Explore Middle Keys Florida 33042 Homes for Sale 26 Active $275,000 701 Spanish Main Drive 457, Cudjoe, FL 2 Beds1 Baths664 SqFt 33 Active $345,000 701 Spanish Main Drive 21, Cudjoe, FL 1 Beds1 Baths690 SqFt 19 Active $349,000 701 Spanish Main Drive 62, Cudjoe, FL 2 Beds1 Baths756 SqFt 29 Open House Active $399,000 28131 Helen Avenue , Little Torch, FL 2 Beds1 Baths856 SqFt 21 Active $399,900 27848 Lobster Tail Trail , Little Torch, FL 2 Beds1 Baths552 SqFt 47 Active $425,000 701 Spanish Main Drive 414, Cudjoe, FL 2 Beds2 Baths675 SqFt 43 Active $425,000 701 Spanish Main Drive 145, Cudjoe, FL 2 Beds2 Baths556 SqFt 55 Active $427,000 701 Spanish Main Drive 543, Cudjoe, FL 2 Beds2 Baths748 SqFt 26 Active $429,000 27873 Coral Shores Road , Little Torch, FL 2 Beds1 Baths686 SqFt 50 Active $449,000 701 Spanish Main Drive 635, Cudjoe, FL 2 Beds2 Baths864 SqFt 1 Active $450,000 37 Yardarm Lane N 1, Cudjoe, FL 2 Beds2 Baths980 SqFt 51 Active $459,000 701 Spanish Main Drive 280, Cudjoe, FL 1 Beds1 Baths816 SqFt 30 Active $470,000 701 Spanish Main Drive 342, Cudjoe, FL 1 Beds1 Baths748 SqFt 32 Active $477,000 701 Spanish Main Drive 22, Cudjoe, FL 2 Beds2 Baths814 SqFt 39 Active $495,000 701 Spanish Main Drive 182, Cudjoe, FL 1 Beds1 Baths754 SqFt 60 Active $499,000 701 Spanish Main Drive 234, Cudjoe, FL 2 Beds2 Baths604 SqFt 34 Active $530,000 27969 Lobster Tail Trail , Little Torch, FL 2 Beds2 Baths863 SqFt 25 Active $533,995 701 Spanish Main Drive 335, Cudjoe, FL 2 Beds1 Baths718 SqFt 46 Active $549,000 701 Spanish Main Drive 659, Cudjoe, FL 2 Beds2 Baths864 SqFt 46 Active $549,000 27853 Coral Shores Road , Little Torch, FL 2 Beds2 Baths960 SqFt 15 Active $550,000 20151 Kings Row , Sugarloaf, FL 1 Beds1 Baths672 SqFt 32 Active $559,000 701 Spanish Main Drive 602, Cudjoe, FL 2 Beds1 Baths667 SqFt 31 Active $559,000 701 Spanish Main Drive 453, Cudjoe, FL 2 Beds2 Baths816 SqFt 71 Active $569,000 701 Spanish Main Drive 417, Cudjoe, FL 2 Beds2 Baths758 SqFt 26 Active $585,000 27858 Lobster Tail Trail , Little Torch, FL 3 Beds3 Baths1,747 SqFt 46 Contingent/Show $589,000 701 Spanish Main Drive 415, Cudjoe, FL 2 Beds2 Baths754 SqFt 16 Active $599,000 538 Powell Avenue , Little Torch, FL 2 Beds2 Baths912 SqFt 46 Active $599,000 701 Spanish Main Drive 510, Cudjoe, FL 2 Beds2 Baths816 SqFt 24 Active $599,000 701 Spanish Main Drive 343, Cudjoe, FL 2 Beds2 Baths816 SqFt 24 Active $606,995 701 Spanish Main Drive 79, Cudjoe, FL 2 Beds2 Baths816 SqFt 34 Active $620,000 19557 Mayan Street , Sugarloaf, FL 2 Beds2 Baths989 SqFt 33 Active $625,000 28130 Dorothy Avenue , Little Torch, FL 3 Beds2 Baths1,413 SqFt 61 Active $637,000 701 Spanish Main Drive 604, Cudjoe, FL 2 Beds2 Baths816 SqFt 50 Active $642,000 701 Spanish Main Drive 631, Cudjoe, FL 2 Beds2 Baths864 SqFt 31 Active $645,000 701 Spanish Main Drive 324, Cudjoe, FL 2 Beds1 Baths740 SqFt 23 Active $650,000 27390 Barbados Lane , Ramrod, FL 2 Beds2 Baths1,120 SqFt 35 Active $655,000 19616 Aztec Street , Sugarloaf, FL 2 Beds2 Baths1,129 SqFt 19 Active $675,000 701 Spanish Main Drive 466, Cudjoe, FL 2 Beds2 Baths816 SqFt 33 Active $675,000 701 Spanish Main Drive 444, Cudjoe, FL 2 Beds2 Baths861 SqFt 42 Active $685,999 701 Spanish Main Drive 30, Cudjoe, FL 2 Beds2 Baths840 SqFt 53 Active $685,999 701 Spanish Main Drive 29, Cudjoe, FL 2 Beds2 Baths840 SqFt 35 Contingent/Show $695,000 87 Lake Drive N , Summerland, FL 2 Beds1 Baths1,024 SqFt 52 Active $699,000 701 Spanish Main Drive 573, Cudjoe, FL 2 Beds2 Baths816 SqFt 54 Active $699,000 701 Spanish Main Drive 131, Cudjoe, FL 2 Beds2 Baths864 SqFt 52 Active $699,000 701 Spanish Main Drive 437, Cudjoe, FL 2 Beds2 Baths864 SqFt 46 Contingent $699,000 25022 Palm Lane , Summerland, FL 3 Beds2 Baths1,200 SqFt 42 Active $719,000 21161 Old State Road 4A Road , Cudjoe, FL 2 Beds2 Baths855 SqFt 34 Active $725,000 27941 Porgie Path , Little Torch, FL 2 Beds2 Baths1,104 SqFt 41 Active $745,000 22882 Buccaneer Lane , Cudjoe, FL 2 Beds2 Baths1,120 SqFt 31 Active $749,000 27373 Antigua Lane , Ramrod, FL 3 Beds2 Baths1,188 SqFt 34 Contingent $775,000 27373 Anguila Lane , Ramrod, FL 3 Beds2 Baths1,077 SqFt 49 Active $790,999 27317 Cayman Lane , Ramrod, FL 2 Beds2 Baths1,029 SqFt 39 Active $792,500 27255 Mariposa Road , Ramrod, FL 3 Beds2 Baths1,440 SqFt 37 Active $799,000 27312 Anguila Lane , Ramrod, FL 2 Beds2 Baths1,148 SqFt 30 Active $799,000 27138 Dolphin Road , Ramrod, FL 3 Beds2 Baths1,320 SqFt 31 Active $799,000 701 Spanish Main Drive 333,334, Cudjoe, FL 2 Beds2 Baths814 SqFt 36 Active $820,000 701 Spanish Main Drive 77, Cudjoe, FL 2 Beds1 Baths864 SqFt 31 Active $820,000 4099 Egret Lane , Big Torch, FL 2 Beds2 Baths1,040 SqFt 70 Active $824,000 22933 Buccaneer Lane , Cudjoe, FL 2 Beds2 Baths1,088 SqFt 45 Contingent/Show $839,000 25093 Center Street , Summerland, FL 3 Beds2 Baths1,584 SqFt 9 Active $849,000 22920 Privateer Drive , Cudjoe, FL 3 Beds2 Baths1,560 SqFt 30 Active $849,900 701 Spanish Main Drive 468, Cudjoe, FL 2 Beds2 Baths864 SqFt 48 Active $850,000 701 Spanish Main Drive 172, Cudjoe, FL 2 Beds2 Baths842 SqFt 30 Active $855,000 26868 Mariposa Road , Ramrod, FL 4 Beds2 Baths1,456 SqFt 68 Active $874,000 19569 Tequesta Street , Sugarloaf, FL 3 Beds2 Baths1,560 SqFt 40 Active $875,000 25121 Center Street , Summerland, FL 2 Beds2 Baths960 SqFt 27 Contingent/Show $875,000 27417 Cayman Lane , Ramrod, FL 2 Beds1 Baths1,085 SqFt 30 Active $877,000 24827 Park Drive , Summerland, FL 3 Beds2 Baths1,274 SqFt 36 Active $879,000 27325 Barbuda Lane , Ramrod, FL 2 Beds2 Baths1,120 SqFt 42 Active $885,000 22739 Buccaneer Lane , Cudjoe, FL 2 Beds2 Baths1,120 SqFt 35 Active $885,000 575 Caribbean Drive E , Summerland, FL 2 Beds2 Baths816 SqFt 16 Active $897,000 27384 Barbuda Lane , Ramrod, FL 2 Beds2 Baths1,176 SqFt 40 Active $899,000 260 Airport Drive S , Summerland, FL 2 Beds2 Baths918 SqFt 25 Active $899,000 28465 Jolly Roger Drive , Little Torch, FL 2 Beds1 Baths908 SqFt 55 Active $899,000 701 Spanish Main Drive 97, Cudjoe, FL 2 Beds2 Baths640 SqFt 34 Active $900,000 726 Jamaica Lane , Little Torch, FL 3 Beds2 Baths1,568 SqFt 48 Active $915,000 701 Spanish Main Drive 49, Cudjoe, FL 2 Beds1 Baths806 SqFt 31 Active $929,000 853 Indies Road , Ramrod, FL 3 Beds2 Baths1,248 SqFt 44 Active $935,000 21650 Overseas Highway 102, Cudjoe, FL 2 Beds3 Baths1,156 SqFt 39 Active $939,000 27468 Haiti Lane , Ramrod, FL 3 Beds2 Baths1,320 SqFt 16 Active $949,000 27215 Mariposa Road , Ramrod, FL 3 Beds2 Baths1,500 SqFt 59 Contingent/Show $949,000 701 Spanish Main Drive 198, Cudjoe, FL 2 Beds2 Baths864 SqFt 38 Contingent $949,900 22971 Hawkins Lane , Cudjoe, FL 3 Beds3 Baths1,142 SqFt 43 Active $950,000 873 Indies Road , Ramrod, FL 3 Beds2 Baths1,081 SqFt 30 Active $970,000 27376 Tobago Lane , Ramrod, FL 4 Beds2 Baths1,344 SqFt 42 Active $975,000 17214 La Brisa Lane E , Sugarloaf, FL 2 Beds1 Baths1,344 SqFt 35 Contingent/Show $975,000 17182 Starfish Lane W , Sugarloaf, FL 2 Beds2 Baths1,265 SqFt 60 Active $979,000 76 Shore Drive W , Summerland, FL 3 Beds2 Baths1,028 SqFt 45 Active $995,000 701 Spanish Main Drive 51, Cudjoe, FL 2 Beds2 Baths888 SqFt 40 Active $995,000 763 Diane Avenue , Little Torch, FL 3 Beds2 Baths1,188 SqFt 25 Active $995,000 17245 Jamaica Lane , Sugarloaf, FL 3 Beds2 Baths1,248 SqFt 35 Active $995,000 22922 Blackbeard Lane , Cudjoe, FL 3 Beds2 Baths1,195 SqFt 66 Open House Active $998,000 246 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,541 SqFt 43 Active $999,000 17425 Jamaica Lane , Sugarloaf, FL 3 Beds2 Baths1,440 SqFt 42 Active $1,025,000 701 Spanish Main Drive 221, Cudjoe, FL 2 Beds2 Baths864 SqFt 47 Active $1,030,000 786 Jamaica Lane , Little Torch, FL 3 Beds2 Baths1,440 SqFt 29 Active $1,039,000 463 Lesrohde Drive , Ramrod, FL 3 Beds2 Baths1,500 SqFt 29 Contingent $1,048,000 1107 Hawksbill Lane , Sugarloaf, FL 3 Beds2 Baths1,152 SqFt 30 Active $1,049,000 25074 5th Street , Summerland, FL 3 Beds2 Baths1,680 SqFt View All Listings