33036 Homes for Sale — Upper Matecumbe Key Islamorada, FL

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 (25 listings); for the ZIP’s values, taxes and growth see the 33036 housing scorecard.

33036 at a glance

ZIP 33036 is Upper Matecumbe Key Islamorada, Monroe County, FL. The numbers below are computed from MLS closings and live listings for every community in the ZIP and refresh with each data pull.

Where it isUpper Matecumbe Key Islamorada, Monroe County, FL
Communities79 MLS communities, 38 with 12-month sales data
Median sold price, 12 months$1.24M (+20.2% year over year)
Days to contract (median)97
New construction share of sales8%
Sale-to-original-list90.9%
Communities with the most salesVENETIAN SHORES ($2.61M), BUTTONWOOD BAY ($1.15M), PORT ANTIGUA ($2.5M)

33036 housing market tracker · all homes for sale in Upper Matecumbe Key Islamorada, FL · Monroe County property tax

27 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 $2,485,000. , built 1988; 2 came on the market in the last 7 days and 33% are new construction.

Newest homes for sale in 33036

18 Pen Key Club, home for sale in Upper Matecumbe Key Islamorada 33036
$3,900,000 New
3 bd · 3 ba · built 1962
18 Pen Key Club
Listing courtesy of Coldwell Banker Schmitt Islamorada
154 Carroll Street, home for sale in Upper Matecumbe Key Islamorada 33036
$2,699,000 New
4 bd · 4 ba · built 2017
154 Carroll Street
Listing courtesy of Ocean Sotheby's International Realty
33 Pen Key Club Drive, home for sale in Upper Matecumbe Key Islamorada 33036
$2,195,000
3 bd · 3.5 ba · built 1987
33 Pen Key Club Drive
Listing courtesy of Ocean Sotheby's International Realty
36 Park Road, home for sale in Upper Matecumbe Key Islamorada 33036
$1,495,000
4 bd · 3 ba · built 2025
36 Park Road
Listing courtesy of Palm House Real Estate
80902 Old Highway, home for sale in Upper Matecumbe Key Islamorada 33036
$2,950,000
4 bd · 3 ba · built 1961
80902 Old Highway
Listing courtesy of Coldwell Banker Schmitt Islamorada
81250 Overseas Highway # 5, home for sale in Upper Matecumbe Key Islamorada 33036
$2,290,000
4 bd · 3 ba · built 1985
81250 Overseas Highway # 5
Listing courtesy of Palm House Real Estate
82779 Old Highway #1, home for sale in Upper Matecumbe Key Islamorada 33036
$4,750,000
4 bd · 4.5 ba · built 2020
82779 Old Highway #1
Listing courtesy of Ocean Sotheby's International Realty
81250 Overseas Highway #2, home for sale in Upper Matecumbe Key Islamorada 33036
$2,485,000
3 bd · 3 ba · built 1985
81250 Overseas Highway #2
Listing courtesy of Palm House Real Estate
81801 Overseas Highway #716, home for sale in Upper Matecumbe Key Islamorada 33036
$549,500
1 bd · 1 ba · built 1988
81801 Overseas Highway #716
Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
81801 Overseas Highway #715, home for sale in Upper Matecumbe Key Islamorada 33036
$549,500
1 bd · 1 ba · built 1988
81801 Overseas Highway #715
Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
81801 Old Highway #754, home for sale in Upper Matecumbe Key Islamorada 33036
$649,000
1 bd · 1 ba · built 1988
81801 Old Highway #754
Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate
19 Avacado Street, home for sale in Upper Matecumbe Key Islamorada 33036
$13,750,000
5 bd · 6 ba · built 2019
19 Avacado Street
Listing courtesy of The Agency Florida Keys
143 N Hammock Road, home for sale in Upper Matecumbe Key Islamorada 33036
$1,199,000
3 bd · 3 ba · built 2020
143 N Hammock Road
Listing courtesy of Flat Fee MLS Realty
81801 Overseas Highway #637, home for sale in Upper Matecumbe Key Islamorada 33036
$715,000
1 bd · 1 ba · built 1988
81801 Overseas Highway #637
Listing courtesy of Ocean Sotheby's International Realty
80450 Overseas Highway #204, home for sale in Upper Matecumbe Key Islamorada 33036
$550,000
2 bd · 2 ba · built 1983
80450 Overseas Highway #204
Listing courtesy of Palm House Real Estate
1101 Mastic Street, home for sale in Upper Matecumbe Key Islamorada 33036
$6,999,000
8 bd · 6 ba · built 1984
1101 Mastic Street
Listing courtesy of LoKation Real Estate
81801 Overseas Highway ## 729, home for sale in Upper Matecumbe Key Islamorada 33036
$699,000
1 bd · 1 ba · built 1988
81801 Overseas Highway ## 729
Listing courtesy of Coldwell Banker Schmitt Key Largo
82779 Old Highway #7, home for sale in Upper Matecumbe Key Islamorada 33036
$4,000,000
4 bd · 4.5 ba · built 2020
82779 Old Highway #7
Listing courtesy of Ocean Sotheby's International Realty
82779 Old Highway #8, home for sale in Upper Matecumbe Key Islamorada 33036
$4,000,000
4 bd · 4.5 ba · built 2020
82779 Old Highway #8
Listing courtesy of Ocean Sotheby's International Realty
82779 Old Highway #15, home for sale in Upper Matecumbe Key Islamorada 33036
$3,800,000
4 bd · 4.5 ba · built 2020
82779 Old Highway #15
Listing courtesy of Ocean Sotheby's International Realty
150 List Street, home for sale in Upper Matecumbe Key Islamorada 33036
$4,499,500
1 bd · 1 ba · built 1950
150 List Street
Listing courtesy of Ocean Sotheby's International Realty
20 Avacado Street, home for sale in Upper Matecumbe Key Islamorada 33036
$15,950,000
6 bd · 7.5 ba · built 2005
20 Avacado Street
Listing courtesy of Beycome of Florida, LLC
80450 Overseas Highway #Apt 106, home for sale in Upper Matecumbe Key Islamorada 33036
$550,000
2 bd · 2.5 ba · built 1983
80450 Overseas Highway #Apt 106
Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
81486 Overseas Highway, home for sale in Upper Matecumbe Key Islamorada 33036
$22,500,000
7 bd · 8 ba · built 2026
81486 Overseas Highway
Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate
81906 Overseas Highway #2, home for sale in Upper Matecumbe Key Islamorada 33036
$2,495,000
3 bd · 3.5 ba · built 2020
81906 Overseas Highway #2
Listing courtesy of Ocean Sotheby's International Realty
189 Carroll Street, home for sale in Upper Matecumbe Key Islamorada 33036
$1,250,000
3 bd · 3 ba · built 2009
189 Carroll Street
Listing courtesy of Ocean Sotheby's International Realty
191 Carroll Street, home for sale in Upper Matecumbe Key Islamorada 33036
$1,250,000
3 bd · 3 ba · built 2009
191 Carroll Street
Listing courtesy of Ocean Sotheby's International Realty

Every home for sale in 33036 right now (27)

All 27 active listings in ZIP 33036 with a detail page, newest first, refreshed twice a day from the MLS.

Homes for sale in 33036 by price

Price bandFor saleShare
$500K–$750K726%
$750K+2074%

How to read this

Counts and medians are from active MLS listings with a 33036 mailing ZIP as of October 11, 2026; property mix Single-family 74%, Condo 26%. 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.

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