Homes for Sale in Islamorada

Property Listings

Price

Living Area

$42,000,000

88041 Old Highway, Plantation Key, FL 33036

6 Beds 9 Baths 9,843 Sq.Ft.

$35,000,000

90400 Overseas Highway, Plantation Key, FL 33070

8 Baths 29,330 Sq.Ft.

$27,800,000

89505 Old Highway, Plantation Key, FL 33070

7 Beds 10 Baths 8,988 Sq.Ft.

$25,000,000

82768 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036

7 Beds 10 Baths 6,935 Sq.Ft.

$24,995,000

87895 Old Highway, Plantation Key, FL 33036

5 Beds 8 Baths 9,011 Sq.Ft.

$24,995,000

82719 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

7 Beds 10 Baths 10,182 Sq.Ft.

$22,500,000

81486 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036

7 Beds 9 Baths 8,878 Sq.Ft.

$21,500,000

87429 Old Highway, Plantation Key, FL 33036

6 Beds 8 Baths 6,692 Sq.Ft.

$18,000,000

96 Madeira Road, Upper Matecumbe Key Islamorada, FL 33036

2 Baths 4,750 Sq.Ft.

$15,990,000

88351 Old Highway, Plantation Key, FL 33036

6 Beds 9 Baths 7,590 Sq.Ft.

$15,950,000

20 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036

6 Beds 8 Baths 6,680 Sq.Ft.

$14,950,000

75840 Overseas Highway, Lower Matecumbe, FL 33036

7 Beds 7 Baths 5,900 Sq.Ft.

$14,900,000

236 Costa Bravo Drive, Lower Matecumbe, FL 33036

5 Beds 8 Baths 6,367 Sq.Ft.

$12,500,000

89251 Old Highway, Plantation Key, FL 33070

3 Beds 3 Baths 1,243 Sq.Ft.

$11,000,000

75280 Overseas Highway, Lower Matecumbe, FL 33036

4 Beds 4 Baths 5,100 Sq.Ft.

$10,900,000

186 & 165 Bayview Drive, Lower Matecumbe, FL 33036

6 Beds 5 Baths 4,394 Sq.Ft.

$8,950,000

162 Bayview Drive, Lower Matecumbe, FL 33036

8 Beds 10 Baths 5,392 Sq.Ft.

$7,995,000

91 Iroquois Drive, Lower Matecumbe, FL 33036

4 Beds 5 Baths 4,048 Sq.Ft.

$7,800,000

75931 Overseas Highway, Lower Matecumbe, FL 33036

5 Beds 6 Baths 4,770 Sq.Ft.

$7,800,000

80201 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036

5 Beds 6 Baths 4,764 Sq.Ft.

$7,795,000

89701 Old Highway, Plantation Key, FL 33070

5 Beds 5 Baths 3,841 Sq.Ft.

$7,500,000

88547 Old Highway, Plantation Key, FL 33070

4 Beds 3 Baths 4,103 Sq.Ft.

$7,450,000

144 N Rolling Hill Road, Plantation Key, FL 33070

4 Beds 5 Baths 3,284 Sq.Ft.

$7,300,000

228 Tide Avenue, Plantation Key, FL 33070

4 Beds 5 Baths 2,629 Sq.Ft.

$6,999,999

82749 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

3 Beds 3 Baths 1,485 Sq.Ft.

$6,995,000

200 Treasure Harbor Drive, Plantation Key, FL 33036

4 Baths 1,069 Sq.Ft.

$6,800,000

90311 Old Highway, Plantation Key, FL 33070

2 Beds 2 Baths 10,714 Sq.Ft.

$6,750,000

82900 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

$6,750,000

83407 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

6 Beds 5 Baths 4,566 Sq.Ft.

$6,700,000

109 Columbus Drive, Lower Matecumbe, FL 33036

4 Beds 5 Baths 3,860 Sq.Ft.

$6,500,000

430 Palm Drive, Lower Matecumbe, FL 33036

5 Beds 7 Baths 5,153 Sq.Ft.

$6,500,000

81910 & 81908 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036

$6,495,000

75131 Overseas Highway, Lower Matecumbe, FL 33036

$6,490,000

137 Sapodilla Drive, Lower Matecumbe, FL 33036

5 Beds 6 Baths 5,456 Sq.Ft.

$6,250,000

206 Plantation Avenue, Plantation Key, FL 33070

5 Beds 6 Baths 3,945 Sq.Ft.

Active Under Contract

$6,150,000

134 N Rolling Hill Road, Plantation Key, FL 33070

4 Beds 5 Baths 2,346 Sq.Ft.

Islamorada Listings Map

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Duck Key

Duck Key

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Key Colony Beach

Marathon

Marathon

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Buying or selling waterfront property requires more than paperwork — it requires clarity, timing, and trusted guidance. Michelle partners closely with her clients to create intentional strategy, navigate complex decisions, and deliver results with confidence. Schedule a private consultation.

Contact Details

Michelle Ann Wininger

Phone

(860) 707-5389

Email

[email protected]

Address

11050 Overseas Hwy Marathon FL 33050

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