last updated October 30, 2026
Listing courtesy of Compass Florida LLC · 239-268-8976
The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Copyright 2026 M.L.S. of Naples, Inc. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Displayed under License No. SL3295589.
Property taxes for a new owner
That is about the same as the seller’s bill on the county’s 2026 roll.
If you make this home your primary residence, a homestead exemption would lower this figure. If you have also had a Florida homestead in any of the last three years, you may be able to carry up to $500,000 of its capped-value savings to this home, which Florida calls “portability.” Both are applied for with the Property Appraiser by March 1.
How a new owner’s property taxes are set is explained in the Costs & Taxes chapter of the 2027 Naples Buyer’s Guide.
Estimated from the Collier County Property Appraiser’s 2026 value of this home and its tax rate, plus its 2025 charges not based on value from the Collier County Tax Collector’s roll. The county sets a new value each January 1, so a new owner’s first full bill can differ.
Destinations & driving times from 371 Bayside Ave
Every destination named here is described in the Destinations chapter of the 2027 Naples Buyer’s Guide.
Driving times are estimated from this home’s location, using OpenStreetMap road data.
| Name | Miles | ETA |
|---|---|---|
| Mercato | 2 mi | 6 min |
| Galleria Shoppes at Vanderbilt | 3.7 mi | 9 min |
| Waterside Shops | 4.2 mi | 9 min |
| Venetian Village | 6 mi | 12 min |
| Coastland Center | 7.4 mi | 15 min |
| Fifth Avenue South | 9.1 mi | 17 min |
| Third Street South | 10.3 mi | 21 min |
| Coconut Point | 11.4 mi | 20 min |
| Miromar Outlets | 17.9 mi | 28 min |
| Gulf Coast Town Center | 22.3 mi | 32 min |
| Name | Miles | ETA |
|---|---|---|
| Nearest beach access: Vanderbilt Beach Park | 0.9 mi | |
| Delnor-Wiggins Pass State Park | 1.5 mi | 4 min |
| Clam Pass Park | 5 mi | 11 min |
| Barefoot Beach Preserve | 6.5 mi | 16 min |
| Bonita Beach | 6.7 mi | 16 min |
| Via Miramar Beach | 7.5 mi | 15 min |
| Lowdermilk Park | 8.1 mi | 16 min |
| Naples Municipal Beach and Pier | 10.4 mi | 21 min |
| Lovers Key State Park | 11.4 mi | 26 min |
| Fort Myers Beach | 18.2 mi | 43 min |
| Name | Miles | ETA |
|---|---|---|
| Artis—Naples | 4.1 mi | 8 min |
| Sugden Community Theatre | 9.2 mi | 18 min |
| Gulfshore Playhouse | 9.3 mi | 17 min |
| Barbara B. Mann Performing Arts Hall | 23.5 mi | 40 min |
| Music & Arts Community Center | 27.1 mi | 38 min |
| Name | Miles | ETA |
|---|---|---|
| North Collier Regional Park | 6.8 mi | 16 min |
| Fred W. Coyle Freedom Park | 8 mi | 16 min |
| Gordon River Greenway Park | 8.1 mi | 15 min |
| Naples Zoo | 8.1 mi | 17 min |
| Baker Park | 9.3 mi | 18 min |
| Cambier Park | 9.4 mi | 19 min |
| Sugden Regional Park | 12.4 mi | 24 min |
| Naples Botanical Garden | 12.8 mi | 25 min |
| Paradise Coast Sports Complex | 15.5 mi | 28 min |
| Big Corkscrew Island Regional Park | 17.2 mi | 31 min |
| Corkscrew Swamp Sanctuary | 22.7 mi | 40 min |
| Name | Miles | ETA |
|---|---|---|
| NCH North Naples Hospital | 3.3 mi | 8 min |
| Physicians Regional Pine Ridge Rd. | 8.5 mi | 18 min |
| NCH Baker Downtown | 8.7 mi | 17 min |
| Physicians Regional Collier Blvd. | 17.5 mi | 30 min |
| Name | Miles | ETA |
|---|---|---|
| Naples Airport (APF) | 10.2 mi | 20 min |
| Marco Island Executive Airport (MKY) | 23.8 mi | 45 min |
| Southwest Florida International Airport (RSW) | 28.5 mi | 41 min |
Flood zones & evacuation
Two different things, measured by two different agencies. Evacuation zones are about storm surge and who leaves first. Flood zones are FEMA’s insurance rating, and they vary from home to home.
Zone A Collier
The first zone ordered to evacuate, and the one called in the weakest storms.
Zone AE
1% annual chance, with a set base flood elevation
The lot is inside a Special Flood Hazard Area, where a federally backed mortgage requires flood insurance.
FEMA flood maps and Collier County Emergency Management. A revised Collier County flood map is in preparation and may change these zones.
Flood zones, evacuation, and insurance are explained in the Risk, Resilience & Insurance chapter of the 2027 Naples Buyer’s Guide.
Jeffrey Waldman
REALTOR® and Owner, Naples Abodes
Call (239) 450-3763 Text (239) 450-3763
Florida License SL3295589
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