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For sale
  • Price cut: $100K (7/1)
    $1,399,000

    22939 Gasparilla Ln, Cudjoe Key, FL 33042

    3beds
    1,434sqft
    : 
    $8,173/mo
    Get pre-qualified
    Single Family Residence
    Built in 1999
    6,098 Square Feet Lot
    $-- Zestimate®
    $976/sqft
    $-- HOA

    What's special

    New metal roofCovered parkingRich wooden ceilingsRooftop deckUnforgettable ocean vistasOpen living spacesFenced grounds
    Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfectly positioned on a canal in the Lower Keys with easy boating access, Rooftop Retreat captures the essence of waterfront living with unforgettable ocean vistas and an inviting coastal atmosphere. Whether you're searching for a private island getaway, a second home, or an exceptional investment opportunity, this property delivers the very best of the Keys lifestyle.
    111 days
    |
    639
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    35
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    Zillow last checked:

    Listing updated:

    Listed by:

    Donna Pezzi 305-304-2602,

    Keller Williams Key West Compass Realty

    Source: FLKMLS,MLS#: 619835MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Bedroom 1
      • Description: Bedroom - canal side
      • Level: Main
      • Area: 105.67 Square Feet
      • Dimensions: 10.75 x 9.83
      Bedroom 2
      • Description: Middle Bedroom
      • Level: Main
      • Area: 88.46 Square Feet
      • Dimensions: 11.67 x 7.58
      Bedroom 3
      • Description: Bedroom - street side
      • Level: Main
      • Area: 113.78 Square Feet
      • Dimensions: 11.67 x 9.75
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: Washer, Dryer, Dishwasher, Refrigerator, Range
      Interior area
      • Total structure area: 1,434
      • Total interior livable area: 1,434 sqft

      Property

      Parking
      • Parking features: Open, RV Access/Parking, Storage
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Roof Top Deck
      • Fencing: Fenced
      • On waterfront: Yes
      Lot
      • Size: 6,098 Square Feet
      • Dimensions: 60 X 100
      Details
      • Parcel number: 00182700000000
      • Zoning: IS - Improved Subivision District

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1999

      Utilities & green energy

      • Utilities for property: Water Separate Meter

      Community & HOA

      Community
      • Subdivision: Cutthroat Harbor Est (23.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Cudjoe Key

      Financial & listing details

      • Price per square foot: $976/sqft
      • Tax assessed value: $820,808
      • Annual tax amount: $7,973
      • Date on market: 5/9/2026
      • Listing terms: Cash,Conventional,FHA

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/1/2026Price change$1,399,000-6.7%$976/sqft
        Source: Key West AOR #619835 Report a problem
        5/9/2026Listed for sale$1,499,000+48.9%$1,045/sqft
        Source: Key West AOR #619835 Report a problem
        12/28/2023Sold$1,006,436-12.4%$702/sqft
        Source: FLKMLS #605565 Report a problem
        11/13/2023Contingent$1,149,000$801/sqft
        Source: MLKAR #605565 Report a problem
        10/23/2023Price change$1,149,000-4.3%$801/sqft
        Source: MLKAR #605565 Report a problem
        6/6/2023Listed for sale$1,200,000+66.9%$837/sqft
        Source: MLKAR #605565 Report a problem
        10/1/2020Listing removed$719,000$501/sqft
        Source: Century 21 Island Life - Key West #588966 Report a problem
        2/7/2020Price change$719,000-4%$501/sqft
        Source: CENTURY 21 Island Life #588966 Report a problem
        1/4/2020Listed for sale$749,000+35%$522/sqft
        Source: Century 21 Island Life - Key West #588966 Report a problem
        5/31/2019Sold$555,000$387/sqft
        Source: FLKMLS #584802 Report a problem
        4/17/2019Price change$555,000-5.5%$387/sqft
        Source: Coastal Collection Real Estate Inc. #584802 Report a problem
        4/12/2019Price change$587,000-0.8%$409/sqft
        Source: Coastal Collection Real Estate Inc. #584802 Report a problem
        4/5/2019Price change$592,000-0.8%$413/sqft
        Source: Coastal Collection Real Estate Inc. #584802 Report a problem
        3/18/2019Listed for sale$597,000+70.6%$416/sqft
        Source: Coastal Collection Real Estate Inc. #584802 Report a problem
        3/18/2013Sold$350,000$244/sqft
        Source: Public Record Report a problem
        1/22/2013Listed for sale$350,000+27.3%$244/sqft
        Source: APA Investment Group, Inc. #A1683344 Report a problem
        9/26/2012Listing removed$275,000$192/sqft
        Source: APA Investment Group, Inc. #A1683344 Report a problem
        9/1/2012Listed for sale$275,000-68.7%$192/sqft
        Source: APA Investment Group, Inc. #A1683344 Report a problem
        5/19/2005Sold$879,000+2219.3%$613/sqft
        Source: Public Record Report a problem
        6/12/1995Sold$37,900$26/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$7,973 +4.1%$820,808 +1.6%
        2024$7,660 +19.8%$807,938 +39.7%
        2023$6,395 +17.1%$578,293 +10%
        2022$5,459 +7.6%$525,721 +10%
        2021$5,075 +1.6%$477,928 +2.8%
        2020$4,996 $464,952 -1.4%
        2019$4,996 -1.5%$471,318 +5.6%
        2018$5,070 +2.3%$446,497 +2.2%
        2017$4,956 +3.4%$437,022 +11.2%
        2016$4,795 +6.1%$392,919 +6.6%
        2015$4,521 $368,458
        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.
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        Climate risks

        Neighborhood: 33042

        Getting around

        14 / 100
        Car-Dependent

        Nearby schools

        GreatSchools rating

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