Waterfront Homes for Sale in Islamorada, FL

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  /72

  $3,850,000

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

  74049 Overseas Hwy, Islamorada, FL 33036

  Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing

  74049 Overseas Hwy, Islamorada, FL 33036
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  /53

  $2,900,000

  $275K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  154 Milano Dr, Islamorada, FL 33036

  What does everyone want? The smallest house in a great neighborhood! THIS IS THE ONE! Tucked away in the sought-after Venetian Shores neighborhood of Islamorada, this solid CBS waterfront home is perfectly positioned for enjoying the effortless boating lifestyle the Keys are known for. With 100 feet of dockage, a 15,000 lb. boat lift, and a fish cleaning station, this home is just one lot from

  Alina Davis Coldwell Banker Schmitt Islamorada

  154 Milano Dr, Islamorada, FL 33036
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  /34

  $549,500

  • 1 Bed
  • 1 Bath
  • 358 Sq Ft

  81801 Overseas Hwy Unit 715, Islamorada, FL 33036

  Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  81801 Overseas Hwy Unit 715, Islamorada, FL 33036
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  /54

  $1,549,000

  $441K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  164 Venetian Dr, Islamorada, FL 33036

  Boater’s dream home in White Marlin Beach, Islamorada. Unique 2-story single-family home with split layout, two 800 square feet 2BD/1BA units. Separate entrances and laundry in each unit, 70' dock with private boat ramp on a tranquil mangrove canal. This property is facing mangrove with maximum privacy, just 7 homes from the bay! Plenty of parking for RVs/trailers. Enjoy access to the White

  Po Yen Hsueh Compass Florida, LLC

  164 Venetian Dr, Islamorada, FL 33036
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  /2

  $1,600,000

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  102 Venetian Dr, Islamorada, FL 33036

  Boaters paradise in Isla Morada Florida the Sport Fishing Capital of the World, this 3 bedroom 02 bath home is ready to enjoy. Own a piece of paradise in the Florida Keys a Marine Sanctuary. This home is located is the sought after community of Marlin Beach adjacent to Port Antigua. It has private dockage for your boat as well as access to the Atlantic Ocean within minutes from your backyard.

  102 Venetian Dr, Islamorada, FL 33036
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  /63

  $4,600,000

  • 5 Beds
  • 5.5 Baths
  • 4,636 Sq Ft

  157 Valencia Dr, Islamorada, FL 33036

  Located in sought-after Venetian Shores subdivision in Islamorada, this canal-front home was renovated in 2022. Sought after location - just one lot in from Snake Creek, offering exceptional boating access, 100' of deep water dockage with a 20k boat lift. With approximately 4,600sf of living space, 5 bedrooms and 5.5 bathrooms, the home is situated above base flood elevation and offers an

  Claire Johnson Exit Realty Florida Keys TAV

  157 Valencia Dr, Islamorada, FL 33036
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  /29

  $27,000,000

  New Construction

  • 5 Beds
  • 8 Baths
  • 8,200 Sq Ft

  88845 Old Hwy, Tavernier, FL 33070

  Set on over 2 acres along prestigious Millionaire's Row in Tavernier, this newly constructed oceanfront estate represents a rare convergence of scale, design, and functionality in the Upper Florida Keys. Encompassing 8,200 square feet of interior living space and over 16,000 square feet total, the residence is thoughtfully designed to accommodate both elevated everyday living and large-scale

  Courtney Conley Serhant Florida LLC - Coconut Grove

  88845 Old Hwy, Tavernier, FL 33070
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  /63

  $699,000

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  81801 Overseas Hwy Unit 729, Islamorada, FL 33036

  Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential.Set within one of the Florida Keys' most celebrated resorts, owners and

  Diana Fiddes Coldwell Banker Schmitt Key Largo

  81801 Overseas Hwy Unit 729, Islamorada, FL 33036
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  /54

  $3,450,000

  $250K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,204 Sq Ft

  168 Indian Mound Trail, Tavernier, FL 33070

  This exceptional waterfront estate on a deep water canal with a 50ft dock on a double lot is situated in the heart of Plantation Key. The property features a grand three story residence framed by established palm trees and a striking, patterned paver driveway. The expansive grounds are clean but unplanted, offering a clear blank canvas for you to design your ultimate custom tropical landscaping

  Caroline Hendrix Coldwell Banker Schmitt Real E

  168 Indian Mound Trail, Tavernier, FL 33070
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  /37

  $485,000

  $14K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 950 Sq Ft

  92550 Overseas Hwy Unit 214, Tavernier, FL 33070

  PRICE REDUCTION AND 5K SELLER INCENTIVE OFFERED! ADDITIONAL 5K WITH PREFERRED LENDER! Excellent investment opportunity in the Florida Keys! This updated condo features a 2024 aluminum roof, fresh interior and exterior paint, updated bathrooms, new bedroom carpeting, and two ocean-view balconies. Enjoy private beach access, multiple dock slips, and a prime bayside location near popular

  George CancioBello Lifestyle International Realty

  92550 Overseas Hwy Unit 214, Tavernier, FL 33070
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  /41

  $3,499,999

  $300K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,130 Sq Ft

  188 Orange Blossom Rd, Tavernier, FL 33070

  Experience true oceanfront living in the Florida Keys with this exceptional home in Tavernier. Showcasing breathtaking 180-degree ocean views, this property offers a front-row seat to some of the most stunning scenery in the Keys—all from the comfort of your own deck. Set on a rare, expansive lot, there’s ample space to entertain family and friends, making it perfect for gatherings and relaxing

  Christian Salgado MDZ Realty, LLC.

  188 Orange Blossom Rd, Tavernier, FL 33070
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  /100

  $6,999,000

  $1M PRICE DROP

  • 8 Beds
  • 6 Baths
  • 3,649 Sq Ft

  1101 Mastic St Unit 1, Islamorada, FL 33036

  Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available.Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct

  Tracey Petrusha LoKation

  1101 Mastic St Unit 1, Islamorada, FL 33036
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  /48

  $3,875,000

  • 4 Beds
  • 3 Baths
  • 3,088 Sq Ft

  109 Giardino Dr, Islamorada, FL 33036

  Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled with natural light, highlighted by a dramatic floor-to-ceiling wall of windows in the living area that brings the outdoors in. An inviting entrance foyer welcomes you inside, with interior stairs to the main living level. The

  Alina Davis Coldwell Banker Schmitt Islamorada

  109 Giardino Dr, Islamorada, FL 33036
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  /65

  $3,000,000

  • 3 Beds
  • 3 Baths
  • 2,850 Sq Ft

  148 Riviera Dr, Tavernier, FL 33070

  Discover effortless Keys living in this beautifully designed three-story home on the ocean side of Plantation Key, offering protected dockage and immediate ocean access. Thoughtfully designed for both relaxed living and waterfront entertaining, the home features an open floor plan, 9-foot ceilings, and expansive 8-foot sliding glass doors that bring the outdoors in. Drive in and the home welcomes

  Alina Davis Coldwell Banker Schmitt Islamorada

  148 Riviera Dr, Tavernier, FL 33070
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  /65

  $5,999,999

  $490K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,456 Sq Ft

  137 Sapodilla Dr, Islamorada, FL 33036

  Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral

  137 Sapodilla Dr, Islamorada, FL 33036
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  /82

  $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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  /41

  $3,199,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  75071 Overseas Hwy, Islamorada, FL 33036

  Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscaping. This exceptional concrete stilt home has undergone a spectacular extensive coastal renovation, blending modern luxury with the relaxed elegance of the Florida Keys lifestyle.The residence features 3 bedrooms and 3

  Derek Rodberg Cypress Realty, Inc.

  75071 Overseas Hwy, Islamorada, FL 33036
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  /48

  $40,000,000

  New Construction

  • 8 Beds
  • 11 Baths
  • 9,704 Sq Ft

  88845 Old Hwy, Tavernier, FL 33070

  A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatched combination of scale, privacy, and future development flexibility in the Florida Keys. At 88845, a newly constructed 8,200SF estate sets a new standard for modern coastal luxury. Thoughtfully designed for both grand

  Courtney Conley Serhant Florida LLC - Coconut Grove

  88845 Old Hwy, Tavernier, FL 33070
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  /36

  $439,000

  $21K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 981 Sq Ft

  87465 Old Hwy 215 Hwy Unit 215, Plantation Key, FL 33036

  WELCOME TO PARADISE BY THE SEA! THIS SPACIOUS CONDO LOCATED ON MILLIONAIRE'S ROW IN AN OCEANFRONT BUILDING OFFERS THE PERFECT BLEND OF COMFORT & CONVENIENCE, THIS BEAUTY FEATURES AN OPEN CONCEPT LIVING AREA, WELL APPOINTED KITCHEN WITH WOOD CABINETS, & A 1/2 BATH DOWNSTAIRS. WALK UPSTAIRS TO A COZY SPLIT BEDROOM FLOOR PLAN FOR PRIVACY. PRIMARY SUITE INCLUDES A WALK-IN CLOSET. OUTSIDE OFFERS

  Nancy Garcia The Keyes Company

  87465 Old Hwy 215 Hwy Unit 215, Plantation Key, FL 33036
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  /18

  $1,300,000

  $50K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,376 Sq Ft

  104 Anglers Way, Islamorada, FL 33036

  Exclusive Anglers Reef Resort-style oceanfront home in Islamorada -- a rare coastal gem. Nestled inside a gated community with resort-caliber amenities, a private marina and two sandy beaches, this fully furnished two-story single-family retreat offers 2 bedrooms and 2.5 baths -- ideal for saltwater lovers or savvy investors.Thoughtfully upgraded with elegant, durable finishes: impact-rated

  Rayden Vega Casa Miami Real Estate

  104 Anglers Way, Islamorada, FL 33036
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  /30

  $439,000

  • 1 Bed
  • 1 Bath
  • 406 Sq Ft

  84961 Old Hwy Unit A1, Islamorada, FL 33036

  Charming concrete bungalow in the heart of Islamorada! Move right into this beautifully updated 1BR/1BA retreat featuring fabulous ocean views from your private rooftop deck. Blending timeless Florida Keys charm with modern finishes, this home offers durable concrete construction with beautiful interior finishes, impact windows, an updated electrical panel, and parking for two vehicles. Relax

  Claudette Mell Century 21 Circle- Islamorada

  84961 Old Hwy Unit A1, Islamorada, FL 33036
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  /42

  $439,000

  $21K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  87465 Old Hwy Unit 215, Islamorada, FL 33036

  WELCOME TO PARADISE BY THE SEA! THIS SPACIOUS CONDO LOCATED IN HIGHLY DESIRED PLANTATION KEY/SLAMORADA ON MILLIONAIRE'S ROW. THIS OCEANFRONT BUILDING OFFERS THE PERFECT BLEND OF COMFORT & CONVENIENCE, THIS BEAUTY FEATURES AN OPEN CONCEPT LIVING AREA THAT LIGHT AND BRIGHT! WELL APPOINTED KITCHEN WITH WOOD CABINETS, & FIRST FLOOR HALF BATHROOM. WALK UPSTAIRS TO A COZY SPLIT BEDROOM FLOOR PLAN FOR

  Anthony Garcia The Keyes Company

  87465 Old Hwy Unit 215, Islamorada, FL 33036
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  /37

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  87200 Overseas Hwy Unit J6, Islamorada, FL 33036

  Discover easy bayfront living in this beautifully updated townhome at Executive Bay Club, where breathtaking views of Florida Bay take center stage. The open living area and kitchen enjoy beautiful, unobstructed bay views, while the upstairs primary bedroom offers its own spectacular waterfront perspective.The main living level features level tile flooring and a comfortable, inviting layout

  Alina Davis Coldwell Banker Schmitt Islamorada

  87200 Overseas Hwy Unit J6, Islamorada, FL 33036
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  /18

  $298,000

  $37K PRICE DROP

  • 1 Bed
  • 1 Bath

  84961 Old17, Islamorada, FL 33036

  Escape to your own slice of paradise with this cozy and beautifully kept 1-bedroom, 1-bath Jayco RV. Whether you’re looking for a peaceful weekend retreat, a seasonal getaway, or a spot with great rental potential, this charming hideaway has it all. Wake up to the soothing sounds of the Atlantic and enjoy unforgettable sunrises and sunsets right from the jetty. Nestled in a rare, intimate

  Stanley Samy Luft Realty

  84961 Old17, Islamorada, FL 33036
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  /34

  $640,000

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,063 Sq Ft

  200 Harborview Dr Unit 101, Tavernier, FL 33070

  NEW LOWER PRICE!! This beautiful 2-bedroom, 2.5-bathroom condo offers everything you need for an stress-free retreat or your full-time piece of paradise. Step inside to a light and bright interior filled with upgrades and thoughtful finishing touches. Two screened lanais provide the perfect spot to relax, unwind, and soak in the stunning views of the lush tropical landscaping, sparkling pool, BBQ

  Krissy Carnahan Paradise Florida Keys Real Estate, a Luxury Brand

  200 Harborview Dr Unit 101, Tavernier, FL 33070
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  /67

  $725,000

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft

  323 Bay View Ave, Key Largo, FL 33037

  Without Leaving South Florida: Private Key Largo Home With Boat Ramp & Bay Access This legal 3-bedroom Key Largo home that is increasingly difficult to find: privacy, parking, low HOA fees and easy Florida Bay access without waterfront pricing. Walk approximately 800 feet to the private homeowners' beach, dock and boat ramp. Bring the boat, RV and weekend bags. With only one neighboring property,

  Steven Koleno Beycome of Florida LLC

  323 Bay View Ave, Key Largo, FL 33037
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  /29

  $5,850,000

  • 5 Beds
  • 4 Baths
  • 2,688 Sq Ft

  233 Aberdeen Ct, Tavernier, FL 33070

  Completely transformed down to the studs and scheduled for completion in late 2026, this extraordinary bay front estate represents the pinnacle of modern Florida Keys luxury. Meticulously rebuilt with elevated design, superior craftsmanship, and today's most coveted finishes, every detail has been thoughtfully curated to deliver an unparalleled waterfront lifestyle. Experience the ultimate

  Mike Figueiras The Keyes Company

  233 Aberdeen Ct, Tavernier, FL 33070
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  /50

  $2,345,000

  $150K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,716 Sq Ft

  127 Seaside Ave, Key Largo, FL 33037

  Ocean views, deepwater dockage, dock is being replaced with a lift 9/26, and the rare ability to legally operate nightly rentals - it doesn't get any better! The seller has approval for a 20,000lb boat lift and improvement of the dock. There is also approval for an observation deck into the open ocean. This exceptional oceanfront estate offers a standout turnkey investment opportunity, combining

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

  127 Seaside Ave, Key Largo, FL 33037
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  /7

  $365,000

  $85K PRICE DROP

  1 Tdr, Upper Matecumbe Key Islamorada, FL 33036

  1 OF 7 WATERFRONT TDR'S FOR SALE IN THE VILLAGE OF ISLANDS. WHY WAIT? START BUILDING TODAY! Secure a rare TRANSFERABLE DEVELOPMENT RIGHT [TDR] for new single-family market-rate construction within the Village of Islands. Each TDR may be applied toward the construction of one new waterfront residence on an eligible receiver site, subject to Village approval. Buyer shall verify that the proposed

  Karan Moeller Ocean Sotheby's International Realty

  1 Tdr, Upper Matecumbe Key Islamorada, FL 33036
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  /34

  $3,500

  • 2 Beds
  • 2.5 Baths
  • 1,063 Sq Ft

  200 Harborview Dr Unit 101, Tavernier, FL 33070

  Nice furnished 2 bedroom 2.5 bath condo on the bay with dockage up to 30 feet. Convenient to Miami. Call for more information. First Last and Security required.

  Krissy Carnahan Paradise Florida Keys Real Estate, a Luxury Brand

  200 Harborview Dr Unit 101, Tavernier, FL 33070

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