Plantation Key, FL Homes

• 

  

  

  /16

  $1,595,000

  • Land
  • 20,908 Sq Ft
  • $3,322,917 per Acre

  229 Coral Rd, Islamorada, FL 33036

  DIRECT OCEANFRONT LOT IN ISLAMORADA WITH ACTIVE BUILDING PERMIT! A rare opportunity to own a beautifully situated direct oceanfront parcel in the heart of Islamorada, offering breathtaking panoramic views of the Atlantic Ocean. An active building permit is already in place, allowing you to begin construction of your dream waterfront estate immediately, or take advantage of the Village of

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  229 Coral Rd, Islamorada, FL 33036
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  /38

  $1,050,000

  Sold May 01, 2026

  83201 Old Hwy Unit 405, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft
  • Built 1982

  Last Sold Summary

  • 12% Below List Price
  • $824/SF
  • 197 Days On Market

  Current Estimated Value $1,061,150

  Last Listing Agent Danielle Cockerham Coastal Realty of the Florida Keys

  83201 Old Hwy Unit 405, Islamorada, FL 33036
• 

  

  

  /68

  Est $1,365,000

  Not Listed For Sale

  84745 Old Hwy Unit 14, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft
  • Built 2023

  84745 Old Hwy Unit 14, Islamorada, FL 33036

  Last Sold Summary

  • 86 Days On Market
• 

  

  

  /32

  $2,500,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,368 Sq Ft

  109 Milano Dr, Islamorada, FL 33036

  Located in the highly desirable Venetian Shores neighborhood in Islamorada, this canal front home offers 70 feet of dockage with a brand new concrete dock and seawall, making it an excellent opportunity for boating enthusiasts.Enjoy quick and convenient access to both the Atlantic Ocean and Florida Bay through Snake Creek, one of the most sought-after boating access points in the Florida Keys.

  Jamie Engel Coldwell Banker Schmitt Islamorada

  109 Milano Dr, Islamorada, FL 33036
• 

  

  

  /81

  $6,050,000

  Sold Jan 30, 2026

  118 Villa Bella Dr, Islamorada, FL 33036

  • 5 Beds
  • 5.5 Baths
  • 5,195 Sq Ft
  • Built 2021

  Last Sold Summary

  • 14% Below List Price
  • $1,165/SF
  • 239 Days On Market

  Current Estimated Value $6,227,714

  Last Listing Agent Karan Moeller Ocean Sotheby's International Realty

  118 Villa Bella Dr, Islamorada, FL 33036
• 

  /2

  Not Listed For Sale

  207 Carroll St, Islamorada, FL 33036

  • 8 Beds
  • 6 Baths
  • 4,931 Sq Ft
  • Built 1961

  207 Carroll St, Islamorada, FL 33036
• 

  

  /60

  $2,195,000

  • 3 Beds
  • 3.5 Baths
  • 4,537 Sq Ft

  33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036

  Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort‑style living awaits in this Key West-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined

  Eric Rizzo Ocean Sotheby's International Realty

  33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
• 

  

  /43

  $1,150,000

  Sold Aug 04, 2025

  116 Anglers Way, Islamorada, FL 33036

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $710/SF
  • 104 Days On Market

  Current Estimated Value $1,304,458

  Last Listing Agent Kimberly Gray LoKation Real Estate - Pompano Beach

  116 Anglers Way, Islamorada, FL 33036
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  /44

  Est $1,365,000

  Not Listed For Sale

  84745 Old Hwy Unit 15, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Built 2023

  84745 Old Hwy Unit 15, Islamorada, FL 33036

  Last Sold Summary

  • 14 Days On Market
• 

  

  /45

  $999,000

  • 2 Beds
  • 2 Baths
  • 793 Sq Ft

  84961 Old Hwy Unit 18, Islamorada, FL 33036

  Beautiful Atlantic Ocean views surround this newer concrete home featuring an open-concept floor plan with 2 bedrooms and 2 bathrooms. Tastefully furnished with a coastal flair, the spacious living area flows into a kitchen appointed with custom wood cabinetry, quartz countertops, stainless steel appliances, and a high-end water filtration system. Impact windows and doors, plantation shutters,

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  84961 Old Hwy Unit 18, Islamorada, FL 33036
• 

  

  /42

  $1,150,000

  Sold Nov 14, 2025

  130 Anglers Way, Islamorada, FL 33036

  • 2 Beds
  • 2.5 Baths
  • 1,170 Sq Ft
  • Built 2007

  Last Sold Summary

  • 12% Below List Price
  • $983/SF
  • 45 Days On Market

  Current Estimated Value $1,175,553

  Last Listing Agent Scott Ofstein Berkshire Hathaway HomeServices Florida Realty - Coral Springs

  130 Anglers Way, Islamorada, FL 33036
• 

  /2

  Est $1,150,991

  Not Listed For Sale

  84745 Old Hwy Unit 2, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft
  • Built 2023

  84745 Old Hwy Unit 2, Islamorada, FL 33036
• 

  

  /36

  $369,000

  • 2 Beds
  • 1.5 Baths
  • 989 Sq Ft

  87455 Old Hwy Unit 244, Islamorada, FL 33036

  Located in Plantation by the Sea, this Islamorada townhouse offers 2 bedrooms, 1.5 bathrooms, covered parking, and a storage unit in a gated oceanfront complex.Inside, the unit has been updated with renovated kitchen, bathrooms, and flooring. Both upstairs bedrooms feature open balconies, along with an additional balcony off the living room for added outdoor space. The upstairs layout

  Claire Johnson Exit Realty Florida Keys TAV

  87455 Old Hwy Unit 244, Islamorada, FL 33036
• 

  

  /31

  $2,900,000

  Sold Mar 05, 2026

  105 Carroll St Unit 6, Islamorada, FL 33036

  • 4 Beds
  • 4.5 Baths
  • 2,576 Sq Ft
  • Built 2023

  Last Sold Summary

  • 9% Below List Price
  • $1,126/SF
  • 1,065 Days On Market

  Last Listing Agent Ralph Sanchez Century 21 All Keys Inc (KW)

  105 Carroll St Unit 6, Islamorada, FL 33036
• 

  

  /36

  Est $391,471

  Not Listed For Sale

  87455 Old Hwy Unit 123, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 993 Sq Ft
  • Built 1977

  87455 Old Hwy Unit 123, Islamorada, FL 33036

  Last Sold Summary

  • 258 Days On Market
• 

  

  /93

  $469,000

  $121K PRICE DROP

  • 2 Beds
  • 2 Baths

  79901 Overseas Higway 204 Unit 204, Islamorada, FL 33036

  Spectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal-clear Atlantic. Perfectly situated near Bud & Mary's Marina and just minutes from Islamorada's

  79901 Overseas Higway 204 Unit 204, Islamorada, FL 33036
• 

  

  /25

  $600,000

  Sold Jun 26, 2026

  130 N Hammock Rd, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1962

  Last Sold Summary

  • 31% Below List Price
  • $436/SF
  • 30 Days On Market

  Current Estimated Value $739,138

  Last Listing Agent The Jude Lindback Te Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  130 N Hammock Rd, Islamorada, FL 33036
• 

  

  /48

  Est $1,686,796

  Not Listed For Sale

  84 Johnston Ave Unit 1, Islamorada, FL 33036

  • 3 Beds
  • 3.5 Baths
  • 1,680 Sq Ft
  • Built 2016

  84 Johnston Ave Unit 1, Islamorada, FL 33036

  Last Sold Summary

  • 75 Days On Market
• 

  

  /53

  $3,995,000

  • 5 Beds
  • 3 Baths
  • 2,640 Sq Ft

  105 Palo de Oro Dr, Islamorada, FL 33036

  Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling

  Jamie Engel Coldwell Banker Schmitt Islamorada

  105 Palo de Oro Dr, Islamorada, FL 33036
• 

  

  /40

  $405,000

  Sold Jun 29, 2026

  87465 Old Hwy Unit 102, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Below List Price
  • $392/SF
  • 168 Days On Market

  Current Estimated Value $417,001

  Last Listing Agent Anthony Garcia The Keyes Company

  87465 Old Hwy Unit 102, Islamorada, FL 33036
• 

  /2

  Est $1,126,944

  Not Listed For Sale

  87851 Old Hwy Unit K3 Boat Slip 46, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1989

  87851 Old Hwy Unit K3 Boat Slip 46, Islamorada, FL 33036
• 

  

  /20

  $475,000

  • 2 Beds
  • 1.5 Baths
  • 981 Sq Ft

  87465 Old Hwy Unit 218, Islamorada, FL 33036

  Condo for Sale - Islamorada, Plantation by The Sea 2 Bedrooms | 1.5 Bathrooms | Furnished | Two-Story Townhouse Style Experience the unique lifestyle of the Florida Keys in this spectacular furnished condo at Plantation by The Sea! Located in prestigious and convenient Islamorada, this exclusive two-story townhouse-style condo is the perfect retreat for those seeking comfort and authentic coastal

  Florentina Antigua EXP Realty LLC

  87465 Old Hwy Unit 218, Islamorada, FL 33036
• 

  

  /26

  $629,000

  Sold Apr 13, 2026

  80450 Overseas Hwy Unit 302, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1983

  Last Sold Summary

  • $484/SF
  • 9 Days On Market

  Current Estimated Value $622,760

  Last Listing Agent Jamie Engel Coldwell Banker Schmitt Islamorada

  80450 Overseas Hwy Unit 302, Islamorada, FL 33036
• 

  

  /60

  Est $1,365,000

  Not Listed For Sale

  84745 Old Hwy Unit 6, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Built 2023

  84745 Old Hwy Unit 6, Islamorada, FL 33036

  Last Sold Summary

  • 98 Days On Market
• 

  

  /34

  $299,000

  Under Contract

  • 2 Beds
  • 1.5 Baths
  • 989 Sq Ft

  87455 Old Hwy Unit 235, Islamorada, FL 33036

  ISLAMORADA OCEANFRONT LIVING! Located in the highly desirable Plantation by the Sea community, this rare opportunity allows you to create your own island retreat. Currently gutted and ready for renovation, this 2-bedroom, 1.5-bathroom townhome offers a blank canvas to design and finish to your personal taste within one of Islamorada's premier gated oceanfront communities. The floor plan features

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  87455 Old Hwy Unit 235, Islamorada, FL 33036
• 

  

  /42

  $515,000

  Sold Oct 20, 2025

  87200 Overseas Hwy Unit C3, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $381/SF
  • 27 Days On Market

  Current Estimated Value $525,709

  Last Listing Agent Joy Martin American Caribbean Real Estate, Christie's International Real Estate

  87200 Overseas Hwy Unit C3, Islamorada, FL 33036
• 

  

  /65

  Not Listed For Sale

  84745 Old Hwy Unit 12, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft
  • Built 2023

  84745 Old Hwy Unit 12, Islamorada, FL 33036

  Last Sold Summary

  • 112 Days On Market
• 

  

  /92

  $3,495,000

  • 4 Beds
  • 4.5 Baths
  • 2,539 Sq Ft

  80639 Old Hwy Unit 201, Islamorada, FL 33036

  Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open

  Jennifer Gomez EXP Realty, LLC

  80639 Old Hwy Unit 201, Islamorada, FL 33036
• 

  

  /35

  $768,000

  Sold Aug 29, 2025

  128 E Ridge Rd, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $582/SF
  • 148 Days On Market

  Current Estimated Value $867,408

  Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

  128 E Ridge Rd, Islamorada, FL 33036
• 

  /2

  Est $1,308,051

  Not Listed For Sale

  111 San Marco Dr Unit and boat slip, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1987

  111 San Marco Dr Unit and boat slip, Islamorada, FL 33036
• 

  

  /82

  $3,800,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,574 Sq Ft

  82779 Old Hwy Unit 8, Islamorada, FL 33036

  The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open,

  The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  82779 Old Hwy Unit 8, Islamorada, FL 33036
• 

  

  /13

  $1,200,000

  Sold Nov 20, 2025

  218 Matecumbe Ave, Islamorada, FL 33036

  • 3 Beds
  • 2.5 Baths
  • 1,071 Sq Ft
  • Built 1953

  Last Sold Summary

  • $1,120/SF
  • 43 Days On Market

  Current Estimated Value $1,207,634

  Last Listing Agent Rocio Hathorn VRNR, LLC

  218 Matecumbe Ave, Islamorada, FL 33036
• 

  /2

  Est $1,210,939

  Not Listed For Sale

  87462 Old Hwy, Plantation Key, FL 33036

  • Studio

  87462 Old Hwy, Plantation Key, FL 33036
• 

  

  /33

  $3,995,000

  • 5 Beds
  • 4 Baths
  • 4,014 Sq Ft

  87445 Old Hwy, Islamorada, FL 33036

  Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number

  Cheri Tindall American Caribbean Real Estate, Christie's International Real Estate

  87445 Old Hwy, Islamorada, FL 33036
• 

  

  /40

  $405,000

  Sold Jun 29, 2026

  87465 Old Hwy 102 Hwy Unit 102, Plantation Key, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Below List Price
  • $392/SF
  • 121 Days On Market

  Current Estimated Value $417,001

  Last Listing Agent Anthony Garcia The Keyes Company

  87465 Old Hwy 102 Hwy Unit 102, Plantation Key, FL 33036
• 

  

  /63

  Not Listed For Sale

  84745 Old Hwy Unit 5, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft
  • Built 2023

  84745 Old Hwy Unit 5, Islamorada, FL 33036

  Last Sold Summary

  • 46 Days On Market
• 

  

  /40

  $1,590,000

  New Construction $109K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,277 Sq Ft

  36 Park Rd, Upper Matecumbe Key Islamorada, FL 33036

  Stunning new custom pool home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space. Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features

  AJ Vetter Palm House Real Estate

  36 Park Rd, Upper Matecumbe Key Islamorada, FL 33036
• 

  

  /42

  $1,300,000

  Sold Dec 01, 2025

  143 Palermo Dr, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,568 Sq Ft
  • Built 1980

  Last Sold Summary

  • 18% Below List Price
  • $829/SF
  • 66 Days On Market

  Current Estimated Value $1,838,217

  Last Listing Agent The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  143 Palermo Dr, Islamorada, FL 33036
• 

  

  /75

  Not Listed For Sale

  28 Pen Key Club, Islamorada, FL 33036

  • 4 Beds
  • 4 Baths
  • 3,044 Sq Ft
  • Built 1964

  28 Pen Key Club, Islamorada, FL 33036

  Last Sold Summary

  • 771 Days On Market
• 

  

  /48

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  32 Park Rd, Islamorada, FL 33036

  Ideally located in the heart of Islamorada, this charming home is perfectly updated with a harmonious blend of old and new Keys characteristics and a light and airy layout and enclosed sun room that brings the lovely landscaping inside! A serene pool and oversized backyard with plenty of privacy provide book ends to lovely days of beat the heat splashes during the day and evenings of peace and

  The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  32 Park Rd, Islamorada, FL 33036

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