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Home Florida Upper Matecumbe Key

Upper Matecumbe Key

Showing 1-8 of 8 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

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

For Sale

$22,500,000

7 Beds | 9.0 Baths | 8,878 Sqft

81486 Overseas Highway, 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: 02/09/2026

Ad#: 7242805 • Added: 02/07/2026 • Updated: 02/09/2026

For Sale

$5,700,000

3 Beds | 3.0 Baths | 3,019 Sqft

100 List Street, Upper Matecumbe Key, FL, 33036

Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built in 2014, this concrete fortress is storm-resilient...

Ad#: 6864183

Added: 11/21/2025 • Updated: 02/22/2026

Ad#: 6864183 • Added: 11/21/2025 • Updated: 02/22/2026

For Sale

$2,495,000

3 Beds | 4.0 Baths | 4,537 Sqft

33 Pen Key Drive, 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#: 7175842

Added: 01/23/2026 • Updated: 01/23/2026

Ad#: 7175842 • Added: 01/23/2026 • Updated: 01/23/2026

For Sale

$1,199,000

2 Beds | 2.0 Baths | 1,275 Sqft

83201 Old Highway UNIT 405, Upper Matecumbe Key, FL, 33036

Unparalleled amenities are what seperates Beacon Reef condo complex from any other complex on Upper Matecumbe Key. Premium oceanside dockage, resort style pool, a well-appointed gym with sweeping...

Ad#: 6720358

Added: 10/13/2025 • Updated: 01/19/2026

Ad#: 6720358 • Added: 10/13/2025 • Updated: 01/19/2026

For Sale

$950,000

2 Beds | 2.0 Baths | 1,275 Sqft

83201 Old Highway 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: 12/22/2025

Ad#: 7013952 • Added: 12/22/2025 • Updated: 12/22/2025

For Sale

$850,000

2 Beds | 2.0 Baths | 1,275 Sqft

83201 Old Highway UNIT 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...

Ad#: 6939653

Added: 12/10/2025 • Updated: 01/23/2026

Ad#: 6939653 • Added: 12/10/2025 • Updated: 01/23/2026

Open House 03/03 For Sale

$580,000

2 Beds | 2.0 Baths | 981 Sqft

79901 Overseas Highway 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...

Ad#: 7156474

Added: 01/19/2026 • Updated: 02/19/2026

Ad#: 7156474 • Added: 01/19/2026 • Updated: 02/19/2026

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