Homes for Sale in Upper Matecumbe Key Islamorada, FL 33036

Every active MLS listing in Upper Matecumbe Key Islamorada’s 33036 ZIP code, refreshed nightly, with the price bands, the property mix and the communities that have the most homes for sale. For the whole city see homes for sale in Upper Matecumbe Key Islamorada, FL (26 listings); for the ZIP’s values, taxes and growth see the 33036 housing scorecard.

25 homes are for sale in ZIP 33036 (Upper Matecumbe Key Islamorada, FL) right now, from $550,000 to $13,750,000 for the middle 80%, at a median asking price of $2,195,000. , built 1988; 1 came on the market in the last 7 days and 32% are new construction.

Newest homes for sale in 33036

$4,750,000

4 bd · 4.5 ba · built 2020

82779 Old Highway #1

Listing courtesy of Ocean Sotheby's International Realty

$2,485,000

3 bd · 3 ba · built 1985

81250 Overseas Highway #2

Listing courtesy of Palm House Real Estate

$549,500

1 bd · 1 ba · built 1988

81801 Overseas Highway #716

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$549,500

1 bd · 1 ba · built 1988

81801 Overseas Highway #715

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$649,000

1 bd · 1 ba · built 1988

81801 Old Highway #754

Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate

$13,750,000

5 bd · 6 ba · built 2019

19 Avacado Street

Listing courtesy of The Agency Florida Keys

$1,199,000

3 bd · 3 ba · built 2020

143 N Hammock Road

Listing courtesy of Flat Fee MLS Realty

$715,000

1 bd · 1 ba · built 1988

81801 Overseas Highway #637

Listing courtesy of Ocean Sotheby's International Realty

$550,000

2 bd · 2 ba · built 1983

80450 Overseas Highway #204

Listing courtesy of Palm House Real Estate

$6,999,000

8 bd · 6 ba · built 1984

1101 Mastic Street

Listing courtesy of Venture Realty Group

$699,000

1 bd · 1 ba · built 1988

81801 Overseas Highway ## 729

Listing courtesy of Coldwell Banker Schmitt Key Largo

$2,195,000

3 bd · 3.5 ba · built 1987

33 Pen Key

Listing courtesy of Ocean Sotheby's International Realty

$585,000

1 bd · 1 ba · built 1988

81801 Overseas Highway #727

Listing courtesy of Coldwell Banker Schmitt Islamorada

$4,000,000

4 bd · 4.5 ba · built 2020

82779 Old Highway #7

Listing courtesy of Ocean Sotheby's International Realty

$4,000,000

4 bd · 4.5 ba · built 2020

82779 Old Highway #8

Listing courtesy of Ocean Sotheby's International Realty

$3,800,000

4 bd · 4.5 ba · built 2020

82779 Old Highway #15

Listing courtesy of Ocean Sotheby's International Realty

$4,499,500

1 bd · 1 ba · built 1950

150 List Street

Listing courtesy of Ocean Sotheby's International Realty

$15,950,000

6 bd · 7.5 ba · built 2005

20 Avacado Street

Listing courtesy of Beycome of Florida, LLC

$550,000

2 bd · 2.5 ba · built 1983

80450 Overseas Highway #Apt 106

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$22,500,000

7 bd · 8 ba · built 2026

81486 Overseas Highway

Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate

$2,495,000

3 bd · 3.5 ba · built 2020

81906 Overseas Highway #2

Listing courtesy of Ocean Sotheby's International Realty

$1,250,000

3 bd · 3 ba · built 2009

189 Carroll Street

Listing courtesy of Ocean Sotheby's International Realty

$1,250,000

3 bd · 3 ba · built 2009

191 Carroll Street

Listing courtesy of Ocean Sotheby's International Realty

$1,550,000

4 bd · 3 ba · built 2025

36 Park Road

Listing courtesy of Palm House Real Estate

Homes for sale in 33036 by price

How to read this

Counts and medians are from active MLS listings with a 33036 mailing ZIP as of September 18, 2026; property mix Single-family 68%, Condo 32%. Prices are asking prices. Listings are shown with the courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also homes for sale in Monroe County. More: Upper Matecumbe Key Islamorada condos, luxury homes in Upper Matecumbe Key Islamorada.