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For sale
  • $3,495,000

    414 Caribbean Dr E, Summerland Key, FL 33042

    4beds
    2,766sqft
    : 
    $21,562/mo
    Get pre-qualified
    Single Family Residence
    Built in 1970
    6,534 Square Feet Lot
    $3,268,700 Zestimate®
    $1,264/sqft
    $-- HOA

    What's special

    Private balconyOceanfront retreatPrivate oceanfront oasisMetal roofSeparate laundry roomBeautiful newly painted exteriorImmediate boating access
    OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful newly painted exterior, this elevated 4 bed 3.5 bath home offers 2,766 sq. ft. of beautifully designed living space where soaring ceilings and walls of glass frame endless turquoise water views. Rare 3 bedroom suites with ensuite bathrooms, and a 4th bedroom with ensuite half bath. The expansive open-concept living and entertaining areas create a seamless indoor-outdoor flow perfect for relaxing or hosting guests after a day on the water. Separate laundry room is a bonus. A rare concrete dock with a protected cut-in boat slip provides quick deep-water access to the Atlantic with no long canal commute--placing you minutes from world-class offshore fishing, reef diving, sandbars, and endless boating adventures. Step outside to your private oceanfront oasis featuring a sparkling pool and spa, expansive lounging decks, and a poolside kitchen designed for sunset entertaining and waterfront gatherings. Panoramic open-water views and ocean breezes create the perfect Keys atmosphere. Upstairs, the spacious primary suite offers stunning ocean views, a private balcony, and a peaceful retreat overlooking the Atlantic. Additional features include impact windows and doors, a metal roof, a chef's kitchen with granite countertops and stainless steel appliances, plus convenient access to the nearby Summerland Key Cove Airport for easy fly-in/fly-out travel in light aircraft. This rare offering combines luxury living, protected deep-water dockage, immediate ocean access, and unforgettable open-water views in one of the Florida Keys' most sought-after waterfront communities.
    61 days
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    753
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    37
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    Zillow last checked:

    Listing updated:

    Listed by:

    Lisa Swanson 305-924-3777,

    The Agency Florida Keys

    Source: FLKMLS,MLS#: 620024MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Heating
      • Has Heating (Unspecified Type)
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Wine Cooler, Stainless Steel Appliance(s)
      • Laundry: Laundry Room
      Features
      • Granite Counters, Walk-in Closet(s), Media Room
      • Flooring: Tile, Carpet
      Interior area
      • Total structure area: 2,766
      • Total interior livable area: 2,766 sqft

      Property

      Parking
      • Parking features: Open
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Open Porch/Balcony, Patio, Lanai
      • Exterior features: Built-in Barbecue, Outdoor Kitchen, Storage
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Has spa: Yes
      • Spa features: Heated
      • Fencing: Fenced
      • On waterfront: Yes
      Lot
      • Size: 6,534 Square Feet
      • Dimensions: 60 X 100
      Details
      • Parcel number: 00192910000000
      • Zoning: IS - Improved Subivision District

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Combo Construction
      Condition
      • Year built: 1970

      Community & HOA

      Community
      • Subdivision: Summerland Key Cove (25.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Summerland Key

      Financial & listing details

      • Price per square foot: $1,264/sqft
      • Tax assessed value: $2,415,171
      • Annual tax amount: $21,751
      • Date on market: 5/24/2026

        Estimated market value

        $3,268,700

        $3.11M - $3.43M

        $6,479/mo

        Price history

        DateEventPrice
        5/24/2026Listed for sale$3,495,000-4.9%$1,264/sqft
        Source: Key West AOR #620024 Report a problem
        4/18/2026Listing removed$3,675,000$1,329/sqft
        Source: Key West AOR #617413 Report a problem
        4/11/2026Price change$3,675,000-5.2%$1,329/sqft
        Source: FLKMLS #617413 Report a problem
        11/21/2025Listed for sale$3,875,000+15.7%$1,401/sqft
        Source: Key West AOR #617413 Report a problem
        4/12/2022Sold$3,350,000-4.1%$1,211/sqft
        Source: FLKMLS #599675 Report a problem
        3/29/2022Contingent$3,495,000$1,264/sqft
        Source: FLKMLS #599675 Report a problem
        3/4/2022Price change$3,495,000-7.9%$1,264/sqft
        Source: FLKMLS #599675 Report a problem
        2/15/2022Listed for sale$3,795,000+119.5%$1,372/sqft
        Source: FLKMLS #599675 Report a problem
        6/15/2020Listing removed$1,729,000$625/sqft
        Source: Coldwell Banker Schmitt RE Co. Lower Keys Office #587599 Report a problem
        10/6/2019Price change$1,729,000+1.7%$625/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #587599 Report a problem
        4/4/2019Price change$1,700,000+3.3%$615/sqft
        Source: Coastal Collection Real Estate Inc. #578894 Report a problem
        3/15/2019Price change$1,645,000-8.6%$595/sqft
        Source: Coastal Collection Real Estate Inc. #578894 Report a problem
        2/23/2018Listed for sale$1,800,000-5.2%$651/sqft
        Source: Coastal Collection Real Estate Inc. #578894 Report a problem
        1/19/2018Listing removed$1,899,000$687/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #571400 Report a problem
        6/15/2017Price change$1,899,000-5%$687/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #571400 Report a problem
        11/23/2016Price change$1,999,000-4.8%$723/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #571400 Report a problem
        7/13/2016Listed for sale$2,100,000+25.7%$759/sqft
        Source: Coldwell Banker Schmitt RE Co. Lower Keys Office #571400 Report a problem
        2/24/2015Sold$1,670,000-1.7%$604/sqft
        Source: FLKMLS #563776 Report a problem
        2/9/2015Pending sale$1,699,000$614/sqft
        Source: Coldwell Banker Schmitt RE Co. Lower Keys Office #563776 Report a problem
        3/16/2014Listed for sale$1,699,000-5.6%$614/sqft
        Source: Coldwell Banker Schmitt Real Estate Co #563776 Report a problem
        10/3/2013Listing removed$1,799,999$651/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #550466 Report a problem
        4/24/2013Price change$1,799,999+2.9%$651/sqft
        Source: Coldwell Banker Schmitt Real Estate Co #550466 Report a problem
        4/23/2013Price change$1,749,999-5.4%$633/sqft
        Source: Coldwell Banker Schmitt Real Estate Co #550466 Report a problem
        12/4/2011Listed for sale$1,849,999+5.7%$669/sqft
        Source: Coldwell Banker Schmitt R.E. - Mar #550466 Report a problem
        10/7/2011Listing removed$1,749,999$633/sqft
        Source: Coldwell Banker Schmitt R.E. - Mar #550466 Report a problem
        5/9/2011Listed for sale$1,749,999+84.2%$633/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #550466 Report a problem
        2/22/2006Sold$950,000$343/sqft
        Source: Public Record Report a problem
        3/19/2004Sold$950,000+251.9%$343/sqft
        Source: Public Record Report a problem
        12/31/1996Sold$270,000$98/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$21,752 +5.3%$2,415,171 +2.8%
        2024$20,652 -1.6%$2,349,585 -1.7%
        2023$20,978 +41.3%$2,389,599 +48.1%
        2022$14,844 +5.3%$1,613,380 +10%
        2021$14,093 +3.2%$1,466,709 +4.4%
        2020$13,659 $1,404,805 -6.2%
        2019$13,659 -6.3%$1,498,014 -2.5%
        2018$14,578 -4.5%$1,536,584 +11%
        2017$15,266 +10.8%$1,383,716 -0.3%
        2016$13,783 -3.1%$1,387,552 +39.9%
        2015$14,222 $991,847
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 33042

        Getting around

        24 / 100
        Car-Dependent
        50 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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