Islamorada, FL Homes for Sale with Garage

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  $2,495,000

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

  33 Pen Key Dr, 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 Dr, Upper Matecumbe Key Islamorada, FL 33036
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  $1,499,000

  • 3 Beds
  • 1.5 Baths
  • 992 Sq Ft

  106 Plantation Ave, Tavernier, FL 33070

  Offered at a compelling market price this canal front home delivers exceptional value with extensive recent upgrades and a turn key appeal. Enjoy 60 feet of dockage with davits, direct canal access and a brand new 24' inground pool complemented by a Lage tiki hut and expansive outdoor entertaining space. The long 110 foot lot creates the perfect setting for gatherings with endless opportunities

  Kelly Randin RE/MAX All Keys Real Estate

  106 Plantation Ave, Tavernier, FL 33070
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  $1,499,000 New Construction

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

  84745 Old Hwy Unit 7, Islamorada, FL 33036

  Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a newly developed gated coastal 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

  Ernesto Portuondo American Caribbean Real Estate, Christie's International Real Estate

  84745 Old Hwy Unit 7, Islamorada, FL 33036
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  $6,975,000 Open Thu 10AM - 12PM

  • 4 Beds
  • 4.5 Baths
  • 2,629 Sq Ft

  228 Tide Ave, Tavernier, FL 33070

  Very few things in life live up to the hype--but living on ''The Creek'' exceeds it. The location is world-class, the people-watching and boating scene never gets old, and the level of construction top-notch. What makes this property even more extraordinary is that the home itself now matches the setting. Following a meticulous two-year, top-to-bottom renovation, this residence was completely

  AJ Vetter Palm House Real Estate

  228 Tide Ave, Tavernier, FL 33070
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  $24,995,000

  • 7 Beds
  • 10.5 Baths
  • 10,182 Sq Ft

  82719 Old Hwy, Islamorada, FL 33036

  The Chateau on the Ocean is a private oceanfront estate in Islamorada, where world-class design meets unmatched amenities. Completely renovated in 2023, this gated estate spans 10,182 sqft & offers 7 bedrooms & 10.5 baths. Set along a pristine private coastline, it features a 100-ft private dock & an expansive rooftop terrace with breathtaking Atlantic views. Interiors showcase soaring ceilings,

  Margarita Franco

  82719 Old Hwy, Islamorada, FL 33036
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  $5,950,000

  • 5 Beds
  • 6.5 Baths
  • 3,978 Sq Ft

  75851 Overseas Hwy, Islamorada, FL 33036

  Welcome to your private tropical retreat in the heart of Islamorada, Florida Keys. This stunning gated oceanfront estate showcases unparalleled beauty with a private walk-in sandy beach, offering direct access to crystal-clear waters. Designed for both relaxation and recreation, the property features 5 spacious bedrooms, 6.5 luxurious bathrooms, a resort-style pool, a pickleball court, and a

  Leslie Leopold Ocean Sotheby's International Realty

  75851 Overseas Hwy, Islamorada, FL 33036
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  $2,390,000

  • 4 Beds
  • 3 Baths
  • 2,508 Sq Ft

  140 Fairwich Ct, Tavernier, FL 33070

  PRICE IMPROVEMENT' MOTIVATED SELLER! Selling 'Fully Furnished'. Bay Views from every corner of this home in Hammer Point! MM93 in Tavernier, 4-bedroom, 3-bath, one house away from the open bay. The second floor 1/1 & the third floor 3/2 having the Master Suite w/ 2 guest bedrooms. Private 37-foot dock, w/platform lift! The property has meticulous landscaping & low-maintenance artificial turf. ALL

  Lidia Yoham Anchor Realty of FL, LLC.

  140 Fairwich Ct, Tavernier, FL 33070
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  $6,500,000

  • 5 Beds
  • 7 Baths
  • 5,153 Sq Ft

  430 Palm Dr, Islamorada, FL 33036

  Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf of thoughtfully designed living space, set just 2 lots from the bay and across from a tranquil mangrove preserve that enhances both privacy and natural beauty.Boaters will love the setup - 100' of dockage with 2 elevator boat

  Claire Johnson Coastal Realty of the Florida Keys

  430 Palm Dr, Islamorada, FL 33036
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  $7,795,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,841 Sq Ft

  89701 Old Hwy, Tavernier, FL 33070

  San Roc is a stunning, gated oceanfront estate set on 2.34 lush tropical acres with 130 feet of direct ocean frontage. This exceptional new-construction residence, completed in 2024, offers 3,841 square feet of elegant living space. Enter the property through a private gate and a winding, tree lined drive. The main home features four bedrooms, four bathrooms, and a separate guest ensuite.Inside,

  Cheri Tindall Ocean Sotheby's International Realty

  89701 Old Hwy, Tavernier, FL 33070
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  $15,990,000 New Construction

  • 6 Beds
  • 9 Baths
  • 7,590 Sq Ft

  88351 Old Hwy, Islamorada, FL 33036

  Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590

  Jason Zarco BHHS EWM Realty

  88351 Old Hwy, Islamorada, FL 33036
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  $635,000 Open Sat 11:30AM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 1,079 Sq Ft

  112 Cortez Dr Unit B1, Islamorada, FL 33036

  Welcome to 112 Cortez Drive, a beautifully updated 2 bedroom, 2 bath townhouse-style condo tucked along a quiet street on Lower Matecumbe Key. This inviting updated residence offers a multi-level design that provides wonderful separation of space & a naturally bright, coastal ambiance throughout. The main living area features an open layout with comfortable gathering spaces, as well as a

  Melissa Nowell Coldwell Banker Schmitt Islamorada

  112 Cortez Dr Unit B1, Islamorada, FL 33036
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  $3,995,000

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

  87445 Old Hwy, Islamorada, FL 33036

  This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this

  Cheri Tindall Ocean Sotheby's International Realty

  87445 Old Hwy, Islamorada, FL 33036
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  $4,495,000

  • 6 Beds
  • 5 Baths
  • 4,964 Sq Ft

  153 Stromboli Dr, Islamorada, FL 33036

  Exquisite Tri-Level Waterfront Estate in Islamorada! Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence offers an open-concept floor plan with soaring ceilings, a fireplace and a grand living area. Enjoy seamless

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  153 Stromboli Dr, Islamorada, FL 33036
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  $5,000,000

  • 3 Beds
  • 3 Baths
  • 2,876 Sq Ft

  171 Kahiki Dr, Tavernier, FL 33070

  An exceptional and increasingly rare opportunity to own a coveted stretch of waterfront on Tavernier Creek, one of the Florida Keys' most treasured waterways. Set along protected open water in the heart of Plantation Key, this refined residence offers immediate access to both the Atlantic Ocean and Florida Bay, a privilege few properties can claim in the Upper Keys. Thoughtfully reimagined with

  TEAM Walters Gloria, Rachel and Michae Ocean Sotheby's International Realty

  171 Kahiki Dr, Tavernier, FL 33070
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  $1,495,000 Open Thu 10AM - 12PM

  • 2 Beds
  • 2 Baths
  • 1,279 Sq Ft

  251 Azalea St, Tavernier, FL 33070

  Located on a tranquil canal-front setting in the desirable Plantation Key Colony, this impeccably updated, turnkey ground-level residence offers two bedrooms, two baths, 50 ft of coveted dockage, and boat slip with immediate bay access. Meticulously maintained and ready for carefree island living. The home's concrete, ground-level construction enhances both durability and ease of maintenance,

  Sebastian Del Negro Ocean Sotheby's International Realty

  251 Azalea St, Tavernier, FL 33070
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  $2,950,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,938 Sq Ft

  124 Orchid St, Tavernier, FL 33070

  Brand-new contemporary waterfront home in premier Plantation Key with 60 ft of protected deep-water dockage and seawall, offering direct canal access to Tavernier Creek, the Atlantic Ocean, and Florida Bay. Ground level features an open-air two-car garage and spacious covered area. First living level offers a large recreation room opening to the poolside patio with full cabana bath, perfect for

  Alexander Rojas The Lab Realty Group, LLC

  124 Orchid St, Tavernier, FL 33070
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  $14,950,000 New Construction

  • 7 Beds
  • 7 Baths

  75840 Overseas Hwy, Islamorada, FL 33036

  Experience the ultimate in coastal luxury and sophistication in this brand-new magnificent bayfront estate designed to impress at every turn. Set on over 2 acres of direct bayfront property with an idyllic rare white sandy private beach in prestigious Lower Matecumbe, this 7-bedroom, 7-bathroom residence spans nearly 6,000 square feet of immaculate living space. Two completely separate guest

  Lisa Swanson The Agency Florida Keys

  75840 Overseas Hwy, Islamorada, FL 33036
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  /19

  $6,000,000 New Construction

  • 5 Beds
  • 6 Baths
  • 3,332 Sq Ft

  120 Captains Ct, Tavernier, FL 33070

  Welcome to 120 Captains Ct, a rare waterfront new construction opportunity in Islamorada. Situated on a quiet Kahiki Harbor cul de sac, this nearly quarter acre property with 165' of deep canal frontage, provides the backdrop for a classic Keys sanctuary.Inspired by timeless Florida Keys estates, the 5 bedroom, 6 bath CBTConstruction built home offers every element you have been searching for in

  AJ Vetter Palm House Real Estate

  120 Captains Ct, Tavernier, FL 33070
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  $8,950,000

  • 8 Beds
  • 10 Baths
  • 5,392 Sq Ft

  162 Bayview Dr, Islamorada, FL 33036

  Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boater's paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning

  Nancy Muniz Coldwell Banker Realty - Coral Gables

  162 Bayview Dr, Islamorada, FL 33036
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  $3,398,000

  • 4 Beds
  • 3 Baths
  • 3,481 Sq Ft

  136 Giardino Dr, Islamorada, FL 33036

  Venetian Shores Has It All! Welcome to your slice of paradise in the heart of Islamorada's most sought-after boating community. This beautiful 4 bedroom, 3 bath coastal retreat is designed for both relaxation and entertainment, featuring 70 feet of deep-water dockage along a 100-foot wide canal - just seconds from open water via Snake Creek. Step inside the front door to access the elevator and

  Alina Davis Coldwell Banker Schmitt Islamorada

  136 Giardino Dr, Islamorada, FL 33036
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  $7,995,000

  • 4 Beds
  • 5 Baths
  • 4,048 Sq Ft

  91 Iroquois Dr, Islamorada, FL 33036

  Discover paradise in Islamorada, where you can enjoy beautiful ocean views, protected dockage, and resort-style amenities. This home blends luxury living with the Florida Keys lifestyle and is designed with both entertainment and relaxation in mind. Concrete construction and equipped with impact windows/doors, Interlock Aluminum Slate Roofing and a solar generator, this home can weather any

  Eric Smith Coastal Realty of the Florida Keys

  91 Iroquois Dr, Islamorada, FL 33036
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  $260,000

  • 1 Bath
  • 398 Sq Ft

  88500 Overseas Hwy Unit 205, Tavernier, FL 33070

  Great opportunity to own a piece of paradise, in the Florida Keys. Updated studio unit in Summer Sea Condo (MM88), turnkey unit ready for occupancy. Building grounds are incredible, featuring dock space (First come first serve), boat ramp, oversized pool area/deck, gym, kids community room, adult billiards room, large party/event room, beach area, barbeque areas, fish cleaning stations, area to

  Nerida Deza Keller Williams Capital Realty

  88500 Overseas Hwy Unit 205, Tavernier, FL 33070
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  $2,220,000 New Construction

  • 5 Beds
  • 3 Baths
  • 2,450 Sq Ft

  115 Azalea St, Tavernier, FL 33070

  New construction waterfront home featuring 5 bedrooms and 3 bathrooms with a flexible split-level layout ideal for guests or extended family. The property offers a private pool, outdoor kitchen and grill area, and spacious outdoor entertaining space. Boaters will appreciate the 40-foot private dock with easy access to the open water. Additional features include a garage and ample storage. A great

  Merlin Perez Golden International Realty

  115 Azalea St, Tavernier, FL 33070
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  $27,800,000

  • 7 Beds
  • 10 Baths
  • 8,988 Sq Ft

  89505 Old Hwy, Tavernier, FL 33070

  Escape to Palm Paradise, a one-of-a-kind oceanfront estate in Islamorada, Florida Keys, where luxury and privacy intertwine on 7.64 secluded acres. This magnificent property boasts 369 feet of pristine ocean frontage, revealing breathtaking panoramic views from nearly every corner. The sprawling 8,988 square foot main residence boasts five spacious bedrooms, five full bathrooms, three half

  Leslie Leopold Ocean Sotheby's International Realty

  89505 Old Hwy, Tavernier, FL 33070
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  $3,800,000 New Construction

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

  82779 Old Hwy Unit 15, 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 15, Islamorada, FL 33036
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  $4,799,000

  • 5 Beds
  • 4.5 Baths
  • 3,556 Sq Ft

  128 Leoni Dr, Islamorada, FL 33036

  SPECTACULAR HOME IN VENETIAN SHORES! 70' concrete dock on deep water canal which opens directly to Snake Creek for easy and quick access to bay or ocean; 5 bedrooms/4.5 baths; private master retreat with gorgeous bath on third level; marble floors throughout; elevator; FABULOUS chef's kitchen with Wolf gas range and huge island; large terraces and fantastic entertaining spaces; sound system

  Emily Romberg Real Estate Sales Force - Coral Gables

  128 Leoni Dr, Islamorada, FL 33036
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  $6,250,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,945 Sq Ft

  206 Plantation Ave, Islamorada, FL 33070

  BRAND NEW CONSTRUCTION WITH BAY VIEWS! Welcome to a stunning new construction residence that redefines luxury waterfront living in the Florida Keys. This elegant three-story home offers 5 bedrooms, 5.5 bathrooms, pool and spa, office, garage, outdoor kitchen and 70 feet of dockage--perfectly positioned to capture sweeping views of the Florida Bay and iconic Keys sunsets.Thoughtfully designed for

  Mike Jones Fairchild Partners, Inc.

  206 Plantation Ave, Islamorada, FL 33070

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