Explore Middle Keys Florida 33036 Homes for Sale 30 Contingent/Show $325,000 84961 Old Highway A1, ISLAMORADA, FL 1 Beds1 Baths406 SqFt 46 Contingent/Show $360,000 87465 Old Highway 223, ISLAMORADA, FL 2 Beds2 Baths1,041 SqFt 54 Contingent/Show $390,000 87455 Old Highway 118, ISLAMORADA, FL 2 Beds2 Baths980 SqFt 30 Active $399,000 119 Cortez Drive G5, ISLAMORADA, FL 1 Beds1 Baths518 SqFt 20 Contingent/Show $399,500 79901 Overseas Highway 101, ISLAMORADA, FL 1 Beds1 Baths409 SqFt 31 Active $449,900 87465 Old Highway 102, ISLAMORADA, FL 2 Beds2 Baths1,100 SqFt 34 Active $475,000 134 Nautilus Drive , ISLAMORADA, FL 5 Beds4 Baths2,900 SqFt 33 Contingent/Show $480,000 87455 Old Highway 116, ISLAMORADA, FL 2 Beds2 Baths1,036 SqFt 15 Active $495,000 84961 Old Highway 19, ISLAMORADA, FL 2 Beds2 Baths800 SqFt 27 Active $589,000 87200 Overseas Highway M4, ISLAMORADA, FL 2 Beds2 Baths1,358 SqFt 97 Active $598,500 87200 Overseas Highway N9, ISLAMORADA, FL 2 Beds2 Baths1,355 SqFt 41 Active $599,000 120 Cortez Drive F1, ISLAMORADA, FL 2 Beds2 Baths1,079 SqFt 33 Active $599,000 87200 Overseas Highway S8, ISLAMORADA, FL 2 Beds2 Baths1,365 SqFt 51 Active $599,000 87200 Overseas Highway M9, ISLAMORADA, FL 3 Beds2 Baths1,358 SqFt 46 Active $615,000 87200 Overseas Highway F4, ISLAMORADA, FL 2 Beds3 Baths1,350 SqFt 14 Active $649,000 81801 Overseas Highway 751, ISLAMORADA, FL 1 Beds1 Baths358 SqFt 56 Active $659,900 87200 Overseas Highway P8, ISLAMORADA, FL 2 Beds2 Baths1,359 SqFt 46 Active $665,000 87200 Overseas Highway B9, ISLAMORADA, FL 2 Beds2 Baths1,343 SqFt 39 Contingent $689,000 63 Cortez Lane , ISLAMORADA, FL 2 Beds2 Baths1,152 SqFt 34 Active $700,000 87200 Overseas Highway O8, ISLAMORADA, FL 2 Beds3 Baths1,365 SqFt 28 Active $716,000 87465 Old Highway 225, ISLAMORADA, FL 2 Beds2 Baths988 SqFt 39 Active $720,000 81801 Overseas Highway 709, ISLAMORADA, FL 1 Beds1 Baths550 SqFt 47 Active $725,000 81801 Overseas Highway 712, ISLAMORADA, FL 1 Beds1 Baths550 SqFt 36 Active $744,800 88181 Old Highway G1, ISLAMORADA, FL 3 Beds2 Baths1,593 SqFt 42 Active $749,000 118 Cortez Drive A, ISLAMORADA, FL 2 Beds2 Baths1,079 SqFt 39 Active $750,000 88181 Old Highway 41G, ISLAMORADA, FL 3 Beds2 Baths1,593 SqFt 62 Active $769,000 87200 Overseas Highway V9, ISLAMORADA, FL 3 Beds2 Baths1,355 SqFt 31 Active $775,000 79901 Overseas Highway 512, ISLAMORADA, FL 2 Beds2 Baths981 SqFt 23 Active $775,000 60 Cortez Lane , ISLAMORADA, FL 3 Beds2 Baths1,152 SqFt 11 Active $795,000 81801 Overseas Highway 612, ISLAMORADA, FL 1 Beds1 Baths550 SqFt 30 Active $799,000 88181 Old Highway F4 slip 65, ISLAMORADA, FL 2 Beds2 Baths1,330 SqFt 32 Active $799,000 110 Knowles Street , ISLAMORADA, FL 3 Beds2 Baths2,016 SqFt 29 Contingent/Show $825,000 302 North Drive , ISLAMORADA, FL 3 Beds2 Baths1,794 SqFt 37 Active $850,000 88181 Old Highway G43 30' slip 52, ISLAMORADA, FL 3 Beds2 Baths1,593 SqFt 43 Active $889,000 88181 Old Highway B2 slip 45, ISLAMORADA, FL 2 Beds2 Baths1,224 SqFt 32 Active $899,000 75811 Overseas Highway 1, ISLAMORADA, FL 3 Beds2 Baths975 SqFt 21 Contingent/Show $899,000 81801 Overseas Highway 208, ISLAMORADA, FL 1 Beds1 Baths840 SqFt 38 Active $925,000 88181 Old Highway 2A, ISLAMORADA, FL 3 Beds2 Baths1,553 SqFt 44 Active $935,000 81801 Overseas Highway 416, ISLAMORADA, FL 1 Beds1 Baths840 SqFt 44 Active $937,000 87200 Overseas Highway J4, ISLAMORADA, FL 2 Beds3 Baths1,403 SqFt 25 Active $985,000 101 Gulfview Drive 202 & 40' Boat slip, ISLAMORADA, FL 2 Beds3 Baths1,473 SqFt 51 Active $994,000 140 Aregood Lane C2, ISLAMORADA, FL 2 Beds3 Baths1,248 SqFt 48 Active $999,000 136 Aregood Lane 2A, ISLAMORADA, FL 2 Beds3 Baths1,152 SqFt 60 Contingent $999,000 121 Gumbo Limbo Road , ISLAMORADA, FL 3 Beds2 Baths1,804 SqFt 47 Active $1,000,000 88181 Old Highway 21H, ISLAMORADA, FL 2 Beds2 Baths1,672 SqFt 30 Active $1,050,000 55 Harbor Drive , ISLAMORADA, FL 2 Beds2 Baths1,075 SqFt 27 Active $1,075,000 142 Gulfview Drive , ISLAMORADA, FL 3 Beds4 Baths1,888 SqFt 44 Active $1,100,000 88181 Old Highway 24G Slip 5, ISLAMORADA, FL 3 Beds2 Baths1,593 SqFt 41 Active $1,100,000 110 Pippin Drive , ISLAMORADA, FL 3 Beds2 Baths1,682 SqFt 47 Active $1,100,000 88181 Old Highway A43 slip #29, ISLAMORADA, FL 3 Beds2 Baths1,553 SqFt 52 Contingent $1,100,000 125 Hammock Road N , ISLAMORADA, FL 3 Beds2 Baths1,518 SqFt 49 Active $1,195,000 192 Ridge Road E , ISLAMORADA, FL 3 Beds2 Baths1,152 SqFt 38 Active $1,199,999 102 Anglers Way , ISLAMORADA, FL 2 Beds3 Baths1,376 SqFt 40 Active $1,225,000 83201 Old Highway 405, ISLAMORADA, FL 2 Beds2 Baths1,275 SqFt 46 Active $1,225,000 101 Gulfview Drive 116D & 30' Boat Slip, ISLAMORADA, FL 3 Beds2 Baths2,026 SqFt 33 Active $1,225,000 101 Gulfview Drive 114D & 30' boat slip with lift, ISLAMORADA, FL 3 Beds3 Baths2,026 SqFt 51 Active $1,239,000 88181 Old Highway 3F, ISLAMORADA, FL 2 Beds2 Baths1,330 SqFt 41 Active $1,295,000 82260 Overseas Highway , ISLAMORADA, FL 3 Beds3 Baths2,808 SqFt 34 Contingent/Show $1,299,999 135 Anglers Way , ISLAMORADA, FL 2 Beds3 Baths1,314 SqFt 42 Active $1,325,000 115 Toner Lane , ISLAMORADA, FL 2 Beds2 Baths1,200 SqFt 31 Active $1,350,000 107 Carroll Street , ISLAMORADA, FL 4 Beds3 Baths1,459 SqFt 31 Active $1,350,000 107 Carroll Street all units, ISLAMORADA, FL 4 Beds3 Baths1,459 SqFt 31 Active $1,350,000 81216 Old Highway , ISLAMORADA, FL 3 Beds3 Baths960 SqFt 40 Active $1,395,000 87851 Old Highway M35, ISLAMORADA, FL 2 Beds2 Baths1,736 SqFt 30 Contingent $1,399,000 109 Nautilus Drive , ISLAMORADA, FL 2 Beds1 Baths900 SqFt 65 Active $1,425,000 87851 Old Highway M26, ISLAMORADA, FL 3 Beds2 Baths1,800 SqFt 47 Contingent/Show $1,495,000 87851 Old Highway K36, ISLAMORADA, FL 3 Beds2 Baths1,813 SqFt 55 Active $1,499,000 158 Iroquois Drive , ISLAMORADA, FL 3 Beds3 Baths1,920 SqFt 57 Open House Active $1,550,000 209 Matecumbe Avenue , ISLAMORADA, FL 2 Beds2 Baths1,556 SqFt 47 Active $1,550,000 141 Aregood Lane C 1, ISLAMORADA, FL 2 Beds3 Baths1,248 SqFt 18 Active $1,650,000 121 Venetian Drive , ISLAMORADA, FL 3 Beds2 Baths1,278 SqFt 32 Contingent/Show $1,650,000 87851 Old Highway P22, ISLAMORADA, FL 3 Beds2 Baths2,119 SqFt 52 Active $1,660,000 102 VENETIAN Drive , ISLAMORADA, FL 3 Beds2 Baths1,380 SqFt 32 Active $1,799,000 84 Johnston Avenue 3, ISLAMORADA, FL 3 Beds4 Baths1,680 SqFt 51 Active $1,895,000 190 Gulfview Drive , ISLAMORADA, FL 4 Beds3 Baths1,629 SqFt 46 Active $1,895,000 178 Gulfview Drive , ISLAMORADA, FL 3 Beds3 Baths1,804 SqFt 47 Active $1,950,000 143 Palermo Drive , ISLAMORADA, FL 3 Beds3 Baths1,568 SqFt 57 Active $1,950,000 106 San Juan Drive , ISLAMORADA, FL 3 Beds3 Baths2,055 SqFt 32 Active $1,999,999 144 Anglers Way , ISLAMORADA, FL 2 Beds3 Baths1,674 SqFt 76 Active $2,089,000 155 Plantation Avenue , ISLAMORADA, FL 3 Beds3 Baths1,295 SqFt 41 Active $2,100,000 75621 Overseas Highway , ISLAMORADA, FL 2 Beds2 Baths1,322 SqFt 69 Active $2,399,000 126 Columbus Drive , ISLAMORADA, FL 3 Beds3 Baths1,827 SqFt 58 Active $2,400,000 76412 Overseas Highway , ISLAMORADA, FL 3 Beds3 Baths2,000 SqFt 26 Active $2,450,000 71 Plaza Del Lago W , ISLAMORADA, FL 4 Beds3 Baths2,082 SqFt 57 Open House Active $2,500,000 186 Biscayne Boulevard , ISLAMORADA, FL 2 Beds2 Baths1,178 SqFt 81 Active $2,695,000 105 Buena Vista Court , ISLAMORADA, FL 4 Beds3 Baths2,095 SqFt 59 Active $2,800,000 33 Pen Key Drive , ISLAMORADA, FL 3 Beds4 Baths4,537 SqFt 77 Active $2,900,000 109 Porto Vista Court , ISLAMORADA, FL 3 Beds4 Baths2,432 SqFt 61 Active $2,950,000 81250 Overseas Highway 5, ISLAMORADA, FL 4 Beds3 Baths2,072 SqFt 39 Active $2,995,000 117 Buena Vista Court , ISLAMORADA, FL 4 Beds3 Baths2,683 SqFt 31 Active $3,150,000 105 Carroll Street 6, ISLAMORADA, FL 4 Beds5 Baths2,576 SqFt 44 Active $3,200,000 85331 Overseas Highway , ISLAMORADA, FL 4 Beds3 Baths2,880 SqFt 47 Active $3,250,000 75055 Overseas Highway , ISLAMORADA, FL 3 Beds2 Baths1,400 SqFt 48 Active $3,350,800 122 Court Contessa , ISLAMORADA, FL 3 Beds3 Baths2,374 SqFt 50 Active $3,375,000 75061 Overseas Highway , ISLAMORADA, FL 3 Beds3 Baths1,616 SqFt 51 Active $3,390,000 72 Plaza Granada W , ISLAMORADA, FL 4 Beds4 Baths2,937 SqFt 72 Active $3,450,000 96 Plaza Del Sol W , ISLAMORADA, FL 4 Beds4 Baths3,004 SqFt 47 Active $3,495,000 80639 Old Highway 201, ISLAMORADA, FL 4 Beds5 Baths2,539 SqFt 61 Active $3,500,000 105 Palo De Oro Drive , ISLAMORADA, FL 5 Beds3 Baths2,640 SqFt View All Listings