Luxury Homes for Sale in Lower Matecumbe, FL

The luxury market in Lower Matecumbe starts at $2,500,000 — about 0.6× the city’s median asking price. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see all homes for sale in Lower Matecumbe.

20 luxury homes are for sale in Lower Matecumbe, FL at $2,500,000 and up — median asking $4,625,000, the top listing at $29,000,000. 100% of the luxury inventory is waterfront; 10% is new construction. Median days on market: 159.

Newest luxury listings in Lower Matecumbe

75433 Overseas Highway, luxury home for sale in Lower Matecumbe
$3,999,000 New
4 bd · 4 ba · built 1970
75433 Overseas Highway, 33036
Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
75751 Overseas Highway, luxury home for sale in Lower Matecumbe
$11,000,000
5 bd · 4.5 ba · built 1997
75751 Overseas Highway, 33036
Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
74049 Overseas Highway, luxury home for sale in Lower Matecumbe
$3,850,000
4 bd · 4 ba · built 1970
74049 Overseas Highway, 33036
Listing courtesy of Luxe Properties, LLC.
101 Madeira Court, luxury home for sale in Lower Matecumbe
$2,890,000
3 bd · 3 ba · built 1983
101 Madeira Court, 33036
Listing courtesy of Coldwell Banker Schmitt Islamorada
77350 Overseas Highway, luxury home for sale in Lower Matecumbe
$11,700,000
6 bd · 7 ba · built 2025
77350 Overseas Highway, 33036
Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate
117 El Capitan Drive, luxury home for sale in Lower Matecumbe
$3,100,000
5 bd · 3 ba · built 1991
117 El Capitan Drive, 33036
Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
75090 Overseas Highway, luxury home for sale in Lower Matecumbe
$29,000,000
4 bd · 5.5 ba · built 2011
75090 Overseas Highway, 33036
Listing courtesy of Ocean Sotheby's International Realty
44 W Plaza Del Lago, luxury home for sale in Lower Matecumbe
$4,750,000
4 bd · 4.5 ba · built 1986
44 W Plaza Del Lago, 33036
Listing courtesy of Pine River Realty, LLC
194 Buttonwood Lane, luxury home for sale in Lower Matecumbe
$6,150,000
6 bd · 7 ba · built 2025
194 Buttonwood Lane, 33036
Listing courtesy of Fairchild Partners, Inc.
75071 Overseas Highway, luxury home for sale in Lower Matecumbe
$3,199,000
3 bd · 2 ba · built 1988
75071 Overseas Highway, 33036
Listing courtesy of Coastal Realty of the Florida Keys
77340 Overseas Highway, luxury home for sale in Lower Matecumbe
$3,999,999
2 bd · 2 ba · built 1963
77340 Overseas Highway, 33036
Listing courtesy of Coldwell Banker Schmitt Islamorada
75131 Overseas Highway, luxury home for sale in Lower Matecumbe
$3,999,000
3 ba · built 1957
75131 Overseas Highway, 33036
Listing courtesy of Century 21 Circle- Islamorada
110 Gulfview Drive, luxury home for sale in Lower Matecumbe
$3,524,000
7 bd · 4 ba · built 1999
110 Gulfview Drive, 33036
Listing courtesy of EXP Realty, LLC
137 Sapodilla Drive, luxury home for sale in Lower Matecumbe
$5,999,999
5 bd · 5.5 ba · built 2000
137 Sapodilla Drive, 33036
Listing courtesy of Ocean Sotheby's International Realty
186 & 165 Bayview Drive, luxury home for sale in Lower Matecumbe
$10,900,000
6 bd · 4.5 ba · built 1991
186 & 165 Bayview Drive, 33036
Listing courtesy of Ocean Sotheby's International Realty
75280 Overseas Highway, luxury home for sale in Lower Matecumbe
$11,000,000
4 bd · 4 ba · built 1993
75280 Overseas Highway, 33036
Listing courtesy of Ocean Sotheby's International Realty
88 W Plaza Del Lago, luxury home for sale in Lower Matecumbe
$4,450,000
5 bd · 5 ba · built 2023
88 W Plaza Del Lago, 33036
Listing courtesy of Ocean Sotheby's International Realty
75761 Overseas Highway, luxury home for sale in Lower Matecumbe
$4,500,000
4 bd · 4 ba · built 1998
75761 Overseas Highway, 33036
Listing courtesy of Engel & Völkers Marathon
162 Bayview Drive, luxury home for sale in Lower Matecumbe
$7,950,000
8 bd · 9 ba · built 2014
162 Bayview Drive, 33036
Listing courtesy of Coldwell Banker Realty - Coral Gables
75131 Overseas Highway, luxury home for sale in Lower Matecumbe
$5,999,000
3 bd · 3 ba · built 1957
75131 Overseas Highway, 33036
Listing courtesy of Century 21 Circle- Islamorada

The most expensive homes for sale in Lower Matecumbe

ListingAskingSq ft$ / sq ftCommunity
75090 Overseas Highway$29,000,000
77350 Overseas Highway$11,700,000
75751 Overseas Highway$11,000,000
75280 Overseas Highway$11,000,000
186 & 165 Bayview Drive$10,900,000
162 Bayview Drive$7,950,000
194 Buttonwood Lane$6,150,000
137 Sapodilla Drive$5,999,999
75131 Overseas Highway$5,999,000
44 W Plaza Del Lago$4,750,000

Luxury inventory by price

BandFor saleShare
$2,000,000–$3,000,00015%
$3,000,000–$5,000,0001050%
$5,000,000+945%

How to read this

Luxury is defined here as asking prices at or above $2,500,000. Counts, medians and closings come from active and closed MLS listings as of September 18, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 23 homes for sale in Lower Matecumbe.

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Common questions

How many luxury homes are for sale in Lower Matecumbe?

20 homes are listed at $2,500,000 or more in Lower Matecumbe, FL as of September 18, 2026, with a median asking price of $4,625,000.

What is the most expensive home for sale in Lower Matecumbe?

The highest asking price right now is $29,000,000.

Which Lower Matecumbe communities have the most luxury listings?

See the table above.