Summerland Key Real Estate
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Summerland Key Communities

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31 Results
Active

$21,900,000
5 Beds | 4 Baths | 3,392 sf
($6,456 / SqFt)
Howell Key
Summerland, FL 33042
Summerland, FL 33042
Active

$8,955,000
-12.01%
(-$960,000)
5 Beds | 4 Baths | 3,952 sf
($2,266 / SqFt)
1151 Ocean Drive
Summerland, FL 33042
Summerland, FL 33042
1 Price Changes
/ 17 Days Ago
Active

$6,490,000
6 Beds | 5 Baths | 4,981 sf
($1,303 / SqFt)
220 Caribbean Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$5,600,000
4 Beds | 3 Baths | 5,608 sf
($999 / SqFt)
974 Flagship Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$5,500,000
3 Beds | 3 Baths | 2,088 sf
($2,634 / SqFt)
481 Shore Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$4,950,000
7 Beds | 4 Baths | 4,531 sf
($1,092 / SqFt)
815 Shore Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$3,899,000
5 Beds | 5 Baths | 3,119 sf
($1,250 / SqFt)
231 Shore Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$2,985,000
4 Beds | 3 Baths | 2,416 sf
($1,236 / SqFt)
835 Gulf Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$2,300,000
3 Beds | 2 Baths | 2,256 sf
($1,020 / SqFt)
441 Airport Drive #N
Summerland, FL 33042
Summerland, FL 33042
Active

$2,292,500
4 Beds | 4 Baths | 2,638 sf
($869 / SqFt)
22925 John Avery Lane
Summerland, FL 33042
Summerland, FL 33042
Active

$2,250,000
-2.17%
(-$50,000)
3 Beds | 3 Baths | 2,010 sf
($1,119 / SqFt)
948 Gulf Drive
Summerland, FL 33042
Summerland, FL 33042
1 Price Changes
/ 1 Days Ago
Active

$2,100,000
2 Beds | 1 Baths | 792 sf
($2,652 / SqFt)
20141 Kings Row
Summerland, FL 33042
Summerland, FL 33042
Active

$1,999,900
-6.98%
(-$150,100)
3 Beds | 2 Baths | 2,156 sf
($928 / SqFt)
1165 Lagoon Drive
Summerland, FL 33042
Summerland, FL 33042
3 Price Changes
/ 2 Days Ago
Active

$1,999,000
-8.93%
(-$196,000)
3 Beds | 2 Baths | 1,664 sf
($1,201 / SqFt)
474 Caribbean Drive
Summerland, FL 33042
Summerland, FL 33042
1 Price Changes
/ 58 Days Ago
Active

$1,950,000
3 Beds | 2 Baths | 1,248 sf
($1,563 / SqFt)
28538 John Silver Rd TORCH KEY Road
Summerland, FL 33042
Summerland, FL 33042
Active

$1,899,900
-9.51%
(-$199,600)
4 Beds | 2 Baths | 1,440 sf
($1,319 / SqFt)
1082 Bay Drive
Summerland, FL 33042
Summerland, FL 33042
2 Price Changes
/ 156 Days Ago
Active

$1,499,000
3 Beds | 2 Baths | 1,400 sf
($1,071 / SqFt)
947 Gulf Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$1,425,000
-1.72%
(-$25,000)
3 Beds | 2 Baths | 1,880 sf
($758 / SqFt)
361 Caribbean Drive
Summerland, FL 33042
Summerland, FL 33042
1 Price Changes
/ 2 Days Ago
Active

$1,350,000
2 Beds | 2 Baths | 1,171 sf
($1,153 / SqFt)
1050 Gulf Drive
Summerland, FL 33042
Summerland, FL 33042
Active

$1,285,000
-3.02%
(-$40,000)
2 Beds | 2 Baths | 864 sf
($1,487 / SqFt)
1021 Caribbean Drive
Summerland, FL 33042
Summerland, FL 33042
1 Price Changes
/ 9 Days Ago
Active

$1,195,000
2 Beds | 2 Baths | 960 sf
($1,245 / SqFt)
529 Shore Drive
Summerland, FL 33042
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.