Explore Middle Keys Florida33042 Homes for Sale 69 Contingent/Show$17,999,9001300 Sunset Boulevard , Summerland, FL 6 Beds8 Baths7,720 SqFt 77 Active$14,495,00021540 21470 Overseas Highway , Cudjoe, FL 31 Beds19 Baths 78 Contingent/Show$7,499,00016750 Old State Road 4A , Sugarloaf, FL 6 Beds5 Baths5,208 SqFt 66 Active$5,900,0001141 Ocean Drive , Summerland, FL 5 Beds5 Baths3,421 SqFt 16 Contingent$5,900,000220 Caribbean Drive E , Summerland, FL 5 Beds7 Baths4,981 SqFt 121 Active$5,699,000681 Sugarloaf Boulevard , Sugarloaf, FL 6 Beds4 Baths3,208 SqFt 132 Active$5,600,000815 Shore Drive E , Summerland, FL 7 Beds6 Baths4,531 SqFt 54 Active$5,600,000974 Flagship Drive , Summerland, FL 4 Beds4 Baths5,608 SqFt 73 Contingent$4,299,000783 Pattison Drive , Cudjoe, FL 3 Beds3 Baths2,388 SqFt 70 Active$4,299,00022572 Jolly Roger Drive , Cudjoe, FL 6 Beds4 Baths3,225 SqFt 117 Active$4,195,000733 Trinidad Lane , Little Torch, FL 3 Beds2 Baths1,636 SqFt 60 Active$3,995,000225 Colson Drive , Cudjoe, FL 6 Beds7 Baths4,976 SqFt 37 Active$3,399,000281 Indies Drive W , Ramrod, FL 3 Beds4 Baths2,914 SqFt 62 Active$3,260,000361 Ave D , Summerland, FL 2 Beds3 Baths1,818 SqFt 44 Active$3,200,00017398 Dolphin Street E , Sugarloaf, FL 4 Beds3 Baths2,404 SqFt 68 Active$3,199,000431 Shore Drive E , Summerland, FL 4 Beds3 Baths2,715 SqFt 61 Contingent/Show$3,100,00020886 4Th Avenue W , Cudjoe, FL 4 Beds3 Baths3,042 SqFt 55 Active$3,000,000531 Seminole Drive , Cudjoe, FL 4 Beds3 Baths2,604 SqFt 53 Active$2,999,000961 Indies Drive W , Ramrod, FL 4 Beds3 Baths2,006 SqFt 48 Active$2,950,00017279 Pinetree Lane , Sugarloaf, FL 2 Beds2 Baths1,016 SqFt 42 Active$2,850,000271 Indies Drive W , Ramrod, FL 4 Beds4 Baths2,358 SqFt 45 Active$2,750,000340 Point Drive S , Sugarloaf, FL 4 Beds4 Baths2,935 SqFt 31 Active$2,600,0001151 Sugarloaf Boulevard , Sugarloaf, FL 3 Beds2 Baths2,144 SqFt 31 Active$2,599,00028573 Le Grand Road , Little Torch, FL 3 Beds3 Baths1,998 SqFt 66 Active$2,499,000320 Point Drive S , Sugarloaf, FL 5 Beds3 Baths2,471 SqFt 54 Active$2,499,00017270 Old State Road 4A, Sugarloaf, FL 2 Beds2 Baths1,202 SqFt 37 Active$2,499,00020864 4th Avenue W , Cudjoe, FL 3 Beds4 Baths3,056 SqFt 38 Active$2,499,000489 Sawyer Drive , Cudjoe, FL 2 Beds2 Baths1,281 SqFt 19 Active$2,495,00024931 Overseas Highway , Summerland, FL 2 Beds4 Baths1,965 SqFt 53 Active$2,375,000205 Point Drive S , Sugarloaf, FL 5 Beds4 Baths2,772 SqFt 31 Active$2,299,00028573 Le Grand Road , Little Torch, FL 3 Beds3 Baths1,998 SqFt 7 Active$2,200,000620 Barry Avenue , Little Torch, FL 4 Beds3 Baths1,943 SqFt 63 Active$2,199,0001040 Gulf Drive , Summerland, FL 4 Beds3 Baths2,233 SqFt 44 Active$2,199,00019527 Indian Mound Drive , Sugarloaf, FL 3 Beds3 Baths1,752 SqFt 8 Active$2,100,00027433 Antigua Lane , Ramrod, FL 4 Beds3 Baths1,943 SqFt 33 Active$2,099,5001082 Bay Drive , Summerland, FL 4 Beds3 Baths1,440 SqFt 37 Active$2,095,000474 Caribbean Drive E , Summerland, FL 3 Beds2 Baths1,664 SqFt 45 Active$1,999,99920942 6Th Avenue W , Cudjoe, FL 3 Beds3 Baths2,772 SqFt 64 Active$1,875,0003127 Stewart Road , Middle Torch, FL 3 Beds2 Baths1,841 SqFt 50 Active$1,799,90021025 Hamilton Avenue , Cudjoe, FL 6 Beds4 Baths4,060 SqFt 68 Active$1,799,000559 Powell Avenue , Little Torch, FL 3 Beds2 Baths1,196 SqFt 47 Active$1,790,000591 Blackbeard Road , Little Torch, FL 4 Beds5 Baths2,512 SqFt 52 Active$1,750,000570 La Fitte Road None, Little Torch, FL 3 Beds2 Baths2,080 SqFt 43 Active$1,699,999695 La Fitte Road , Little Torch, FL 3 Beds3 Baths1,527 SqFt 48 Active$1,699,0001330 Ocean Drive , Summerland, FL 2 Beds2 Baths1,144 SqFt 52 Active$1,695,000241 Indies Drive W , Ramrod, FL 4 Beds3 Baths2,008 SqFt 39 Contingent/Show$1,599,99921076 3rd Avenue , Cudjoe, FL 3 Beds3 Baths1,732 SqFt 66 Active$1,599,000246 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,541 SqFt 37 Active$1,549,000243 Indies Road , Ramrod, FL 4 Beds3 Baths1,920 SqFt 50 Active$1,549,00043 Venetian Way , Sugarloaf, FL 3 Beds2 Baths1,250 SqFt 32 Active$1,500,000980 Caribbean Drive E , Summerland, FL 3 Beds3 Baths2,202 SqFt 14 Active$1,499,00022970 Gasparilla Lane , Cudjoe, FL 3 Beds2 Baths1,450 SqFt 33 Active$1,499,000361 Caribbean Drive E , Summerland, FL 3 Beds3 Baths1,880 SqFt 45 Active$1,499,000696 Heck Avenue , Little Torch, FL 3 Beds2 Baths1,488 SqFt 57 Active$1,499,000559 Powell Avenue , Little Torch, FL 3 Beds2 Baths1,196 SqFt 29 Active$1,499,00028565 Anne Bonny Road , Little Torch, FL 3 Beds2 Baths2,392 SqFt 63 Active$1,495,000165 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,560 SqFt 39 Active$1,495,00066 Colson Drive , Cudjoe, FL 3 Beds2 Baths1,764 SqFt 94 Active$1,475,00019512 Aztec Street , Sugarloaf, FL 2 Beds3 Baths1,760 SqFt 55 Active$1,399,000887 Grenada Lane , Little Torch, FL 2 Beds2 Baths936 SqFt 52 Contingent/Show$1,395,000733 Pirates Road , Little Torch, FL 3 Beds2 Baths1,464 SqFt 45 Active$1,389,00027397 Tobago Lane , Ramrod, FL 3 Beds2 Baths1,500 SqFt 39 Active$1,365,999146 Sugarloaf Drive , Sugarloaf, FL 3 Beds2 Baths1,859 SqFt 44 Active$1,350,00027984 Barton Avenue , Little Torch, FL 2 Beds2 Baths1,100 SqFt 46 Active$1,329,000137 Caribbean Drive E , Summerland, FL 2 Beds2 Baths1,120 SqFt 49 Active$1,325,00023018 Sailfish Lane , Cudjoe, FL 3 Beds2 Baths1,280 SqFt 49 Active$1,295,00021790 Spain Boulevard , Cudjoe, FL 4 Beds3 Baths1,744 SqFt 41 Active$1,295,000421 Indies W , Ramrod, FL 2 Beds2 Baths1,124 SqFt 46 Active$1,295,000840 Lagoon Drive , Summerland, FL 2 Beds3 Baths1,528 SqFt 36 Contingent/Show$1,275,000969 Caribbean Drive E , Summerland, FL 2 Beds2 Baths1,250 SqFt 53 Active$1,275,000845 Gulf Drive , Summerland, FL 2 Beds2 Baths1,008 SqFt 45 Contingent/Show$1,250,00023058 Sailfish Lane , Cudjoe, FL 3 Beds3 Baths1,280 SqFt 97 Contingent/Show$1,250,0001342 Ocean Drive , Summerland, FL 2 Beds2 Baths992 SqFt 40 Contingent/Show$1,250,000367 Sawyer Drive , Cudjoe, FL 2 Beds2 Baths900 SqFt 55 Active$1,249,000103 Shore Drive , Sugarloaf, FL 3 Beds2 Baths1,128 SqFt 19 Active$1,200,00025074 5th Street , Summerland, FL 3 Beds2 Baths1,680 SqFt 63 Contingent/Show$1,199,000105 Point Drive S , Sugarloaf, FL 3 Beds2 Baths1,544 SqFt 20 Active$1,198,00020770 1St Avenue , Cudjoe, FL 2 Beds2 Baths2,160 SqFt 38 Active$1,190,000757 La Fitte Road , Little Torch, FL 2 Beds1 Baths768 SqFt 46 Active$1,185,000701 Spanish Main Drive 51, Cudjoe, FL 2 Beds2 Baths888 SqFt 40 Contingent/Show$1,175,00022983 Anne Bonny Lane , Cudjoe, FL 2 Beds2 Baths1,320 SqFt 55 Active$1,150,00028550 Doubloon Road , Little Torch, FL 3 Beds2 Baths2,371 SqFt 42 Contingent$1,150,000321 Indies Drive W , Ramrod, FL 3 Beds2 Baths1,474 SqFt 28 Active$1,145,00023022 Snapper Lane , Cudjoe, FL 3 Beds2 Baths1,225 SqFt 35 Active$1,100,000701 Spanish Main Drive 221, Cudjoe, FL 2 Beds2 Baths864 SqFt 28 Active$1,100,00027725 Sea Whip Street , Little Torch, FL 3 Beds2 Baths1,400 SqFt 36 Contingent/Show$1,099,00017055 Kingfish Lane W , Sugarloaf, FL 2 Beds2 Baths1,184 SqFt 46 Active$1,085,000701 Spanish Main Drive 49, Cudjoe, FL 2 Beds1 Baths806 SqFt 35 Active$1,075,00027285 Mariposa Road , Ramrod, FL 3 Beds2 Baths1,152 SqFt 24 Active$1,049,00017236 Keystone Road , Sugarloaf, FL 2 Beds2 Baths1,155 SqFt 43 Active$1,025,000447 Pirates Road , Little Torch, FL 3 Beds2 Baths1,014 SqFt 56 Active$999,999873 Hawksbill Lane , Sugarloaf, FL 3 Beds2 Baths1,467 SqFt 31 Active$999,00022953 John Silver Lane , Cudjoe, FL 2 Beds2 Baths960 SqFt 13 Active$985,00027373 Antigua Lane , Ramrod, FL 3 Beds2 Baths1,188 SqFt 46 Active$975,00027384 Barbuda Lane , Ramrod, FL 2 Beds2 Baths1,176 SqFt 32 Active$959,00024833 Park Drive , Summerland, FL 2 Beds2 Baths1,166 SqFt 36 Active$950,00021066 3Rd Avenue , Cudjoe, FL 2 Beds1 Baths1,245 SqFt 33 Active$949,00022957 Drake Lane , Cudjoe, FL 2 Beds2 Baths1,008 SqFt 23 Active$939,00022988 Long Ben Lane , Cudjoe, FL 3 Beds2 Baths1,196 SqFt View All Listings
