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 $4.5M
Lowest Price $1.8K
Highest Price $29.5M
Total Listings 47
Avg. Days On Market 147
Avg. Price/SQFT $1.4K

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

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New
82260 Overseas Highway, ISLAMORADA

$1,150,000

82260 Overseas Highway, ISLAMORADA

3 Beds 3 Baths 2,808 SqFt Residential MLS® # 615095

Sutter & Nugent, Inc.

New
80151 Overseas Highway, ISLAMORADA

$4,250,000

80151 Overseas Highway, ISLAMORADA

2 Beds 2 Baths 1,578 SqFt Residential MLS® # 615069

Serhant Florida LLC - Delray Beach Office

81250 Overseas Highway 2, ISLAMORADA

$2,850,000

81250 Overseas Highway 2, ISLAMORADA

3 Beds 3 Baths 2,072 SqFt Residential MLS® # 615038

Palm House Real Estate

83201 Old Highway 409, ISLAMORADA

$1,200,000

83201 Old Highway 409, ISLAMORADA

2 Beds 2 Baths 1,275 SqFt Residential MLS® # 614971

Palm House Real Estate

81216 Old Highway, ISLAMORADA

$1,300,000

81216 Old Highway, ISLAMORADA

3 Beds 3 Baths 960 SqFt Residential MLS® # 614871

Coldwell Banker Schmitt Islamorada

176 N Carroll Street, ISLAMORADA

$5,250

176 N Carroll Street, ISLAMORADA

5 Beds 3 Baths 2,236 SqFt Rental Long Term MLS® # 614749

Realty One Group Engage the Keys

82762 Overseas Highway 3, ISLAMORADA

$2,695,000

82762 Overseas Highway 3, ISLAMORADA

4 Beds 4 Baths 2,728 SqFt Residential MLS® # 614741

Coldwell Banker Schmitt Islamorada

100 Seashore Drive, ISLAMORADA

$1,600,000

100 Seashore Drive, ISLAMORADA

3 Beds 2 Baths 2,128 SqFt Residential MLS® # 614725

American Caribbean Real Estate, Christie's International Real Estate

81801 Overseas Highway 726, ISLAMORADA

$695,000

81801 Overseas Highway 726, ISLAMORADA

1 Bed 1 Bath 550 SqFt Residential MLS® # 614669

Coldwell Banker Schmitt Islamorada

82719 Old Highway, ISLAMORADA

$29,500,000

82719 Old Highway, ISLAMORADA

5 Beds 10 Baths 8,680 SqFt Residential MLS® # 614564

Serhant Florida LLC - Delray Beach Office

82779 Old Highway 8, ISLAMORADA

$4,250,000

82779 Old Highway 8, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 614560

Serhant Florida LLC - Delray Beach Office

82779 Old Highway 3, ISLAMORADA

$5,990,000

82779 Old Highway 3, ISLAMORADA

4 Beds 5 Baths 2,574 SqFt Residential MLS® # 614561

Serhant Florida LLC - Delray Beach Office

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