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969 E Caribbean Drive Property Photo 1
36
OPEN HOUSE 4/20
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. (KW)
$1,275,000
969 E Caribbean Drive 
Summerland Key, FL 33042
  • Beds2
  • Baths 2 Total 2 Total
  • SqFt1,2501.3k
  • Built1995
93 Palm Drive Property Photo 1
32
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. (KW)
$1,094,000
93 Palm Drive 
Saddlebunch, FL 33040
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt1,3251.3k
  • Built2016
17396 Jamaica Lane Property Photo 1
50
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. (KW)
$899,000
17396 Jamaica Lane 
Sugarloaf Key, FL 33042
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt1,2241.2k
  • Built1992
1300 Sunset Boulevard Property Photo 1
69
Truman & Co. (KW) Logo
Listing Provided By: Truman & Co. (KW)
$17,999,900
1300 Sunset Boulevard 
Summerland Key, FL 33042
  • Beds6
  • Baths 8 Total 8 Total
  • SqFt7,7207.7k
  • Built2015
16750 Old State Road 4a Property Photo 1
78
NEW
Listing Provided By: Coldwell Banker Schmitt Lower Keys (KW)
$7,499,000
16750 Old State Road 4A 
Sugarloaf Key, FL 33042
  • Beds6
  • Baths 5 Total 5 Total
  • SqFt5,2085.2k
  • Built1959
1446 Calle Bogota Property Photo 1
59
Florida Keys Real Estate Group Logo
Listing Provided By: Florida Keys Real Estate Group
$6,249,000
1446 Calle Bogota 
Summerland Key, FL 33042
  • Beds4
  • Baths 4 Total 4 Total
  • SqFt4,7064.7k
  • Built2010
220 E Caribbean Drive Property Photo 1
16
Island Real Estate Company Florida Keys Logo
Listing Provided By: Island Real Estate Company Florida Keys
$5,900,000
220 E Caribbean Drive 
Summerland Key, FL 33042
  • Beds5
  • Baths 7 Total 7 Total
  • SqFt4,9815.0k
  • Built2023
1141 Ocean Drive Property Photo 1
66
NEW
Premier Brokers International Logo
Listing Provided By: Premier Brokers International
$5,900,000
1141 Ocean Drive 
Summerland Key, FL 33042
  • Beds5
  • Baths 5 Total 5 Total
  • SqFt3,4213.4k
  • Built2005
681 Sugarloaf Boulevard Property Photo 1
121
Berkshire Hathaway Knight & Gardner Logo
Listing Provided By: Berkshire Hathaway Knight & Gardner
$5,699,000
681 Sugarloaf Boulevard 
Sugarloaf Key, FL 33042
  • Beds6
  • Baths 4 Total 4 Total
  • SqFt3,2083.2k
  • Built1971
974 Flagship Drive Property Photo 1
54
KeyIsle Realty Logo
Listing Provided By: KeyIsle Realty
$5,600,000
974 Flagship Drive 
Summerland Key, FL 33042
  • Beds4
  • Baths 4 Total 4 Total
  • SqFt5,6085.6k
  • Built2001
815 E Shore Drive Property Photo 1
132
Better Homes and Gardens Real Estate Destinations Logo
Listing Provided By: Better Homes and Gardens Real Estate Destinations
$5,600,000
815 E Shore Drive 
Summerland Key, FL 33042
  • Beds7
  • Baths 6 Total 6 Total
  • SqFt4,5314.5k
  • Built1961
999 Flagship Drive Property Photo 1
59
KeyIsle Realty Logo
Listing Provided By: KeyIsle Realty
$5,299,000
999 Flagship Drive 
Summerland Key, FL 33042
  • Beds3
  • Baths 4 Total 4 Total
  • SqFt3,5313.5k
  • Built2024
9 Bay Drive Property Photo 1
73
Key West Luxury Real Estate Inc (KW) Logo
Listing Provided By: Key West Luxury Real Estate Inc (KW)
$4,250,000
9 Bay Drive 
Saddlebunch, FL 33040
  • Beds5
  • Baths 5 Total 5 Total
  • SqFt3,2723.3k
  • Built2014
17398 E Dolphin Street Property Photo 1
44
Sunny Keys Realty LLC Logo
Listing Provided By: Sunny Keys Realty LLC
$3,845,000
17398 E Dolphin Street 
Sugarloaf Key, FL 33042
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,4042.4k
  • Built2021
361 Ave D Property Photo 1
62
Island Real Estate Company Florida Keys Logo
Listing Provided By: Island Real Estate Company Florida Keys
$3,260,000
361 Ave D 
Summerland Key, FL 33042
  • Beds2
  • Baths 3 Total 3 Total
  • SqFt1,8181.8k
  • Built2022
17279 Pinetree Lane Property Photo 1
48
Key West Luxury Real Estate Inc (KW) Logo
Listing Provided By: Key West Luxury Real Estate Inc (KW)
$2,950,000
17279 Pinetree Lane 
Sugarloaf Key, FL 33042
  • Beds2
  • Baths 2 Total 2 Total
  • SqFt1,0161.0k
  • Built1956
70 Bay Drive Property Photo 1
79
Keller Williams Key West Compass Realty Logo
Listing Provided By: Keller Williams Key West Compass Realty
$2,625,000
70 Bay Drive 
Saddlebunch, FL 33040
  • Beds5
  • Baths 2 Total 2 Total
  • SqFt2,4502.5k
  • Built1993
1151 Sugarloaf Boulevard Property Photo 1
31
Truman & Co. (KW) Logo
Listing Provided By: Truman & Co. (KW)
$2,600,000
1151 Sugarloaf Boulevard 
Sugarloaf Key, FL 33042
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt2,1442.1k
  • Built1959
15800 Old State Road 4a Road, 4a Property Photo 1
37
Expert Realty LLC (HQ) Logo
Listing Provided By: Expert Realty LLC (HQ)
$2,599,000
15800 Old State Road 4A Road, 4A 
Sugarloaf Key, FL 33042
  • Beds2
  • Baths 3 Total 3 Total
  • SqFt1,5481.5k
  • Built2006
17054 Coral Drive Property Photo 1
42
Keller Williams Key West Compass Realty Logo
Listing Provided By: Keller Williams Key West Compass Realty
$2,499,000
17054 Coral Drive 
Sugarloaf Key, FL 33042
  • Beds4
  • Baths 4 Total 4 Total
  • SqFt2,4222.4k
  • Built2004
17270 Old State Road, 4a Property Photo 1
54
Expert Realty LLC (HQ) Logo
Listing Provided By: Expert Realty LLC (HQ)
$2,499,000
17270 Old State Road, 4A 
Sugarloaf Key, FL 33042
  • Beds2
  • Baths 2 Total 2 Total
  • SqFt1,2021.2k
  • Built1988
320 S Point Drive Property Photo 1
66
Berkshire Hathaway Knight & Gardner Logo
Listing Provided By: Berkshire Hathaway Knight & Gardner
$2,499,000
320 S Point Drive 
Sugarloaf Key, FL 33042
  • Beds5
  • Baths 3 Total 3 Total
  • SqFt2,4712.5k
  • Built1979
24931 Overseas Highway Property Photo 1
19
Island Real Estate Company Florida Keys Logo
Listing Provided By: Island Real Estate Company Florida Keys
$2,495,000
24931 Overseas Highway 
Summerland Key, FL 33042
  • Beds2
  • Baths 4 Total 4 Total
  • SqFt1,9652.0k
  • Built1975
948 Gulf Drive Property Photo 1
47
Listing Provided By: Coldwell Banker Schmitt Real Estate Co.
$2,399,000
948 Gulf Drive 
Summerland Key, FL 33042
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt2,0102.0k
  • Built2000
205 S Point Drive Property Photo 1
53
LoKation Real Estate Logo
Listing Provided By: LoKation Real Estate
$2,375,000
205 S Point Drive 
Sugarloaf Key, FL 33042
  • Beds5
  • Baths 4 Total 4 Total
  • SqFt2,7722.8k
  • Built1985
1040 Gulf Drive Property Photo 1
64
Berkshire Hathaway Knight & Gardner Logo
Listing Provided By: Berkshire Hathaway Knight & Gardner
$2,299,000
1040 Gulf Drive 
Summerland Key, FL 33042
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt2,2332.2k
  • Built2003
19527 Indian Mound Drive Property Photo 1
44
Listing Provided By: Coldwell Banker Schmitt Lower Keys (KW)
$2,199,000
19527 Indian Mound Drive 
Sugarloaf Key, FL 33042
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt1,7521.8k
  • Built1996
474 E Caribbean Drive Property Photo 1
37
Listing Provided By: Coldwell Banker Schmitt Lower Keys (KW)
$2,195,000
474 E Caribbean Drive 
Summerland Key, FL 33042
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt1,6641.7k
  • Built1973
17153 W Buttonwood Drive Property Photo 1
42
Century 21 Circle - Key West Logo
Listing Provided By: Century 21 Circle - Key West
$2,150,000
17153 W Buttonwood Drive 
Sugarloaf Key, FL 33042
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt1,4241.4k
  • Built1998
1165 Lagoon Drive Property Photo 1
51
Island Welcome Real Estate Logo
Listing Provided By: Island Welcome Real Estate
$2,150,000
1165 Lagoon Drive 
Summerland Key, FL 33042
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt2,1562.2k
  • Built1995
1082 Bay Drive Property Photo 1
33
OPEN HOUSE 4/20
Listing Provided By: Coldwell Banker Schmitt Lower Keys (KW)
$2,099,500
1082 Bay Drive 
Summerland Key, FL 33042
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt1,4401.4k
  • Built1980
17150 La Brisa Court Property Photo 1
57
Listing Provided By: Coldwell Banker Schmitt Lower Keys (KW)
$1,999,999
17150 La Brisa Court 
Sugarloaf Key, FL 33042
  • Beds4
  • Baths 3 Total 3 Total
  • SqFt1,8101.8k
  • Built1980
15 Bay Drive Property Photo 1
62
Truman & Co. (KW) Logo
Listing Provided By: Truman & Co. (KW)
$1,999,750
15 Bay Drive 
Saddlebunch, FL 33040
  • Beds3
  • Baths 2 Total 2 Total
  • SqFt2,0282.0k
  • Built1990
6 Shore Drive Property Photo 1
49
Berkshire Hathaway HomeServices Keys Real Estate - Islamorada Logo
Listing Provided By: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
$1,799,000
6 Shore Drive 
Saddlebunch, FL 33040
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt1,5891.6k
  • Built2006
980 E Caribbean Drive Property Photo 1
32
NEW
Keller Williams Key West Compass Realty Logo
Listing Provided By: Keller Williams Key West Compass Realty
$1,600,000
980 E Caribbean Drive 
Summerland Key, FL 33042
  • Beds3
  • Baths 3 Total 3 Total
  • SqFt2,2022.2k
  • Built1989
19512 Aztec Street Property Photo 1
94
Royal Palms Realty (KW) Logo
Listing Provided By: Royal Palms Realty (KW)
$1,590,000
19512 Aztec Street 
Sugarloaf Key, FL 33042
  • Beds2
  • Baths 3 Total 3 Total
  • SqFt1,7601.8k
  • Built1968