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 $5.1M
Lowest Price $1.8K
Highest Price $29.5M
Total Listings 50
Avg. Days On Market 185
Avg. Price/SQFT $1.5K

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

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New
Waterfront Tdr Building Right For Sale Road, ISLAMORADA

$400,000

Waterfront Tdr Building Right For Sale Road, ISLAMORADA

0 Beds 0 Baths 0 SqFt Vacant Land MLS® # 619014

Coldwell Banker Schmitt Islamorada

New
150 List Street, ISLAMORADA

$4,900,000

150 List Street, ISLAMORADA

0 Beds 0 Baths 34,000 SqFt Vacant Land MLS® # 618920

Ocean Sotheby's International Realty

New
150 List Street, ISLAMORADA

$4,900,000

150 List Street, ISLAMORADA

1 Bed 1 Bath 946 SqFt Residential MLS® # 618918

Ocean Sotheby's International Realty

80639 Old Highway 309, ISLAMORADA

$2,999,000

80639 Old Highway 309, ISLAMORADA

3 Beds 3 Baths 2,275 SqFt Residential MLS® # 618876

Ocean Sotheby's International Realty

20 Avacado Street, ISLAMORADA

$15,950,000

20 Avacado Street, ISLAMORADA

6 Beds 8 Baths 6,680 SqFt Residential MLS® # 618816

Beycome of Florida, LLC

105 Palm Avenue, ISLAMORADA

$4,600,000

105 Palm Avenue, ISLAMORADA

1 Bed 4 Baths 2,965 SqFt Commercial Sale MLS® # 618814

Paradise Florida Keys Real Estate, a Luxury Brand

96 Madeira Road, ISLAMORADA

$18,000,000

96 Madeira Road, ISLAMORADA

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

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

80450 Overseas Highway Apt 106, ISLAMORADA

$585,000

80450 Overseas Highway Apt 106, ISLAMORADA

2 Beds 3 Baths 1,303 SqFt Residential MLS® # 618784

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

81486 Overseas Highway, ISLAMORADA

$22,500,000

81486 Overseas Highway, ISLAMORADA

7 Beds 9 Baths 8,878 SqFt Residential MLS® # 618525

American Caribbean Real Estate, Christie's International Real Estate

82779 Old Highway 14, ISLAMORADA

$3,800,000

82779 Old Highway 14, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 618400

Ocean Sotheby's International Realty

33 Pen Key Drive, ISLAMORADA

$2,495,000

33 Pen Key Drive, ISLAMORADA

3 Beds 4 Baths 4,537 SqFt Residential MLS® # 618190

Ocean Sotheby's International Realty

Open House
79901 Overseas Highway 204, ISLAMORADA

$569,000

↓ $21,000

79901 Overseas Highway 204, ISLAMORADA

2 Beds 2 Baths 981 SqFt Residential MLS® # 618199

Venture Realty Group

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