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 $2.4M
Lowest Price $2.1K
Highest Price $25M
Total Listings 48
Avg. Days On Market 109
Avg. Price/SQFT $895

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

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New
81250 Overseas Highway 2, ISLAMORADA

$2,850,000

81250 Overseas Highway 2, ISLAMORADA

3 Beds 3 Baths 2,072 SqFt Residential MLS® # 609215

Coastal Realty of the Florida Keys

New
81801 Overseas Highway 709, ISLAMORADA

$775,000

81801 Overseas Highway 709, ISLAMORADA

1 Bed 1 Bath 550 SqFt Residential MLS® # 609208

Coldwell Banker Schmitt Islamorada

New
207 Russell Street A, ISLAMORADA

$3,200

207 Russell Street A, ISLAMORADA

2 Beds 1 Bath 928 SqFt Rental MLS® # 609207

Realty One Group Engage the Keys

New
207 Russell Street B, ISLAMORADA

$2,200

207 Russell Street B, ISLAMORADA

1 Bed 1 Bath 496 SqFt Rental MLS® # 609206

Realty One Group Engage the Keys

210 Palm Avenue, ISLAMORADA

$1,200,000

210 Palm Avenue, ISLAMORADA

3 Beds 2 Baths 2,912 SqFt Residential MLS® # 605023

RE/MAX Advance Realty Inc.

79901 Overseas Highway 101, ISLAMORADA

$400,000

79901 Overseas Highway 101, ISLAMORADA

1 Bed 1 Bath 409 SqFt Residential MLS® # 609064

Realty ONE Group Destination (ISL)

18 Avacado Street, ISLAMORADA

$5,875,000

18 Avacado Street, ISLAMORADA

5 Beds 4 Baths 2,845 SqFt Residential MLS® # 608986

Ocean Sotheby's International Realty

81801 Overseas Highway 751, ISLAMORADA

$649,000

81801 Overseas Highway 751, ISLAMORADA

1 Bed 1 Bath 358 SqFt Residential MLS® # 608876

Ocean Sotheby's International Realty

81801 Overseas Highway 612, ISLAMORADA

$795,000

81801 Overseas Highway 612, ISLAMORADA

1 Bed 1 Bath 550 SqFt Residential MLS® # 608878

Ocean Sotheby's International Realty

107 Carroll Street A And B, ISLAMORADA

$1,650,000

107 Carroll Street A And B, ISLAMORADA

3 Beds 3 Baths 1,459 SqFt Residential MLS® # 608826

Coldwell Banker Schmitt Islamorada

80459 Old Highway, ISLAMORADA

$5,250,000

80459 Old Highway, ISLAMORADA

5 Beds 4 Baths 2,358 SqFt Residential MLS® # 608791

Coldwell Banker Schmitt Islamorada

81801 Overseas Highway 631, ISLAMORADA

$624,000

↓ $25,000

81801 Overseas Highway 631, ISLAMORADA

1 Bed 1 Bath 358 SqFt Residential MLS® # 608764

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

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