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Upper Matecumbe Key Islamorada Real Estate

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Currently 34 Properties For Sale in Upper Matecumbe Key Islamorada
We are experiencing a shortage of properties for sale throughout the Florida Keys. We have off-market listings that we make available to our clients, if you have the need for a specific type of property please contact us below.
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34 Results

Active
Listing Image
$25,000,000
 
7 Beds | 9 Baths | 6,935 sf ($3,605 / SqFt)
82768 Overseas Highway
ISLAMORADA, FL 33036
 
Active
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$13,995,000
 
7 Beds | 8 Baths | 6,696 sf ($2,090 / SqFt)
83283 Old Highway
ISLAMORADA, FL 33036
 
Active
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$10,250,000
-4.65% (-$500,000)  
6 Beds | 5 Baths | 6,866 sf ($1,493 / SqFt)
82238 Overseas Highway
ISLAMORADA, FL 33036
1 Price Changes / 2 Days Ago  
Active
Listing Image
$7,495,000
 
3 Beds | 2 Baths | 3,019 sf ($2,483 / SqFt)
100 List Street
ISLAMORADA, FL 33036
 
Active
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$6,750,000
 
6 Beds | 5 Baths | 4,566 sf ($1,478 / SqFt)
83407 Old Highway
ISLAMORADA, FL 33036
 
Active
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$6,125,000
 
4 Beds | 4 Baths | 2,573 sf ($2,380 / SqFt)
82779 Old Highway #21
ISLAMORADA, FL 33036
 
Active
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$5,500,000
 
4 Beds | 4 Baths | 2,573 sf ($2,138 / SqFt)
82779 Old Highway #3
ISLAMORADA, FL 33036
 
Active
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$4,950,000
 
4 Beds | 4 Baths | 2,573 sf ($1,924 / SqFt)
82779 Old Highway #16
ISLAMORADA, FL 33036
 
Contingent/Show
Listing Image
$4,675,000
-2.60% (-$125,000)  
1 Beds | 1 Baths | 946 sf ($4,942 / SqFt)
150 List Street
ISLAMORADA, FL 33036
1 Price Changes / 12 Days Ago  
Active
Listing Image
$4,200,000
 
5 Beds | 4 Baths | 2,358 sf ($1,781 / SqFt)
80459 Old Highway
ISLAMORADA, FL 33036
 
Active
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$3,500,000
 
5 Beds | 3 Baths | 2,640 sf ($1,326 / SqFt)
105 Palo De Oro Drive
ISLAMORADA, FL 33036
 
Active
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$3,495,000
 
4 Beds | 4 Baths | 2,539 sf ($1,377 / SqFt)
80639 Old Highway #201
ISLAMORADA, FL 33036
 
Active
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$3,150,000
-1.56% (-$50,000)  
4 Beds | 4 Baths | 2,576 sf ($1,223 / SqFt)
105 Carroll Street #6
ISLAMORADA, FL 33036
2 Price Changes / 45 Days Ago  
Active
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$2,950,000
 
4 Beds | 3 Baths | 2,072 sf ($1,424 / SqFt)
81250 Overseas Highway #5
ISLAMORADA, FL 33036
 
Active
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$2,800,000
 
3 Beds | 3 Baths | 4,537 sf ($617 / SqFt)
33 Pen Key Drive
ISLAMORADA, FL 33036
 
Active
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$1,799,000
 
3 Beds | 3 Baths | 1,680 sf ($1,071 / SqFt)
84 Johnston Avenue #3
ISLAMORADA, FL 33036
 
Active
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$1,550,000
-3.13% (-$50,000)  
2 Beds | 1 Baths | 1,556 sf ($996 / SqFt)
209 Matecumbe Avenue
ISLAMORADA, FL 33036
1 Price Changes / 15 Days Ago  
Active
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$1,350,000
 
3 Beds | 3 Baths | 1,550 sf ($871 / SqFt)
191 Carroll Street
ISLAMORADA, FL 33036
 
Active
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$1,350,000
 
4 Beds | 3 Baths | 1,459 sf ($925 / SqFt)
107 Carroll Street #all units
ISLAMORADA, FL 33036
 
Active
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$1,350,000
 
4 Beds | 3 Baths | 1,459 sf ($925 / SqFt)
107 Carroll Street
ISLAMORADA, FL 33036
 
Active
Listing Image
$1,350,000
-3.57% (-$50,000)  
3 Beds | 3 Baths | 960 sf ($1,406 / SqFt)
81216 Old Highway
ISLAMORADA, FL 33036
3 Price Changes / 38 Days Ago  
The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 02-10-2025.
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