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 122
Avg. Price/SQFT $924

Property Types (active listings)

Browse Upper Matecumbe Real Estate Listings

Click the links below to sort results by price range.

Sort by:
28 Pen Key Drive, ISLAMORADA

$4,195,000

↓ $255,000

28 Pen Key Drive, ISLAMORADA

4 Beds 4 Baths 3,044 SqFt Residential MLS® # 599529

Coldwell Banker Schmitt Islamorada

105 Carroll Street 6, ISLAMORADA

$3,195,000

↓ $5,000

105 Carroll Street 6, ISLAMORADA

4 Beds 5 Baths 2,576 SqFt Residential MLS® # 604613

Century 21 All Keys Inc (KW)

80639 Old Highway 204, ISLAMORADA

$3,195,000

↓ $55,000

80639 Old Highway 204, ISLAMORADA

4 Beds 5 Baths 2,539 SqFt Residential MLS® # 605011

Coldwell Banker Schmitt Islamorada

80639 Old Highway 308, ISLAMORADA

$1,875,000

↓ $100,000

80639 Old Highway 308, ISLAMORADA

3 Beds 3 Baths 2,251 SqFt Residential MLS® # 605738

Ocean Sotheby's International Realty

80639 Old Highway 201, ISLAMORADA

$3,500,000

80639 Old Highway 201, ISLAMORADA

4 Beds 5 Baths 2,539 SqFt Residential MLS® # 606541

Coldwell Banker Schmitt Islamorada

84961 Old Highway 26, ISLAMORADA

$695,000

↓ $44,000

84961 Old Highway 26, ISLAMORADA

3 Beds 1 Bath 400 SqFt Residential MLS® # 606618

Coldwell Banker Schmitt Key Largo

83283 Old Highway, ISLAMORADA

$14,000,000

83283 Old Highway, ISLAMORADA

7 Beds 9 Baths 6,696 SqFt Residential MLS® # 606946

Coldwell Banker Schmitt Islamorada

82900 Old Highway, ISLAMORADA

$6,750,000

82900 Old Highway, ISLAMORADA

0 Beds 0 Baths 339,102 SqFt Vacant Land MLS® # 607307

Ocean Sotheby's International Realty

80925 Overseas Highway, ISLAMORADA

$90,000

↓ $39,000

80925 Overseas Highway, ISLAMORADA

0 Beds 2 Baths 11,747 SqFt Business Opportunity MLS® # 607355

Berkshire Hathaway Knight & Gardner

80450 Overseas Highway 101, ISLAMORADA

$589,000

80450 Overseas Highway 101, ISLAMORADA

2 Beds 3 Baths 1,232 SqFt Residential MLS® # 607429

Coastal Realty of the Florida Keys

36 Park Road, ISLAMORADA

$650,000

36 Park Road, ISLAMORADA

0 Beds 0 Baths 11,317 SqFt Vacant Land MLS® # 607549

Coastal Realty of the Florida Keys

81801 Overseas Highway 727, ISLAMORADA

$649,000

↓ $31,000

81801 Overseas Highway 727, ISLAMORADA

1 Bed 1 Bath 358 SqFt Residential MLS® # 607644

Ocean Sotheby's International Realty

Browse all Florida Keys islands here


Pink sunset over waterfront with pier in the Florida Keys

What's my Florida Keys home worth?

Use our Home Evaluation tool to get a free estimated market value of your Florida Keys home. We'll calculate a home valuation based on similar properties in your area.


Better Homes and Gardens Florida Keys logo

Your Florida Keys Home Search Starts With Destinations.

Local agents, professional service. Better Homes and Gardens Real Estate Destinations
can help you find your dream home in the Florida Keys. Trust the team that puts clients first.

Let's Chat