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Home Florida Upper Matecumbe Key

Upper Matecumbe Key

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Showing 1-7 of 7 Homes For Sale

For Sale

$25,000,000

7 Beds | 10.0 Baths | 6,935 Sqft

82768 Overseas Highway, Upper Matecumbe Key, FL, 33036

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling...

Ad#: 5716151 • Added: 01/17/2025 • Updated: 10/15/2025

Open House 04/29 For Sale

$24,995,000

7 Beds | 11.0 Baths | 10,182 Sqft

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...

Ad#: 7578575 • Added: 04/16/2026 • Updated: 04/16/2026

For Sale

$22,500,000

7 Beds | 9.0 Baths | 8,878 Sqft

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...

Ad#: 7242805 • Added: 02/07/2026 • Updated: 04/23/2026

For Sale

$2,195,000

3 Beds | 4.0 Baths | 4,537 Sqft

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 resort‑style living awaits in this Key West-inspired residence, set...

Ad#: 7603365 • Added: 04/21/2026 • Updated: 04/21/2026

For Sale

$940,000

2 Beds | 2.0 Baths | 1,275 Sqft

83201 Old Hwy UNIT 504, Upper Matecumbe Key, FL, 33036

Exclusive Beacon Reef Unit 504 presents a rare opportunity in the heart of downtown Islamorada. This updated top-floor residence offers higher ceilings, enhanced views, and a larger porch--creating a...

Ad#: 7013952 • Added: 12/22/2025 • Updated: 04/02/2026

For Sale

$585,000

1 Beds | 1.0 Baths | 358 Sqft

81801 Overseas Hwy UNIT 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 large living...

Ad#: 7524203 • Added: 04/05/2026 • Updated: 04/22/2026

Open House 04/23 For Sale

$549,000

2 Beds | 2.0 Baths | 981 Sqft

79901 Overseas Hwy UNIT 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...

Ad#: 7156474 • Added: 01/19/2026 • Updated: 04/21/2026

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