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Upper Matecumbe Key

Showing 1-9 of 9 Homes For Sale

$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

Ad#: 6939653 •

Added: 25/12/2025 • Updated: 25/12/2025

Ad#: 6939653 • Added: 25/12/2025 • Updated: 25/12/2025

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

Ad#: 6864183 •

Added: 25/11/2025 • Updated: 25/11/2025

Ad#: 6864183 • Added: 25/11/2025 • Updated: 25/11/2025

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

$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

Ad#: 6821096 •

Added: 25/11/2025 • Updated: 25/11/2025

Ad#: 6821096 • Added: 25/11/2025 • Updated: 25/11/2025

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

$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

Ad#: 6720358 •

Added: 25/10/2025 • Updated: 25/10/2025

Ad#: 6720358 • Added: 25/10/2025 • Updated: 25/10/2025

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

$449,900

1 Beds | 2.0 Baths | 827 Sqft

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

Lowest priced unit at The Palms of Islamorada, one of the area's

Ad#: 6603242 •

Added: 25/09/2025 • Updated: 25/09/2025

Ad#: 6603242 • Added: 25/09/2025 • Updated: 25/09/2025

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

$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

Ad#: 6476507 •

Added: 25/08/2025 • Updated: 25/10/2025

Ad#: 6476507 • Added: 25/08/2025 • Updated: 25/10/2025

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

$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

Ad#: 6389604 •

Added: 25/07/2025 • Updated: 25/10/2025

Ad#: 6389604 • Added: 25/07/2025 • Updated: 25/10/2025

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

$639,000

1 Beds | 1.0 Baths | 550 Sqft

81801 Overseas Highway UNIT 754, Upper Matecumbe Key, FL, 33036

Escape to island elegance in your own spacious King Suite at

Ad#: 6249813 •

Added: 25/06/2025 • Updated: 25/08/2025

Ad#: 6249813 • Added: 25/06/2025 • Updated: 25/08/2025

Listed by Corie McGraw-Abel at Coastal Realty of the Florida • 305-393-6864

$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

Ad#: 5716151 •

Added: 25/01/2025 • Updated: 25/10/2025

Ad#: 5716151 • Added: 25/01/2025 • Updated: 25/10/2025

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

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