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For sale
    • Price cut: $500K (6/5)
    $5,400,000

    371 Bayside AVE, NAPLES, FL 34108

    4beds
    3,447sqft
    : 
    $33,748/mo
    Get pre-qualified
    Single Family Residence
    Built in 1998
    0.58 Acres Lot
    $-- Zestimate®
    $1,567/sqft
    $-- HOA

    What's special

    Covered boathouseSun deckCorner tip lotWestern exposure sunsetsNew seawall and dock
    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.
    330 days
    |
    338
    |
    10
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    Zillow last checked:

    Listing updated:

    Listed by:

    Debbie Pappas-Burback, PA 239-404-4900,

    Compass Florida LLC

    Source: SWFLMLS,MLS#: 225072095MLS LogoOriginating MLS: Naples

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Rooms
      • Room types: Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Office, Screened Balcony, Screened Lanai/Porch, Workshop, 4 Bed
      Primary bedroom
      • Dimensions: 30.6 x 14
      Bedroom
      • Dimensions: 12 x 11
      Bedroom
      • Dimensions: 11.9 x 12.6
      Bedroom
      • Dimensions: 11.9 x 11
      Dining room
      • Dimensions: 12 x 11
      Family room
      • Dimensions: 18 x 15.9
      Garage
      • Dimensions: 46 x 20.8
      Kitchen
      • Dimensions: 11.3 x 12.9
      Other
      • Dimensions: 16.8 x 30.6
      Living room
      • Dimensions: 16.6 x 14.9
      Heating
      • Central
      Cooling
      • Ceiling Fan(s), Central Air
      Appliances
      • Included: Electric Cooktop, Dishwasher, Disposal, Microwave, Refrigerator/Freezer, Self Cleaning Oven, Washer
      • Laundry: Inside
      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, Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Screened Balcony, Screened Lanai/Porch, Workshop
      • Flooring: Concrete, Tile, Wood
      • Doors: Zero/Corner Door Sliders
      • Windows: Window Coverings, Shutters Electric, Shutters - Manual
      • Has fireplace: No
      Interior area
      • Total structure area: 11,087
      • Total interior livable area: 3,447 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 4
      • Parking features: Circular Driveway, Attached
      • Attached garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Levels: Multi/Split
      • Stories: 2
      • Patio & porch: Deck, Screened Lanai/Porch
      • Exterior features: Dock, Boat Slip, Balcony, Outdoor Shower, Boat Canopy/Cover, Boat Lift, Elec Avail at dock, Hoist/Davit, Water Avail at Dock
      • Has private pool: Yes
      • Pool features: In Ground, Concrete, Equipment Stays, Electric Heat
      • Has spa: Yes
      • Spa features: In Ground, Equipment Stays, Heated, Bath
      • Has view: Yes
      • View description: Bay, Gulf and Bay, Partial Gulf
      • Has water view: Yes
      • Water view: Bay,Gulf and Bay,Partial Gulf
      • Waterfront features: Bay, Canal Front, Intersecting Canal, Navigable Water, Seawall
      • Frontage type: Bay/Harbor
      Lot
      • Size: 0.58 Acres
      • Features: Cul-De-Sac, Oversize
      Details
      • Additional structures: Boat House
      • Parcel number: 27583080009

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Concrete, Frame, Stucco, Vinyl Siding
      • Foundation: Concrete Block, Poured Concrete
      • Roof: Metal
      Condition
      • New construction: No
      • Year built: 1998

      Utilities & green energy

      • Gas: Propane
      • Water: Central

      Community & HOA

      Community
      • Features: Fishing, Street Lights, Boating
      • Security: Smoke Detector(s)
      • Subdivision: CONNERS
      HOA
      • Has HOA: No
      • Amenities included: Fish Cleaning Station, Fishing Pier, Internet Access, Streetlight, Underground Utility
      Location
      • Region: Naples

      Financial & listing details

      • Price per square foot: $1,567/sqft
      • Tax assessed value: $6,644,968
      • Annual tax amount: $24,468
      • Date on market: 9/30/2025
      • Lease term: Buyer Finance/Cash

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/5/2026Price change$5,400,000-8.5%$1,567/sqft
        Source: SWFLMLS #225072095 Report a problem
        1/23/2026Price change$5,900,000-4.8%$1,712/sqft
        Source: SWFLMLS #225072095 Report a problem
        9/30/2025Listed for sale$6,200,000-4.6%$1,799/sqft
        Source: SWFLMLS #225072095 Report a problem
        7/28/2025Listing removed$6,500,000$1,886/sqft
        Source: SWFLMLS #225011611 Report a problem
        4/18/2025Price change$6,500,000-13.3%$1,886/sqft
        Source: SWFLMLS #225011611 Report a problem
        1/30/2025Listed for sale$7,500,000-18.5%$2,176/sqft
        Source: SWFLMLS #225011611 Report a problem
        9/17/2024Listing removed$9,200,000$2,669/sqft
        Source: SWFLMLS #224045163 Report a problem
        9/3/2024Listed for sale$9,200,000$2,669/sqft
        Source: SWFLMLS #224045163 Report a problem
        8/21/2024Listing removed$9,200,000$2,669/sqft
        Source: SWFLMLS #224045163 Report a problem
        8/9/2024Price change$9,200,000-14.4%$2,669/sqft
        Source: SWFLMLS #224045163 Report a problem
        6/7/2024Price change$10,750,000-6.5%$3,119/sqft
        Source: SWFLMLS #224045163 Report a problem
        5/24/2024Listed for sale$11,500,000+3185.7%$3,336/sqft
        Source: SWFLMLS #224045163 Report a problem
        1/22/1999Sold$350,000-73%$102/sqft
        Source: Public Record Report a problem
        3/9/1998Sold$1,298,000$377/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$68,538 +179%$6,644,968 +177.3%
        2024$24,568 +1.4%$2,396,105 +3%
        2023$24,219 -3.1%$2,326,316 +3%
        2022$24,990 -1%$2,258,559 +3%
        2021$25,237 +2.4%$2,192,776 +1.4%
        2020$24,653 +1.6%$2,162,501 +2.3%
        2019$24,259 +6.6%$2,113,882 +3.7%
        2018$22,752 -0.9%$2,039,227 +2.1%
        2017$22,965 +1.4%$1,997,284 +2.1%
        2016$22,658 +2.2%$1,956,204 +0.7%
        2015$22,160 -0.8%$1,942,606 +3.5%
        2014$22,330 +0.5%$1,876,688 +1.5%
        2013$22,212 +0.5%$1,848,207 +1.7%
        2012$22,108 -1.1%$1,816,469 -1.7%
        2011$22,360 -24.1%$1,847,028 -14.1%
        2010$29,470 +6.4%$2,149,836 -13.3%
        2009$27,709 $2,479,465 -1.9%
        2008$27,709 -6%$2,527,438 +3%
        2007$29,476 -2.9%$2,453,823 +2.5%
        2006$30,367 $2,393,974 +3%
        2005$30,367 +2.2%$2,324,247 +3%
        2004$29,719 -0.4%$2,256,550 +1.9%
        2003$29,844 +23%$2,214,475 +25.9%
        2002$24,266 -42.8%$1,758,462 +12.5%
        2001$42,428 +143.4%$1,563,536
        2000$17,434 --
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.
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        Climate risks

        Neighborhood: 34108

        Getting around

        21 / 100
        Car-Dependent
        46 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: NAPLES PARK ELEMENTARY SCHOOL
        • Middle: PINE RIDGE MIDDLE SCHOOL
        • High: BARRON COLLIER HIGH SCHOOL

        Source: SWFLMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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