Homes over $1M in Islamorada, FL

68 for sale · 112 homes listed · Updated September 25, 2026 · Page 2 of 3

• 101 madeira court, Islamorada 33036 $2,890,000 · 3 bd · 3 ba · 1,947 sqft
• 109 valencia drive, Islamorada 33036 $4,650,000 · 5 bd · 6 ba · 4,354 sqft
• 82891 overseas highway, Islamorada 33036 $2,100,000 · 3 bd · 4 ba · 2,036 sqft
• 74049 overseas highway, Islamorada 33036 $3,850,000 · 4 bd · 4 ba · 2,596 sqft
• 82779 old highway 1, Islamorada 33036 $4,750,000 · 4 bd · 5 ba · 2,574 sqft
• 75751 overseas highway, Islamorada 33036 $11,000,000 · 5 bd · 5 ba · 3,421 sqft
• 155 plantation avenue, Islamorada 33070 $2,000,000 · 3 bd · 3 ba · 1,771 sqft
• 144 north rolling hill road, Islamorada 33036 $6,195,000 · 4 bd · 5 ba · 3,284 sqft
• 316 north drive, Islamorada 33036 $2,400,000 · 3 bd · 4 ba · 2,309 sqft
• 148 giardino drive, Islamorada 33036 $3,952,000 · 5 bd · 3 ba · 2,328 sqft
• 107 valencia drive, Islamorada 33036 $2,500,000 · 3 bd · 3 ba · 1,632 sqft
• 313 north drive, Islamorada 33036 $3,700,000 · 3 bd · 3 ba · 1,729 sqft
• 102 venetian drive, Islamorada 33036 $1,600,000 · 3 bd · 2 ba · 1,380 sqft
• 75433 overseas highway, Islamorada 33036 $3,999,000 · 4 bd · 4 ba · 2,624 sqft
• 81250 overseas highway 5, Islamorada 33036 $2,290,000 · 4 bd · 3 ba · 2,464 sqft
• 161 palermo drive, Islamorada 33036 $1,950,000 · 3 bd · 2 ba · 1,190 sqft
• 101 buena vista court, Islamorada 33036 $3,999,999 · 4 bd · 4 ba · 2,873 sqft
• 87429 old highway, Islamorada 33036 $18,999,000 · 6 bd · 8 ba · 6,692 sqft
• 80639 old highway 201, Islamorada 33036 Pending $3,495,000 · 4 bd · 5 ba · 2,539 sqft
• 166 bayview drive, Islamorada 33036 Pending $4,700,000 · 4 bd · 4 ba
• 113 san juan drive boat slip, Islamorada 33036 Pending $1,695,000 · 3 bd · 2 ba · 1,490 sqft
• 155 palo de oro drive, Islamorada 33036 Pending $4,500,000 · 4 bd · 6 ba
• 136 giardino drive, Islamorada 33036 Active Under Contract $3,250,000 · 4 bd · 3 ba · 3,481 sqft
• 142 gulfview drive, Islamorada 33036 Active Under Contract $1,075,000 · 3 bd · 4 ba · 1,888 sqft
• 87950 overseas highway, Islamorada 33036 Active Under Contract $3,800,000 · 5 bd · 3 ba · 2,464 sqft
• 82779 old highway 14, Islamorada 33036 Active Under Contract $3,950,000 · 4 bd · 5 ba · 2,574 sqft
• 186 165 bayview drive, Islamorada 33036 Active Under Contract $10,900,000 · 6 bd · 5 ba · 4,394 sqft
• 109 milano drive, Islamorada 33036 Active Under Contract $2,500,000 · 3 bd · 3 ba · 1,368 sqft
• 105 palo de oro drive, Islamorada 33036 Active Under Contract $3,995,000 · 5 bd · 3 ba · 2,640 sqft
• 87851 old highway m3, Islamorada 33036 Active Under Contract $1,075,000 · 2 bd · 2 ba · 1,536 sqft
• 141 canal street, Islamorada 33070 Active Under Contract $3,499,000 · 5 bd · 6 ba · 5,061 sqft
• 131 bayview isle drive, Islamorada 33036 Active Under Contract $3,900,000 · 3 bd · 3 ba · 2,148 sqft
• 75840 overseas highway, Islamorada 33036 Active Under Contract $12,950,000 · 7 bd · 7 ba · 5,900 sqft
• 316 woods avenue, Islamorada 33070 Active Under Contract $2,375,000 · 4 bd · 4 ba · 2,793 sqft
• 87851 old highway m42, Islamorada 33036 Active Under Contract $1,385,000 · 3 bd · 2 ba · 1,736 sqft
• 139 gimpy gulch drive, Islamorada 33036 Active Under Contract $13,900,000 · 6 bd · 9 ba · 6,573 sqft
• 113 villa bella drive, Islamorada 33036 Active Under Contract $2,550,000 · 5 bd · 3 ba · 2,759 sqft
• 87445 old highway, Islamorada 33036 Active Under Contract $3,995,000 · 5 bd · 4 ba · 4,014 sqft
• 430 palm drive, Islamorada 33036 Active Under Contract $5,999,000 · 5 bd · 7 ba · 5,153 sqft
• 321 tollgate shores drive, Islamorada 33036 Active Under Contract $1,100,000 · 2 bd · 2 ba · 1,532 sqft
• 102 anglers way, Islamorada 33036 Active Under Contract $1,150,000 · 2 bd · 3 ba · 1,376 sqft
• 121 severino drive, Islamorada 33036 Active Under Contract $3,000,000 · 3 bd · 3 ba · 1,422 sqft
• 130 palm lane, Islamorada 33036 Active Under Contract $2,250,000 · 3 bd · 3 ba · 2,796 sqft
• 81250 overseas highway 5, Islamorada 33036 Off market since Jul 2026 $2,290,000 · 4 bd · 3 ba · 2,336 sqft
• 316 north drive, Islamorada 33036 Off market since Aug 2026 $2,400,000 · 3 bd · 4 ba · 2,309 sqft
• 80201 overseas highway, Islamorada 33036 Off market since Sep 2026 $7,400,000 · 5 bd · 6 ba · 4,764 sqft
• 122 court contessa, Islamorada 33036 Off market since Sep 2026 $2,740,000 · 3 bd · 3 ba · 2,374 sqft
• 82749 old highway, Islamorada 33036 Off market since Sep 2026 $6,900,000 · 3 bd · 3 ba · 1,485 sqft
• 109 columbus drive, Islamorada 33036 Off market since Aug 2026 $6,700,000 · 4 bd · 5 ba · 3,860 sqft
• 75055 overseas highway, Islamorada 33036 Off market since Sep 2026 $2,790,000 · 3 bd · 2 ba · 1,400 sqft