Lower Matecumbe Key

$13,750,000

75840 Overseas Hwy, Lower Matecumbe Key, FL, 33036

LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering...

$10,900,000

186 & 165 Bayview Dr, Lower Matecumbe Key, FL, 33036

A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over 1/2 acre lot with panoramic water views from every room. Offering 220+ linear feet of...

$8,950,000

162 Bayview Dr, Lower Matecumbe Key, FL, 33036

Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts...

$7,900,000

91 Iroquois Dr, Lower Matecumbe Key, FL, 33036

Discover paradise in Islamorada, with beautiful ocean views, protected canal dockage, and resort-style amenities that you'll never want to leave! Blending luxury living with the Florida Keys...

$6,299,000

137 Sapodilla Dr, Lower Matecumbe Key, FL, 33036

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A...

$5,999,999

181 Nautilus Dr, Lower Matecumbe Key, FL, 33036

Brand new 2026 coastal luxury in Islamorada's White Marlin Beach. 181 Nautilus Dr offers the ultimate Keys lifestyle with 5 bedrooms, 5.5 baths, and 5,320 SF of living area across three levels. Served...

$5,999,000

430 Palm Dr, Lower Matecumbe Key, FL, 33036

Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf of thoughtfully designed...

$4,299,000

241 Tollgate Blvd, Lower Matecumbe Key, FL, 33036

Near-new luxury home in coveted Toll Gate Shores, Islamorada, Florida. Near perfection, describes this newly constructed 3-bedroom, 3-bath residence offering single-level living with elevator access...

$2,790,000

75055 Overseas Hwy, Lower Matecumbe Key, FL, 33036

Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch...

$2,075,000

121 Lisbon Ct, Lower Matecumbe Key, FL, 33036

What does everyone dream of? The smallest house in the best neighborhood - and this one delivers. Welcome to easy, breezy living in Port Antigua, where charm, quality, and location come together...

$1,375,000

101 Gulfview Dr 204 & 30' Boat Slip With Lift, Lower Matecumbe Key, FL, 33036

Experience luxury island living in the heart of Islamorada at Bay Harbour, one of the Florida Keys' most desirable waterfront communities. Unit 204 offers breathtaking ocean and lagoon water views and...