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Recently Sold Homes in Summerland Key, FL

242 homes

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SOLD
FEB 17, 2026
$460,000
2 Beds
840 sqft
701 Spanish Main Dr #369 & 370,
Cudjoe Key, FL 33042
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SOLD
FEB 17, 2026
$220,000
25044 45th St,
Summerland Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
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SOLD
FEB 17, 2026
$257,500
701 Spanish Main Dr #396,
Cudjoe Key, FL 33042
Keller Williams Key West Compass Realty
SOLD
FEB 17, 2026
$750,000
Studio
1,152 sqft
24933 Overseas Hwy,
Summerland Key, FL 33042
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SOLD
FEB 10, 2026
$577,500
3 Beds
2 Baths
1,380 sqft
56 W Shore Dr,
Summerland Key, FL 33042
Genstone Realty LLC
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SOLD
FEB 6, 2026
$1,725,000
4 Beds
3 Baths
1,440 sqft
1082 Bay Dr,
Summerland Key, FL 33042
Berkshire Hathaway HomeServices Knight & Gardner Realty
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SOLD
FEB 6, 2026
$750,000
1 Bed
3 Baths
1,965 sqft
24931 Overseas Hwy,
Summerland Key, FL 33042
Berkshire Hathaway HomeServices Knight & Gardner Realty
SOLD
FEB 5, 2026
$870,000
2 Beds
2 Baths
779 sqft
701 Spanish Main Dr #214,
Cudjoe Key, FL 33042
Bluescape Real Estate
SOLD
JAN 30, 2026
$1,700,000
4 Beds
2 Baths
2,074 sqft
22562 Jolly Roger Dr,
Cudjoe Key, FL 33042
eXp Realty LLC
SOLD
JAN 30, 2026
$1,550,000
3 Beds
2 Baths
1,248 sqft
28538 John Silver Rd,
Little Torch Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
SOLD
JAN 29, 2026
$1,929,430
3 Beds
2 Baths
1,767 sqft
22896 Jolly Roger Dr,
Cudjoe Key, FL 33042
SOLD
JAN 29, 2026
$700,000
3 Beds
2 Baths
1,188 sqft
24830 Park Dr,
Summerland Key, FL 33042
Coldwell Banker Schmitt Lower Keys (KW)
SOLD
JAN 28, 2026
$1,650,000
3 Beds
2 Baths
1,750 sqft
17213 Starfish Ln,
Sugarloaf Key, FL 33042
Truman & Co. (KW)
SOLD
JAN 28, 2026
$1,299,000
3 Beds
2 Baths
1,530 sqft
28532 Dirk Rd,
Little Torch Key, FL 33042
Coldwell Banker Schmitt Lower Keys (KW)
SOLD
JAN 27, 2026
$375,000
2 Beds
2 Baths
828 sqft
701 Spanish Main Dr #401,
Cudjoe Key, FL 33042
SOLD
JAN 23, 2026
$1,800,000
4 Beds
3 Baths
2,422 sqft
17054 Coral Dr,
Sugarloaf Key, FL 33042
Berkshire Hathaway HomeServices Knight & Gardner Realty
SOLD
JAN 22, 2026
$762,000
3 Beds
2 Baths
1,568 sqft
726 Jamaica Ln,
Little Torch Key, FL 33042
Expert Realty LLC (HQ)
SOLD
JAN 21, 2026
$250,000
20812 1st Ave W,
Summerland Key, FL 33042
SOLD
JAN 20, 2026
$935,000
3 Beds
3 Baths
1,859 sqft
146 Sugarloaf Dr,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Lower Keys (KW)
SOLD
JAN 16, 2026
$55,000
State Rd #4A,
Summerland Key, FL 33042
Meyer and Boumerhi Realty LLC
SOLD
JAN 14, 2026
$1,400,000
3 Beds
2 Baths
1,728 sqft
17166 Wahoo Ln,
Summerland Key, FL 33042
Coldwell Banker Schmitt Lower Keys (KW)
SOLD
JAN 14, 2026
$150,000
4 Beds
4 Baths
1,671 sqft
193 Galleon Ln,
Cudjoe Key, FL 33042
SOLD
JAN 12, 2026
$600,000
19535 Indian Mound Dr,
Sugarloaf Key, FL 33042
SOLD
JAN 9, 2026
$700,000
2 Beds
2 Baths
864 sqft
701 Spanish Main Dr #87,
Cudjoe Key, FL 33042
RE/MAX Keys Connection (KW)
SOLD
JAN 9, 2026
$853,000
3 Beds
2 Baths
1,195 sqft
22922 Blackbeard Ln,
Cudjoe Key, FL 33042
eXp Realty LLC
SOLD
JAN 9, 2026
$1,300,000
3 Beds
2 Baths
1,674 sqft
141 Arica Ln,
Cudjoe Key, FL 33042
Expert Realty LLC (HQ)
SOLD
JAN 5, 2026
$5,003,500
5 Beds
5 Baths
3,952 sqft
1151 Ocean Dr,
Summerland Key, FL 33042
The Agency Florida Keys
SOLD
JAN 2, 2026
$1,700,000
4 Beds
3 Baths
2,120 sqft
620 Barry Ave,
Little Torch Key, FL 33042
Bluescape Real Estate
SOLD
DEC 31, 2025
$935,000
3 Beds
2 Baths
1,440 sqft
786 Jamaica Ln,
Little Torch Key, FL 33042
Keller Williams Key West Compass Realty
SOLD
DEC 24, 2025
$175,000
Studio
Vacant lan overseas Hwy,
Cudjoe key, FL 33042
SOLD
DEC 23, 2025
$175,000
Lot 2 Overseas Hwy,
Summerland Key, FL 33042
Coldwell Banker Schmitt Real Estate Co. (KW)
SOLD
DEC 19, 2025
$1,200,000
3 Beds
2 Baths
2,392 sqft
28565 Anne Bonny Rd,
Little Torch Key, FL 33042
Coldwell Banker Schmitt RE Co.
SOLD
DEC 19, 2025
$50,000
4 Old State Rd #A,
Ramrod key, FL 33042
SOLD
DEC 18, 2025
$175,000
Vacant lan overseas Hwy,
Cudjoe key, FL 33042
SOLD
DEC 17, 2025
$850,000
2 Beds
1 Bath
795 sqft
757 La Fitte Rd,
Little Torch Key, FL 33042
SOLD
DEC 12, 2025
$1,164,000
3 Beds
2 Baths
1,400 sqft
164 Tortuga Ln,
Summerland Key, FL 33042
Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
SOLD
DEC 12, 2025
$1,164,000
2 Beds
2 Baths
1,400 sqft
164 Tortuga Ln,
Cudjoe Key, FL 33042
SOLD
DEC 11, 2025
$938,000
3 Beds
2 Baths
1,440 sqft
460 Barry Ave,
Little Torch Key, FL 33042
Tropic Shores Realty
SOLD
DEC 11, 2025
$905,000
2 Beds
2 Baths
1,620 sqft
22852 John Silver Ln,
Cudjoe Key, FL 33042
Ocean Sotheby's International Realty
SOLD
DEC 11, 2025
$340,000
Overseas Hwy,
Summerland key, FL 33042
Island Real Estate Company Florida Keys

MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.