Plantation Key, FL Homes

• 

  

  

  /28

  $1,385,000

  $140K PRICE DROP

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

  87851 Old Hwy Unit M42, Islamorada, FL 33036

  Ocean Harbour condo with Atlantic ocean views and a boat slip in Islamorada. 3 bedroom, 2 bathroom luxury condo offers expansive ocean views and comfortable living space. The thoughtfully redesigned floor plan enhances the primary suite layout, adds a third bedroom, updates both bathrooms, and expands the living area by enclosing the porch as additional interior living space; maximizing

  

  Carolyn Ambler

  American Caribbean Real Estate, Christie's International Real Estate

  87851 Old Hwy Unit M42, Islamorada, FL 33036
• 

  

  

  /26

  $2,850 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Condo for Rent

  87465 Old Hwy 209 Hwy Unit 209, Plantation Key, FL 33036

  LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY ON MILLIONAIRES' ROW IN PLANTATION BY THE SEA! LOCATED IN ISLAMORADA IN THE BEAUTIFUL FLORIDA KEYS! TURN KEY STUNNING AND REMODELED, FULLY FURNISHED 2 BEDROOM 1.5 BATH CONDO IS MOVE IN READY! ALL YOU NEED ARE YOUR CLOTHES AND TOOTHBRUSH! GLASSWARE, STEMWARE, SHEETS, TOWELS, ALL ARE FURNISHED FOR YOU! BEAUTIFUL OPEN CONCEPT KITCHEN HAS A

  Anthony Garcia The Keyes Company

  87465 Old Hwy 209 Hwy Unit 209, Plantation Key, FL 33036
• 

  

  

  /3

  $2,600,000

  Sold Mar 26, 2026

  152 Giardino Dr, Islamorada, FL 33036

  • 2 Beds
  • 3 Baths
  • 1,832 Sq Ft
  • Built 1989

  Last Sold Summary

  • $1,419/SF
  • 0 Days On Market

  Current Estimated Value $2,628,616

  Last Listing Agent Carolyn Ambler American Caribbean Real Estate, Christie's International Real Estate

  152 Giardino Dr, Islamorada, FL 33036
• 

  

  

  /67

  Est $3,790,640

  Not Listed For Sale

  116 Gulfside Dr, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,846 Sq Ft
  • Built 1987

  116 Gulfside Dr, Islamorada, FL 33036

  Last Sold Summary

  • 177 Days On Market
• 

  

  

  /19

  $899,000

  • 1 Bed
  • 1 Bath
  • 468 Sq Ft

  84961 Old Hwy Unit LOT 27, Islamorada, FL 33036

  Memories begin here. Tucked along the ocean's edge and offering the kind of lifestyle buyers spend years searching for, this one-of-a-kind oceanfront retreat delivers the ultimate Florida Keys escape all for under $1M! What is unique about this property is the 40' protected boat slip located right out your back door. This unit is conveniently located offering quick access to the ocean or the bay

  

  Lorie LaLonde

  American Caribbean Real Estate, Christie's International Real Estate

  84961 Old Hwy Unit LOT 27, Islamorada, FL 33036
• 

  

  /29

  $5,400

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,345 Sq Ft
  • Condo for Rent

  87001 Overseas Hwy Unit SI FL2-ID1539601P, Islamorada, FL 33036

  The advertised rate of $5,400/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 15, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  87001 Overseas Hwy Unit SI FL2-ID1539601P, Islamorada, FL 33036
• 

  

  /56

  $880,000

  Sold Apr 15, 2026

  82260 Overseas Hwy, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 2,314 Sq Ft
  • Built 1964

  Last Sold Summary

  • 22% Below List Price
  • $380/SF
  • 276 Days On Market

  Current Estimated Value $955,474

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

  82260 Overseas Hwy, Islamorada, FL 33036
• 

  

  /30

  Est $393,937

  Not Listed For Sale

  84961 Old Hwy Unit A1, Islamorada, FL 33036

  • 1 Bed
  • 1 Bath
  • 406 Sq Ft
  • Built 1948

  84961 Old Hwy Unit A1, Islamorada, FL 33036

  Last Sold Summary

  • 1 Day On Market
• 

  

  /66

  $4,445,000

  $250K PRICE DROP

  • 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.

  136 San Remo Dr, Islamorada, FL 33036
• 

  

  /27

  $2,850 Per Month

  • 2 Beds
  • 1.5 Baths
  • 989 Sq Ft
  • Condo for Rent

  87455 Old Hwy 245 Hwy Unit 245, Plantation Key, FL 33036

  Location! Location! Location! Beautiful 2 bedroom 2 bath furnished condo. Located in oceanfrontbuilding in Islamorada. 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 parking, heated pool, 400 ft. fishing pier/dock for loading and unloading only, club house, gym,

  Anthony Garcia The Keyes Company

  87455 Old Hwy 245 Hwy Unit 245, Plantation Key, FL 33036
• 

  

  /57

  $5,400,000

  Sold May 08, 2026

  100 List St, Islamorada, FL 33036

  • 3 Beds
  • 2.5 Baths
  • 3,019 Sq Ft
  • Built 2014

  Last Sold Summary

  • 8% Below List Price
  • $1,789/SF
  • 138 Days On Market

  Current Estimated Value $5,445,685

  Last Listing Agent Brett Newman Coldwell Banker Schmitt Islamorada

  100 List St, Islamorada, FL 33036
• 

  

  /17

  Est $960,955

  Not Listed For Sale

  33 Flamingo Hammock Rd, Islamorada, FL 33036

  33 Flamingo Hammock Rd, Islamorada, FL 33036

  Last Sold Summary

  • 92 Days On Market
• 

  

  /78

  $1,295,000

  • 6 Beds
  • 3 Baths
  • 2,684 Sq Ft

  81160 Old Hwy, Islamorada, FL 33036

  3 plex ( 3 separate units) in the heart of downtown Islamorada. A total of 6 bedrooms and 3 baths. Two of the units are remodeled. Walk to Shopping, Boutiques, Bars, Restaurants, World Wide Sportsman/Bas Pro Shops, Florida Keys Brewery. Or take your street legal golf cart. Currently fully rented on annual leases. Would make great 30 days rentals or really great employee housing. Do not miss this

  

  Shane Wilson

  Cypress Realty, Inc.

  81160 Old Hwy, Islamorada, FL 33036
• 

  

  /20

  $4,500 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
• 

  

  /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
• 

  

  /26

  Est $338,541

  Not Listed For Sale

  84961 Old Hwy Unit 9, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 400 Sq Ft
  • Built 2023

  84961 Old Hwy Unit 9, Islamorada, FL 33036

  Last Sold Summary

  • 14 Days On Market
• 

  /2

  $450,000

  $25K PRICE DROP

  1 Waterfront Tdr, Lower Matecumbe, FL 33036

  Start building immediately with this Waterfront TDR for use in the Village of Islamorada for a Single Family Residence on the water!Buyer has to verify with the Village if TDR is applicable to vacant lot.Buyer has to pay all closing costs associated with the transaction and the transfer fees to the Village.The letter of Development Rights Determination from the Village is on file and

  

  Bettina Garber

  Ocean Sotheby's International Realty

  1 Waterfront Tdr, Lower Matecumbe, FL 33036
• 

  

  /26

  $2,850 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Condo for Rent

  87465 Old Hwy 209 Hwy 209 Unit 209, Plantation Key, FL 33036

  LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY ON MILLIONAIRES' ROW IN PLANTATION BY THE SEA! LOCATED IN ISLAMORADA IN THE BEAUTIFUL FLORIDA KEYS! TURN KEY STUNNING AND REMODELED, FULLY FURNISHED 2 BEDROOM 1.5 BATH CONDO IS MOVE IN READY! ALL YOU NEED ARE YOUR CLOTHES AND TOOTHBRUSH! GLASSWARE, STEMWARE, SHEETS, TOWELS, ALL ARE FURNISHED FOR YOU! BEAUTIFUL OPEN CONCEPT KITCHEN HAS A

  Anthony Garcia The Keyes Company

  87465 Old Hwy 209 Hwy 209 Unit 209, Plantation Key, FL 33036
• 

  

  /52

  $2,350,000

  Sold Mar 13, 2026

  101 Villa Bella Dr, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1986

  Last Sold Summary

  • 15% Below List Price
  • $1,506/SF
  • 71 Days On Market

  Current Estimated Value $2,412,875

  Last Listing Agent Alina Davis Coldwell Banker Schmitt Islamorada

  101 Villa Bella Dr, Islamorada, FL 33036
• 

  

  /12

  Est $280,353

  Not Listed For Sale

  96 Madeira Rd Unit 26, Islamorada, FL 33036

  • 1 Bed
  • 45 Sq Ft
  • Built 2014

  96 Madeira Rd Unit 26, Islamorada, FL 33036

  Last Sold Summary

  • 21 Days On Market
• 

  

  /100

  $29,500,000

  Under Contract

  • 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 famous Alligator Reef Lighthouse. Surrounded by vivid turquoise waters, this extraordinary sanctuary offers complete privacy and a

  

  Pierre-Marc Bellion

  Ocean Sotheby's International Realty

  79775 Overseas Hwy, Islamorada, FL 33036
• 

  

  /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 $1,038,825

  Last Listing Agent Pierre-Marc Bellion Ocean Sotheby's International Realty

  192 E Ridge Rd, Islamorada, FL 33036
• 

  

  /32

  Est $1,847,555

  Not Listed For Sale

  87851 Old Hwy Unit P43, Islamorada, FL 33036

  • 4 Beds
  • 3 Baths
  • 2,668 Sq Ft
  • Built 1989

  87851 Old Hwy Unit P43, Islamorada, FL 33036

  Last Sold Summary

  • 26 Days On Market
• 

  

  /53

  $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-Marc Bellion

  Ocean Sotheby's International Realty

  81906 Overseas Hwy Unit 2, Islamorada, FL 33036
• 

  

  /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

  Current Estimated Value $650,357

  Last Listing Agent Wiebke Westedt LoKation Real Estate - Pompano Beach

  129 S Rd, Upper Matecumbe Key Islamorada, FL 33036
• 

  

  /54

  Est $388,507

  Not Listed For Sale

  87455 Old Hwy Unit 118, Islamorada, FL 33036

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

  87455 Old Hwy Unit 118, Islamorada, FL 33036

  Last Sold Summary

  • 119 Days On Market
• 

  

  /54

  $2,400,000

  $500K PRICE DROP

  • 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
• 

  

  /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

  Current Estimated Value $8,183,946

  Last Listing Agent Leslie Leopold Ocean Sotheby's International Realty

  19 Avacado St, Islamorada, FL 33036
• 

  

  /21

  Est $899,690

  Not Listed For Sale

  81801 Overseas Hwy Unit 208, Islamorada, FL 33036

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft
  • Built 2010

  81801 Overseas Hwy Unit 208, Islamorada, FL 33036

  Last Sold Summary

  • 117 Days On Market
• 

  

  /43

  $485,900

  • 2 Beds
  • 1.5 Baths
  • 1,354 Sq Ft

  87200 Overseas Hwy Unit 6, Islamorada, FL 33036

  This is the exceptional deal you've been waiting for! Opportunity knocks on this 2 story townhouse in Islamorada's gated bayfront community, Executive Bay Club. These spacious units are highly desired for their well laid out floor plan, perfect for full time residence, a vacation home or as a seasonal rental (30 day minimum) Amenities include a Bayfront sandy beach, newly renovated marina with

  Jaclyn Kelley Prudential Keyswide Properties

  87200 Overseas Hwy Unit 6, Islamorada, FL 33036
• 

  

  /56

  $1,450,000

  Sold Mar 10, 2026

  87851 Old Hwy Unit K21 & 35 ft. Boat Sl, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,813 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $800/SF
  • 65 Days On Market

  Last Listing Agent Seanna Lindback Sea Haven Realty, Inc.

  87851 Old Hwy Unit K21 & 35 ft. Boat Sl, Islamorada, FL 33036
• 

  

  /32

  Not Listed For Sale

  84745 Old Hwy Unit 11, Islamorada, FL 33036

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

  84745 Old Hwy Unit 11, Islamorada, FL 33036

  Last Sold Summary

  • 38 Days On Market
• 

  

  /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

  Kim Thaler Ocean Sotheby's International Realty

  120 Toner Ln, Islamorada, FL 33036
• 

  

  /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
• 

  

  /44

  Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1964

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

  Last Sold Summary

  • 75 Days On Market
• 

  

  /23

  $789,000

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft

  124 S Hammock Rd, Islamorada, FL 33036

  Nestled in the heart of Islamorada, this ground-level residence captures the essence of timeless Old Florida charm with refined modern updates. Offering 3 bedrooms and 2 bathrooms with 1,300sf of living space, the home has been updated with impact windows and doors, metal roof, renovated kitchen and updated bathrooms, and a newer A/C and water heater.The outdoor spaces are equally inviting. A

  Claire Johnson Exit Realty Florida Keys TAV

  124 S Hammock Rd, Islamorada, FL 33036
• 

  

  /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 $1,368,093

  Last Listing Agent Will Langley Langley Knight Gardner Islamorada

  87851 Old Hwy Unit M26, Islamorada, FL 33036
• 

  

  /33

  Est $424,263

  Not Listed For Sale

  87455 Old Hwy Unit 116, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Built 1977

  87455 Old Hwy Unit 116, Islamorada, FL 33036

  Last Sold Summary

  • 137 Days On Market
• 

  

  /92

  $24,995,000

  New Construction

  • 5 Beds
  • 8 Baths
  • 9,011 Sq Ft

  87895 Old Hwy, Islamorada, FL 33036

  Newly completed private oceanfront estate on 2+ acres in Plantation Key, offering an extraordinary combination of scale, privacy, dockage, and resort-style living in the heart of the Florida Keys. Designed for luxury coastal living, entertaining, and extended stays, this exceptional estate features over 9,000 sq. ft. of interior living space and more than 15,000 sq. ft. under roof. Set behind a

  Sam Williams Coldwell Banker Schmitt Real Estate Co.

  87895 Old Hwy, Islamorada, FL 33036
• 

  

  /33

  $1,260,000

  Sold Jun 25, 2026

  310 North Dr, Islamorada, FL 33036

  • 4 Beds
  • 2 Baths
  • 1,975 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $638/SF
  • 7 Days On Market

  Current Estimated Value $1,313,958

  Last Listing Agent The Pinder Team - Jessica & Hank Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  310 North Dr, Islamorada, FL 33036

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