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Upper Matecumbe Key Islamorada, FL
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45 Properties Available

45 Properties Available

The average price in the selected areas has remained stable. Learn more
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81801 Old HWY 754, Upper Matecumbe Key Islamorada, FL 33036
1/47
Active

$649,000

1 Bed1 Bath550 SqFt

81801 Old HWY 754, Upper Matecumbe Key Islamorada, FL 33036

MLS# 620677

Listed by KELLY K SHAW PA American Caribbean Real Estate, Christie's International Real Estate

81486 Overseas HWY, Upper Matecumbe Key Islamorada, FL 33036
1/26
Active

$22,500,000

7 Beds9 Baths8,878 SqFt

81486 Overseas HWY, Upper Matecumbe Key Islamorada, FL 33036

MLS# 618525

Listed by KELLY K SHAW PA American Caribbean Real Estate, Christie's International Real Estate

83265 Old HWY, Upper Matecumbe Key Islamorada, FL 33036
1/29
Open Sun 2PM-3PM

$24,000

3 Beds2 Baths1,686 SqFt

83265 Old HWY, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621767

Listed by Tracey E. Petrusha LoKation Real Estate

1101 Mastic ST, Upper Matecumbe Key Islamorada, FL 33036
1/132
Open Sun 12PM-3PM
3D

$5,999,000

8 Beds6 Baths3,649 SqFt

1101 Mastic ST, Upper Matecumbe Key Islamorada, FL 33036

MLS# 619673

Listed by Tracey E. Petrusha LoKation Real Estate

189 Carroll ST, Upper Matecumbe Key Islamorada, FL 33036
1/37
New

$1,250,000

3 Beds3 Baths1,525 SqFt

189 Carroll ST, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621912

Listed by James V. Mooney Jr. P.A. Ocean Sotheby's International Realty

191 Carroll ST, Upper Matecumbe Key Islamorada, FL 33036
1/40
New

$1,250,000

3 Beds3 Baths1,550 SqFt

191 Carroll ST, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621911

Listed by James V. Mooney Jr. P.A. Ocean Sotheby's International Realty

16 Avacado ST, Upper Matecumbe Key Islamorada, FL 33036
1/182
Active

$23,500,000

9 Beds11 Baths7,372 SqFt

16 Avacado ST, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621766

Listed by AJ Vetter Palm House Real Estate

79901 Overseas HWY 217, Upper Matecumbe Key Islamorada, FL 33036
1/31
Active

$399,000

1 Bed1 Bath827 SqFt

79901 Overseas HWY 217, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621774

Listed by Claire Johnson Coastal Realty of the Florida Keys

79901 Overseas HWY 410, Upper Matecumbe Key Islamorada, FL 33036
1/24
Active

$659,000

2 Beds2 Baths981 SqFt

79901 Overseas HWY 410, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621648

Listed by Natalie Biondoletti Coastal Realty of the Florida Keys

82719 Old HWY, Upper Matecumbe Key Islamorada, FL 33036
1/62
Active

$24,995,000

7 Beds11 Baths10,182 SqFt

82719 Old HWY, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621626

Listed by Pamela DiMartino Coldwell Banker Realty - Aventura

18 Pen Key Club, Upper Matecumbe Key Islamorada, FL 33036
1/64
Active Under Contract
3D

$3,900,000

3 Beds3 Baths2,600 SqFt

18 Pen Key Club, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621575

Listed by Christy Hughes Coldwell Banker Schmitt Islamorada

154 Carroll ST, Upper Matecumbe Key Islamorada, FL 33036
1/62
Active

$2,699,000

4 Beds4 Baths3,315 SqFt

154 Carroll ST, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621562

Listed by Eric M. Rizzo Ocean Sotheby's International Realty

79901 Overseas HWY APT 220, Upper Matecumbe Key Islamorada, FL 33036
1/16
Active

$2,400

1 Bed2 Baths827 SqFt

79901 Overseas HWY APT 220, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621541

Listed by Jamie Gunthner Real Estate Sales Force, Inc.

33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036
1/59
Active

$2,195,000

3 Beds4 Baths4,537 SqFt

33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621487

Listed by Eric M. Rizzo Ocean Sotheby's International Realty

36 Park RD, Upper Matecumbe Key Islamorada, FL 33036
1/41
Active

$1,495,000

4 Beds3 Baths2,277 SqFt

36 Park RD, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621431

Listed by AJ Vetter Palm House Real Estate

80902 Old HWY, Upper Matecumbe Key Islamorada, FL 33036
1/60
Active

$2,950,000

4 Beds3 Baths3,550 SqFt

80902 Old HWY, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621398

Listed by Caroline Hendrix Coldwell Banker Schmitt Islamorada

81250 Overseas HWY 5, Upper Matecumbe Key Islamorada, FL 33036
1/67
Active

$2,290,000

4 Beds3 Baths2,464 SqFt

81250 Overseas HWY 5, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621329

Listed by AJ Vetter Palm House Real Estate

80939 Overseas HWY, Upper Matecumbe Key Islamorada, FL 33036
1/24
Active

$3,900,000

7 Beds7 Baths0.85 Acres Lot

80939 Overseas HWY, Upper Matecumbe Key Islamorada, FL 33036

MLS# 621298

Listed by Daniel Sanchez Century 21 All Keys Inc (KW)

82779 Old HWY 1, Upper Matecumbe Key Islamorada, FL 33036
1/80
Active

$4,750,000

4 Beds5 Baths2,574 SqFt

82779 Old HWY 1, Upper Matecumbe Key Islamorada, FL 33036

MLS# 620933

Listed by Sabrina Wampler & Sarah Ewald Ocean Sotheby's International Realty

81250 Overseas HWY 2, Upper Matecumbe Key Islamorada, FL 33036
1/34
Active

$2,485,000

3 Beds3 Baths2,072 SqFt

81250 Overseas HWY 2, Upper Matecumbe Key Islamorada, FL 33036

MLS# 620704

Listed by Drew Moret Palm House Real Estate

81801 Overseas HWY 715, Upper Matecumbe Key Islamorada, FL 33036
1/34
Active

$549,500

1 Bed1 Bath358 SqFt

81801 Overseas HWY 715, Upper Matecumbe Key Islamorada, FL 33036

MLS# 620633

Listed by Lisa Frins P.A. Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

81801 Overseas HWY 716, Upper Matecumbe Key Islamorada, FL 33036
1/43
Active

$549,500

1 Bed1 Bath358 SqFt

81801 Overseas HWY 716, Upper Matecumbe Key Islamorada, FL 33036

MLS# 620629

Listed by Lisa Frins P.A. Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

19 Avacado ST, Upper Matecumbe Key Islamorada, FL 33036
1/139
Pending
3D

$13,750,000

5 Beds7 Baths5,489 SqFt

19 Avacado ST, Upper Matecumbe Key Islamorada, FL 33036

MLS# 620590

Listed by Lisa Swanson The Agency Florida Keys

143 Hammock RD, Upper Matecumbe Key Islamorada, FL 33036
1/33
Active

$1,199,000

3 Beds3 Baths2,022 SqFt

143 Hammock RD, Upper Matecumbe Key Islamorada, FL 33036

MLS# 619848

Listed by Stephen Hachey Flat Fee MLS Realty

  • 1
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acre logo whtie side
American Caribbean Christie's International Real Estate

Lorie LaLonde License ID: 3211570

+1(305) 522-1837 lorie@lorielalonde.com

81800 Overseas Hwy, Islamorada, FL 33036-3606, USA

 

305-664-4966

81800 Overseas Highway, Islamorada, Florida, 33036, USA

Sales@americancaribbean.com

  • Home
  • Global Partners
    1. Christie's International Real Estate
    2. Who's Who in Luxury Real Estate
  • Buy
    1. Featured Listings
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    3. All Listings
  • About
    1. About Lorie
    2. About Us
    3. Contact Lorie
    4. Reviews
  • Sell
    1. Sell My Home
    2. Home Valuation
  • Market Snapshot

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Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
acre logo whtie side
American Caribbean Christie's International Real Estate

Lorie LaLonde License ID: 3211570

+1(305) 522-1837 lorie@lorielalonde.com

81800 Overseas Hwy, Islamorada, FL 33036-3606, USA

 

305-664-4966

81800 Overseas Highway, Islamorada, Florida, 33036, USA

Sales@americancaribbean.com

  • Home
  • Global Partners
    1. Christie's International Real Estate
    2. Who's Who in Luxury Real Estate
  • Buy
    1. Featured Listings
    2. Featured Listings(copy)
    3. All Listings
  • About
    1. About Lorie
    2. About Us
    3. Contact Lorie
    4. Reviews
  • Sell
    1. Sell My Home
    2. Home Valuation
  • Market Snapshot

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.