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For sale
    • $2,195,000

    33 Pen Key Clb, Islamorada, FL 33036

    3beds
    4,537sqft
    : 
    $13,187/mo
    Get pre-qualified
    Single Family Residence
    Built in 1987
    0.3 Acres Lot
    $-- Zestimate®
    $484/sqft
    $646/mo HOA

    What's special

    Resort-style poolPrivate beachWraparound porchesKey west-inspired residenceTimeless architectural charmKayak launchSpacious three-bedroom layout
    Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort-style living awaits in this Key West-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined by serenity and sophistication. A palm-lined entrance leads to a vibrant exterior with wraparound porches and sun-filled interiors framed by lush garden views. The spacious three-bedroom layout is designed for effortless indoor-outdoor living, with multiple gathering spaces opening to expansive patios ideal for entertaining, unwinding, or savoring golden sunsets. Mature palms, bougainvillea, and the scent of salt air create a secluded sanctuary that feels worlds away. Residents enjoy exclusive access to a resort-style pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to world-class sport fishing and boating, while full-time on-site property management ensures peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. Whether you're seeking a seasonal escape or a long-term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.
    118 days
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    453
    |
    10
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    Zillow last checked:

    Listing updated:

    Listed by:

    Eric M. Rizzo 305-394-3062,

    Ocean Sotheby's International Realty,

    Jamie Daniels 305-522-6872,

    Ocean Sotheby's International Realty

    Source: FLKMLS,MLS#: 619577MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Heating
      • Has Heating (Unspecified Type)
      Cooling
      • Central Air, Ceiling Fans(s), Ductless
      Appliances
      • Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler
      • Laundry: Laundry Room
      Features
      • Built-in Features, Elevator, Storage, Walk-in Closet(s), Quartz Countertops
      • Flooring: Tile, Wood, Carpet
      Interior area
      • Total structure area: 4,537
      • Total interior livable area: 4,537 sqft

      Property

      Parking
      • Parking features: Attached, Garage Door Opener, Open
      • Has attached garage: Yes
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: Accessible Elevator Installed, Parking
      Features
      • Patio & porch: Open Porch/Balcony, Windowed P/B, Screened Patio
      • Exterior features: Rain Gutters, Lighting
      • Has private pool: Yes
      • Pool features: In Ground, Above Ground, Concrete, Decked
      Lot
      • Size: 0.3 Acres
      Details
      • Parcel number: 00402800000000
      • Zoning: R1 - Residential Single Family
      • Other equipment: Satellite Dish, Irrigation Equipment

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Other
      • Property subtype: Single Family Residence
      Materials
      • CBS
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1987

      Utilities & green energy

      • Utilities for property: Cable Available

      Community & HOA

      Community
      • Features: Community Dockage, Manager on Premises, Beach, Other
      • Security: Security Gate
      • Subdivision: Penn Key Club (83.0)
      HOA
      • Has HOA: Yes
      • Services included: Common Area Mnt, Security, Other
      • HOA fee: $646 monthly
      Location
      • Region: Islamorada

      Financial & listing details

      • Price per square foot: $484/sqft
      • Tax assessed value: $1,795,418
      • Annual tax amount: $17,068
      • Date on market: 4/21/2026
      • Listing terms: No Seller Finance,Cash,Conventional

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        4/21/2026Listed for sale$2,195,000-12%$484/sqft
        Source: Key West AOR #619577 Report a problem
        4/20/2026Listing removed$2,495,000$550/sqft
        Source: FLKMLS #618190 Report a problem
        1/23/2026Listed for sale$2,495,000$550/sqft
        Source: FLKMLS #618190 Report a problem
        1/19/2026Listing removed$2,495,000$550/sqft
        Source: Key West AOR #616008 Report a problem
        8/1/2025Listed for sale$2,495,000-10.9%$550/sqft
        Source: Key West AOR #616008 Report a problem
        8/1/2025Listing removed$2,800,000$617/sqft
        Source: Key West AOR #613198 Report a problem
        1/18/2025Listed for sale$2,800,000+243.6%$617/sqft
        Source: Key West AOR #613198 Report a problem
        8/8/2012Sold$815,000-11.9%$180/sqft
        Source: FLKMLS #558712 Report a problem
        3/22/2012Listing removed$925,000$204/sqft
        Source: Mabel Vasniles #546516 Report a problem
        12/2/2011Listed for sale$925,000$204/sqft
        Source: Mabel Vasniles #546516 Report a problem
        8/4/2011Listing removed$925,000$204/sqft
        Source: Moorings Realty Inc. Report a problem
        3/12/2010Price change$925,000-19.6%$204/sqft
        Source: Moorings Realty Inc. Report a problem
        1/10/2009Listed for sale$1,150,000+243.3%$253/sqft
        Source: Homes & Land Report a problem
        4/17/1996Sold$335,000$74/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$17,069 +62.2%$1,795,418 +60.8%
        2024$10,526 +0.7%$1,116,839 +3%
        2023$10,451 +1.5%$1,084,310 +3%
        2022$10,299 -1.2%$1,052,729 +3%
        2021$10,429 +0.9%$1,022,067 +1.4%
        2020$10,336 $1,007,956 +2.3%
        2019$10,336 +0.3%$985,295 +1.9%
        2018$10,302 +2.4%$966,924 +2.1%
        2017$10,060 +4.1%$947,037 +2.1%
        2016$9,667 -3.4%$927,559 -6.3%
        2015$10,010 $989,488
        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: 33036

        Getting around

        42 / 100
        Car-Dependent
        66 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

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