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Pending
  • $5,350,000

    4042 Old Trail WAY, NAPLES, FL 34103

    4beds
    4,049sqft
    : 
    $35,104/mo
    Get pre-qualified
    Single Family Residence
    Built in 2000
    -- sqft lot
    $-- Zestimate®
    $1,321/sqft
    $25/mo HOA

    What's special

    Resort-style poolLarge center islandOutdoor kitchenInviting private oasisIncredibly large backyardSpacious light-filled great roomFire pit
    Situated in the heart of prestigious Park Shore on a quiet cul-de-sac street, this residence was beautifully remodeled and refreshed in 2018 by esteemed custom builder A. Vernon Allen Builder, Inc, with an elegant redesign by Herscoe Hajjar Architects, LLC. The result is an impressive, thoughtfully arranged floor plan that blends quality craftsmanship with the relaxed sophistication of coastal living. Designed for both comfortable daily living and effortless entertaining, the home features 4 bedrooms, a playroom, and an office. A spacious, light-filled great room flows seamlessly into a stunning and well-equipped kitchen appointed with a large center island, Wolf and Sub-Zero appliances, and an expansive butler’s pantry/prep kitchen. The large covered outdoor living area is conveniently accessed either from the great room or from an intimate sitting room also adjacent to the kitchen a charming, relaxed sitting area ideal for quiet moments, watching television, light reading, or seamlessly moving between the kitchen and the outdoor living spaces. Extraordinary for the Park Shore neighborhood, the property offers an incredibly large backyard—an inviting private oasis boasting a resort-style pool, generous pool deck, fire pit, outdoor kitchen, and a charming trellis-covered dining area, all framed by lush, beautifully designed landscaping. Additional modern comforts include retractable screens and shutters, a 24KW generator, security cameras, and more. This property is eligible for membership to the Park Shore Association Beach Park.
    42 days
    76
    3

    Zillow last checked:

    Listing updated:

    Listed by:

    Richard Prebish, II 239-357-6628,

    William Raveis Real Estate,

    Thomas Campbell, Jr. 239-860-4923,

    William Raveis Real Estate

    Source: SWFLMLS,MLS#: 226034529MLS LogoOriginating MLS: Naples

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Rooms
      • Room types: Den - Study, Family Room, Office, 4 Bedrooms Plus Den
      Dining room
      • Features: Breakfast Bar, Dining - Living
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Gas Cooktop, Dishwasher, Dryer, Microwave, Refrigerator/Freezer, Oven, Washer, Wine Cooler
      • Laundry: Inside
      Features
      • Built-In Cabinets, Foyer, Walk-In Closet(s), Den - Study, Family Room, Home Office, Laundry in Residence
      • Flooring: Carpet, Tile, Wood
      • Windows: Storm Protection (Other)
      • Has fireplace: No
      Interior area
      • Total structure area: 5,222
      • Total interior livable area: 4,049 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached
      • Attached garage spaces: 2
      Features
      • Stories: 2
      • Exterior features: Outdoor Grill, Fire Pit, Outdoor Shower
      • Has private pool: Yes
      • Pool features: In Ground
      • Has spa: Yes
      • Spa features: In Ground
      • Has view: Yes
      • View description: Landscaped Area
      • Waterfront features: None
      Details
      • Parcel number: 16005360001
      • Other equipment: Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Frame, Stucco
      • Foundation: Concrete Block
      • Roof: Built-Up,Tile
      Condition
      • New construction: No
      • Year built: 2000

      Utilities & green energy

      • Gas: Propane
      • Water: Central

      Community & HOA

      Community
      • Features: Non-Gated
      • Subdivision: PARK SHORE
      HOA
      • Has HOA: No
      • Amenities included: None
      • HOA fee: $300 annually
      Location
      • Region: Naples

      Financial & listing details

      • Price per square foot: $1,321/sqft
      • Tax assessed value: $3,633,585
      • Annual tax amount: $28,926
      • Date on market: 9/29/2026
      • Lease term: Buyer Finance/Cash

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        10/7/2026Pending sale$5,350,000$1,321/sqft
        Source: SWFLMLS #226034529 Report a problem
        9/29/2026Listed for sale$5,350,000-9.2%$1,321/sqft
        Source: SWFLMLS #226034529 Report a problem
        6/2/2026Listing removed$5,895,000$1,456/sqft
        Source: SWFLMLS #225079376 Report a problem
        11/25/2025Listed for sale$5,895,000+1.9%$1,456/sqft
        Source: SWFLMLS #225079376 Report a problem
        10/19/2023Sold$5,783,000-1.9%$1,428/sqft
        Source: Public Record Report a problem
        5/16/2023Listing removed--
        Source: William Raveis Real Estate, Mortgage & Insurance Report a problem
        3/7/2023Listed for sale$5,895,000+73.6%$1,456/sqft
        Source: SWFLMLS #222077750 Report a problem
        8/26/2020Listing removed$3,395,000$838/sqft
        Source: Premier Sotheby's International Realty #220048181 Report a problem
        8/6/2020Listed for sale$3,395,000+2878.1%$838/sqft
        Source: Premier Sotheby's International Realty #220048181 Report a problem
        4/5/1999Sold$114,000$28/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$28,926 +2.2%$3,239,424 +2.9%
        2024$28,304 +180.1%$3,148,128 +178.5%
        2023$10,104 -2.7%$1,130,246 +3%
        2022$10,382 -1.5%$1,097,326 +3%
        2021$10,541 +2.5%$1,065,365 +1.4%
        2020$10,284 +9.7%$1,050,656 +10.5%
        2019$9,373 +2.2%$950,872 +1.9%
        2018$9,173 $933,142 -0.8%
        2017$9,173 -1.5%$941,022 +2.1%
        2016$9,309 +1.7%$921,667 +0.7%
        2015$9,149 -2%$915,260 +6.7%
        2014$9,340 -0.1%$857,996 +1.6%
        2013$9,345 +0.1%$844,577 +1.8%
        2012$9,341 +3.7%$829,623 +3.2%
        2011$9,005 -11%$804,003 -2.8%
        2010$10,120 +6.7%$827,580 -10.1%
        2009$9,482 $920,369 -5.1%
        2008$9,482 -7%$969,400 +3%
        2007$10,193 -1.8%$941,165 +2.5%
        2006$10,380 $918,210 +3.8%
        2005$10,380 +1.9%$884,422 +3%
        2004$10,183 -0.4%$858,662 +1.9%
        2003$10,224 -5.1%$842,652 -0.9%
        2002$10,769 -42%$850,203 +18.9%
        2001$18,568 +609.9%$715,182
        2000$2,616 --
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        Climate risks

        Neighborhood: Park Shore

        Getting around

        59 / 100
        Somewhat Walkable
        49 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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