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 $3.7M
Lowest Price $1.8K
Highest Price $25M
Total Listings 47
Avg. Days On Market 167
Avg. Price/SQFT $1.2K

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

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83201 Old Highway 405, ISLAMORADA

$1,199,000

83201 Old Highway 405, ISLAMORADA

2 Beds 2 Baths 1,275 SqFt Residential MLS® # 616860

Coastal Realty of the Florida Keys

218 Matecumbe Avenue, ISLAMORADA

$1,199,999

218 Matecumbe Avenue, ISLAMORADA

3 Beds 3 Baths 1,071 SqFt Residential MLS® # 616707

VRNR, LLC

219 Preston Street, ISLAMORADA

$1,250,000

219 Preston Street, ISLAMORADA

4 Beds 3 Baths 1,766 SqFt Residential MLS® # 616583

Coldwell Banker Schmitt Islamorada

80639 Old Highway 201, ISLAMORADA

$3,495,000

80639 Old Highway 201, ISLAMORADA

4 Beds 5 Baths 2,539 SqFt Residential MLS® # 616523

LPT Realty, LLC

82749 Old Highway, ISLAMORADA

$7,750,000

82749 Old Highway, ISLAMORADA

3 Beds 3 Baths 1,485 SqFt Residential MLS® # 616520

Coldwell Banker Schmitt Islamorada

79901 Overseas Highway 218, ISLAMORADA

$449,900

79901 Overseas Highway 218, ISLAMORADA

1 Bed 2 Baths 827 SqFt Residential MLS® # 616424

Realty One Group Engage the Keys

108 Madeira Road, ISLAMORADA

$99,999

108 Madeira Road, ISLAMORADA

0 Beds 1 Bath 0 SqFt Business Opportunity MLS® # 616421

Coastal Realty of the Florida Keys

80201 Overseas Highway, ISLAMORADA

$9,500,000

80201 Overseas Highway, ISLAMORADA

5 Beds 6 Baths 4,764 SqFt Residential MLS® # 616417

Sea Haven Realty, Inc.

0000 Overseas Hwy, ISLAMORADA

$299,900

↓ $50,000

0000 Overseas Hwy, ISLAMORADA

0 Beds 1 Bath 0 SqFt Business Opportunity MLS® # 616289

Coastal Realty of the Florida Keys

84745 Old Highway 4, ISLAMORADA

$1,375,000

84745 Old Highway 4, ISLAMORADA

3 Beds 3 Baths 1,680 SqFt Residential MLS® # 616248

American Caribbean Real Estate, Christie's International Real Estate

81901 Overseas Highway, ISLAMORADA

$2,699,000

81901 Overseas Highway, ISLAMORADA

0 Beds 4 Baths 4,942 SqFt Commercial Sale MLS® # 616246

RE/MAX All Keys Real Estate

80939 Overseas Highway, ISLAMORADA

$350,000

80939 Overseas Highway, ISLAMORADA

0 Beds 0 Baths 37,126 SqFt Vacant Land MLS® # 616211

Century 21 All Keys Inc (KW)

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