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Recently Sold Homes in Summerland Key, FL

208 homes

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SOLD
JUN 9, 2026
$3,150,000
4 Beds
4 Baths
2,375 sqft
270 Caribbean Dr E,
Summerland Key, FL 33042
Island Welcome Real Estate
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SOLD
JUN 5, 2026
$1,937,500
3 Beds
2 Baths
1,767 sqft
1058 Buttonwood Dr,
Summerland Key, FL 33042
The Agency Florida Keys
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SOLD
JUN 5, 2026
$1,300,000
3 Beds
2 Baths
1,944 sqft
20838 5th Ave W,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
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SOLD
JUN 4, 2026
$600,000
22948 Drake Ln,
Cudjoe Key, FL 33042
Preferred Properties (KW)
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SOLD
JUN 3, 2026
$280,000
1 Bed
1 Bath
690 sqft
701 Spanish Main Dr #21,
Cudjoe Key, FL 33042
Expert Realty LLC (HQ)
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SOLD
JUN 1, 2026
$2,675,000
4 Beds
3 Baths
2,951 sqft
20844 4th Ave W,
Summerland Key, FL 33042
Berkshire Hathaway HomeServices Knight & Gardner Realty
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SOLD
MAY 29, 2026
$810,000
3 Beds
2.5 Baths
1,592 sqft
19611 Tequesta St,
Sugarloaf Key, FL 33042
eXp Realty LLC Southernmost Branch
SOLD
MAY 29, 2026
$835,000
2 Beds
2 Baths
960 sqft
154 Cutthroat Dr,
Cudjoe Key, FL 33042
Expert Realty LLC
SOLD
MAY 28, 2026
$1,400,000
3 Beds
2 Baths
1,296 sqft
17195 Hibiscus Ln,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
SOLD
MAY 28, 2026
$525,000
2 Beds
2 Baths
816 sqft
701 Spanish Main Dr #510,
Cudjoe Key, FL 33042
Bluescape Real Estate
SOLD
MAY 28, 2026
$570,000
3 Beds
2 Baths
1,449 sqft
27970 Lobstertail Trl,
Little Torch Key, FL 33042
Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key
SOLD
MAY 28, 2026
$1,425,000
3 Beds
2 Baths
1,528 sqft
17215 Bonita Ln E,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
SOLD
MAY 27, 2026
$475,000
2 Beds
2 Baths
832 sqft
19264 Acosta Trl,
Sugarloaf Key, FL 33042
Bluescape Real Estate
SOLD
MAY 26, 2026
$420,000
701 Spanish Main Dr #574,
Cudjoe Key, FL 33042
Bluescape Real Estate
SOLD
MAY 22, 2026
$2,800,000
3 Beds
3.5 Baths
2,538 sqft
747 La Fitte Rd,
Little Torch Key, FL 33042
Keller Williams Realty Premier Properties - Kendall
SOLD
MAY 20, 2026
$1,375,000
3 Beds
2.5 Baths
1,740 sqft
16823 E Point Dr,
Summerland Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
SOLD
MAY 20, 2026
$649,000
2 Beds
2 Baths
1,040 sqft
19591 Navajo St,
Sugarloaf Key, FL 33042
Internet Realty of the Florida Keys
SOLD
MAY 20, 2026
$205,000
701 Spanish Main Dr #317,
Cudjoe Key, FL 33042
Florida Keys Realty, Inc.
SOLD
MAY 18, 2026
$720,000
3 Beds
2 Baths
1,410 sqft
28151 Helen Ave,
Little Torch Key, FL 33042
EXP Realty LLC
SOLD
MAY 14, 2026
$1,100,000
3 Beds
2 Baths
1,144 sqft
1011 Caribbean Dr E,
Summerland Key, FL 33042
Keller Williams Key West Compass Realty
SOLD
MAY 13, 2026
$1,075,000
2 Beds
2 Baths
1,260 sqft
110 Doubloon Ln,
Cudjoe Key, FL 33042
Island Welcome Real Estate
SOLD
MAY 13, 2026
$849,000
4 Beds
3 Baths
2,100 sqft
25057 7th St,
Summerland Key, FL 33042
Coldwell Banker Schmitt RE Co.
SOLD
MAY 11, 2026
$430,000
2 Beds
1 Bath
415 sqft
21857 Disturbed Pine Rd,
Cudjoe Key, FL 33042
Keller Williams Key West Compass Realty
SOLD
MAY 11, 2026
$1,075,000
3 Beds
2 Baths
1,467 sqft
21855 Spain Blvd,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Lower Keys (KW)
SOLD
MAY 11, 2026
$750,000
2 Beds
2 Baths
984 sqft
744 Blackbeard Rd,
Little Torch Key, FL 33042
Island Welcome Real Estate
SOLD
MAY 7, 2026
$1,425,000
3 Beds
2 Baths
1,144 sqft
1581 State Rd,
Little Torch Key, FL 33042
Realty ONE Group Destination
SOLD
MAY 7, 2026
$50,000
13 Yucatan Ln,
Summerland Key, FL 33042
The Keyes Company
SOLD
MAY 7, 2026
$50,000
12 Trinidad Ln,
Summerland Key, FL 33042
The Keyes Company
SOLD
MAY 6, 2026
$750,000
1 Bed
1 Bath
766 sqft
701 Spanish Main Dr #333,
Cudjoe Key, FL 33042
SOLD
MAY 4, 2026
$405,000
3 Beds
1.5 Baths
1,104 sqft
744 Trinidad Ln,
Little Torch Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
SOLD
MAY 1, 2026
$775,000
3 Beds
2 Baths
1,288 sqft
22939 Privateer Dr,
Cudjoe Key, FL 33042
Brenda Donnelly Real Estate LLC
SOLD
APR 30, 2026
$1,410,000
3 Beds
2 Baths
1,200 sqft
17152 Marlin Dr,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
SOLD
APR 30, 2026
$1,800,000
3 Beds
3.5 Baths
2,100 sqft
23087 Sailfish Ln,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
SOLD
APR 30, 2026
$440,000
2 Beds
1.5 Baths
604 sqft
701 Spanish Main Dr #234,
Cudjoe Key, FL 33042
Bluescape Real Estate
SOLD
APR 30, 2026
$278,000
2 Beds
1 Bath
738 sqft
701 Spanish Main Dr #641,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt RE Co.
SOLD
APR 30, 2026
$425,000
132 Blackbeard Rd,
Little Torch Key, FL 33042
Coldwell Banker Schmitt RE Co.
SOLD
APR 29, 2026
$390,000
2 Beds
2 Baths
864 sqft
701 Spanish Main Dr #635,
Cudjoe Key, FL 33042
Expert Realty LLC (HQ)
SOLD
APR 28, 2026
$1,249,000
2 Beds
2 Baths
1,056 sqft
17170 Amberjack Ln,
Sugarloaf Key, FL 33042
The Agency Florida Keys
SOLD
APR 27, 2026
$268,000
701 Spanish Main Dr #146,
Cudjoe Key, FL 33042
Expert Realty LLC (HQ)
SOLD
APR 27, 2026
$1,100,000
3 Beds
2 Baths
1,204 sqft
857 Caribbean Dr E,
Summerland Key, FL 33042
Keller Williams Key West Compass Realty

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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 Board of Realtors.