74049 Overseas Highway, Islamorada, FL 33036
Local realty services provided by:Better Homes and Gardens Real Estate Destinations
74049 Overseas Highway,Lower Matecumbe, FL 33036
$3,999,999
- 4 Beds
- 4 Baths
- 2,591 sq. ft.
- Single family
- Active
Upcoming open houses
- Sat, Jun 2710:00 am - 02:00 pm
Listed by: judy rossignol, richard trottnow
Office: paradise florida keys real estate, a luxury brand
MLS#:619687
Source:FL_FKBOR
Price summary
- Price:$3,999,999
- Price per sq. ft.:$1,543.81
About this home
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....
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Home facts
- Year built:1970
- Listing ID #:619687
- Added:53 day(s) ago
- Updated:June 22, 2026 at 02:43 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:4
- Kitchen Description:Quartz Countertops
- Living area:2,591 sq. ft.
Heating and cooling
- Cooling:Ceiling Fans(s), Central Air
Structure and exterior
- Year built:1970
- Building area:2,591 sq. ft.
- Lot area:0.48 Acres
- Construction Materials:Concrete
- Exterior Features:Fencing, Lighting, Sandy Beach
Finances and disclosures
- Price:$3,999,999
- Price per sq. ft.:$1,543.81
- Tax amount:$20,640
Features and amenities
- Amenities:Drapes Included, Storage
Parking
- Parking description:Off Street
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