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Upper Matecumbe Key

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$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

Listed by Sabrina Wampler & Sarah Ewald at Ocean Sotheby's International Realty • 305-393-0585

$5,900,000

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 by the current owner in 2014, this concrete fortress...

Ad#: 6864183 •

Added: 11/21/2025 • Updated: 11/21/2025

Ad#: 6864183 • Added: 11/21/2025 • Updated: 11/21/2025

Listed by Brett Newman at Coldwell Banker Schmitt Islamorada • 305-393-1770

$2,495,000

3 Beds | 3.0 Baths | 4,537 Sqft

33 Pen Key Drive, Upper Matecumbe Key, FL, 33036

Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where...

Ad#: 6476507 •

Added: 08/01/2025 • Updated: 10/15/2025

Ad#: 6476507 • Added: 08/01/2025 • Updated: 10/15/2025

Listed by Eric M. Rizzo at Ocean Sotheby's International Realty • 305-394-3062

$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: 10/13/2025

Ad#: 6720358 • Added: 10/13/2025 • Updated: 10/13/2025

Listed by Danielle P. Cockerham at Coastal Realty of the Florida • 305-304-9107

$999,000

2 Beds | 2.0 Baths | 1,275 Sqft

83201 Old Highway UNIT 409, Upper Matecumbe Key, FL, 33036

Welcome to Unit #409 at Beacon Reef, an oceanfront gem located in the heart of Islamorada. Beacon Reef is well-run, meticulously maintained, and units are rarely available for a reason. Beacon Reef...

Ad#: 6821096 •

Added: 11/10/2025 • Updated: 11/10/2025

Ad#: 6821096 • Added: 11/10/2025 • Updated: 11/10/2025

Listed by AJ Vetter at Palm House Real Estate • 305-304-8841

$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

Listed by Drew Moret at Palm House Real Estate • 305-393-3331

$899,000

3 Beds | 3.0 Baths | 2,314 Sqft

82260 Overseas Highway, Upper Matecumbe Key, FL, 33036

This renovated treehouse retreat is your picture-perfect getaway or forever island home! Discover a rare opportunity to own a beautifully reimagined Keys haven in the heart of Islamorada. Nestled...

Ad#: 6389604 •

Added: 07/08/2025 • Updated: 10/15/2025

Ad#: 6389604 • Added: 07/08/2025 • Updated: 10/15/2025

Listed by Sabrina Wampler & Sarah Ewald at Ocean Sotheby's International Realty • 305-393-0585

$895,000

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: 12/14/2025

Ad#: 6939653 • Added: 12/10/2025 • Updated: 12/14/2025

Listed by Sabrina Wampler & Sarah Ewald at Ocean Sotheby's International Realty • 305-393-0585

$399,900

1 Beds | 2.0 Baths | 827 Sqft

79901 Overseas Highway UNIT 218, Upper Matecumbe Key, FL, 33036

LET'S MAKE A DEAL! Seller has just reduced this condo by $50,000. At this price, this updated 1BR/1.5BA condo is the largest one bedroom condo available for sale in the Upper Keys. Located at The...

Ad#: 6603242 •

Added: 09/09/2025 • Updated: 12/15/2025

Ad#: 6603242 • Added: 09/09/2025 • Updated: 12/15/2025

Listed by Andrea (Andi) Saylor at Realty ONE Group Engage the Keys • 305-407-4326

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