How many active listings are available in this area?

There are 10 active listings in this area.

What is the average listing price in this area?

The average listing price for the displayed results is $6,277,200.

How many active listings are available in this area?

There are 10 active listings in this area.

What is the average listing price in this area?

The average listing price for the displayed results is $6,277,200.

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Upper Matecumbe Key

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For Sale

Experience unparalleled oceanfront living at the Chateau on the - photo 1

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$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: 07/10/2026

For Sale

Introducing Isla House. A truly exceptional waterfront estate in - photo 1

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$22,500,000

7 Beds | 8.0 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: 07/10/2026

For Sale

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$6,999,000

8 Beds | 6.0 Baths | 3,649 Sqft

1101 Mastic St, Upper Matecumbe Key, FL, 33036

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its finest in this exceptional Gated...

Ad#: 7641243 • Added: 04/28/2026 • Updated: 07/21/2026

For Sale

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$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 resortstyle living awaits in this Key West-inspired residence, set within one...

Ad#: 7603365 • Added: 04/21/2026 • Updated: 05/31/2026

For Sale

Welcome to your island King suite overlooking the beautiful - photo 1

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$735,000

1 Beds | 1.0 Baths | 550 Sqft

81801 Overseas Hwy 637, Upper Matecumbe Key, FL, 33036

Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals...

Ad#: 7679812 • Added: 05/06/2026 • Updated: 07/10/2026

For Sale

Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 1

Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 2

Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 3

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Attention Investors! Own a piece of the legendary Cheeca Lodge - photo 23

$585,000

1 Beds | 1.0 Baths | 358 Sqft

81801 Overseas Hwy 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 spacious...

Ad#: 7524203 • Added: 04/05/2026 • Updated: 05/23/2026

For Sale

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in - photo 1

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$549,500

1 Beds | 1.0 Baths | 358 Sqft

81801 Overseas Hwy 715, Upper Matecumbe Key, FL, 33036

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the...

Ad#: 7625577 • Added: 07/14/2026 • Updated: 07/15/2026

For Sale

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in - photo 35

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$549,500

1 Beds | 1.0 Baths | 358 Sqft

81801 Overseas Hwy 716, Upper Matecumbe Key, FL, 33036

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the...

Ad#: 7626165 • Added: 07/14/2026 • Updated: 07/15/2026

For Sale

Spectacular Direct Ocean Views! Islamorada's Best-Kept Secret! - photo 1

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$469,000

2 Beds | 2.0 Baths | 981 Sqft

79901 Overseas Hwy 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 waterfront...

Ad#: 7156474 • Added: 01/19/2026 • Updated: 06/13/2026

Sale Pending

Maison Residences #204, a 4 bedroom residence with 4.5 bathrooms - photo 1

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Maison Residences #204, a 4 bedroom residence with 4.5 bathrooms - photo 42

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Maison Residences #204, a 4 bedroom residence with 4.5 bathrooms - photo 46

$3,195,000

4 Beds | 5.0 Baths | 2,539 Sqft

80639 Old Hwy 204, Upper Matecumbe Key, FL, 33036

Maison Residences #204, a 4 bedroom residence with 4.5 bathrooms features an open floor plan with a grand room and oversized covered terraces for oceanside living. So open and airy! The grand living...

Ad#: 5245775 • Added: 08/08/2024 • Updated: 05/21/2026

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