45
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371 Bayside Avenue
About This Property
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.
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What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
How much can I actually make?
Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
How is cap rate calculated?
Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Oct 23, 2026 | Price Decreased |
$3,600,000
↓ $2M
(33.3%) | |
| Price Decreased | |||
| Jun 6, 2026 | Price Decreased |
$5,400,000
↓ $500K
(8.5%) | |
| Price Decreased | |||
| Jan 24, 2026 | Price Decreased |
$5,900,000
↓ $300K
(4.8%) | |
| Price Decreased | |||
| Sep 29, 2025 | Listed by Compass Florida LLC | $6,200,000 | |
| Listed by Compass Florida LLC | |||
| Jul 29, 2025 | Temporarily off market | - | |
| Temporarily off market | |||
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Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017