388 Listings
Gated, Any price, 1+ beds, 0+ baths Reset Filters
Sort
$42,000,000
Virtual Tour
88041 Old Hwy, Islamorada, FL 33036
9,843 SqFt
6 Beds | 9 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$27,500,000
2405 Coco Plum Dr, Marathon, FL 33050
19,124 SqFt
9 Beds | 10 Baths
Listing Provided By: American Caribbean Real Estate 
$24,995,000
82719 Old Hwy, Islamorada, FL 33036
10,182 SqFt
7 Beds | 10 Baths
Listing Provided By: Compass Florida 
$24,995,000
87895 Old Hwy, Islamorada, FL 33036
9,011 SqFt
5 Beds | 8 Baths
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. 
$23,900,000
Virtual Tour
19 Sunset Key Dr, Key West, FL 33040
6,532 SqFt
4 Beds | 6 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$15,990,000
88351 Old Hwy, Islamorada, FL 33036
7,590 SqFt
6 Beds | 9 Baths
Listing Provided By: Berkshire Hathaway Homeservices Ewm Realty 
$14,495,000
Virtual Tour
44 Card Sound Rd, Key Largo, FL 33037
7,358 SqFt
7 Beds | 8 Baths
Listing Provided By: Swenson & Ecuyer Realty 
$12,500,000
89251 Old Hwy, Islamorada, FL 33070
1,243 SqFt
3 Beds | 3 Baths
Listing Provided By: Coldwell Banker Schmitt Islamorada 
$12,450,000
Virtual Tour
301 Ixora St, Duck, FL 33050
5,390 SqFt
5 Beds | 7 Baths
Listing Provided By: Berkshire Hathaway Homeservices Keys Real Estate 
$11,995,000
1355-1350 Coury Dr, Key Colony, FL 33051
4,752 SqFt
4 Beds | 5 Baths
Listing Provided By: Coldwell Banker Schmitt Lower Keys (kw) 
$11,000,000
Virtual Tour
75280 Overseas Hwy, Islamorada, FL 33036
5,100 SqFt
4 Beds | 4 Baths
Listing Provided By: Ocean Sotheby's International Realty
$9,995,000
1355 Coury Dr, Key Colony, FL 33051
4,752 SqFt
4 Beds | 5 Baths
Listing Provided By: Coldwell Banker Schmitt Lower Keys (kw) 
$9,975,000
65760 Overseas Hwy, Layton, FL 33001
5,048 SqFt
5 Beds | 5 Baths
Listing Provided By: Florida Keys Real Estate Group 
$9,950,000
Virtual Tour
16750 Old State Road 4a, Sugarloaf, FL 33042
5,208 SqFt
6 Beds | 5 Baths
Listing Provided By: The Agency Florida Keys 
$9,950,000
104 Coastal Dr, Key Largo, FL 33037
6,083 SqFt
5 Beds | 8 Baths
Listing Provided By: American Caribbean Real Estate 
$9,950,000
6500-6600 Overseas Hwy, Marathon, FL 33050
10,852 SqFt
6 Beds | 11 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$9,500,000
95351 Overseas Hwy, Key Largo, FL 33037
2,489 SqFt
7 Beds | 4 Baths
Listing Provided By: Buccaneer R.E. 
$7,900,000
95480 & 90 Overseas Hwy, Key Largo, FL 33037
5,392 SqFt
10 Beds | 9 Baths
Listing Provided By: Coldwell Banker Schmitt Islamorada 
$7,795,000
Virtual Tour
89701 Old Hwy, Tavernier, FL 33070
3,841 SqFt
5 Beds | 5 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$6,950,000
545 Ocean Cay Dr, Key Largo, FL 33037
4,728 SqFt
3 Beds | 4 Baths
Listing Provided By: American Caribbean Real Estate 
$6,500,000
430 Palm Dr, Islamorada, FL 33036
5,153 SqFt
5 Beds | 7 Baths
Listing Provided By: Coastal Realty Of The Florida Keys 
$6,490,000
Virtual Tour
137 Sapodilla Dr, Islamorada, FL 33036
5,456 SqFt
5 Beds | 6 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$6,290,000
21470 Overseas Hwy, Cudjoe, FL 33042
n/a SqFt
13 Beds | 7 Baths
Listing Provided By: Select Properties Of Nwfl 
$6,200,000
36 Cannon Royal Dr, Shark Key, FL 33040
4,624 SqFt
5 Beds | 5 Baths
Listing Provided By: Brenda Donnelly Real Estate LLC 
$6,200,000
Virtual Tour
42 Cannon Royal Dr, Shark Key, FL 33040
4,000 SqFt
4 Beds | 4 Baths
Listing Provided By: Berkshire Hathaway Homeservices Knight & Gardner Realty 
$6,200,000
24200 Overseas Hwy, Summerland, FL 33042
3,000 SqFt
5 Beds | 6 Baths
Listing Provided By: Keller Williams Key West Compass Realty 
$6,150,000
134 N Rolling Hill Rd, Tavernier, FL 33070
2,346 SqFt
4 Beds | 5 Baths
Listing Provided By: American Caribbean Real Estate 
$5,999,999
Virtual Tour
181 Nautilus Dr, Islamorada, FL 33036
5,320 SqFt
5 Beds | 6 Baths
Listing Provided By: Coldwell Banker Realty - Coral Gables 
$5,995,000
Virtual Tour
126 Sunrise Dr, Marathon, FL 33050
3,448 SqFt
5 Beds | 4 Baths
Listing Provided By: Lokation Real Estate - Pompano Beach 
$5,995,000
Virtual Tour
910-914 Watson St, Key West, FL 33040
4,387 SqFt
5 Beds | 7 Baths
Listing Provided By: Truman & Co. (kw) 
$5,950,000
723 Eaton St, Key West, FL 33040
4,094 SqFt
6 Beds | 8 Baths
Listing Provided By: Preferred Properties (kw) 
$5,950,000
Virtual Tour
75851 Overseas Hwy, Islamorada, FL 33036
3,978 SqFt
5 Beds | 7 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$5,750,000
Virtual Tour
30 Cannon Royal Dr, Shark Key, FL 33040
5,180 SqFt
4 Beds | 5 Baths
Listing Provided By: Berkshire Hathaway Homeservices Knight & Gardner Realty 
$5,750,000
22 S Island Dr, Key Largo, FL 33037
2,208 SqFt
3 Beds | 3 Baths
Listing Provided By: Swenson & Ecuyer Realty 
$5,700,000
Virtual Tour
100 List St, Islamorada, FL 33036
3,019 SqFt
3 Beds | 3 Baths
Listing Provided By: Coldwell Banker Schmitt Islamorada 
$5,390,000
Virtual Tour
3742 Seagrape St, Big Pine, FL 33043
4,687 SqFt
3 Beds | 3 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$5,200,000
Virtual Tour
17013 Coral Dr, Sugarloaf, FL 33042
2,660 SqFt
4 Beds | 4 Baths
Listing Provided By: Coldwell Banker Schmitt Lower Keys (kw) 
$4,999,900
75761 Overseas Hwy, Islamorada, FL 33036
3,001 SqFt
4 Beds | 4 Baths
Listing Provided By: Engel & Völkers Marathon 
$4,997,000
113 Court Contessa, Islamorada, FL 33036
3,597 SqFt
5 Beds | 7 Baths
Listing Provided By: Taylor & Assoc. RE 
$4,850,000
74501 Overseas Hwy, Islamorada, FL 33036
3,772 SqFt
5 Beds | 4 Baths
Listing Provided By: Engel & Völkers Marathon 
$4,699,000
Virtual Tour
58213 Morton St, Marathon, FL 33050
4,000 SqFt
3 Beds | 5 Baths
Listing Provided By: Coldwell Banker Schmitt Lower Keys (kw) 
$4,695,000
Virtual Tour
24 Cannon Royal Dr, Shark Key, FL 33040
4,176 SqFt
5 Beds | 4 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$4,690,000
810 39th Street Gulf, Marathon, FL 33050
3,026 SqFt
5 Beds | 5 Baths
Listing Provided By: RE/MAX Alliance Group 
$4,600,000
Virtual Tour
1227 Washington St, Key West, FL 33040
3,066 SqFt
4 Beds | 4 Baths
Listing Provided By: Location 3 Real Estate Of Kw Inc (kw) 
$4,595,000
Virtual Tour
1217 Johnson St, Key West, FL 33040
3,650 SqFt
5 Beds | 6 Baths
Listing Provided By: Truman & Co. (kw) 
$4,595,000
924 Flagler Ave, Key West, FL 33040
2,064 SqFt
4 Beds | 3 Baths
Listing Provided By: Preferred Properties (kw) 
$4,500,000
Virtual Tour
115 Windy Point Cir, Marathon, FL 33050
2,623 SqFt
3 Beds | 3 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$4,400,000
231 E Shore Dr Unit 5, Summerland, FL 33042
3,119 SqFt
5 Beds | 6 Baths
Listing Provided By: Serhant Florida LLC - Delray Beach Office
$4,375,000
231 E Shore Dr Unit 3, Summerland, FL 33042
3,119 SqFt
5 Beds | 6 Baths
Listing Provided By: Serhant Florida LLC - Delray Beach Office
$4,375,000
231 E Shore Dr Unit 6, Summerland, FL 33042
3,119 SqFt
5 Beds | 6 Baths
Listing Provided By: Serhant Florida LLC - Delray Beach Office
$4,375,000
231 E Shore Dr Unit 4, Summerland, FL 33042
3,119 SqFt
5 Beds | 6 Baths
Listing Provided By: Serhant Florida LLC - Delray Beach Office 
$4,350,000
202 Admirals Ln, Key West, FL 33040
3,148 SqFt
5 Beds | 4 Baths
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. (kw) 
$4,300,000
2125 Avenue H, Marathon, FL 33050
3,262 SqFt
5 Beds | 4 Baths
Listing Provided By: Florida Keys Real Estate Group
$4,150,000
231 E Shore Dr Unit 2, Summerland, FL 33042
3,119 SqFt
5 Beds | 6 Baths
Listing Provided By: Serhant Florida LLC - Delray Beach Office 
$3,999,000
Virtual Tour
17015 W Wahoo Ln, Sugarloaf, FL 33042
2,096 SqFt
3 Beds | 3 Baths
Listing Provided By: Coldwell Banker Schmitt Lower Keys (kw)
$3,995,900
231 E Shore Dr Unit 1, Summerland, FL 33042
3,119 SqFt
5 Beds | 6 Baths
Listing Provided By: Serhant Florida LLC - Delray Beach Office 
$3,995,000
Virtual Tour
87445 Old Hwy, Islamorada, FL 33036
4,014 SqFt
5 Beds | 4 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$3,995,000
802 Bonito Ln, Key Largo, FL 33037
2,669 SqFt
4 Beds | 4 Baths
Listing Provided By: Coastal Realty Of The Florida Keys 
$3,995,000
813 Thomas St, Key West, FL 33040
2,271 SqFt
4 Beds | 3 Baths
Listing Provided By: Brenda Donnelly Real Estate LLC 
$3,995,000
141 Grassy Rd, Key Largo, FL 33037
3,600 SqFt
5 Beds | 5 Baths
Listing Provided By: American Caribbean Real Estate 
$3,995,000
105 Palo De Oro Dr, Islamorada, FL 33036
2,640 SqFt
5 Beds | 3 Baths
Listing Provided By: Coldwell Banker Schmitt Islamorada 
$3,950,000
Virtual Tour
59720 Overseas Hwy Unit 13, Marathon, FL 33050
3,011 SqFt
5 Beds | 5 Baths
Listing Provided By: Internet Realty Of The Florida Keys Inc 
$3,900,000
Virtual Tour
48 E Playa Largo Blvd, Key Largo, FL 33037
2,807 SqFt
4 Beds | 5 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$3,879,000
906 Southard St, Key West, FL 33040
2,188 SqFt
3 Beds | 3 Baths
Listing Provided By: RE/MAX Keys Connection (kw)
$3,825,000
Virtual Tour
46 E Playa Largo Blvd, Key Largo, FL 33037
2,807 SqFt
4 Beds | 5 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$3,800,000
Virtual Tour
82779 Old Hwy Unit 14, Islamorada, FL 33036
2,574 SqFt
4 Beds | 5 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$3,699,000
Virtual Tour
17183 Coral Dr, Sugarloaf, FL 33042
1,744 SqFt
4 Beds | 4 Baths
Listing Provided By: Coldwell Banker Schmitt RE Co. 
$3,695,000
680 Elma Ave, Big Pine, FL 33043
2,050 SqFt
4 Beds | 4 Baths
Listing Provided By: Island Welcome Real Estate 
$3,675,000
224 W Seaview Cir, Duck, FL 33050
1,658 SqFt
3 Beds | 2 Baths
Listing Provided By: Trustpoint Realty 
$3,600,000
Virtual Tour
1401 51st Street Gulf, Marathon, FL 33050
2,428 SqFt
3 Beds | 3 Baths
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. 
$3,524,000
110 Gulfview Dr, Islamorada, FL 33036
3,524 SqFt
7 Beds | 4 Baths
Listing Provided By: Exp Realty 
$3,490,000
Virtual Tour
996 97th Street Ocean, Marathon, FL 33050
1,999 SqFt
3 Beds | 3 Baths
Listing Provided By: Berkshire Hathaway Homeservices Keys Real Estate 
$3,450,000
111 Brian Rd, Marathon, FL 33050
4,256 SqFt
4 Beds | 4 Baths
Listing Provided By: Berkshire Hathaway Homeservices Keys Real Estate 
$3,400,000
59720 Overseas Hwy Unit 9, Marathon, FL 33050
3,011 SqFt
4 Beds | 5 Baths
Listing Provided By: Compass Florida LLC - Tavernier 
$3,400,000
Virtual Tour
205 Stirrup Key Blvd, Marathon, FL 33050
3,414 SqFt
4 Beds | 3 Baths
Listing Provided By: Coldwell Banker Schmitt Islamorada 
$3,295,000
Virtual Tour
418 William St, Key West, FL 33040
1,852 SqFt
4 Beds | 3 Baths
Listing Provided By: Truman & Co. (kw) 
$3,150,000
Virtual Tour
3720 Flagler Ave, Key West, FL 33040
2,426 SqFt
4 Beds | 2 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$3,050,000
Virtual Tour
25 E Playa Largo Blvd, Key Largo, FL 33037
2,502 SqFt
3 Beds | 3 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$2,999,500
401 Emma St Apt H, Key West, FL 33040
1,770 SqFt
2 Beds | 2 Baths
Listing Provided By: Century 21 All Keys Inc (kw) 
$2,999,000
Virtual Tour
80639 Old Hwy Unit 309, Islamorada, FL 33036
2,275 SqFt
3 Beds | 3 Baths
Listing Provided By: Ocean Sotheby's International Realty
$2,950,000
Virtual Tour
59720 Overseas Hwy Unit 7, Marathon, FL 33050
3,013 SqFt
5 Beds | 5 Baths
Listing Provided By: Internet Realty Of The Florida Keys Inc 
$2,900,000
Virtual Tour
111 Windy Point Cir, Marathon, FL 33050
2,446 SqFt
3 Beds | 4 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$2,890,000
Virtual Tour
75055 Overseas Hwy, Islamorada, FL 33036
1,400 SqFt
3 Beds | 2 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$2,850,000
81250 Overseas Hwy Unit 2, Islamorada, FL 33036
2,072 SqFt
3 Beds | 3 Baths
Listing Provided By: Palm House Real Estate 
$2,825,000
525 Louisa St, Key West, FL 33040
1,902 SqFt
3 Beds | 3 Baths
Listing Provided By: Keller Williams Key West Compass Realty 
$2,795,000
502 Porter Ln, Key West, FL 33040
1,920 SqFt
4 Beds | 3 Baths
Listing Provided By: Keller Williams Key West Compass Realty 
$2,789,000
3206 Riviera Dr, Key West, FL 33040
2,212 SqFt
3 Beds | 3 Baths
Listing Provided By: Berkshire Hathaway Homeservices Knight & Gardner Realty 
$2,750,000
Virtual Tour
120 Pirates Cove Dr, Marathon, FL 33050
3,476 SqFt
4 Beds | 4 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$2,700,000
Virtual Tour
316 North Dr, Islamorada, FL 33036
2,309 SqFt
3 Beds | 4 Baths
Listing Provided By: RE/MAX All Keys Real Estate 
$2,699,000
Virtual Tour
1233 Avenue A, Big Pine, FL 33043
1,456 SqFt
3 Beds | 2 Baths
Listing Provided By: Coldwell Banker Schmitt Lower Keys (kw) 
$2,650,000
1500 Atlantic Blvd Unit 414, Key West, FL 33040
2,038 SqFt
3 Beds | 3 Baths
Listing Provided By: Keller Williams Key West Compass Realty 
$2,600,000
139 Marina Ave, Key Largo, FL 33037
2,485 SqFt
4 Beds | 6 Baths
Listing Provided By: American Caribbean Real Estate 
$2,550,000
815 39th St Gulf St, Marathon, FL 33050
2,266 SqFt
4 Beds | 4 Baths
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. 
$2,499,000
409 Grinnell St, Key West, FL 33040
1,628 SqFt
4 Beds | 2 Baths
Listing Provided By: Berkshire Hathaway Homeservices Knight & Gardner Realty 
$2,495,000
1616 Atlantic Blvd Unit 15, Key West, FL 33040
3,118 SqFt
4 Beds | 6 Baths
Listing Provided By: Truman & Co. (kw) 
$2,495,000
Virtual Tour
33 Pen Key Dr, Islamorada, FL 33036
4,537 SqFt
3 Beds | 4 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$2,495,000
Virtual Tour
81906 Overseas Hwy Unit 2, Islamorada, FL 33036
1,829 SqFt
3 Beds | 4 Baths
Listing Provided By: Ocean Sotheby's International Realty 
$2,425,000
818 39th St, Marathon, FL 33050
2,298 SqFt
5 Beds | 4 Baths
Listing Provided By: Coldwell Banker Schmitt Real Estate Co. 
