Summerland Key Real Estate

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Currently 38 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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Summerland Key Communities

Dobies Subdivision (4) Misc Summerland Key (1) Niles Channel Subdivision (1) S Summerland Key Yac (1) Snug Harbor Subdivision (3) Summerland Beach (3) Summerland Cove Isle (8) Summerland Estates (4) Summerland Key Cove (12) Summerland Key Gard (1)

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Search Results

38 Results

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Active

$21,900,000

5 Beds | 4 Baths | 3,392 sf ($6,456 / SqFt)

Howell Key
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

1 Price Changes / 44 Days Ago

Active

$6,249,000

-3.71% (-$241,000)

6 Beds | 5 Baths | 4,981 sf ($1,255 / SqFt)

220 Caribbean Drive
Summerland, FL 33042

1 Price Changes / 31 Days Ago

Active

$5,600,000

4 Beds | 3 Baths | 5,608 sf ($999 / SqFt)

974 Flagship Drive
Summerland, FL 33042

Active

$5,500,000

3 Beds | 3 Baths | 2,088 sf ($2,634 / SqFt)

481 Shore Drive
Summerland, FL 33042

Active

$4,445,000

-10.20% (-$505,000)

7 Beds | 4 Baths | 4,531 sf ($981 / SqFt)

815 Shore Drive
Summerland, FL 33042

1 Price Changes / 33 Days Ago

Active

$3,899,000

5 Beds | 5 Baths | 3,119 sf ($1,250 / SqFt)

231 Shore Drive
Summerland, FL 33042

Active

$3,399,000

4 Beds | 3 Baths | 2,950 sf ($1,152 / SqFt)

23971 Henry Street
Summerland, FL 33042

Active

$3,199,000

2 Beds | 2 Baths | 2,232 sf ($1,433 / SqFt)

23941 Henry Street
Summerland, FL 33042

Active

$2,985,000

4 Beds | 3 Baths | 2,416 sf ($1,236 / SqFt)

835 Gulf Drive
Summerland, FL 33042

Active

$2,699,000

3 Beds | 2 Baths | 1,792 sf ($1,506 / SqFt)

943 Flagship Drive
Summerland, FL 33042

Active

$2,300,000

3 Beds | 2 Baths | 2,256 sf ($1,020 / SqFt)

441 Airport Drive #N
Summerland, FL 33042

Active

$2,299,000

-0.28% (-$6,500)

4 Beds | 4 Baths | 2,638 sf ($871 / SqFt)

22925 John Avery Lane
Summerland, FL 33042

1 Price Changes / 2 Days Ago

Active

$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 / 6 Days Ago

Active

$2,100,000

2 Beds | 1 Baths | 792 sf ($2,652 / SqFt)

20141 Kings Row
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

3 Price Changes / 2 Days Ago

Contingent/Show

$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 / 110 Days Ago

Active

$1,800,000

-7.69% (-$150,000)

3 Beds | 2 Baths | 1,248 sf ($1,442 / SqFt)

28538 John Silver Rd TORCH KEY Road
Summerland, FL 33042

1 Price Changes / 2 Days Ago

Active

$1,799,900

-14.27% (-$299,600)

4 Beds | 2 Baths | 1,440 sf ($1,250 / SqFt)

1082 Bay Drive
Summerland, FL 33042

3 Price Changes / 10 Days Ago

Active

$1,499,000

3 Beds | 2 Baths | 1,400 sf ($1,071 / SqFt)

947 Gulf Drive
Summerland, FL 33042

Active

$1,399,900

3 Beds | 2 Baths | 1,380 sf ($1,014 / SqFt)

1032 Caribbean 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 03-21-2025.