Explore Middle Keys Florida 33042 Homes for Sale 25 Active $339,000 28232 Dorothy Avenue , Little Torch, FL 2 Beds2 Baths1,064 SqFt 19 Active $349,000 701 Spanish Main Drive 62, Cudjoe, FL 2 Beds1 Baths756 SqFt 41 Active $349,900 701 Spanish Main Drive 625, Cudjoe, FL 2 Beds1 Baths720 SqFt 47 Active $389,000 701 Spanish Main Drive 537, Cudjoe, FL 1 Beds1 Baths520 SqFt 22 Active $392,500 27954 Tarpon Terrace , Little Torch, FL 2 Beds2 Baths735 SqFt 47 Contingent/Show $449,000 701 Spanish Main Drive 414, Cudjoe, FL 2 Beds2 Baths675 SqFt 50 Active $469,000 701 Spanish Main Drive 635, Cudjoe, FL 2 Beds2 Baths864 SqFt 32 Active $497,000 701 Spanish Main Drive 22, Cudjoe, FL 2 Beds2 Baths814 SqFt 21 Active $499,000 27848 Lobster Tail Trail , Little Torch, FL 2 Beds1 Baths552 SqFt 43 Active $529,000 701 Spanish Main Drive 440, Cudjoe, FL 2 Beds2 Baths773 SqFt 34 Active $530,000 27969 Lobster Tail Trail , Little Torch, FL 2 Beds2 Baths863 SqFt 58 Active $550,000 701 Spanish Main Drive 329, Cudjoe, FL 1 Beds1 Baths320 SqFt 38 Active $550,000 27883 Coral Shores Road , Little Torch, FL 2 Beds1 Baths720 SqFt 15 Active $550,000 20151 Kings Row , Summerland, FL 1 Beds1 Baths672 SqFt 48 Active $559,900 701 Spanish Main Drive 154, Cudjoe, FL 2 Beds2 Baths836 SqFt 44 Active $575,000 701 Spanish Main Drive 659, Cudjoe, FL 2 Beds2 Baths864 SqFt 24 Active $575,000 701 Spanish Main Drive 343, Cudjoe, FL 2 Beds2 Baths816 SqFt 73 Active $575,000 701 Spanish Main Drive 417, Cudjoe, FL 2 Beds2 Baths758 SqFt 12 Active $585,000 27858 Lobster Tail Trail , Little Torch, FL 2 Beds2 Baths1,747 SqFt 33 Active $625,000 28130 Dorothy Avenue , Little Torch, FL 3 Beds2 Baths1,413 SqFt 48 Active $629,000 701 Spanish Main Drive 510, Cudjoe, FL 2 Beds2 Baths816 SqFt 23 Active $635,000 19572 Aztec Street , Sugarloaf, FL 2 Beds2 Baths1,110 SqFt 40 Active $649,000 701 Spanish Main Drive 366, Cudjoe, FL 2 Beds2 Baths816 SqFt 25 Active $649,000 701 Spanish Main Drive 335, Cudjoe, FL 2 Beds1 Baths718 SqFt 31 Active $659,000 701 Spanish Main Drive 324, Cudjoe, FL 2 Beds1 Baths740 SqFt 19 Active $675,000 701 Spanish Main Drive 466, Cudjoe, FL 2 Beds2 Baths816 SqFt 50 Active $675,000 701 Spanish Main Drive 631, Cudjoe, FL 2 Beds2 Baths864 SqFt 35 Contingent/Show $695,000 87 Lake Drive N , Summerland, FL 2 Beds1 Baths1,024 SqFt 35 Open House Active $699,000 19616 Aztec Street , Sugarloaf, FL 2 Beds2 Baths1,129 SqFt 44 Contingent/Show $699,000 27999 Lobster Tail Trail , Little Torch, FL 3 Beds2 Baths1,176 SqFt 21 Active $699,000 19518 Caloosa Street , Sugarloaf, FL 3 Beds2 Baths1,143 SqFt 43 Active $699,000 701 Spanish Main Drive 30, Cudjoe, FL 2 Beds2 Baths864 SqFt 42 Active $699,000 701 Spanish Main Drive 29, Cudjoe, FL 2 Beds2 Baths864 SqFt 44 Active $699,000 268 Spanish Main Drive , Cudjoe, FL 2 Beds2 Baths1,056 SqFt 44 Contingent/Show $699,999 28233 Helen Avenue , Little Torch, FL 3 Beds2 Baths1,512 SqFt 52 Active $710,000 701 Spanish Main Drive 437, Cudjoe, FL 2 Beds2 Baths864 SqFt 54 Active $715,000 701 Spanish Main Drive 131, Cudjoe, FL 2 Beds2 Baths864 SqFt 33 Active $725,000 701 Spanish Main Drive 444, Cudjoe, FL 2 Beds2 Baths861 SqFt 24 Active $728,000 701 Spanish Main Drive 79, Cudjoe, FL 2 Beds2 Baths816 SqFt 41 Active $749,000 21161 Old State Road 4A Road , Cudjoe, FL 2 Beds2 Baths820 SqFt 30 Contingent/Show $750,000 124 Yardarm Road , Cudjoe, FL 3 Beds2 Baths1,064 SqFt 50 Active $759,000 701 Spanish Main Drive 573, Cudjoe, FL 2 Beds2 Baths816 SqFt 27 Active $775,000 27230 Brown Drive , Ramrod, FL 3 Beds2 Baths1,242 SqFt 33 Open House Active $789,000 22918 Cudjoe Drive , Cudjoe, FL 3 Beds2 Baths1,431 SqFt 34 Contingent/Show $799,000 191 Doubloon Lane , Cudjoe, FL 2 Beds2 Baths1,340 SqFt 18 Active $799,000 27438 Haiti Lane , Ramrod, FL 2 Beds2 Baths816 SqFt 41 Active $799,000 22882 Buccaneer Lane , Cudjoe, FL 2 Beds2 Baths1,120 SqFt 40 Active $799,000 701 Spanish Main Drive 333,334, Cudjoe, FL 2 Beds2 Baths814 SqFt 34 Active $815,000 27373 Anguila Lane , Ramrod, FL 3 Beds2 Baths1,077 SqFt 31 Active $820,000 4099 Egret Lane , Big Torch, FL 2 Beds2 Baths1,040 SqFt 39 Active $829,000 23930 Overseas Highway , Summerland, FL 3 Beds3 Baths1,360 SqFt 31 Active $829,999 27373 Antigua Lane , Ramrod, FL 3 Beds2 Baths1,188 SqFt 36 Active $840,000 19533 Mayan Drive , Sugarloaf, FL 3 Beds2 Baths1,372 SqFt 44 Active $850,000 701 Spanish Main Drive 374, Cudjoe, FL 2 Beds2 Baths816 SqFt 48 Active $850,000 701 Spanish Main Drive 172, Cudjoe, FL 2 Beds2 Baths842 SqFt 30 Active $875,000 26868 Mariposa Road , Ramrod, FL 4 Beds2 Baths1,456 SqFt 20 Active $875,000 27370 Indies Drive W , Ramrod, FL 3 Beds2 Baths1,200 SqFt 36 Active $879,000 27325 Barbuda Lane , Ramrod, FL 2 Beds2 Baths1,120 SqFt 40 Active $895,000 17236 Keystone Road , Sugarloaf, FL 2 Beds2 Baths1,155 SqFt 33 Open House Active $899,000 27394 Saint Lucie Lane , Ramrod, FL 3 Beds2 Baths1,078 SqFt 38 Contingent/Show $899,000 27416 Cayman Lane , Ramrod, FL 2 Beds2 Baths1,116 SqFt 33 Active $899,000 24833 Park Drive , Summerland, FL 2 Beds2 Baths1,166 SqFt 31 Active $899,000 22727 Jolly Roger Drive , Cudjoe, FL 3 Beds2 Baths1,008 SqFt 30 Active $899,000 701 Spanish Main Drive 468, Cudjoe, FL 2 Beds2 Baths864 SqFt 34 Open House Active $899,900 22957 Drake Lane , Cudjoe, FL 2 Beds2 Baths1,008 SqFt 49 Active $899,999 27317 Cayman Lane , Ramrod, FL 2 Beds2 Baths1,029 SqFt 50 Active $925,000 487 489 Pirates Road , Little Torch, FL 4 Beds4 Baths1,638 SqFt 40 Active $925,000 22994 Anne Bonny Lane , Cudjoe, FL 3 Beds2 Baths1,184 SqFt 44 Active $935,000 21650 Overseas Highway 102, Cudjoe, FL 2 Beds3 Baths1,156 SqFt 31 Active $965,000 27417 Cayman Lane , Ramrod, FL 2 Beds1 Baths1,085 SqFt 43 Contingent/Show $975,000 447 Pirates Road , Little Torch, FL 3 Beds2 Baths984 SqFt 35 Active $985,000 346 Blackbeard Road , Little Torch, FL 3 Beds2 Baths1,188 SqFt 48 Active $985,000 701 Spanish Main Drive 49, Cudjoe, FL 2 Beds1 Baths806 SqFt 31 Active $999,000 853 Indies Road , Ramrod, FL 3 Beds2 Baths1,248 SqFt 55 Active $1,050,000 701 Spanish Main Drive 97, Cudjoe, FL 2 Beds2 Baths640 SqFt 45 Active $1,085,000 701 Spanish Main Drive 51, Cudjoe, FL 2 Beds2 Baths888 SqFt 38 Active $1,090,000 757 La Fitte Road , Little Torch, FL 2 Beds1 Baths768 SqFt 48 Active $1,090,000 66 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,764 SqFt 60 Active $1,095,000 76 Shore Drive W , Summerland, FL 3 Beds2 Baths1,028 SqFt 44 Active $1,097,000 701 Spanish Main Drive 214, Cudjoe, FL 2 Beds2 Baths779 SqFt 43 Open House Active $1,099,000 786 Jamaica Lane , Little Torch, FL 3 Beds2 Baths1,440 SqFt 28 Active $1,100,000 27725 Sea Whip Street , Little Torch, FL 3 Beds2 Baths1,400 SqFt 30 Active $1,100,000 25074 5th Street , Summerland, FL 3 Beds2 Baths1,680 SqFt 40 Active $1,100,000 20914 7Th Avenue W , Cudjoe, FL 2 Beds2 Baths1,312 SqFt 35 Active $1,100,000 22922 Blackbeard Lane , Cudjoe, FL 3 Beds2 Baths1,195 SqFt 35 Active $1,100,000 285 Blackbeard Road , Little Torch, FL 3 Beds2 Baths1,576 SqFt 41 Active $1,118,000 23022 Snapper Lane , Cudjoe, FL 3 Beds2 Baths1,225 SqFt 50 Active $1,119,000 184 Cutthroat Drive , Cudjoe, FL 6 Beds3 Baths2,320 SqFt 42 Active $1,135,000 22837 Calico Jack Circle , Cudjoe, FL 2 Beds2 Baths1,008 SqFt 66 Active $1,145,000 246 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,541 SqFt 29 Active $1,149,000 463 Lesrohde Drive , Ramrod, FL 3 Beds2 Baths1,500 SqFt 52 Contingent/Show $1,175,000 1348 Ocean Drive , Summerland, FL 2 Beds3 Baths930 SqFt 40 Active $1,189,000 146 Sugarloaf Drive , Sugarloaf, FL 3 Beds2 Baths1,859 SqFt 51 Active $1,199,000 27984 Barton Avenue , Little Torch, FL 2 Beds2 Baths1,225 SqFt 41 Open House Active $1,199,999 22852 John Silver Lane , Cudjoe, FL 2 Beds2 Baths1,620 SqFt 21 Active $1,200,000 419 Blackbeard Road , Little Torch, FL 2 Beds2 Baths1,050 SqFt 92 Active $1,249,000 27436 Tobago Lane , Ramrod, FL 3 Beds2 Baths1,232 SqFt 39 Active $1,250,000 17215 Bonita Lane E , Sugarloaf, FL 3 Beds2 Baths1,528 SqFt 45 Contingent/Show $1,259,000 27379 Jamaica Lane , Ramrod, FL 3 Beds2 Baths1,376 SqFt View All Listings