$5,400,000
4 Bed Pool Home for Sale in Conners
371 Bayside Avenue, Naples, FL, 34108
About this home
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.
Property details
- Type
- SingleFamilyResidence
- Year built
- 1998
- Interior
- 3,447 sqft
- Lot size
- 25,264.8 sqft
- Acreage
- 0.58 acres
- Garage
- 4 car
- Days on market
- 273
- Total association fees
- None
- CDD
- None
- Est. taxes (1.4%)
- $75,600/yr
- Flood zone (area est.)
- Not available
- Storm protection
- None listed
- Exposure
- West
- Waterfront
- Yes
- Gulf access
- Yes
- Gulf access type
- Indirect — bridges/locks
- Pool
- Yes
- Spa
- Yes
- Natural gas
- No
- Water
- Public
- Sewer
- Public Sewer
- New construction
- No
- Pets
- Yes
- County
- Collier
Amenities
Based on the $/sqft of 4 comparable homes sold nearby in the last 12 months. Indicative, not an appraisal.
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Recently sold nearby
Closed comparable sales within ~1 mile in the last 12 months, similar price, size, beds/baths, and age.
| Address | Sold | Sold price | Beds/Baths | Sq ft | $/sqft |
|---|---|---|---|---|---|
| 8473 Bay Colony Drive 1904 | Apr 2026 | $5,100,000 | 3/3 | 3,325 | $1,534 |
| 8473 Bay Colony Drive 1704 | Dec 2025 | $5,000,000 | 3/3 | 3,325 | $1,504 |
| 8171 Bay Colony Drive 2004 | Dec 2025 | $5,255,000 | 3/3 | 3,274 | $1,605 |
| 8231 Bay Colony Drive 1101 | Jan 2026 | $6,000,000 | 3/3 | 3,380 | $1,775 |
| Average | 4 comps | $5,338,750 | $1,605 |
Market trends, Conners
Live community medians from the MLS · see all listings. Indicative, not an appraisal.
Price & status history
Down $800,000 (12.9%) from the original list price.
| Jun 5, 2026 | Price reducedfrom $5,900,000 | $5,400,000 |
| Sep 30, 2025 | Listed | $6,200,000 |
The good, the trade-offs & the location
- Private pool
- Gulf access (Indirect — bridges/locks)
- 4-car garage
- Built 1998 — pre-2002 construction may carry older wind codes and higher insurance
Straight-line distances to major SWFL amenities, approximate; actual drive times vary.
Nearby schools
Get more information on their programs, scores, and extracurriculars on each school's page · browse the full schools directory.
Similar communities
Matched by amenities, price tier, and location to Conners.
Listing information is provided in part by the Florida Gulf Coast Multiple Listing Service (MLS) through its Broker Reciprocity / Internet Data Exchange (IDX) program. Properties displayed may be listed by brokerages other than SWFL Relocation Team. Data is deemed reliable but is not guaranteed accurate by the MLS or this brokerage and should be independently verified. Fees, flood zones, taxes, square footage, and school assignments are estimates from the feed and must be confirmed. © 2026 SWFL Relocation Team. All rights reserved.