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For sale
    • Price cut: $200K (8/6)
    $4,995,000

    336 AVENIDA DE MAYO, SARASOTA, FL 34242

    8beds
    3,811sqft
    : 
    $32,335/mo
    Get pre-qualified
    Single Family Residence
    Built in 2019
    5,392 Square Feet Lot
    $-- Zestimate®
    $1,311/sqft
    $-- HOA

    What's special

    Heated poolWell-appointed guest suitesPrivate elevatorExpansive layoutLarge gathering islandHigh-end finishesPrivate baths
    Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
    140 days
    |
    259
    |
    7
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Samantha Callaway 630-865-3189,

    RE/MAX ALLIANCE GROUP 941-954-5454,

    Sabrina Ullmann 203-300-8181,

    RE/MAX ALLIANCE GROUP

    Source: Stellar MLS,MLS#: A4687301MLS LogoOriginating MLS: Sarasota - Manatee

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 8
      • Bathrooms: 9
      • Full bathrooms: 8
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: Second
      • Area: 224 Square Feet
      • Dimensions: 16x14
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 224 Square Feet
      • Dimensions: 14x16
      Other
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: Second
      • Area: 99 Square Feet
      • Dimensions: 11x9
      Other
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: Third
      • Area: 150 Square Feet
      • Dimensions: 15x10
      Other
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: Third
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Bedroom 2
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: Upper
      • Area: 108 Square Feet
      • Dimensions: 12x9
      Bedroom 3
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: Second
      • Area: 132 Square Feet
      • Dimensions: 12x11
      Bedroom 4
      • Features: En Suite Bathroom, Built-in Closet
      • Level: Second
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Bedroom 5
      • Features: En Suite Bathroom, Built-in Closet
      • Level: Second
      • Area: 99 Square Feet
      • Dimensions: 11x9
      Dining room
      • Level: Upper
      • Area: 140 Square Feet
      • Dimensions: 14x10
      Kitchen
      • Features: Kitchen Island
      • Level: Upper
      • Area: 140 Square Feet
      • Dimensions: 10x14
      Living room
      • Features: Ceiling Fan(s)
      • Level: Upper
      • Area: 320 Square Feet
      • Dimensions: 16x20
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Oven, Dishwasher, Disposal, Microwave, Refrigerator
      • Laundry: Laundry Room
      Features
      • Built-in Features, Ceiling Fan(s), Elevator, Thermostat, Walk-In Closet(s), Wet Bar
      • Flooring: Other, Hardwood
      • Doors: Sliding Doors
      • Windows: Window Treatments
      • Has fireplace: No
      Interior area
      • Total structure area: 6,086
      • Total interior livable area: 3,811 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Guest, Off Street
      • Attached garage spaces: 2
      Features
      • Levels: Three Or More
      • Stories: 3
      • Exterior features: Balcony, Irrigation System, Lighting, Private Entrance, Sidewalk
      • Has private pool: Yes
      • Pool features: Gunite, Heated, In Ground, Tile
      • Has spa: Yes
      • Spa features: Heated, In Ground
      Lot
      • Size: 5,392 Square Feet
      • Residential vegetation: Trees/Landscaped
      Details
      • Parcel number: 0082040038
      • Zoning: RMF1
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Coastal,Elevated,Florida
      • Property subtype: Single Family Residence
      Materials
      • Stucco, Wood Siding
      • Foundation: Slab
      • Roof: Metal
      Condition
      • New construction: No
      • Year built: 2019

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Water Connected

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: SARASOTA BEACH
      HOA
      • Has HOA: No
      Location
      • Region: Sarasota

      Financial & listing details

      • Price per square foot: $1,311/sqft
      • Tax assessed value: $2,206,400
      • Annual tax amount: $25,684
      • Date on market: 3/25/2026
      • Cumulative days on market: 135 days
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/6/2026Price change$4,995,000-3.8%$1,311/sqft
        Source: Stellar MLS #A4687301 Report a problem
        6/11/2026Price change$5,195,000-3.7%$1,363/sqft
        Source: Stellar MLS #A4687301 Report a problem
        5/18/2026Price change$5,395,000-3.6%$1,416/sqft
        Source: Stellar MLS #A4687301 Report a problem
        4/16/2026Price change$5,595,000-1.8%$1,468/sqft
        Source: Stellar MLS #A4687301 Report a problem
        3/25/2026Listed for sale$5,695,000-12.3%$1,494/sqft
        Source: Stellar MLS #A4687301 Report a problem
        7/9/2025Listing removed$6,495,000$1,704/sqft
        Source: Stellar MLS #A4646579 Report a problem
        4/1/2025Listed for sale$6,495,000$1,704/sqft
        Source: Stellar MLS #A4646579 Report a problem
        9/27/2024Listing removed$6,495,000$1,704/sqft
        Source: Stellar MLS #A4614865 Report a problem
        7/9/2024Listed for sale$6,495,000-14.9%$1,704/sqft
        Source: Stellar MLS #A4614865 Report a problem
        10/1/2022Listing removed--
        Source: Stellar MLS #A4529768 Report a problem
        3/31/2022Listed for sale$7,635,000+739%$2,003/sqft
        Source: Stellar MLS #A4529768 Report a problem
        8/15/2016Sold$910,000-5.1%$239/sqft
        Source: Stellar MLS #A4149197 Report a problem
        5/12/2016Pending sale$959,000$252/sqft
        Source: ERA Waterside Realty #A4132785 Report a problem
        3/25/2016Price change$959,000-3.6%$252/sqft
        Source: ERA Waterside Realty #A4132785 Report a problem
        1/21/2016Listed for sale$995,000$261/sqft
        Source: ERA Waterside Realty #A4132785 Report a problem
        1/15/2016Pending sale$995,000$261/sqft
        Source: ERA Waterside Realty #A4132785 Report a problem
        9/28/2015Listed for sale$995,000+55.5%$261/sqft
        Source: ERA WATERSIDE REALTY #A4132785 Report a problem
        9/16/2014Sold$640,000-12.2%$168/sqft
        Source: Public Record Report a problem
        6/14/2014Listing removed$729,000$191/sqft
        Source: POE & ASSOCIATES REALTY, LLC #M5836741 Report a problem
        4/10/2014Listed for sale$729,000$191/sqft
        Source: POE & ASSOCIATES REALTY, LLC #M5836741 Report a problem
        12/16/2013Listing removed$729,000$191/sqft
        Source: POE & ASSOCIATES REALTY, LLC #M5836741 Report a problem
        8/4/2013Price change$729,000-5.2%$191/sqft
        Source: POE & ASSOCIATES REALTY, LLC #M5836741 Report a problem
        4/12/2013Listed for sale$769,000+29.2%$202/sqft
        Source: POE & ASSOCIATES REALTY, LLC #M5836741 Report a problem
        1/19/2013Listing removed$595,000$156/sqft
        Source: Michael Saunders & Company - Licensed Real Estate Broker Report a problem
        5/10/2011Pending sale$595,000$156/sqft
        Source: Michael Saunders & Company - Licensed Real Estate Broker Report a problem
        4/16/2011Listed for sale$595,000+142.9%$156/sqft
        Source: Michael Saunders & Company - Licensed Real Estate Broker Report a problem
        6/30/2004Sold$245,000-33.3%$64/sqft
        Source: Public Record Report a problem
        3/8/2002Sold$367,500$96/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$24,826 -3.3%$1,948,808 +10%
        2024$25,684 +1%$1,771,644 +10%
        2023$25,439 +16.1%$1,610,585 +10%
        2022$21,906 +26.7%$1,464,168 +10%
        2021$17,289 +7.5%$1,331,062 +10%
        2020$16,087 +155.7%$1,210,056 +192.2%
        2019$6,292 $414,051 -24.6%
        2018$6,292 +3.3%$548,800 -23.4%
        2017$6,089 -19.9%$716,800 +1.8%
        2016$7,599 $704,400 +32.6%
        2015$7,599 $531,400 +18.5%
        2014$7,599 +14.3%$448,580
        2013$6,650 +10.6%$448,580 +10%
        2012$6,014 +2.4%$407,800 +0.8%
        2011$5,875 -5.1%$404,500 -2.8%
        2010$6,193 +3.8%$416,100 -7.7%
        2009$5,964 $450,600 +4.6%
        2008$5,964 -19.6%$430,700 -20.7%
        2007$7,422 $543,400 +15.6%
        2006-- $470,000 +27.2%
        2005-- $369,600 +34.1%
        2004$4,564 +5.4%$275,700 +9.6%
        2003$4,331 +6.7%$251,500 +7.4%
        2002$4,061 +58.2%$234,200 +39.7%
        2001$2,567 +7%$167,615 +9.5%
        2000$2,399 $153,007
        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.
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        Climate risks

        Neighborhood: 34242

        Getting around

        66 / 100
        Somewhat Walkable
        0 / 100
        No Nearby Transit
        72 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Phillippi Shores Elementary
        • Middle: Brookside Middle
        • High: Sarasota High

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

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