Explore Middle Keys Florida 33036 Homes for Sale 30 Active $399,000 119 Cortez Drive G5, ISLAMORADA, FL 1 Beds1 Baths518 SqFt 30 Active $428,000 87465 Old Highway 102, ISLAMORADA, FL 2 Beds2 Baths1,100 SqFt 15 Active $449,000 84961 Old Highway 19, ISLAMORADA, FL 2 Beds2 Baths800 SqFt 33 Active $475,000 134 Nautilus Drive Share A, ISLAMORADA, FL 5 Beds4 Baths2,900 SqFt 41 Contingent/Show $575,000 120 Cortez Drive F1, ISLAMORADA, FL 2 Beds2 Baths1,079 SqFt 43 Active $575,000 87200 Overseas Highway C3, ISLAMORADA, FL 2 Beds2 Baths1,352 SqFt 37 Active $575,000 87200 Overseas Highway R6, ISLAMORADA, FL 2 Beds2 Baths1,335 SqFt 27 Active $589,000 87200 Overseas Highway M4, ISLAMORADA, FL 2 Beds2 Baths1,358 SqFt 33 Active $594,000 87200 Overseas Highway S8, ISLAMORADA, FL 2 Beds2 Baths1,365 SqFt 4 Contingent $595,000 202 Hibiscus Street , Tavernier, FL 2 Beds2 Baths1,338 SqFt 46 Active $615,000 87200 Overseas Highway F4, ISLAMORADA, FL 2 Beds3 Baths1,350 SqFt 46 Active $665,000 87200 Overseas Highway B9, ISLAMORADA, FL 2 Beds2 Baths1,343 SqFt 34 Active $690,999 87200 Overseas Highway O8, ISLAMORADA, FL 2 Beds3 Baths1,365 SqFt 20 Active $695,000 81801 Overseas Highway 726, ISLAMORADA, FL 1 Beds1 Baths550 SqFt 36 Contingent/Show $699,000 79901 Overseas Highway 403, ISLAMORADA, FL 2 Beds2 Baths981 SqFt 32 Active $700,000 110 Knowles Street , ISLAMORADA, FL 3 Beds2 Baths2,016 SqFt 28 Active $716,000 87465 Old Highway 225, ISLAMORADA, FL 2 Beds2 Baths988 SqFt 42 Active $720,000 118 Cortez Drive A, ISLAMORADA, FL 2 Beds2 Baths1,079 SqFt 31 Active $725,000 79901 Overseas Highway 512, ISLAMORADA, FL 2 Beds2 Baths981 SqFt 62 Active $725,000 87200 Overseas Highway V9, ISLAMORADA, FL 3 Beds2 Baths1,355 SqFt 40 Active $725,000 81801 Overseas Highway 712, ISLAMORADA, FL 1 Beds1 Baths550 SqFt 21 Active $750,000 60 Cortez Lane , ISLAMORADA, FL 3 Beds2 Baths1,152 SqFt 37 Active $799,000 88181 Old Highway G43 30' slip 52, ISLAMORADA, FL 3 Beds2 Baths1,593 SqFt 35 Active $799,995 128 Ridge Road E , ISLAMORADA, FL 3 Beds2 Baths1,320 SqFt 36 Active $825,000 87200 Overseas Highway H4, ISLAMORADA, FL 2 Beds2 Baths1,359 SqFt 31 Active $845,000 100 Parker Drive , ISLAMORADA, FL 2 Beds2 Baths1,095 SqFt 38 Active $899,000 88181 Old Highway 2A, ISLAMORADA, FL 3 Beds2 Baths1,553 SqFt 46 Active $937,000 87200 Overseas Highway J4, ISLAMORADA, FL 2 Beds3 Baths1,403 SqFt 47 Active $949,000 88181 Old Highway 21H, ISLAMORADA, FL 2 Beds2 Baths1,672 SqFt 50 Active $954,000 140 Aregood Lane C2, ISLAMORADA, FL 2 Beds3 Baths1,248 SqFt 25 Active $985,000 101 Gulfview Drive 202 & 30' Boat slip, ISLAMORADA, FL 2 Beds3 Baths1,473 SqFt 50 Active $995,000 136 Aregood Lane 2A, ISLAMORADA, FL 2 Beds3 Baths1,152 SqFt 40 Contingent/Show $1,050,000 55 Harbor Drive , ISLAMORADA, FL 2 Beds2 Baths1,075 SqFt 55 Active $1,050,000 160 Ridge Road E , ISLAMORADA, FL 3 Beds3 Baths2,034 SqFt 27 Active $1,075,000 142 Gulfview Drive , ISLAMORADA, FL 3 Beds4 Baths1,888 SqFt 65 Active $1,099,000 84745 Old Highway 1, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 41 Active $1,100,000 110 Pippin Drive , ISLAMORADA, FL 3 Beds2 Baths1,682 SqFt 33 Active $1,125,000 101 Gulfview Drive 114D & 30' boat slip with lift, ISLAMORADA, FL 3 Beds3 Baths2,026 SqFt 49 Active $1,195,000 192 Ridge Road E , ISLAMORADA, FL 3 Beds2 Baths1,152 SqFt 56 Active $1,195,000 87851 Old Highway M32, ISLAMORADA, FL 2 Beds2 Baths1,536 SqFt 42 Active $1,199,000 115 Toner Lane , ISLAMORADA, FL 2 Beds2 Baths1,200 SqFt 38 Active $1,199,999 102 Anglers Way , ISLAMORADA, FL 2 Beds3 Baths1,376 SqFt 65 Active $1,200,000 83201 Old Highway 409, ISLAMORADA, FL 2 Beds2 Baths1,275 SqFt 34 Active $1,200,000 87851 Old Highway K33, ISLAMORADA, FL 3 Beds2 Baths1,536 SqFt 46 Active $1,225,000 101 Gulfview Drive 116D & 30' Boat Slip, ISLAMORADA, FL 3 Beds2 Baths2,026 SqFt 51 Active $1,239,000 88181 Old Highway 3F, ISLAMORADA, FL 2 Beds2 Baths1,330 SqFt 43 Active $1,275,000 116 Anglers Way , ISLAMORADA, FL 2 Beds3 Baths1,620 SqFt 35 Active $1,300,000 81216 Old Highway , ISLAMORADA, FL 3 Beds3 Baths960 SqFt 41 Contingent/Show $1,300,000 137 Venetian Way , ISLAMORADA, FL 5 Beds3 Baths2,240 SqFt 40 Active $1,395,000 87851 Old Highway M35, ISLAMORADA, FL 2 Beds2 Baths1,736 SqFt 41 Active $1,399,000 141 Aregood Lane C1, ISLAMORADA, FL 2 Beds3 Baths1,248 SqFt 34 Active $1,400,000 131 Ocean Lane , ISLAMORADA, FL 3 Beds3 Baths897 SqFt 65 Active $1,425,000 87851 Old Highway M26, ISLAMORADA, FL 3 Beds2 Baths1,800 SqFt 52 Active $1,450,000 176 Iroquois Drive , ISLAMORADA, FL 2 Beds2 Baths960 SqFt 65 Contingent $1,499,000 84745 Old Highway 12, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 65 Active $1,599,000 84745 Old Highway 7, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 43 Active $1,600,000 100 Seashore Drive , ISLAMORADA, FL 3 Beds2 Baths2,128 SqFt 32 Active $1,629,000 87851 Old Highway P22, ISLAMORADA, FL 3 Beds2 Baths2,119 SqFt 62 Active $1,649,000 84745 Old Highway 13, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 18 Active $1,650,000 121 Venetian Drive , ISLAMORADA, FL 3 Beds2 Baths1,278 SqFt 52 Active $1,660,000 102 VENETIAN Drive , ISLAMORADA, FL 3 Beds2 Baths1,380 SqFt 47 Active $1,690,000 143 Palermo Drive , ISLAMORADA, FL 3 Beds3 Baths1,568 SqFt 66 Active $1,749,000 84745 Old Highway 8, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 42 Contingent/Show $1,775,000 88181 Old Hwy. C-44 & 50' Slip #7, ISLAMORADA, FL 3 Beds2 Baths1,593 SqFt 51 Active $1,795,000 190 Gulfview Drive , ISLAMORADA, FL 4 Beds3 Baths1,629 SqFt 32 Active $1,999,999 144 Anglers Way , ISLAMORADA, FL 2 Beds3 Baths1,674 SqFt 76 Active $2,049,000 155 Plantation Avenue , ISLAMORADA, FL 3 Beds3 Baths1,295 SqFt 41 Active $2,100,000 75621 Overseas Highway , ISLAMORADA, FL 2 Beds2 Baths1,322 SqFt 43 Active $2,100,000 157 Venetian Drive , ISLAMORADA, FL 3 Beds2 Baths1,263 SqFt 36 Active $2,260,000 125 Cortez Drive , ISLAMORADA, FL 2 Beds2 Baths1,071 SqFt 41 Active $2,299,000 150 Columbus Drive , ISLAMORADA, FL 3 Beds2 Baths1,802 SqFt 57 Active $2,300,000 186 Biscayne Boulevard , ISLAMORADA, FL 2 Beds2 Baths1,178 SqFt 58 Active $2,300,000 159 Iroquois Drive , ISLAMORADA, FL 3 Beds3 Baths2,150 SqFt 58 Active $2,300,000 76412 Overseas Highway , ISLAMORADA, FL 3 Beds3 Baths2,000 SqFt 33 Active $2,395,000 121 Lisbon Court , ISLAMORADA, FL 2 Beds2 Baths1,228 SqFt 69 Active $2,399,000 126 Columbus Drive , ISLAMORADA, FL 3 Beds3 Baths1,827 SqFt 48 Active $2,495,000 64 Plaza Del Sol W , ISLAMORADA, FL 3 Beds2 Baths1,560 SqFt 77 Active $2,499,999 109 Porto Vista Court , ISLAMORADA, FL 3 Beds4 Baths2,432 SqFt 60 Active $2,599,000 189 Gulfview Drive , ISLAMORADA, FL 3 Beds2 Baths2,010 SqFt 57 Active $2,695,000 82762 Overseas Highway 3, ISLAMORADA, FL 4 Beds4 Baths2,728 SqFt 59 Active $2,800,000 33 Pen Key Drive , ISLAMORADA, FL 3 Beds4 Baths4,537 SqFt 49 Active $2,850,000 81250 Overseas Highway 2, ISLAMORADA, FL 3 Beds3 Baths2,072 SqFt 52 Active $2,950,000 124 Palermo Drive , ISLAMORADA, FL 4 Beds3 Baths2,229 SqFt 61 Active $2,950,000 81250 Overseas Highway 5, ISLAMORADA, FL 4 Beds3 Baths2,072 SqFt 72 Active $2,995,000 415 Palm Drive , ISLAMORADA, FL 4 Beds2 Baths2,928 SqFt 39 Active $2,995,000 117 Buena Vista Court , ISLAMORADA, FL 4 Beds3 Baths2,683 SqFt 47 Active $2,999,999 75055 Overseas Highway , ISLAMORADA, FL 3 Beds2 Baths1,400 SqFt 31 Active $3,150,000 105 Carroll Street 6, ISLAMORADA, FL 4 Beds5 Baths2,576 SqFt 51 Active $3,175,000 72 Plaza Granada W , ISLAMORADA, FL 4 Beds4 Baths2,937 SqFt 59 Active $3,225,000 112 Leoni Drive , ISLAMORADA, FL 4 Beds4 Baths2,478 SqFt 48 Active $3,230,000 122 Court Contessa , ISLAMORADA, FL 3 Beds3 Baths2,374 SqFt 39 Active $3,249,000 188 Indian Mound Trail , Tavernier, FL 3 Beds3 Baths2,250 SqFt 55 Active $3,275,000 109 South Drive , ISLAMORADA, FL 4 Beds3 Baths2,782 SqFt 62 Active $3,450,000 117 El Capitan Drive , ISLAMORADA, FL 5 Beds3 Baths3,052 SqFt 55 Contingent/Show $3,450,000 128 Plaza Del Sol W , ISLAMORADA, FL 6 Beds4 Baths2,843 SqFt 47 Active $3,495,000 80639 Old Highway 201, ISLAMORADA, FL 4 Beds5 Baths2,539 SqFt 51 Active $3,750,000 145 Venetian Drive , ISLAMORADA, FL 4 Beds4 Baths3,182 SqFt 81 Active $3,800,000 133 Sunset Drive , ISLAMORADA, FL 4 Beds3 Baths2,519 SqFt 68 Active $3,875,000 96 Plaza Del Sol W , ISLAMORADA, FL 4 Beds4 Baths3,004 SqFt View All Listings