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Summerland Key Real Estate

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Currently 31 Properties For Sale in Summerland Key
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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31 Results

Active
Listing Image
$21,900,000
 
5 Beds | 4 Baths | 3,392 sf ($6,456 / SqFt)
Howell Key
Summerland, FL 33042
 
Active
Listing Image
$8,955,000
-12.01% (-$960,000)  
5 Beds | 4 Baths | 3,952 sf ($2,266 / SqFt)
1151 Ocean Drive
Summerland, FL 33042
1 Price Changes / 17 Days Ago  
Active
Listing Image
$6,490,000
 
6 Beds | 5 Baths | 4,981 sf ($1,303 / SqFt)
220 Caribbean Drive
Summerland, FL 33042
 
Active
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$5,600,000
 
4 Beds | 3 Baths | 5,608 sf ($999 / SqFt)
974 Flagship Drive
Summerland, FL 33042
 
Active
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$5,500,000
 
3 Beds | 3 Baths | 2,088 sf ($2,634 / SqFt)
481 Shore Drive
Summerland, FL 33042
 
Active
Listing Image
$4,950,000
 
7 Beds | 4 Baths | 4,531 sf ($1,092 / SqFt)
815 Shore Drive
Summerland, FL 33042
 
Active
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$3,899,000
 
5 Beds | 5 Baths | 3,119 sf ($1,250 / SqFt)
231 Shore Drive
Summerland, FL 33042
 
Active
Listing Image
$2,985,000
 
4 Beds | 3 Baths | 2,416 sf ($1,236 / SqFt)
835 Gulf Drive
Summerland, FL 33042
 
Active
Listing Image
$2,300,000
 
3 Beds | 2 Baths | 2,256 sf ($1,020 / SqFt)
441 Airport Drive #N
Summerland, FL 33042
 
Active
Listing Image
$2,292,500
 
4 Beds | 4 Baths | 2,638 sf ($869 / SqFt)
22925 John Avery Lane
Summerland, FL 33042
 
Active
Listing Image
$2,250,000
-2.17% (-$50,000)  
3 Beds | 3 Baths | 2,010 sf ($1,119 / SqFt)
948 Gulf Drive
Summerland, FL 33042
1 Price Changes / 1 Days Ago  
Active
Listing Image
$2,100,000
 
2 Beds | 1 Baths | 792 sf ($2,652 / SqFt)
20141 Kings Row
Summerland, FL 33042
 
Active
Listing Image
$1,999,900
-6.98% (-$150,100)  
3 Beds | 2 Baths | 2,156 sf ($928 / SqFt)
1165 Lagoon Drive
Summerland, FL 33042
3 Price Changes / 2 Days Ago  
Active
Listing Image
$1,999,000
-8.93% (-$196,000)  
3 Beds | 2 Baths | 1,664 sf ($1,201 / SqFt)
474 Caribbean Drive
Summerland, FL 33042
1 Price Changes / 58 Days Ago  
Active
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$1,950,000
 
3 Beds | 2 Baths | 1,248 sf ($1,563 / SqFt)
28538 John Silver Rd TORCH KEY Road
Summerland, FL 33042
 
Active
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$1,899,900
-9.51% (-$199,600)  
4 Beds | 2 Baths | 1,440 sf ($1,319 / SqFt)
1082 Bay Drive
Summerland, FL 33042
2 Price Changes / 156 Days Ago  
Active
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$1,499,000
 
3 Beds | 2 Baths | 1,400 sf ($1,071 / SqFt)
947 Gulf Drive
Summerland, FL 33042
 
Active
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$1,425,000
-1.72% (-$25,000)  
3 Beds | 2 Baths | 1,880 sf ($758 / SqFt)
361 Caribbean Drive
Summerland, FL 33042
1 Price Changes / 2 Days Ago  
Active
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$1,350,000
 
2 Beds | 2 Baths | 1,171 sf ($1,153 / SqFt)
1050 Gulf Drive
Summerland, FL 33042
 
Active
Listing Image
$1,285,000
-3.02% (-$40,000)  
2 Beds | 2 Baths | 864 sf ($1,487 / SqFt)
1021 Caribbean Drive
Summerland, FL 33042
1 Price Changes / 9 Days Ago  
Active
Listing Image
$1,195,000
 
2 Beds | 2 Baths | 960 sf ($1,245 / SqFt)
529 Shore Drive
Summerland, FL 33042
 
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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