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For discerning investors seeking to enhance their luxury portfolio, “Southern Paradise” in the Florida Keys offers an unparalleled opportunity.

83283 Old Hwy, Upper Matecumbe Key, FL 33036


83283 Old Hwy, Upper Matecumbe Key


Nestled at Mile Marker 83, this exquisite property epitomizes elegance with its casual coastal design and breathtaking Atlantic Ocean backdrop. The estate’s prime location provides direct access to the ‘Old Road,’ ideal for walking, biking, and carting, further accentuating its unique charm and appeal.

Spanning over 1.5 acres with more than 200 feet of pristine beachfront, “Southern Paradise” is a haven of tranquility and luxury. The main residence boasts over 5,600 square feet of living space under air, featuring sunny verandas, five bedrooms, and 6.5 baths, each designed with meticulous attention to detail and comfort. A separate guest cottage offers an additional two bedrooms and two baths, perfect for accommodating family and guests with privacy and elegance.

83283 Old Hwy, Upper Matecumbe Key
83283 Old Hwy, Upper Matecumbe Key


A paved ‘old brick’ driveway leads to both the main and guest residences, culminating in a spacious two-car garage. The entrance, framed by inviting French doors, opens to reveal stunning views of the sky, beach, and ocean, setting the stage for an unforgettable living experience. The first-floor layout promotes an indoor-outdoor lifestyle, with direct access to a cool grassy lanai, beach, lap-pool, and hot tub. Expansive patios ensure ample space for entertaining, allowing guests to savor the Caribbean breezes.

The property is equipped with a pier, skiff lift, and kayak launch, offering effortless ocean access. Inside, the main residence impresses with high ceilings and vast spaces ideal for gatherings. The thoughtful floor plan includes an East wing and a newly added West wing, with each bedroom featuring its own ensuite bath, ensuring privacy and luxury for all occupants.

83283 Old Hwy, Upper Matecumbe Key
83283 Old Hwy, Upper Matecumbe Key
83283 Old Hwy, Upper Matecumbe Key


The first-floor houses an open-concept great room leading to a kitchen equipped with a Wolf gas range, double SubZero refrigeration, and an attached wine cellar centered around a large island counter. An adjoining wet bar and powder room add convenience, while the West wing houses an exercise room with a full ensuite spa bath and the master bedroom, which boasts ocean views, a soaking bathtub, and dual vanities.

On the second floor, two guest rooms share a sitting room, wet bar, and terrace, completing the layout of this magnificent residence. “Southern Paradise” is more than a home; it’s a lifestyle, offering privacy, luxury, and direct ocean access in one of the most coveted locations in the Florida Keys. For private jet travelers seeking to add a distinguished property to their collection, this estate promises a blend of casual elegance and sophisticated coastal living, making it a truly exceptional investment.

83283 Old Hwy, Upper Matecumbe Key, FL 33036 is offered at $14,000,000.

For more information and a private showing, please contact:

Patti Stanley
Luxury Estate Broker Associate
Coldwell Banker Schmitt Islamorada
T: +1 305.393.4433

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