Upper Matecumbe Key

$24,995,000

82719 Old Hwy, Upper Matecumbe Key, FL, 33036

Experience unparalleled oceanfront living at the Chateau on the Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication...

$22,500,000

81486 Overseas Hwy, Upper Matecumbe Key, FL, 33036

Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla...

$8,490,000

1101 Mastic St, Upper Matecumbe Key, FL, 33036

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of...

$2,195,000

33 Pen Key, Upper Matecumbe Key, FL, 33036

Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resortstyle living awaits in this Key West-inspired residence, set within one...

$735,000

81801 Overseas Hwy 637, Upper Matecumbe Key, FL, 33036

Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals...

$585,000

81801 Overseas Hwy 727, Upper Matecumbe Key, FL, 33036

Attention Investors! Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Sportfishing Capital of the World''. This spacious Two Queen bed Suite offers a spacious...

$499,000

79901 Overseas Hwy 204, Upper Matecumbe Key, FL, 33036

Spectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront...

$3,195,000

80639 Old Hwy 204, Upper Matecumbe Key, FL, 33036

Maison Residences #204, a 4 bedroom residence with 4.5 bathrooms features an open floor plan with a grand room and oversized covered terraces for oceanside living. So open and airy! The grand living...

$850,000

83201 Old Hwy 301, Upper Matecumbe Key, FL, 33036

Beacon Reef is calling your name! This beautifully designed 2-bedroom, 2-bath residence spans approximately 1,275 square feet of light-filled living space. Enjoy the charming balcony with a steady...

$439,000

79901 Overseas Hwy 320, Upper Matecumbe Key, FL, 33036

The Palms of Islamorada is one of Islamorada's true sweet spots! Enjoy the oceanfront pool with nearby steps leading directly into the water where you can take a refreshing dip while soaking in...