Islamorada Real Estate

102 matches found

$2,195,000
33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
View Photos (60)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 4
Square Footage: 4537
Year Built: 1987
Area: 23 - Upper Matecumbe
Subdivision: Penn Key Club (83.0)
Description: Welcome to your legacy retreat in Islamorada's premier gated waterfront com...
Listing Office: Ocean Sotheby's International Realty
Last Updated: April - 21 - 2026
IDX
$549,000
79901 Overseas Highway 204, Upper Matecumbe Key Islamorada, FL 33036
View Photos (85)Videos (1)
Open House (04/21/2026 - 6:00 pm)
Property Type: Residential
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 981
Year Built: 1976
Area: 23 - Upper Matecumbe
Subdivision: Palms of Isla (80.0)
Description: 🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best-Kep...
Listing Office: Venture Realty Group
Last Updated: April - 21 - 2026
IDX
$2,999,000
Updated, pool, spa, tiki, 12,000 lb boat lift, fish cleaning station, CBS, concrete roof, room for boat trailers, kayaks etc.
View Photos (66)Videos (1)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 1830
Year Built: 1983
Area: 22 - Lower Matecumbe
Subdivision: Port Antigua (74.5)
Description: Welcome to your coastal retreat in the highly sought-after Port Antigua nei...
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: April - 21 - 2026
IDX
$789,000
124 S Hammock Road, Upper Matecumbe Key Islamorada, FL 33036
View Photos (23)
Open House (04/23/2026 - 11:00 am)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 2
Square Footage: 1305
Year Built: 1960
Area: 23 - Upper Matecumbe
Subdivision: Hammock (83.5)
Description: Nestled in the heart of Islamorada, this ground-level residence captures th...
Listing Office: Coastal Realty of the Florida Keys
Last Updated: April - 20 - 2026
IDX
$24,995,000
82719 Old Highway, Upper Matecumbe Key Islamorada, FL 33036
View Photos (60)
Open House (04/29/2026 - 12:00 pm)
Property Type: Residential
# of Bedrooms: 7
# of Bathrooms: 11
Square Footage: 10182
Year Built: 1995
Area: 23 - Upper Matecumbe
Subdivision: Strattons (82.5)
Description: Experience unparalleled oceanfront living at the Chateau on the Ocean, a tu...
Listing Office: Coldwell Banker Realty - Aventura
Last Updated: April - 20 - 2026
IDX
$450,000
134 Nautilus Drive, Lower Matecumbe, FL 33036
View Photos (33)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 4
Square Footage: 2907
Year Built: 2021
Area: 22 - Lower Matecumbe
Subdivision: White Marlin Bch (74.5)
Description: New co-ownership opportunity: Own one-eighth of this professionally managed...
Listing Office: Pacaso Inc.
Last Updated: April - 20 - 2026
IDX
$6,500,000
82749 Old Highway, Upper Matecumbe Key Islamorada, FL 33036
View Photos (39)Videos (1)
Property Type: Residential
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 1485
Year Built: 1978
Area: 23 - Upper Matecumbe
Subdivision: Russell Estates (83.2)
Description: Welcome to Casa Mar Azul, a one-of-a-kind oceanfront estate located along t...
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: April - 20 - 2026
IDX
$13,950,000
Property Type: Residential
# of Bedrooms: 7
# of Bathrooms: 7
Square Footage: 5900
Year Built: 2025
Area: 22 - Lower Matecumbe
Subdivision: Mat Ocean Bay (75.0)
Description: Experience the ultimate in coastal luxury and sophistication in this brand-...
Listing Office: The Agency Florida Keys
Last Updated: April - 20 - 2026
IDX
$3,200,000
Property Type: Residential
# of Bedrooms: 4
# of Bathrooms: 3
Square Footage: 2519
Year Built: 1974
Area: 22 - Lower Matecumbe
Subdivision: Lower Mat Bch (74.0)
Description: The Ospreys are back! Welcome to The Osprey's Nest; your perch by the Ocean...
Listing Office: Ocean Sotheby's International Realty
Last Updated: April - 19 - 2026
IDX
$3,200,000
117 El Capitan Drive, Lower Matecumbe, FL 33036
View Photos (58)Virtual Tours (1)
Property Type: Residential
# of Bedrooms: 5
# of Bathrooms: 3
Square Footage: 3052
Year Built: 1991
Area: 22 - Lower Matecumbe
Subdivision: Port Antigua (74.5)
Description: Newly remodeled waterfront home located in the highly desirable Port Antigu...
Listing Office: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
Last Updated: April - 19 - 2026
IDX

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The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.