Explore Middle Keys Florida33042 Homes for Sale 41 Active$289,000701 Spanish Main Drive 423, Cudjoe, FL 1 Beds1 Baths316 SqFt 23 Active$299,00081 Johnson Road , Sugarloaf, FL 2 Beds1 Baths600 SqFt 31 Active$325,000701 Spanish Main Drive 457, Cudjoe, FL 2 Beds1 Baths664 SqFt 13 Contingent$345,00027950 Porgie , Little Torch, FL 2 Beds2 Baths840 SqFt 31 Active$349,000701 Spanish Main Drive 62, Cudjoe, FL 2 Beds1 Baths756 SqFt 33 Active$359,000701 Spanish Main Drive 625, Cudjoe, FL 2 Beds1 Baths720 SqFt 47 Active$399,000701 Spanish Main Drive 537, Cudjoe, FL 1 Beds1 Baths520 SqFt 39 Active$499,00027848 Lobster Tail Trail , Little Torch, FL 2 Beds1 Baths552 SqFt 13 Active$499,00027007 Angelfish Road , Ramrod, FL 1,201 SqFt 44 Active$539,000701 Spanish Main Drive 440, Cudjoe, FL 2 Beds2 Baths773 SqFt 48 Active$549,00019461 Canal Drive , Sugarloaf, FL 3 Beds1 Baths1,136 SqFt 73 Active$580,000701 Spanish Main Drive 417, Cudjoe, FL 2 Beds2 Baths758 SqFt 24 Active$595,000701 Spanish Main Drive 343, Cudjoe, FL 2 Beds2 Baths816 SqFt 44 Active$599,000701 Spanish Main Drive 154, Cudjoe, FL 2 Beds2 Baths836 SqFt 50 Active$599,00027732 Astrangia Avenue , Little Torch, FL 2 Beds2 Baths1,092 SqFt 25 Active$649,000701 Spanish Main Drive 335, Cudjoe, FL 2 Beds1 Baths718 SqFt 31 Active$650,000701 Spanish Main Drive 247, Cudjoe, FL 2 Beds2 Baths860 SqFt 48 Active$659,00027018 Angelfish Road , Ramrod, FL 2 Beds2 Baths960 SqFt 62 Active$659,000701 Spanish Main Drive 366, Cudjoe, FL 2 Beds2 Baths816 SqFt 56 Active$675,000701 Spanish Main Drive 466, Cudjoe, FL 2 Beds2 Baths816 SqFt 30 Active$699,000701 Spanish Main Drive 392, Cudjoe, FL 2 Beds2 Baths864 SqFt 21 Contingent/Show$699,00019518 Caloosa Street , Sugarloaf, FL 3 Beds2 Baths1,143 SqFt 32 Active$699,000753 Diane Avenue , Little Torch, FL 2 Beds2 Baths900 SqFt 24 Active$728,000701 Spanish Main Drive 79, Cudjoe, FL 2 Beds2 Baths816 SqFt 16 Active$729,900268 Spanish Main Drive , Cudjoe, FL 2 Beds2 Baths1,056 SqFt 29 Contingent$734,90091 Frazier Lane , Sugarloaf, FL 4 Beds2 Baths1,544 SqFt 24 Active$735,00019570 Mayan Street , Sugarloaf, FL 3 Beds2 Baths1,544 SqFt 35 Active$739,90087 Lake Drive N , Summerland, FL 2 Beds1 Baths1,024 SqFt 43 Active$749,00028150 Dorothy Avenue , Little Torch, FL 4 Beds2 Baths1,608 SqFt 53 Active$749,50028233 Helen Avenue , Little Torch, FL 3 Beds2 Baths1,512 SqFt 44 Active$749,90027999 Lobster Tail Trail , Little Torch, FL 3 Beds2 Baths1,176 SqFt 44 Active$749,900701 Spanish Main Drive 30, Cudjoe, FL 2 Beds2 Baths865 SqFt 5 Active$755,000134 Shore Lane , Sugarloaf, FL 10 Active$769,000124 Yardarm Road , Cudjoe, FL 3 Beds2 Baths1,064 SqFt 44 Active$774,90022903 Jolly Roger Drive , Cudjoe, FL 3 Beds2 Baths1,152 SqFt 33 Active$775,00028551 Buccaneer Road , Little Torch, FL 2 Beds2 Baths841 SqFt 21 Active$775,000134 Tortuga Lane , Cudjoe, FL 3 Beds2 Baths1,056 SqFt 33 Active$795,00022918 Cudjoe Drive , Cudjoe, FL 3 Beds2 Baths1,431 SqFt 46 Contingent/Show$795,000910 Shore Drive E , Summerland, FL 3 Beds2 Baths1,872 SqFt 46 Active$799,000743 Indies Road , Ramrod, FL 2 Beds2 Baths984 SqFt 23 Contingent/Show$799,000283 Pirates Road , Little Torch, FL 2 Beds1 Baths768 SqFt 61 Active$799,900701 Spanish Main Drive 167, Cudjoe, FL 2 Beds2 Baths864 SqFt 31 Active$820,0004099 Egret Lane , Big Torch, FL 2 Beds2 Baths1,040 SqFt 36 Active$840,00019533 Mayan Drive , Sugarloaf, FL 3 Beds2 Baths1,372 SqFt 40 Active$845,00023930 Overseas Highway , Summerland, FL 3 Beds3 Baths1,360 SqFt 44 Active$850,000701 Spanish Main Drive 374, Cudjoe, FL 2 Beds2 Baths816 SqFt 36 Active$874,99927392 Anguila Lane , Ramrod, FL 2 Beds1 Baths825 SqFt 20 Active$875,00027370 Indies Drive W , Ramrod, FL 3 Beds2 Baths1,200 SqFt 31 Active$899,00027373 Antigua Lane , Ramrod, FL 3 Beds2 Baths1,188 SqFt 31 Active$899,00022727 Jolly Roger Drive , Cudjoe, FL 3 Beds2 Baths1,008 SqFt 33 Active$899,00024833 Park Drive , Summerland, FL 2 Beds2 Baths1,166 SqFt 34 Active$899,90022957 Drake Lane , Cudjoe, FL 2 Beds2 Baths1,008 SqFt 32 Contingent/Show$899,900663 Indies Road , Ramrod, FL 2 Beds2 Baths1,056 SqFt 47 Active$905,000589 Powell Avenue , Little Torch, FL 4 Beds2 Baths1,568 SqFt 31 Active$949,00028571 Buccaneer Road , Little Torch, FL 3 Beds2 Baths1,034 SqFt 30 Contingent/Show$975,00026868 Mariposa Road , Ramrod, FL 4 Beds2 Baths1,456 SqFt 31 Active$975,00027417 Cayman Lane , Ramrod, FL 2 Beds1 Baths1,085 SqFt 36 Active$985,000346 Blackbeard Road , Little Torch, FL 3 Beds2 Baths1,188 SqFt 43 Active$985,000701 Spanish Main Drive 49, Cudjoe, FL 2 Beds1 Baths806 SqFt 40 Active$998,00017236 Keystone Road , Sugarloaf, FL 2 Beds2 Baths1,155 SqFt 45 Active$1,085,000701 Spanish Main Drive 51, Cudjoe, FL 2 Beds2 Baths888 SqFt 60 Active$1,095,00076 Shore Drive W , Summerland, FL 3 Beds2 Baths1,028 SqFt 44 Active$1,097,000701 Spanish Main Drive 214, Cudjoe, FL 2 Beds2 Baths779 SqFt 28 Active$1,100,00027725 Sea Whip Street , Little Torch, FL 3 Beds2 Baths1,400 SqFt 34 Contingent/Show$1,100,00027486 Martinique Lane , Ramrod, FL 3 Beds2 Baths1,056 SqFt 11 Active$1,114,200622 Diane Avenue , Little Torch, FL 3 Beds2 Baths1,320 SqFt 55 Active$1,125,00028550 Doubloon Road , Little Torch, FL 3 Beds2 Baths2,371 SqFt 41 Active$1,150,00022837 Calico Jack Circle , Cudjoe, FL 2 Beds2 Baths1,008 SqFt 64 Active$1,189,000184 Cutthroat Drive , Cudjoe, FL 6 Beds3 Baths2,320 SqFt 38 Active$1,190,000757 La Fitte Road , Little Torch, FL 2 Beds1 Baths768 SqFt 60 Active$1,190,0001342 Ocean Drive , Summerland, FL 2 Beds2 Baths992 SqFt 44 Active$1,195,000285 Blackbeard Road , Little Torch, FL 3 Beds2 Baths1,576 SqFt 33 Contingent/Show$1,195,00027397 Tobago Lane , Ramrod, FL 3 Beds2 Baths1,494 SqFt 49 Active$1,199,00023018 Sailfish Lane , Cudjoe, FL 3 Beds2 Baths1,280 SqFt 35 Active$1,200,00021024 2Nd Avenue , Cudjoe, FL 2 Beds2 Baths1,313 SqFt 19 Active$1,200,00025074 5th Street , Summerland, FL 3 Beds2 Baths1,680 SqFt 10 Active$1,249,000335 Pirates Road , Little Torch, FL 3 Beds2 Baths1,320 SqFt 56 Active$1,249,000589 Powell Avenue , Little Torch, FL 4 Beds2 Baths1,568 SqFt 39 Active$1,250,00066 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,764 SqFt 34 Active$1,250,00027376 Tobago Lane , Ramrod, FL 4 Beds2 Baths1,344 SqFt 38 Contingent/Show$1,250,00017165 Wahoo Lane W , Sugarloaf, FL 3 Beds2 Baths1,600 SqFt 25 Active$1,250,000529 Powell Avenue , Little Torch, FL 4 Beds2 Baths1,568 SqFt 40 Open House Active$1,269,900146 Sugarloaf Drive , Sugarloaf, FL 3 Beds2 Baths1,859 SqFt 38 Contingent/Show$1,275,0001327 Hudgins Drive , Summerland, FL 2 Beds2 Baths957 SqFt 47 Active$1,275,000133 Galleon Lane , Cudjoe, FL 3 Beds2 Baths1,780 SqFt 66 Active$1,285,000246 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,541 SqFt 36 Active$1,295,00027328 Jamaica Lane , Ramrod, FL 3 Beds3 Baths1,518 SqFt 55 Active$1,299,000887 Grenada Lane , Little Torch, FL 2 Beds2 Baths936 SqFt 39 Active$1,300,00017215 Bonita Lane E , Sugarloaf, FL 3 Beds2 Baths1,528 SqFt 53 Active$1,330,00022521 Jolly Roger Drive , Cudjoe, FL 4 Beds3 Baths1,728 SqFt 20 Active$1,375,000267 La Fitte Road , Little Torch, FL 2 Beds2 Baths1,152 SqFt 31 Active$1,399,00028565 Anne Bonny Road , Little Torch, FL 3 Beds2 Baths2,392 SqFt 40 Active$1,399,00022841 Buccaneer Lane , Cudjoe, FL 3 Beds3 Baths1,920 SqFt 65 Active$1,399,000165 Cutlass Lane , Cudjoe, FL 4 Beds3 Baths2,448 SqFt 55 Active$1,430,00016941 Driftwood Lane , Sugarloaf, FL 3 Beds3 Baths1,700 SqFt 38 Active$1,499,000947 Gulf Drive , Summerland, FL 3 Beds2 Baths1,400 SqFt 50 Active$1,499,00043 Venetian Way , Sugarloaf, FL 3 Beds2 Baths1,250 SqFt 39 Active$1,550,000591 Blackbeard Road , Little Torch, FL 4 Beds5 Baths2,512 SqFt 105 Active$1,587,00019512 Aztec Street , Sugarloaf, FL 3 Beds3 Baths1,760 SqFt View All Listings