Islamorada, FL Homes for Sale with Garage

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  /33

  $1,599,000

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

  121 Venetian Dr, Islamorada, FL 33036

  Discover the ultimate waterfront retreat in the heart of Islamorada, in the highly sought after neighborhood of White Marlin Beach. This captivating 3-bedroom, 2-bathroom gem is a dream come true. The interior features an open floor plan with 9-foot ceilings and ceramic tile. Embrace the coastal lifestyle with stunning water views right from your backyard and revel in the convenience of a private

  Ray Palacios TruRes Real Estate, Inc.

  121 Venetian Dr, Islamorada, FL 33036
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  /33

  $12,500,000

  • 3 Beds
  • 3 Baths
  • 1,243 Sq Ft

  89251 Old Hwy, Tavernier, FL 33070

  Pure magic. Every step on this property is like a step back in time. Once you pass through the gated coral rock entrance you are instantly transported back to the Old Keys as you wind down the driveway through the shady tropical hammock and meander your way to the settler's beach home circa 1934. The charming 3/3 fishing cabin was meticulously updated to add modern comforts but still maintain its

  Brett Newman Coldwell Banker Schmitt Islamorada

  89251 Old Hwy, Tavernier, FL 33070
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  /55

  $3,299,000

  • 4 Beds
  • 3.5 Baths
  • 3,817 Sq Ft

  111 Spoonbill Rd, Tavernier, FL 33070

  This canal-front pool home is an absolute beauty, combining timeless elegance with coastal sophistication. Renovated in 2022 and offered furnished or not, this home is filled with light-filled indoor and outdoor living spaces.Enter through the legal ground-level entrance into the indoor entertaining area, elevated above flood level and offering plenty of space for activities. Large windows and

  Javier Dapena Lifestyle International Realty

  111 Spoonbill Rd, Tavernier, FL 33070
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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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  $1,075,000

  • 3 Beds
  • 2.5 Baths
  • 2,026 Sq Ft

  101 Gulfview Dr Unit 114, Islamorada, FL 33036

  Luxury Condo with Boat slip and Lift in Islamorada

  Judy Rossignol Paradise Florida Keys Real Est

  101 Gulfview Dr Unit 114, Islamorada, FL 33036
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  $1,567,670

  • 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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  /68

  $1,375,000 New Construction

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

  84745 Old Hwy Unit 4, 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 4, Islamorada, FL 33036
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  /106

  $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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  /64

  $4,000,000

  • 4 Beds
  • 4 Baths
  • 3,004 Sq Ft

  96 W Plaza Del Sol, Islamorada, FL 33036

  Paradise in Port Antigua! Assumable interest rate of 2.625%! New pool going in before Summer 2026! Discover one of Islamorada's best-kept secrets in this spacious 4bd/4ba home, built in 2019. With a modern coastal design, deepwater dockage, and exceptionally low insurance premiums, this home delivers the ultimate Florida Keys lifestyle. A pool permit is already in the works, and the seller is

  Amy Bruggeman American Caribbean Real Estate, Christie's International Real Estate

  96 W Plaza Del Sol, Islamorada, FL 33036
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  /65

  $7,800,000

  • 5 Beds
  • 5.5 Baths
  • 4,764 Sq Ft

  80201 Overseas Hwy, Islamorada, FL 33036

  Experience Islamorada living at its absolute finest with this remodeled oceanfront estate. Situated on 200 feet of sandy waterfront with unobstructed views of the Atlantic Ocean and Alligator Reef Lighthouse, this ground-level residence is designed for resort-style living. Inside, the home features 5 spacious ensuite bedrooms and 5.5 baths, highlighted by a luxurious primary suite with a coffee

  Seanna Lindback Sea Haven Realty, Inc.

  80201 Overseas Hwy, Islamorada, FL 33036
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  /60

  $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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  /73

  $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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  $3,290,000 New Construction

  • 4 Beds
  • 5 Baths
  • 3,467 Sq Ft

  114 Royal Ln, Islamorada, FL 33036

  Pickle Ball Estate is a stunning new luxury retreat in the heart of Islamorada, masterfully crafted by 4 Keys Construction. This brand-new four-bedroom, five-bathroom residence is a true standout, blending refined coastal design with resort-style living.Designed for both relaxation and entertainment, the home features a private pickleball court, making it a rare and exciting find in the Florida

  Alexander Pinero Pine River Realty, LLC

  114 Royal Ln, Islamorada, FL 33036
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  /10

  $895,000

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft

  101 Gulfview Dr Unit 202, Islamorada, FL 33036

  Luxury Condo in Islamorada with Ocean view

  Judy Rossignol Paradise Florida Keys Real Est

  101 Gulfview Dr Unit 202, Islamorada, FL 33036
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  $689,000

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

  118 Cortez Dr Unit A, Islamorada, FL 33036

  Charming, light-filled townhouse-style condo featuring 2 bedrooms and 2 baths, tucked away on a quiet cul-de-sac on Lower Matecumbe Key. Enjoy resort-style amenities and excellent boating and fishing access to both the Ocean and the Bay.The open-concept living and dining area flows seamlessly into a well-designed kitchen. Each bedroom and bathroom occupies its own level, providing exceptional

  Bettina Garber Ocean Sotheby's International Realty

  118 Cortez Dr Unit A, Islamorada, FL 33036
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  /48

  $644,900

  • 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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  /33

  $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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  /79

  $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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  /73

  $5,000,000

  • 3 Beds
  • 3 Baths
  • 1,980 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

  • 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

  • 3 Beds
  • 3.5 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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  $4,750,000

  • 4 Beds
  • 4.5 Baths
  • 4,464 Sq Ft

  44 W Plaza Del Lago, Islamorada, FL 33036

  Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating

  Alexander Pinero Pine River Realty, LLC.

  44 W Plaza Del Lago, Islamorada, FL 33036
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  $15,750,000 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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  /51

  $3,649,000

  • 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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  /73

  $4,299,999

  • 4 Beds
  • 4 Baths
  • 2,596 Sq Ft

  74049 Overseas Hwy, Islamorada, FL 33036

  Incredible opportunity to own an amazing large home directly on the ocean in the Florida Keys, Islamorada. Use this property or rent it with significant short term rental income in demand all year round. A huge 21,600 sft lot has pool, sports area, bbq area, storage, and plenty of gated parking. Home is 2,500+sft. The tranquility of this charming area and private street make this home the perfect

  George Theodore Address Real Estate LLC

  74049 Overseas Hwy, Islamorada, FL 33036
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  /58

  $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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  /33

  $2,220,000 New Construction

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

  115 Azalea St, Tavernier, FL 33070

  Merlin Perez Golden International Realty

  115 Azalea St, Tavernier, FL 33070
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  $1,900,000

  • 4 Beds
  • 4 Baths
  • 2,728 Sq Ft

  82762 Overseas Hwy Unit 3, Islamorada, FL 33036

  Open Bay Views, Boat Dockage, Pool and more... all in the Heart of Downtown Islamorada! Have you been dreaming of living downtown, but can't find a home with dedicated boat dockage and open water views? If so, this custom 4/4 home in Madeira Bay is your dream come true! Enjoy open water views from the porch, living room, kitchen, loft and bedroom plus soaring ceilings and nearly 3,000 sf of

  Brett Newman Coldwell Banker Schmitt Islamorada

  82762 Overseas Hwy Unit 3, Islamorada, FL 33036
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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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  /29

  $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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  $24,995,000

  • 7 Beds
  • 9.5 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 2022, this gated estate spans 10,182 sqft & offers 7 bedrooms & 9.5 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,

  Chad Carroll Compass Florida, LLC

  82719 Old Hwy, Islamorada, FL 33036

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