Skip main navigation
For sale
  • $3,999,999

    74049 Overseas Hwy, Islamorada, FL 33036

    4beds
    2,591sqft
    : 
    $24,529/mo
    Get pre-qualified
    Single Family Residence
    Built in 1970
    0.5 Acres Lot
    $3,623,300 Zestimate®
    $1,544/sqft
    $-- HOA

    What's special

    Direct ocean accessOceanfront sanctuaryPrivate gated resort-style compoundExpansive open-water viewsImpact windows
    Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represents one of the rarest opportunities in the Upper Keys: a private, gated, resort-style compound offering expansive open-water views, unmatched privacy, and the timeless charm of classic Florida Keys architecture. Set on a generous parcel with a sandy beach, and direct ocean access, Casa Matecumbe delivers the ultimate coastal lifestyle--one defined by serenity, natural beauty, and the freedom to enjoy the water at a moment's notice. The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Lower-Level Finished area of 1,065 is included in square footage. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.
    84 days
    |
    1,045
    |
    40
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Judy Rossignol 305-393-0523,

    Paradise Florida Keys Real Estate, a Luxury Brand,

    Richard Trottnow 305-842-1151,

    Paradise Florida Keys Real Estate, a Luxury Brand

    Source: FLKMLS,MLS#: 619687MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Cooling
      • Central Air, Ceiling Fans(s)
      Appliances
      • Included: Washer, Dryer, Dishwasher, Range, Oven, Microwave
      Features
      • Storage, Quartz Countertops
      • Flooring: Tile, Combination
      Interior area
      • Total structure area: 2,591
      • Total interior livable area: 2,591 sqft
      Video & virtual tour

      Property

      Features
      • Patio & porch: Open Porch/Balcony, Deck
      • Exterior features: Lighting, Sandy Beach
      • Has private pool: Yes
      • Pool features: In Ground, Concrete
      • Fencing: Fenced
      • On waterfront: Yes
      Lot
      • Size: 0.5 Acres
      Details
      • Parcel number: 00389650000000
      • Zoning: R1 - Residential Single Family

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS, Concrete
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1970

      Utilities & green energy

      • Utilities for property: Elect Separate Meter, Cable Available

      Community & HOA

      Community
      • Features: Beach, Bike Paths
      • Security: Security Gate
      • Subdivision: Lower Mat Bch (74.0)
      HOA
      • Has HOA: No
      • Services included: None, Other
      Location
      • Region: Islamorada

      Financial & listing details

      • Price per square foot: $1,544/sqft
      • Tax assessed value: $2,272,746
      • Annual tax amount: $20,640
      • Date on market: 4/29/2026
      • Listing terms: No Seller Finance,Cash,Conventional,FHA

        Estimated market value

        $3,623,300

        $3.44M - $3.80M

        $7,827/mo

        Price history

        DateEventPrice
        4/29/2026Listed for sale$3,999,999-7%$1,544/sqft
        Source: FLKMLS #619687 Report a problem
        3/3/2026Listing removed$4,299,999$1,660/sqft
        Source: MIAMI #A11918242 Report a problem
        11/21/2025Listed for sale$4,299,999+95.5%$1,660/sqft
        Source: MIAMI #A11918242 Report a problem
        10/18/2013Listing removed$2,199,000$849/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #549979 Report a problem
        10/21/2012Listed for sale$2,199,000$849/sqft
        Source: Coldwell Banker Schmitt Islamorada #549979 Report a problem
        7/15/2011Listing removed$2,199,000$849/sqft
        Source: Coldwell Banker Schmitt #549979 Report a problem
        12/20/2009Price change$2,199,000-2.2%$849/sqft
        Source: Schmitt Real Estate Co. #549979 Report a problem
        12/19/2009Price change$2,249,000+2.3%$868/sqft
        Source: Coldwell Banker Schmitt R.E. - Isl #123456 Report a problem
        11/13/2009Price change$2,199,000-2.7%$849/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #549979 Report a problem
        11/7/2009Price change$2,259,000+0.4%$872/sqft
        Source: Coldwell Banker Schmitt Real Estate Co. #549979 Report a problem
        9/5/2009Listed for sale$2,249,000-19.7%$868/sqft
        Source: Coldwell Banker Schmitt R.E. - Isl #123456 Report a problem
        11/4/2008Listing removed$2,800,000$1,081/sqft
        Source: Homes & Land #542671 Report a problem
        3/9/2008Price change$2,800,000-3.4%$1,081/sqft
        Source: NCI #542671 Report a problem
        1/31/2008Listed for sale$2,900,000+752.9%$1,119/sqft
        Source: NCI #542671 Report a problem
        9/6/1995Sold$340,000$131/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$21,327 +3.3%$2,272,746 +2.8%
        2024$20,641 -0.1%$2,210,100 +2.3%
        2023$20,652 +2.1%$2,160,897 +3.2%
        2022$20,227 -1.4%$2,092,893 +3.2%
        2021$20,515 +1.8%$2,028,438 +6%
        2020$20,151 $1,912,921 +0.2%
        2019$20,151 +10.6%$1,909,995 +26.4%
        2018$18,219 $1,510,969 -5.4%
        2017-- $1,597,514 +2%
        2016-- $1,566,213 +27.2%
        2015-- $1,230,954
        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.
        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 33036

        Getting around

        12 / 100
        Car-Dependent
        47 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes