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 $3.1M
Lowest Price $2.1K
Highest Price $25M
Total Listings 44
Avg. Days On Market 126
Avg. Price/SQFT $1K

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

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New
79901 Overseas Highway 404, ISLAMORADA

$599,900

79901 Overseas Highway 404, ISLAMORADA

2 Beds 2 Baths 981 SqFt Residential MLS® # 610888

Realty One Group Engage the Keys

82779 Old Highway 13, ISLAMORADA

$5,500,000

82779 Old Highway 13, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 610874

Ocean Sotheby's International Realty

82779 Old Highway 15, ISLAMORADA

$4,950,000

82779 Old Highway 15, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 610875

Ocean Sotheby's International Realty

82779 Old Highway 22, ISLAMORADA

$6,125,000

82779 Old Highway 22, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 610876

Ocean Sotheby's International Realty

82779 Old Highway 4, ISLAMORADA

$5,500,000

82779 Old Highway 4, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 610872

Ocean Sotheby's International Realty

82779 Old Highway 9, ISLAMORADA

$5,250,000

82779 Old Highway 9, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 610873

Ocean Sotheby's International Realty

82779 Old Highway 2, ISLAMORADA

$5,950,000

82779 Old Highway 2, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 610871

Ocean Sotheby's International Realty

New
82238 Overseas Highway, ISLAMORADA

$10,750,000

82238 Overseas Highway, ISLAMORADA

6 Beds 7 Baths 6,866 SqFt Residential MLS® # 610851

Ocean Sotheby's International Realty

81888 Overseas Highway C1, ISLAMORADA

$2,750

81888 Overseas Highway C1, ISLAMORADA

0 Beds 0 Baths 7,810 SqFt Commercial MLS® # 610741

Ocean Sotheby's International Realty

87200 Overseas Highway V9, ISLAMORADA

$995,000

87200 Overseas Highway V9, ISLAMORADA

3 Beds 2 Baths 1,355 SqFt Residential MLS® # 610663

Premier Properties

84961 Old Highway 19, ISLAMORADA

$599,000

↓ $40,000

84961 Old Highway 19, ISLAMORADA

0 Beds 0 Baths 1,495 SqFt Vacant Land MLS® # 610652

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

153 List Street, ISLAMORADA

$599,000

153 List Street, ISLAMORADA

1 Bed 1 Bath 525 SqFt Residential MLS® # 610464

Coastal Realty of the Florida Keys

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