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For sale
  • Price cut: $155K (8/19)
    $3,495,000

    58652 Overseas Hwy, Grassy Key, FL 33050

    4beds
    2,429sqft
    : 
    $21,637/mo
    Get pre-qualified
    Single Family Residence
    Built in 1981
    0.85 Acres Lot
    $3,256,300 Zestimate®
    $1,439/sqft
    $-- HOA

    What's special

    Fruit treesLibrary loftFresh herbsPrivate oceanfront retreatBougainvillea-lined gatesCustom millworkWhite sand beach
    Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key offering expansive water views, a white sand beach, and resort-style living. A strong-producing vacation rental with established history and future bookings in place, this exceptional estate presents an attractive investment opportunity. Set on more than 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, Casa Feliz is designed for relaxation and entertaining. An observation pier provides access for kayaking, paddleboarding, fishing, and enjoying abundant marine life. Dockage is available nearby at Duck Key Marina or Grassy Key Marina, if desired. The property's unique orientation captures both sunrise and sunset views, a rare feature in the Keys. Outdoor amenities include a saltwater pool with cascading waterfalls, spillover spa, and a fully equipped poolside cabana featuring a wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit offer inviting spaces to gather beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was redesigned to maximize ocean views throughout. Four custom bedroom suites, each with a private en-suite bath, comfortably accommodate guests. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Accordion impact-glass doors create a seamless connection between indoor and outdoor living. The gourmet kitchen features Café appliances, an induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, and a mural by a local artist. Come discover why Grassy Key is the place to be.
    107 days
    1,406
    81

    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 Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Cooling
      • Ceiling Fans(s)
      Appliances
      • Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Wine Cooler, Stainless Steel Appliance(s)
      • Laundry: Laundry Room
      Features
      • Quartz Countertops
      • Flooring: Tile, Wood
      • Furnished: Yes
      Interior area
      • Total structure area: 2,429
      • Total interior livable area: 2,429 sqft
      Video & virtual tour

      Property

      Features
      • Patio & porch: Open Porch/Balcony
      • Exterior features: Built-in Barbecue, Fruit Tree(s), Rain Gutters, Lighting, Outdoor Kitchen, Outdoor Shower, Sandy Beach, Storage, Water Display
      • Has private pool: Yes
      • Pool features: In Ground, Lap, Concrete, Decked
      • Has spa: Yes
      • Spa features: Heated
      • Fencing: Privacy
      • On waterfront: Yes
      Lot
      • Size: 0.85 Acres
      • Dimensions: 60 X 410
      Details
      • Parcel number: 00366860000000
      • Zoning: RM - Residential Medium
      • Other equipment: Home Theater, Irrigation Equipment

      Construction

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

      Utilities & green energy

      • Utilities for property: Cable Available

      Community & HOA

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

      Financial & listing details

      • Price per square foot: $1,439/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

        $3,256,300

        $3.09M - $3.42M

        $6,137/mo

        Price history

        DateEventPrice
        8/19/2026Price change$3,495,000-4.2%$1,439/sqft
        Source: FLKMLS #619913 Report a problem
        7/24/2026Price change$3,650,000-2.7%$1,503/sqft
        Source: Key West AOR #619913 Report a problem
        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

        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: 33050

        Getting around

        7 / 100
        Car-Dependent
        43 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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