Islamorada

Upper Matecumbe Key



Upper Matecumbe Key is located within the Village of Islamorada between the islands of Windley Key and Upper Matecumbe Key. Beginning at mile marker 83.5 on the Southwestern side of Whale harbor Channel and ending at mile marker 79 at Teatable relief channel. 


Upper Matecumbe Key might be the most synonymous to Islamorada's visitors with the Islamorada Village Center being here. On Upper Matecumbe Key you'll find the Arts District on Industrial Way and the Old Highway. Home to some of our communities world renowned artists and establishments. Stop by the Florida Keys Brewery for a local brew and tour the Art Gallery by Pasta Pantaleo, The Blue Marlin Jewerly Store and many more. Every Third Thursday of the month all the stores and galleries open up for a festive time known as "The Art Walk". Many will end up at The Whistle Stop for "Whistle Pizza" or Hog Heaven for some fun tunes. For an upscale fine dining experience head over to Ziggie and Mad Dog's, Kiayo Grill or Chef Michaels. Sunsets are most well known at Pierre's Morada Bay, The Lorelei, or The Islamorada Fish Company. All of these amazing options are location on Upper Matecumbe Key! Also home to a Publix supermarket, The Trading Post, several small clothing boutiques Miss Monroe or Wild Lily and the History of Diving Museum! Spend a week or a lifetime with no two days ever being the same! 

Upper Matecumbe Key real estate trends

Average Price $3.9M
Lowest Price $30K
Highest Price $25M
Total Listings 48
Avg. Days On Market 162
Avg. Price/SQFT $1.4K

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

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96 Madeira Road, ISLAMORADA

$23,000,000

96 Madeira Road, ISLAMORADA

0 Beds 2 Baths 4,750 SqFt Commercial MLS® # 613627

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

81213 Overseas Highway, ISLAMORADA

$2,100,000

81213 Overseas Highway, ISLAMORADA

0 Beds 0 Baths 0 SqFt Commercial MLS® # 613620

Coldwell Banker Schmitt Islamorada

83201 Old Highway 405, ISLAMORADA

$1,225,000

83201 Old Highway 405, ISLAMORADA

2 Beds 2 Baths 1,275 SqFt Residential MLS® # 610929

Coastal Realty of the Florida Keys

80459 Old Highway, ISLAMORADA

$4,200,000

80459 Old Highway, ISLAMORADA

5 Beds 4 Baths 2,358 SqFt Residential MLS® # 613392

Coldwell Banker Schmitt Islamorada

81250 Overseas Highway 5, ISLAMORADA

$2,950,000

81250 Overseas Highway 5, ISLAMORADA

4 Beds 3 Baths 2,072 SqFt Residential MLS® # 613383

Coastal Realty of the Florida Keys

107 Carroll Street, ISLAMORADA

$1,350,000

107 Carroll Street, ISLAMORADA

4 Beds 3 Baths 1,459 SqFt Residential MLS® # 613295

Coldwell Banker Schmitt Islamorada

107 Carroll Street All Units, ISLAMORADA

$1,350,000

107 Carroll Street All Units, ISLAMORADA

4 Beds 3 Baths 1,459 SqFt Residential MLS® # 613294

Coldwell Banker Schmitt Islamorada

33 Pen Key Drive, ISLAMORADA

$2,800,000

33 Pen Key Drive, ISLAMORADA

3 Beds 4 Baths 4,537 SqFt Residential MLS® # 613198

Ocean Sotheby's International Realty

82768 Overseas Highway, ISLAMORADA

$25,000,000

82768 Overseas Highway, ISLAMORADA

7 Beds 10 Baths 6,935 SqFt Residential MLS® # 613195

Ocean Sotheby's International Realty

84961 Old Highway A1, ISLAMORADA

$325,000

84961 Old Highway A1, ISLAMORADA

1 Bed 1 Bath 406 SqFt Residential MLS® # 613189

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

82779 Old Highway 21, ISLAMORADA

$6,125,000

82779 Old Highway 21, ISLAMORADA

4 Beds 5 Baths 2,573 SqFt Residential MLS® # 613178

Ocean Sotheby's International Realty

82779 Old Highway 16, ISLAMORADA

$4,950,000

82779 Old Highway 16, ISLAMORADA

4 Beds 5 Baths 2,573 SqFt Residential MLS® # 613177

Ocean Sotheby's International Realty

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