Plantation Key, FL Homes

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  /44

  $1,190,000

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

  87851 Old Hwy Unit M32, Islamorada, FL 33036

  Welcome to Ocean Harbour Condominiums, one of Islamorada's most sought-after addresses where tropical luxury meets Keys serenity. Built in 1989 and meticulously maintained, this gated oceanfront community is a true hidden gem boasting lush, resort-style grounds with hundreds of swaying palms and panoramic views that stretch endlessly across the caribbean blue Atlantic ocean.This 2-bedroom, 2-bath

  

  Krissy Carnahan

  Realty ONE Group Destination (ISL)

  (786) 551-1072

  87851 Old Hwy Unit M32, Islamorada, FL 33036
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  /27

  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 983 Sq Ft
  • Condo for Rent

  87455 Old Hwy Unit 124, Islamorada, FL 33036

  Location! Location! Location! Beautiful 2 bedroom 2 bath furnished condo all on one level. Located in oceanfront building in Islamorada. Split bedroom plan, wood cabinets in kitchen as well as stainless steel appliances. Dock available for boat to load and unload. Elevator to first floor. Master has a large balcony and walk in closet. Additional storage unit on main floor. Covered parking, guest

  Anthony Garcia The Keyes Company

  87455 Old Hwy Unit 124, Islamorada, FL 33036
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  /3

  $910,000 Sold Dec 31, 2025

  81200 Overseas Hwy Unit 7, 8, 9, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,012 Sq Ft
  • Built 1962

  Last Sold Summary

  • $899/SF
  • 0 Days On Market

  Last Listing Agent Leslie Leopold Ocean Sotheby's International Realty

  81200 Overseas Hwy Unit 7, 8, 9, Islamorada, FL 33036
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  /70

  Est $6,220,462 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,846 Sq Ft

  178 Plantation Blvd, Islamorada, FL 33036

  178 Plantation Blvd, Islamorada, FL 33036
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  /43

  $1,195,000

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

  87851 Old Hwy Unit M24, Islamorada, FL 33036

  Resort-style living at Ocean Harbour. 2BR/2BA oceanfront condo with sweeping Atlantic Ocean views, new kitchen appliances, impact windows/doors and a 6,000-lb boat lift. Boat slip #36 is currently leased from the Association for $100 per month. Boat ramp, trailer storage, and covered parking space included. Enjoy the luxury island lifestyle on 12 gated acres with an oceanfront pool, beach areas,

  

  Carolyn Ambler

  American Caribbean Real Estate, Christie's International Real Estate

  (786) 807-9114

  87851 Old Hwy Unit M24, Islamorada, FL 33036
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  /31

  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 983 Sq Ft
  • Condo for Rent

  87455 Old Hwy 124 Hwy Unit 124, Plantation Key, FL 33036

  Location! Location! Location! Beautiful 2 bedroom 2 bath furnished condo all on one level. Located in oceanfrontbuilding in Islamorada. Split bedroom plan, wood cabinets in kitchen as well as stainless steel appliances. Dockavailable for boat to load and unload. Elevator to first floor. Master has a large balcony and walk in closet.Additional storage unit on main floor. Covered

  Anthony Garcia The Keyes Company

  87455 Old Hwy 124 Hwy Unit 124, Plantation Key, FL 33036
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  /49

  $990,000 Sold Aug 18, 2025

  192 E Ridge Rd, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1965

  Last Sold Summary

  • 17% Below List Price
  • $859/SF
  • 251 Days On Market

  Current Estimated Value $977,406

  Last Listing Agent Pierre Bellion Ocean Sotheby's International Realty

  192 E Ridge Rd, Islamorada, FL 33036
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  /22

  Est $1,725,968 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  120 San Marco Dr, Islamorada, FL 33036

  120 San Marco Dr, Islamorada, FL 33036
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  /100

  $29,500,000

  • 6 Beds
  • 6 Baths
  • 3,104 Sq Ft

  79775 Overseas Hwy, Islamorada, FL 33036

  A once-in-a-lifetime opportunity to own one of South Florida's most iconic properties.Welcome to Tea Table Key, a breathtaking 15-acre private island estate, accessible by car or by boat, located just minutes from downtown Islamorada and directly across from the iconic Alligator Reef Lighthouse.Surrounded by vivid turquoise waters, this extraordinary sanctuary offers complete privacy and a

  

  Pierre Bellion

  Ocean Sotheby's International Realty

  (855) 951-5685

  79775 Overseas Hwy, Islamorada, FL 33036
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  /16

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,016 Sq Ft
  • House for Rent

  87455 Old Hwy 229 Hwy Unit 87455, Plantation Key, FL 33036

  Beautifully maintained 2-bedroom, 2-bath townhouse-style condo located oceanside in the heart of Islamorada. This fully turn-key residence offers effortless island living—just arrive and enjoy. Featuring a newer A/C system (2022), updated appliances (2024), and fully replaced air ducts (2024) for optimal comfort and efficiency. Impact windows provide peace of mind, while electric blackout blinds

  Jose Medina Main Assets Corp

  87455 Old Hwy 229 Hwy Unit 87455, Plantation Key, FL 33036
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  /23

  $650,000 Sold Dec 30, 2025

  129 S Rd, Upper Matecumbe Key Islamorada, FL 33036

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft
  • Built 1958

  Last Sold Summary

  • 27% Below List Price
  • $737/SF
  • 118 Days On Market

  Last Listing Agent Wiebke Westedt LoKation Real Estate

  129 S Rd, Upper Matecumbe Key Islamorada, FL 33036
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  /47

  Est $1,430,166 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,813 Sq Ft

  87851 Old Hwy Unit K36, Islamorada, FL 33036

  87851 Old Hwy Unit K36, Islamorada, FL 33036
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  /66

  $4,695,000

  • 8 Beds
  • 4 Baths
  • 4,681 Sq Ft

  136 San Remo Dr, Islamorada, FL 33036

  Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique

  

  Shane Wilson

  Cypress Realty, Inc.

  (786) 756-7611

  136 San Remo Dr, Islamorada, FL 33036
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  /27

  $35,000 per month

  • 4 Beds
  • 4.5 Baths
  • 5,348 Sq Ft
  • House for Rent

  133 Severino Dr, Islamorada, FL 33036

  Experience luxury living at its finest in this completely renovated four-bedroom, four-bathroom home nestled in one of the most prestigious neighborhoods in the upper Keys. This stunning residence showcases exceptional craftsmanship by a renowned local builder, creating an extraordinary retreat where sophisticated design meets tropical paradise. The home features two separate living areas and

  Pete Riveiro The Firm Realty Group

  133 Severino Dr, Islamorada, FL 33036
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  /104

  $12,000,000 Sold Feb 13, 2026

  19 Avacado St, Islamorada, FL 33036

  • 5 Beds
  • 7 Baths
  • 5,489 Sq Ft
  • Built 2017

  Last Sold Summary

  • 7% Below List Price
  • $2,186/SF
  • 26 Days On Market

  Last Listing Agent Leslie Leopold Ocean Sotheby's International Realty

  19 Avacado St, Islamorada, FL 33036
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  /2

  Est $3,081,148 Not Listed For Sale

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

  80639 Old Hwy Unit 203, Islamorada, FL 33036

  80639 Old Hwy Unit 203, Islamorada, FL 33036
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  /63

  $2,750,000

  • 4 Beds
  • 4 Baths
  • 2,478 Sq Ft

  112 Leoni Dr, Islamorada, FL 33036

  PRICE IMPROVEMENT!!! LOOKING FOR THE PREMIER DEEP WATER OCEAN/BAY ACCESS COMMUNITY? Discover the epitome of waterfront living in the exclusive community of Venetian Shores in Islamorada. Renowned for its expansive 100-foot-wide canals, this neighborhood provides unparalleled access to both the Atlantic Ocean and Florida Bay via Snake Creek--ideal for boating enthusiasts. This meticulously updated

  

  Shane Wilson

  Cypress Realty, Inc.

  (786) 882-9199

  112 Leoni Dr, Islamorada, FL 33036
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  /21

  $2,800 per month

  • 2 Beds
  • 3 Baths
  • Townhouse for Rent

  87200 Overseas Hwy Unit 5, Islamorada, FL 33036

  Available for annual rental only starting November 1st. Beautifully renovated and fully furnished, this 2 bedroom, 3 bath townhouse is ready to move right in. The loft has been thoughtfully set up with two twin beds, making it a great spot for extra guests. More interior photos to come!Executive Bay Club offers everything you could want - tennis courts, a pool, and a private beach with incredible

  Courtney Jeffers Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  87200 Overseas Hwy Unit 5, Islamorada, FL 33036
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  /51

  $3,500,000 Sold Apr 15, 2025

  139 Bayview Isle Dr, Islamorada, FL 33036

  • 4 Beds
  • 4 Baths
  • 2,304 Sq Ft
  • Built 1983

  Last Sold Summary

  • 22% Below List Price
  • $1,519/SF
  • 405 Days On Market

  Current Estimated Value $3,578,785

  Last Listing Agent Brett Newman Coldwell Banker Schmitt Islamorada

  139 Bayview Isle Dr, Islamorada, FL 33036
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  /53

  Est $2,225,095 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,829 Sq Ft

  81906 Overseas Hwy, Islamorada, FL 33036

  81906 Overseas Hwy, Islamorada, FL 33036
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  /47

  $569,000

  • 2 Beds
  • 2 Baths
  • 1,343 Sq Ft

  87200 Overseas Hwy Unit 9, Islamorada, FL 33036

  Welcome to your new home in the heart of Islamorada! This desirable 2-bedroom, 2-bathroom townhouse offers an exceptional blend of comfort and luxury, perfect for those seeking a serene yet vibrant coastal lifestyle.Step inside to discover a spacious living area bathed in natural light, designed with an open-concept layout that flows seamlessly into the outdoor space. The modern kitchen is a

  

  Pierre Bellion

  Ocean Sotheby's International Realty

  (305) 930-7942

  87200 Overseas Hwy Unit 9, Islamorada, FL 33036
• 

  

  /20

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • Townhouse for Rent

  87200 Overseas Hwy Unit 1, Islamorada, FL 33036

  Prestigious Executive Bay Club corner townhouse in Islamorada. Offering 2BD/2Bth and loft. Spacious, updated & completely furnished. Beach front private community with 24 manned gate entrance, private beach to enjoy beautiful sunsets, pool, tennis courts, club house, first come first serve dock. Next door to Founder's Park offering many activities including the famous Nautical flee market. Assoc

  Isabel Ruiz Coldwell Banker Realty

  87200 Overseas Hwy Unit 1, Islamorada, FL 33036
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  /66

  $1,475,000 Sold Dec 29, 2025

  84745 Old Hwy Unit 8, Islamorada, FL 33036

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

  Last Sold Summary

  • 16% Below List Price
  • $878/SF
  • 284 Days On Market

  Last Listing Agent Ernesto Portuondo American Caribbean Real Estate, Christie's International Real Estate

  84745 Old Hwy Unit 8, Islamorada, FL 33036
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  /42

  Est $2,832,797 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,139 Sq Ft

  80639 Old Hwy Unit 403, Islamorada, FL 33036

  80639 Old Hwy Unit 403, Islamorada, FL 33036
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  /55

  $2,495,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,829 Sq Ft

  81906 Overseas Hwy Unit 2, Islamorada, FL 33036

  Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions.Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes

  

  Pierre Bellion

  Ocean Sotheby's International Realty

  (786) 917-2660

  81906 Overseas Hwy Unit 2, Islamorada, FL 33036
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  /64

  $625,000 Sold Nov 20, 2025

  87200 Overseas Hwy Unit 4, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,359 Sq Ft
  • Built 1980

  Last Sold Summary

  • 11% Below List Price
  • $460/SF
  • 230 Days On Market

  Last Listing Agent Paul Tejera Coldwell Banker Schmitt Real E

  87200 Overseas Hwy Unit 4, Islamorada, FL 33036
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  /26

  Est $332,384 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 400 Sq Ft

  84961 Old Hwy Unit 9, Islamorada, FL 33036

  84961 Old Hwy Unit 9, Islamorada, FL 33036
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  /55

  $2,750,000

  • 3 Beds
  • 3.5 Baths
  • 2,309 Sq Ft

  316 North Dr, Islamorada, FL 33036

  Simply the best location, exclusive & extremely private. This is a rare find and a single-family home that's rarely available. It's tucked away in the prestigious ''Plantation Lake Estates,'' a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach,

  Anthony Askowitz RE/MAX All Keys Real Estate

  316 North Dr, Islamorada, FL 33036
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  /64

  $1,400,000 Sold Oct 16, 2025

  87851 Old Hwy Unit M26, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $778/SF
  • 297 Days On Market

  Current Estimated Value $1,408,458

  Last Listing Agent Will Langley Langley Knight Gardner Islamorada

  87851 Old Hwy Unit M26, Islamorada, FL 33036
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  /12

  Est $274,707 Not Listed For Sale

  • 1 Bed
  • 45 Sq Ft

  96 Madeira Rd Unit 26, Islamorada, FL 33036

  96 Madeira Rd Unit 26, Islamorada, FL 33036
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  /65

  $1,375,000

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

  84745 Old Hwy Unit 4, Islamorada, FL 33036

  Peaceful Palms, a newly developed gated community offering 15 exclusive high-end townhomes in the heart of the Florida Keys. This oceanfront retreat boasts breathtaking views of the renowned Sandbar and Alligator Reef Lighthouse, providing the perfect blend of luxury, relaxation, and investment potential. Each three-bedroom, three-bathroom townhome is thoughtfully designed with expansive

  Ernesto Portuondo American Caribbean Real Estate

  84745 Old Hwy Unit 4, Islamorada, FL 33036
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  /65

  $1,250,000 Sold Jun 18, 2025

  84745 Old Hwy Unit 12, Islamorada, FL 33036

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

  Last Sold Summary

  • 17% Below List Price
  • $744/SF
  • 112 Days On Market

  Last Listing Agent Ernesto Portuondo American Caribbean Real Estate, Christie's International Real Estate

  84745 Old Hwy Unit 12, Islamorada, FL 33036
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  /32

  Est $1,944,631 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,668 Sq Ft

  87851 Old Hwy Unit P43, Islamorada, FL 33036

  87851 Old Hwy Unit P43, Islamorada, FL 33036
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  /57

  $5,700,000

  • 3 Beds
  • 2.5 Baths
  • 3,019 Sq Ft

  100 List St, Islamorada, FL 33036

  Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built by the current owner in 2014, this concrete fortress is storm-resilient and also offers a host of sustainability features including a whole-house solar array. Situated on a peninsula with 250+ feet of crystal-clear open waterfront, the gated estate

  Brett Newman Coldwell Banker Schmitt Islamorada

  100 List St, Islamorada, FL 33036
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  /41

  $1,175,000 Sold Jun 03, 2025

  137 Venetian Way, Islamorada, FL 33036

  • 5 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 1992

  Last Sold Summary

  • 16% Below List Price
  • $525/SF
  • 43 Days On Market

  Current Estimated Value $1,249,543

  Last Listing Agent Jan Keller Coldwell Banker Schmitt Islamorada

  137 Venetian Way, Islamorada, FL 33036
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  /32

  Not Listed For Sale

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

  84745 Old Hwy Unit 11, Islamorada, FL 33036

  84745 Old Hwy Unit 11, Islamorada, FL 33036
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  /72

  $5,493,000

  • 4 Beds
  • 4 Baths
  • 3,052 Sq Ft

  120 Toner Ln, Islamorada, FL 33036

  Oceanfront luxury living in Islamorada.Experience the ultimate in coastal elegance with this breathtaking 4-bedroom, 4-bath oceanfront estate in the heart of Islamorada, offering 3,052 square feet of beautifully crafted living space. Nestled on over half an acre, this three-story residence boasts unobstructed 180-degree views of the Atlantic, deep water dockage, a rare, private boat ramp and room

  Kim Thaler Ocean Sotheby's International Realty

  120 Toner Ln, Islamorada, FL 33036
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  /13

  $270,000 Sold Jan 12, 2026

  96 Madeira Rd Unit 9, Islamorada, FL 33036

  • Built 2014

  Last Sold Summary

  • 17% Below List Price
  • 151 Days On Market

  Last Listing Agent Greg Henderson Keller Williams Realty - Marco

  96 Madeira Rd Unit 9, Islamorada, FL 33036
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  /44

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  81200 Overseas Hwy Unit 5, 6, Islamorada, FL 33036

  81200 Overseas Hwy Unit 5, 6, Islamorada, FL 33036
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  /52

  $2,699,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  101 Villa Bella Dr, Islamorada, FL 33036

  Welcome to your Venetian Shores sanctuary--where coastal elegance meets effortless living. This beautifully updated residence invites you in with an open, sunlit floor plan, its living spaces wrapped in impact-rated windows and doors that frame serene tropical views. An updated kitchen features new stainless-steel appliances, including refrigerator, range, and dishwasher, complemented by a

  Alina Davis Coldwell Banker Schmitt Islamorada

  101 Villa Bella Dr, Islamorada, FL 33036

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