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For sale
  • Price cut: $245K (6/28)
    $3,750,000

    58652 Overseas Hwy, Grassy Key, FL 33050

    4beds
    2,429sqft
    : 
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    Single Family Residence
    Built in 1981
    0.85 Acres Lot
    $3,446,100 Zestimate®
    $1,544/sqft
    $-- HOA

    What's special

    Fruit treesPrivate balconyTop-floor penthouse suiteLocal artist muralFire tableLibrary loftCascading waterfalls
    Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key with expansive water views, white sand beach, and a true resort-style experience in the Florida Keys. An exceptional investment opportunity, Casa Feliz is a strong producing vacation rental with rental history and future bookings already in place. Set on over 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, this exceptional estate is designed for both relaxation and entertaining. An observation pier invites kayaking, paddleboarding, fishing, and endless enjoyment of marine life, while the unique orientation captures both breathtaking sunrise and sunset views over the water, a rare and coveted feature in the Keys. Outdoor living is elevated with a resort-style saltwater pool featuring cascading waterfalls, spillover spa, and fully equipped poolside cabana complete with wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit create the ultimate setting for entertaining or unwinding beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was thoughtfully redesigned to maximize sweeping ocean views from nearly every room. Offering four custom bedroom suites, each with private en-suite bath, the home comfortably accommodates guests in luxury. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Expansive accordion impact glass doors seamlessly blend indoor and outdoor living throughout. The gourmet kitchen showcases Cafe appliances, induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas ideal for hosting. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, local artist mural, and more. Discover why Grassy Key is the place to be.
    59 days
    |
    1,350
    |
    105
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Ally Kelley 727-459-0493,

    Ocean Sotheby's International,

    Jo Ann Cook 305-360-7968,

    Ocean Sotheby's International

    Source: FLKMLS,MLS#: 619913MLS LogoOriginating MLS: Marathon/Lower Keys

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Cooling
      • Ceiling Fans(s)
      Appliances
      • Included: Washer, Stainless Steel Appliance(s), Wine Cooler, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
      • Laundry: Laundry Room
      Features
      • Quartz Countertops, Theater Room
      • Flooring: Tile, Wood
      • Doors: Impact Rstnce Doors
      • Windows: Drapes/Blinds Incl, Impact Rstnce Window
      • Furnished: Yes
      Interior area
      • Total interior livable area: 2,429 sqft

      Property

      Parking
      • Parking features: Carport
      • Has carport: Yes
      Features
      • Patio & porch: Open Porch/Balcony
      • Exterior features: Built-in Barbecue, Water Display, Storage, Sprinkler System, Sandy Beach, Outdoor Shower, Outdoor Kitchen, Lighting, Rain Gutters
      • Has private pool: Yes
      • Pool features: Heated, In Ground, Decked, Concrete, Lap
      • Has spa: Yes
      • Spa features: Private
      • Fencing: Privacy
      • Has view: Yes
      • View description: Ocean, Water
      • Has water view: Yes
      • Water view: Ocean,Water
      • Waterfront features: Oceanfront, Open Water, Waterfront, Sandy Beach, Dock: Composite
      Lot
      • Size: 0.85 Acres
      • Dimensions: 60 x 410
      • Features: 1/4 - 1/2 Acre
      • Residential vegetation: Fruit Tree(s)
      Details
      • Parcel number: 00366860000000
      • Zoning: RM
      • Zoning description: Residential Medium

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS
      • Roof: Metal
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1981

      Utilities & green energy

      • Sewer: Municipal Sewer, Public Sewer
      • Utilities for property: FKAA, Propane, Cable Available, Buyer to Verify

      Community & HOA

      Community
      • Security: Security System, Smoke Detector(s)
      • Subdivision: Crains Sub (58.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Grassy Key

      Financial & listing details

      • Price per square foot: $1,544/sqft
      • Tax assessed value: $1,579,131
      • Annual tax amount: $14,033
      • Date on market: 5/15/2026
      • Listing terms: No Seller Finance

        Estimated market value

        $3,446,100

        $3.27M - $3.62M

        $7,149/mo

        Price history

        DateEventPrice
        6/28/2026Price change$3,750,000-6.1%$1,544/sqft
        Source: Key West AOR #619913 Report a problem
        5/15/2026Listed for sale$3,995,000+207.3%$1,645/sqft
        Source: MLKAR #619913 Report a problem
        6/30/2017Sold$1,300,000-3.7%$535/sqft
        Source: FLKMLS #573307 Report a problem
        3/28/2017Price change$1,350,000-9.7%$556/sqft
        Source: RE/MAX All Keys (Marathon) Real Estate #573307 Report a problem
        12/23/2016Listed for sale$1,495,000+121.6%$615/sqft
        Source: RE/MAX All Keys Real Estate #573307 Report a problem
        1/30/2004Sold$674,500+101.3%$278/sqft
        Source: FLKMLS #520194 Report a problem
        11/22/2000Sold$335,000$138/sqft
        Source: MLKAR #504095 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$14,034 -27%$1,579,131 -23.9%
        2024$19,228 +56.2%$2,074,909 +127.7%
        2023$12,310 +25.5%$911,309 +10%
        2022$9,808 +22.9%$828,463 +10%
        2021$7,982 +3.9%$753,148 +2.5%
        2020$7,683 $734,789 -2.4%
        2019$7,683 -2.3%$752,600 -7.8%
        2018$7,861 -3.9%$816,185 -0.8%
        2017$8,180 +3.9%$823,135 +2.1%
        2016$7,870 -1%$806,205 +0.7%
        2015$7,949 $800,601
        Find assessor info on the county website

        Monthly payment

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        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: 33050

        Getting around

        7 / 100
        Car-Dependent
        43 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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