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 $4.7M
Lowest Price $1.2K
Highest Price $29.5M
Total Listings 39
Avg. Days On Market 156
Avg. Price/SQFT $1.6K

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

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New
81001 Overseas Highway, Upper Matecumbe Key Islamorada

$235,000

↑ $232,000

81001 Overseas Highway, Upper Matecumbe Key Islamorada

0 Beds 0 Baths 2,512 SqFt Commercial Lease MLS® # 621122

RE/MAX All Keys Real Estate

New
82779 Old Highway 1, Upper Matecumbe Key Islamorada

$4,750,000

82779 Old Highway 1, Upper Matecumbe Key Islamorada

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 620933

Ocean Sotheby's International Realty

New
84961 Old Highway A1, Windley Key

$439,000

84961 Old Highway A1, Windley Key

1 Bed 1 Bath 406 SqFt Residential MLS® # 620845

Ocean Sotheby's International Realty

New
81250 Overseas Highway 2, Upper Matecumbe Key Islamorada

$2,485,000

81250 Overseas Highway 2, Upper Matecumbe Key Islamorada

3 Beds 3 Baths 2,072 SqFt Residential MLS® # 620704

Palm House Real Estate

81801 Old Highway 754, Upper Matecumbe Key Islamorada

$649,000

81801 Old Highway 754, Upper Matecumbe Key Islamorada

1 Bed 1 Bath 550 SqFt Residential MLS® # 620677

American Caribbean Real Estate, Christie's International Real Estate

New
81801 Overseas Highway 715, Upper Matecumbe Key Islamorada

$549,500

81801 Overseas Highway 715, Upper Matecumbe Key Islamorada

1 Bed 1 Bath 358 SqFt Residential MLS® # 620633

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

New
81801 Overseas Highway 716, Upper Matecumbe Key Islamorada

$549,500

81801 Overseas Highway 716, Upper Matecumbe Key Islamorada

1 Bed 1 Bath 358 SqFt Residential MLS® # 620629

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

New
19 Avacado Street, Upper Matecumbe Key Islamorada

$13,750,000

19 Avacado Street, Upper Matecumbe Key Islamorada

5 Beds 7 Baths 5,489 SqFt Residential MLS® # 620590

The Agency Florida Keys

143 N Hammock Road, Upper Matecumbe Key Islamorada

$1,199,000

143 N Hammock Road, Upper Matecumbe Key Islamorada

3 Beds 3 Baths 2,022 SqFt Residential MLS® # 619848

Flat Fee MLS Realty

81801 Overseas Highway 637, Upper Matecumbe Key Islamorada

$715,000

↓ $10,000

81801 Overseas Highway 637, Upper Matecumbe Key Islamorada

1 Bed 1 Bath 550 SqFt Residential MLS® # 619786

Ocean Sotheby's International Realty

80450 Overseas Highway 204, Upper Matecumbe Key Islamorada

$595,000

↓ $20,000

80450 Overseas Highway 204, Upper Matecumbe Key Islamorada

2 Beds 2 Baths 1,261 SqFt Residential MLS® # 619711

Palm House Real Estate

1101 Mastic Street, Upper Matecumbe Key Islamorada

$6,999,000

↓ $496,000

1101 Mastic Street, Upper Matecumbe Key Islamorada

8 Beds 6 Baths 3,649 SqFt Residential MLS® # 619673

Venture Realty Group

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