Summerland Key Real Estate

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Currently 24 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 (1) S Summerland Key Yac (2) Snug Harbor Subdivision (3) Summerland Beach (3) Summerland Cove Isle (6) Summerland Estates (1) Summerland Key Cove (8)

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24 Results

5 Beds | 4 Baths | 3,952 sf ($2,266 / SqFt)

1151 Ocean Drive
Summerland, FL 33042

1 Price Changes / 44 Days Ago

Active

$5,992,000

-7.67% (-$498,000)

5 Beds | 5 Baths | 4,981 sf ($1,203 / SqFt)

220 Caribbean Drive
Summerland, FL 33042

2 Price Changes / 57 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

$4,200,000

-15.15% (-$750,000)

7 Beds | 4 Baths | 4,531 sf ($927 / SqFt)

815 Shore Drive
Summerland, FL 33042

2 Price Changes / 2 Days Ago

Active

$3,199,000

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

23941 Henry Street
Summerland, FL 33042

Active

$2,895,000

-3.02% (-$90,000)

4 Beds | 3 Baths | 2,416 sf ($1,198 / SqFt)

835 Gulf Drive
Summerland, FL 33042

1 Price Changes / 37 Days Ago

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

$2,159,000

-5.82% (-$133,500)

4 Beds | 4 Baths | 2,638 sf ($818 / SqFt)

22925 John Avery Lane
Summerland, FL 33042

3 Price Changes / 2 Days Ago

Active

$1,999,900

2 Beds | 2 Baths | 2,156 sf ($928 / SqFt)

1165 Lagoon Drive
Summerland, FL 33042

Active

$1,850,000

2 Beds | 2 Baths | 1,410 sf ($1,312 / SqFt)

1323 Hudgins Drive
Summerland, FL 33042

Active

$1,599,900

4 Beds | 3 Baths | 1,704 sf ($939 / SqFt)

951 Lagoon Drive
Summerland, FL 33042

Active

$1,295,000

1 Beds | 4 Baths | 1,965 sf ($659 / SqFt)

24931 Overseas Highway
Summerland, FL 33042

Active

$1,290,000

-0.69% (-$9,000)

3 Beds | 1 Baths | 2,246 sf ($574 / SqFt)

715 Caribbean Drive
Summerland, FL 33042

1 Price Changes / 7 Days Ago

Active

$1,275,000

-8.92% (-$124,900)

3 Beds | 2 Baths | 1,380 sf ($924 / SqFt)

1032 Caribbean Drive
Summerland, FL 33042

4 Price Changes / 2 Days Ago

Active

$1,255,000

2 Beds | 2 Baths | 864 sf ($1,453 / SqFt)

1021 Caribbean Drive
Summerland, FL 33042

Active

$1,049,000

-4.55% (-$50,000)

2 Beds | 2 Baths | 992 sf ($1,057 / SqFt)

1342 Ocean Drive
Summerland, FL 33042

1 Price Changes / 8 Days Ago

Active

$1,049,000

-12.58% (-$151,000)

3 Beds | 2 Baths | 1,680 sf ($624 / SqFt)

25074 5th Street
Summerland, FL 33042

2 Price Changes / 65 Days Ago

Active

$979,000

-10.59% (-$116,000)

3 Beds | 2 Baths | 1,028 sf ($952 / SqFt)

76 Shore Drive
Summerland, FL 33042

2 Price Changes / 2 Days Ago

Active

$894,000

-0.56% (-$5,000)

2 Beds | 2 Baths | 918 sf ($974 / SqFt)

260 Airport Drive
Summerland, FL 33042

1 Price Changes / 13 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 05-18-2025.