Islamorada, FL Homes

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  /33

  $779,000

  $20K PRICE DROP Under Contract

  • 4 Beds
  • 2 Baths
  • 1,496 Sq Ft

  102 Harry Harris Dr, Tavernier, FL 33070

  Legal Duplex, Two electric meters, Two water meters, with two mailboxes and plenty of parking. Concrete building with metal roof. Both apartments have been nicely updated inside & out. Mini split AC's with tankless water heaters. Each apartment is 748 sq. ft. Downstairs is rented at $2,650.00 Upstairs is rented at $2,700.00 per month. Washer & Dryer in Storage building that both tenants can use.

  

  Tom Rodriguez

  American Caribbean Real Estate, Christie's International Real Estate

  102 Harry Harris Dr, Tavernier, FL 33070
• 

  

  

  /29

  $4,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,075 Sq Ft
  • House for Rent

  251 Bougainvillea St, Tavernier, FL 33070

  Enjoy year-round Keys living in this updated 2-bedroom, 2-bath concrete home located in the desirable Plantation Key Colony neighborhood. This two-story waterfront home offers a comfortable and functional layout with a fully fenced yard, screened-in porch, covered carport, and ample off-street parking. For boating enthusiasts, the property features 40 feet of dockage, a private boat ramp, a

  Kenneth Smith American Caribbean Real Estate, Christie's International Real Estate

  251 Bougainvillea St, Tavernier, FL 33070
• 

  

  

  /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 $1,049,549

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

  192 E Ridge Rd, Islamorada, FL 33036
• 

  

  

  /37

  Est $795,918

  Not Listed For Sale

  273 Hibiscus St, Tavernier, FL 33070

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1992

  273 Hibiscus St, Tavernier, FL 33070

  Last Sold Summary

  • 140 Days On Market
• 

  

  

  /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 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
• 

  

  /23

  $3,995 Per Month

  • 4 Beds
  • 2 Baths
  • Property for Rent

  164 Blue Harbor Dr, Tavernier, FL 33070

  PERFECT VACATION HOME! BRING YOUR BOAT! Available Immediately Beautiful & Spacious 4 Bedrooms & 2 Bathrooms POOL HOME with a wraparound porch & Pool Cabana & outdoor kitchen located in Blue Harbor Private Community Home is located Right across from the Boat Ramp Property offers plenty of space for a Big Family to enjoy endless days of fishing and water activities Space for boat and other water

  Ernie Echauri RE/MAX All Keys Real Estate

  164 Blue Harbor Dr, Tavernier, FL 33070
• 

  

  /59

  $2,775,000

  Sold May 22, 2026

  226 S Coconut Palm Blvd, Plantation Key, FL 33070

  • 4 Beds
  • 4 Baths
  • 2,853 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $973/SF
  • 138 Days On Market

  Current Estimated Value $2,813,388

  Last Listing Agent AJ Vetter Palm House Real Estate

  226 S Coconut Palm Blvd, Plantation Key, FL 33070
• 

  

  /17

  Est $890,658

  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
• 

  

  /44

  $719,000

  • 2 Beds
  • 2 Baths
  • 841 Sq Ft

  500 Burton Dr Unit 3406, Tavernier, FL 33070

  TWO oceanfront balconies with Stunning ocean views in this 2/2 D model on the TOP floor. Beautiful ocean views from the living room and the Owners suite bedroom !! Updated kitchen and both bathrooms. Impact windows and sliders. Being sold fully furnished. Jr. Olympic Heated pool with 14 person Spa. Pool Bar is all remodeled and back open !! Full liquor bar for nice frozen drinks by the pool !!

  

  Tom Rodriguez

  American Caribbean Real Estate, Christie's International Real Estate

  500 Burton Dr Unit 3406, Tavernier, FL 33070
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  /9

  $1,675 Per Month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  195 Gardenia St Unit 1, Tavernier, FL 33070

  Available September 1st! Affordable Keys living awaits! This ground-floor 1 bed/1 bath is located in a charming six-unit building on a canal in Plantation Key Colony. Designed for comfortable, low-maintenance living, this home is ideally suited for single occupancy. Enjoy a peaceful waterfront setting just minutes from marinas, restaurants, shopping, and all the conveniences of the Upper Keys. If

  Samantha Arce Better Homes and Gardens Real Estate Destinations

  195 Gardenia St Unit 1, Tavernier, FL 33070
• 

  

  /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 $683,504

  Last Listing Agent Wiebke Westedt LoKation Real Estate - Pompano Beach

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

  

  /28

  Est $698,574

  Not Listed For Sale

  88181 Old Hwy Unit F4 slip 65, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft
  • Built 1979

  88181 Old Hwy Unit F4 slip 65, Islamorada, FL 33036

  Last Sold Summary

  • 102 Days On Market
• 

  

  /28

  $1,385,000

  $140K PRICE DROP Under Contract

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

  87851 Old Hwy Unit M42, Islamorada, FL 33036

  Islamorada top-floor condo at Ocean Harbour with Atlantic ocean views and a boat slip. 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

  87851 Old Hwy Unit M42, 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
• 

  

  /20

  $4,000

  Sold May 14, 2026

  142 Airstream Ln, Tavernier, FL 33070

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 2022

  Last Sold Summary

  • $4/SF
  • 56 Days On Market

  Current Estimated Value $943,885

  Last Listing Agent Megan Jones Coldwell Banker Schmitt Islamorada

  142 Airstream Ln, Tavernier, FL 33070
• 

  

  /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
• 

  

  /41

  $500,000

  • 1 Bed
  • 1 Bath
  • 577 Sq Ft

  500 Burton Dr Unit 4204, Tavernier, FL 33070

  Rare Opportunity in Ocean Pointe! Experience the ultimate in Florida Keys luxury living with this modern, oceanfront 1-bedroom, 1-bath condo—a rare find in the highly sought-after Ocean Pointe community. Located in Building 4 on the 2nd floor, this beautifully appointed unit features a private balcony with serene ocean and mangrove views, offering the perfect spot to unwind. With a strong rental

  

  Ian Trumbach

  FLORIDA PRESTIGIOUS HOMES INC

  500 Burton Dr Unit 4204, Tavernier, FL 33070
• 

  

  /21

  $2,500 Per Month

  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  113 Mockingbird Rd Unit 1, Tavernier, FL 33070

  Modern, turnkey studio offering a bright and open layout with assigned Parking and Washer & Dryer. Near Mariners Hospital and local shops and Restaurants, the space features a cozy sleeping area with a nautical flair, plus a versatile living space for lounging or entertaining. Enjoy a fully equipped kitchen with white shaker cabinets, quartz counters, stainless steel appliances, and a stylish

  Jennifer Gomez EXP Realty, LLC

  113 Mockingbird Rd Unit 1, Tavernier, FL 33070
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  /34

  $960,000

  Sold Apr 21, 2026

  100 Iroquois Dr Unit 5, Islamorada, FL 33036

  • 4 Beds
  • 3 Baths
  • 1,710 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $561/SF
  • 9 Days On Market

  Current Estimated Value $951,733

  Last Listing Agent Nancy Hershoff Coldwell Banker Schmitt Islamorada

  100 Iroquois Dr Unit 5, Islamorada, FL 33036
• 

  

  /12

  Est $287,834

  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
• 

  

  /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
• 

  

  /10

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 9,878 Sq Ft
  • Apartment for Rent

  Unlisted Address

  Outstanding private apartment fully furnished and equipped offer for short term at Tavernier, Key Largo. The apartment features a 3 separated bedrooms and 2 full bathrooms with enclosed showers, full kitchen with cook-top, refrigerator and everything needed for a short term unit.Ideally for whole family travelers or group of friends that want to enjoy the lifestyle of florida keys. Other

  Yohan Barreras Soltura Prime House Realty, Inc.

  Unlisted Address
• 

  

  /8

  Sold Jun 19, 2026

  40 High Point Rd Unit C105, Tavernier, FL 33070

  • 2 Beds
  • 1.5 Baths

  Last Sold Summary

  • 23 Days On Market

  Current Estimated Value $407,169

  Last Listing Agent Sharon Kelly-Brown Reel Keys Realty

  40 High Point Rd Unit C105, Tavernier, FL 33070
• 

  

  /46

  Est $772,627

  Not Listed For Sale

  163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070

  • 6 Beds
  • 4 Baths
  • 2,240 Sq Ft
  • Built 1984

  163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070

  Last Sold Summary

  • 42 Days On Market
• 

  

  /33

  $11,700,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 6,577 Sq Ft

  77350 Overseas Hwy, Islamorada, FL 33036

  Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom

  

  Carolyn Ambler

  American Caribbean Real Estate, Christie's International Real Estate

  77350 Overseas Hwy, 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 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
• 

  

  /22

  $1,457,000

  Sold Jun 02, 2026

  121 Venetian Dr, Islamorada, FL 33036

  • 3 Beds
  • 2 Baths
  • 1,278 Sq Ft
  • Built 2018

  Last Sold Summary

  • 14% Below List Price
  • $1,140/SF
  • 557 Days On Market

  Current Estimated Value $1,636,397

  Last Listing Agent Robert Santana TruRes Real Estate Inc.

  121 Venetian Dr, Islamorada, FL 33036
• 

  

  /32

  Est $1,739,880

  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
• 

  

  /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
• 

  

  /37

  $1,720,000

  Sold Jun 01, 2026

  309 Woods Ave, Tavernier, FL 33070

  • 3 Beds
  • 3 Baths
  • 1,248 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Below List Price
  • $1,378/SF
  • 2 Days On Market

  Current Estimated Value $1,784,502

  Last Listing Agent Jessica Pinder Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  309 Woods Ave, Tavernier, FL 33070
• 

  

  /44

  Est $851,710

  Not Listed For Sale

  103 Costa Bravo Dr Unit 103, Islamorada, FL 33036

  • 2 Beds
  • 1.5 Baths
  • 1,206 Sq Ft
  • Built 1974

  103 Costa Bravo Dr Unit 103, Islamorada, FL 33036

  Last Sold Summary

  • 26 Days On Market
• 

  

  /33

  $530,000

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft

  107 Tavern Dr, Tavernier, FL 33070

  In the heart of Historic Tavernier, this charming Keys cottage offers the kind of character that's getting harder and harder to find. Set on two lots with peekaboo ocean views, the property combines Old Florida charm, outdoor space, and boating convenience in one inviting package. Inside, the two bedroom, one bath home has a cozy, authentic Keys feel. This compact space is full of personality.

  Karin Moerner Cedergren Coldwell Banker Schmitt Islamorada

  107 Tavern Dr, Tavernier, FL 33070
• 

  

  /31

  $775,000

  Sold Aug 11, 2025

  182 Adobe Casa Ct Dr Unit 182-184, Key Largo, FL 33037

  • 4 Beds
  • 2 Baths
  • 1,782 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $435/SF
  • 28 Days On Market

  Current Estimated Value $779,786

  Last Listing Agent Jeannine Cook Rook Realty

  182 Adobe Casa Ct Dr Unit 182-184, Key Largo, FL 33037
• 

  

  /29

  Not Listed For Sale

  215 Antigua Rd, Tavernier, FL 33070

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1970

  215 Antigua Rd, Tavernier, FL 33070

  Last Sold Summary

  • 10 Days On Market
• 

  

  /56

  $875,000

  Open Sat 10AM - 12PM $50K PRICE DROP

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

  88181 Old Hwy Unit B3, Islamorada, FL 33036

  Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just eight buildings, this home sits in a peaceful low-rise building with only three units. As an end unit with no one above or below, it feels very much like a single-family home. Windows on three sides bring in natural light and a

  Christy Hughes Coldwell Banker Schmitt Islamorada

  88181 Old Hwy Unit B3, Islamorada, FL 33036
• 

  

  /47

  $3,200,000

  Sold Jun 10, 2026

  139 Tequesta St, Tavernier, FL 33070

  • 5 Beds
  • 4 Baths
  • 3,559 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $899/SF
  • 7 Days On Market

  Current Estimated Value $3,216,617

  Last Listing Agent Elizabeth Jolin Coldwell Banker Schmitt RE Co

  139 Tequesta St, Tavernier, FL 33070
• 

  

  /54

  Est $376,088

  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
• 

  

  /43

  $485,900

  Under Contract

  • 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
• 

  

  /44

  $670,000

  Sold Jul 24, 2026

  184 Pearl Ave, Tavernier, FL 33070

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft
  • Built 1967

  Last Sold Summary

  • 16% Below List Price
  • $332/SF
  • 29 Days On Market

  Current Estimated Value $707,570

  Last Listing Agent Shane Wilson Cypress Realty, Inc.

  184 Pearl Ave, Tavernier, FL 33070
• 

  

  /40

  Not Listed For Sale

  88540 Overseas and Boat Slip 37 Hwy Unit 727, Plantation Key, FL 33070

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft
  • Built 1985

  88540 Overseas and Boat Slip 37 Hwy Unit 727, Plantation Key, FL 33070

  Last Sold Summary

  • 157 Days On Market

Showing Results 81 - 120, Page 3 of 18