Explore Middle Keys Florida33036 Homes for Sale 135 Active$25,000,00082768 Overseas Highway , ISLAMORADA, FL 7 Beds9 Baths8,288 SqFt 104 Active$25,000,000141 Cortez Drive , ISLAMORADA, FL 10 Beds11 Baths3,772 SqFt 119 Active$19,990,00087429 Old Highway , ISLAMORADA, FL 6 Beds7 Baths6,602 SqFt 62 Active$14,500,00087895 Old Highway , ISLAMORADA, FL 5 Beds8 Baths9,011 SqFt 83 Active$14,000,00083283 Old Highway , ISLAMORADA, FL 7 Beds9 Baths6,696 SqFt 91 Active$11,500,000170 Sapodilla Drive , ISLAMORADA, FL 4 Beds4 Baths4,512 SqFt 113 Active$10,500,00091 Iroquois Drive , ISLAMORADA, FL 6 Beds5 Baths6,100 SqFt 70 Active$9,900,00088011 Old Highway , ISLAMORADA, FL 5 Beds6 Baths7,813 SqFt 65 Active$7,450,000168 Galleon Road , ISLAMORADA, FL 4 Beds5 Baths3,790 SqFt 64 Active$6,999,99975560 Overseas Highway , ISLAMORADA, FL 4 Beds4 Baths3,228 SqFt 36 Active$6,995,00075131 Overseas Highway , ISLAMORADA, FL 3 Beds3 Baths1,500 SqFt 75 Active$6,950,000156 San Remo Drive , ISLAMORADA, FL 4 Beds3 Baths3,542 SqFt 116 Active$6,500,00075261 Overseas Highway , ISLAMORADA, FL 4 Beds3 Baths3,014 SqFt 104 Active$6,500,00080908 Overseas Highway , ISLAMORADA, FL 4 Beds5 Baths5,244 SqFt 64 Active$6,500,000140 Gulfside Drive , ISLAMORADA, FL 3 Beds4 Baths2,972 SqFt 33 Active$5,900,00075730 Overseas Highway , ISLAMORADA, FL 3 Beds2 Baths1,264 SqFt 80 Active$4,975,00080459 Old Highway , ISLAMORADA, FL 5 Beds4 Baths2,358 SqFt 42 Active$4,800,00087950 Overseas Highway , ISLAMORADA, FL 5 Beds3 Baths2,764 SqFt 65 Active$4,750,00074501 Overseas Highway , ISLAMORADA, FL 5 Beds4 Baths3,772 SqFt 53 Active$4,595,000442 Palm Drive , ISLAMORADA, FL 4 Beds3 Baths2,058 SqFt 51 Active$4,495,000139 Bayview Isle Drive , ISLAMORADA, FL 4 Beds4 Baths2,304 SqFt 69 Active$4,470,000190 Biscayne Boulevard , ISLAMORADA, FL 3 Beds2 Baths2,872 SqFt 45 Active$4,290,00096 Plaza Del Sol W , ISLAMORADA, FL 4 Beds4 Baths3,004 SqFt 51 Active$4,250,000218 Gulfview Drive , ISLAMORADA, FL 3 Beds3 Baths3,660 SqFt 76 Contingent/Show$4,195,00028 Pen Key Drive , ISLAMORADA, FL 4 Beds4 Baths3,044 SqFt 49 Active$3,750,00085327 Overseas Highway , ISLAMORADA, FL 4 Beds3 Baths2,880 SqFt 50 Active$3,750,000128 Plaza Del Sol W , ISLAMORADA, FL 6 Beds5 Baths3,202 SqFt 53 Active$3,699,00072 Plaza Granada W , ISLAMORADA, FL 4 Beds4 Baths2,937 SqFt 47 Active$3,500,00080639 Old Highway 201, ISLAMORADA, FL 4 Beds5 Baths2,539 SqFt 41 Active$3,395,000415 Palm Drive , ISLAMORADA, FL 4 Beds2 Baths2,928 SqFt 43 Active$3,250,00085331 Overseas Highway , ISLAMORADA, FL 4 Beds3 Baths2,880 SqFt 49 Active$3,200,000134 Bayview Isle Drive , ISLAMORADA, FL 4 Beds4 Baths2,577 SqFt 20 Active$3,195,000105 Carroll Street 6, ISLAMORADA, FL 4 Beds5 Baths2,576 SqFt 46 Active$3,195,00080639 Old Highway 204, ISLAMORADA, FL 4 Beds5 Baths2,539 SqFt 77 Active$3,150,000109 Porto Vista Court , ISLAMORADA, FL 3 Beds4 Baths2,432 SqFt 64 Active$3,125,00059 Plaza Del Sol W , ISLAMORADA, FL 5 Beds3 Baths2,922 SqFt 63 Active$2,975,000141 Giardino Drive , ISLAMORADA, FL 4 Beds3 Baths2,310 SqFt 35 Active$2,850,00071 Plaza Del Lago W , ISLAMORADA, FL 4 Beds3 Baths2,082 SqFt 79 Active$2,850,000105 Buena Vista Court , ISLAMORADA, FL 4 Beds3 Baths2,095 SqFt 57 Active$2,850,00081250 Overseas Highway 2, ISLAMORADA, FL 3 Beds3 Baths2,072 SqFt 57 Active$2,750,000190 Venetian Drive , ISLAMORADA, FL 3 Beds3 Baths1,200 SqFt 48 Active$2,700,00087901 Old Highway , ISLAMORADA, FL 4 Beds4 Baths2,500 SqFt 53 Contingent/Show$2,700,000125 Giardino Drive , ISLAMORADA, FL 4 Beds5 Baths2,720 SqFt 48 Active$2,700,000113 Bayview Isle Drive , ISLAMORADA, FL 4 Beds3 Baths2,619 SqFt 80 Active$2,650,000150 Valencia Drive , ISLAMORADA, FL 3 Beds3 Baths1,972 SqFt 70 Active$2,575,000132 Stromboli Drive , ISLAMORADA, FL 3 Beds3 Baths2,001 SqFt 41 Open House Active$2,499,999107 Azalea Street , ISLAMORADA, FL 5 Beds3 Baths2,450 SqFt 33 Active$2,495,000121 Lisbon Court , ISLAMORADA, FL 2 Beds2 Baths1,228 SqFt 45 Active$2,350,00075091 Overseas Highway , ISLAMORADA, FL 2 Beds2 Baths1,534 SqFt 44 Active$2,200,000144 Anglers Way , ISLAMORADA, FL 2 Beds3 Baths1,674 SqFt 38 Active$2,000,000115 Vilabella Drive , ISLAMORADA, FL 3 Beds3 Baths1,120 SqFt 71 Active$1,850,00084745 Old Highway 14, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 25 Active$1,825,00080639 Old Highway 308, ISLAMORADA, FL 3 Beds3 Baths2,251 SqFt 199 Active$1,800,00084745 Old Highway 8, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 68 Active$1,750,00084745 Old Highway 7, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 25 Active$1,699,000101 Gulfview Drive 308 and 50' Boat Slip, ISLAMORADA, FL 3 Beds3 Baths2,026 SqFt 52 Active$1,699,00018 Flamingo Hammock Road , ISLAMORADA, FL 3 Beds2 Baths1,774 SqFt 40 Active$1,650,00084745 Old Highway 12, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 33 Active$1,645,000169 Venetian Way , ISLAMORADA, FL 5 Beds4 Baths2,941 SqFt 47 Active$1,625,000141 Aregood Lane C 1, ISLAMORADA, FL 2 Beds3 Baths1,248 SqFt 42 Active$1,624,00087851 Old Highway M36, ISLAMORADA, FL 3 Beds2 Baths2,150 SqFt 82 Active$1,500,00084745 Old Highway 11, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 80 Active$1,500,00084745 Old Highway 5, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 43 Active$1,450,000121 Gumbo Limbo Road , ISLAMORADA, FL 3 Beds2 Baths1,804 SqFt 30 Active$1,440,000117 South Drive , ISLAMORADA, FL 4 Beds3 Baths1,794 SqFt 31 Active$1,400,00081216 Old Highway , ISLAMORADA, FL 3 Beds3 Baths960 SqFt 72 Active$1,400,00084745 Old Highway 10, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 50 Active$1,400,00084745 Old Highway 4, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 67 Active$1,400,00084745 Old Highway 1, ISLAMORADA, FL 3 Beds3 Baths1,680 SqFt 63 Active$1,399,00087851 Old Highway K1, ISLAMORADA, FL 4 Beds2 Baths1,813 SqFt 61 Contingent/Show$1,360,000110 Columbus Drive , ISLAMORADA, FL 2 Beds1 Baths1,107 SqFt 32 Active$1,300,000141 Plantation Boulevard , ISLAMORADA, FL 3 Beds3 Baths1,678 SqFt 33 Active$1,300,000137 Ridge Road E , ISLAMORADA, FL 3 Beds2 Baths1,739 SqFt 48 Active$1,295,000136 Aregood Lane 2A, ISLAMORADA, FL 2 Beds3 Baths1,152 SqFt 46 Active$1,275,000101 Gulfview Drive 116 D, ISLAMORADA, FL 3 Beds2 Baths2,026 SqFt 41 Active$1,273,000101 Gulfview Drive 209 & 30 ft. boatslip, ISLAMORADA, FL 3 Beds3 Baths2,026 SqFt 33 Active$1,250,000207 Russell Street , ISLAMORADA, FL 2 Beds1 Baths928 SqFt 69 Active$1,239,00088181 Old Highway 3F + 50' Slip, ISLAMORADA, FL 2 Beds2 Baths1,330 SqFt 54 Active$1,225,000140 Aregood Lane C2, ISLAMORADA, FL 2 Beds3 Baths1,248 SqFt 37 Active$1,200,000110 Pippin Drive , ISLAMORADA, FL 3 Beds2 Baths1,682 SqFt 29 Active$1,200,00087200 Overseas Highway J5, ISLAMORADA, FL 2 Beds3 Baths1,403 SqFt 28 Contingent/Show$1,175,000200 El Capitan Drive B4, ISLAMORADA, FL 3 Beds3 Baths1,700 SqFt 45 Active$1,100,00087200 Overseas Highway H4, ISLAMORADA, FL 2 Beds2 Baths1,359 SqFt 38 Active$1,100,00080450 Overseas Highway 107, ISLAMORADA, FL 5 Beds3 Baths3,264 SqFt 34 Active$1,100,00087200 Overseas Highway H1, ISLAMORADA, FL 3 Beds3 Baths1,500 SqFt 54 Active$1,099,00075100 Overseas Highway Parcel B1, ISLAMORADA, FL 2 Beds2 Baths1,552 SqFt 64 Active$1,075,00087851 Old Highway M3, ISLAMORADA, FL 2 Beds2 Baths1,536 SqFt 32 Active$1,020,00075811 Overseas Highway 1, ISLAMORADA, FL 3 Beds2 Baths975 SqFt 37 Active$975,00088181 Old Highway 43G and 30' slip 52, ISLAMORADA, FL 3 Beds2 Baths1,593 SqFt 44 Active$935,00081801 Overseas Highway 416, ISLAMORADA, FL 1 Beds1 Baths840 SqFt 39 Active$925,00088181 Old HWY Highway 2A, ISLAMORADA, FL 3 Beds2 Baths1,553 SqFt 57 Active$895,000183 Orlando Drive , ISLAMORADA, FL 4 Beds3 Baths1,596 SqFt 41 Contingent/Show$869,000173 Coral Road , ISLAMORADA, FL 3 Beds2 Baths1,346 SqFt 26 Active$850,000128 Ridge Road E , ISLAMORADA, FL 3 Beds2 Baths1,320 SqFt 51 Active$830,000100 Orange Lane , ISLAMORADA, FL 3 Beds2 Baths1,515 SqFt 36 Active$799,000100 Iroquois Drive 8, ISLAMORADA, FL 3 Beds3 Baths1,440 SqFt 11 Active$795,00081801 Overseas Highway 612, ISLAMORADA, FL 1 Beds1 Baths550 SqFt 33 Active$775,00075710 Overseas Highway 10, ISLAMORADA, FL 2 Beds2 Baths1,104 SqFt 42 Active$775,000120 Cortez Drive F1, ISLAMORADA, FL 2 Beds2 Baths1,079 SqFt View All Listings