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All Islamorada Waterfront Homes for Sale

Every active waterfront home listing in Islamorada, updated every five minutes from the Florida Keys MLS. This includes canalfront, bayfront, and oceanfront properties across Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key.

Islamorada, known as the Village of Islands, draws serious boaters and anglers from around the world. Canalfront homes offer protected dockage with quick access to both the ocean and Florida Bay. Bayfront properties face the backcountry flats. Oceanfront homes sit on the Atlantic side with direct access to world-class offshore fishing.

Contact Jim Signor at 305-394-4449 to set up a personalized search by price, water type, or neighborhood, with instant alerts for new listings.

Frequently Asked Questions

What types of waterfront homes are available in Islamorada?

Islamorada waterfront homes include canalfront, bayfront, and oceanfront properties across Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key.

Which islands make up Islamorada?

Islamorada, known as the Village of Islands, encompasses Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key.

What makes Islamorada waterfront real estate unique?

Islamorada is known as the Sport Fishing Capital of the World. Waterfront homes offer access to world-class offshore fishing on the Atlantic side and backcountry flats fishing on Florida Bay.

How often are Islamorada waterfront listings updated?

Listings are pulled directly from the Florida Keys MLS and updated every five minutes.

Islamorada Homes for Sale

101 Madeira Ct, Islamorada image
101 Madeira Ct, Islamorada $2,890,000

Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenitie...

  • 3 Beds
  • 3 Baths
  • 620743 MLS
202 Plantation Shores Dr, Tavernier image
202 Plantation Shores Dr, Tavernier $6,000,000

Coastal Luxury. Endless Lifestyle. A rare opportunity to own an extraordinary Plantation Key waterfront estate where captivating ocean views, 140 feet of protected docka...

  • 4 Beds
  • 6 Baths
  • 620708 MLS
81250 Overseas Highway Unit 2, Islamorada image
81250 Overseas Highway Unit 2, Islamorada $2,485,000

Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across f...

  • 3 Beds
  • 3 Baths
  • 620704 MLS
77350 Overseas Hwy, Islamorada image
77350 Overseas Hwy, Islamorada $11,700,000

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 s...

  • 6 Beds
  • 8 Baths
  • 620680 MLS
154 Biscayne Blvd, Islamorada image
154 Biscayne Blvd, Islamorada $2,500,000

Welcome to 154 Biscayne Boulevard in the heart of Islamorada. This beautifully maintained 3 bedroom, 2 bathroom concrete home is designed for those who want to enjoy life...

  • 3 Beds
  • 2 Baths
  • 620603 MLS
117 El Capitan Dr, Islamorada image
117 El Capitan Dr, Islamorada $3,100,000

Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathr...

  • 5 Beds
  • 3 Baths
  • 620602 MLS
19 Avacado St, Islamorada image
19 Avacado St, Islamorada $13,750,000

Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by reno...

  • 5 Beds
  • 7 Baths
  • 620590 MLS
280 S Coconut Palm Blvd, Tavernier image
280 S Coconut Palm Blvd, Tavernier $2,095,000

Welcome to one of Tavernier's most desirable waterfront homes, located in the highly sought after Plantation Key Colony neighborhood. Perfectly positioned in a prime boat...

  • 3 Beds
  • 3 Baths
  • 620552 MLS
157 Valencia Dr, Islamorada image
157 Valencia Dr, Islamorada $4,600,000

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...

  • 5 Beds
  • 6 Baths
  • 620549 MLS
154 Redwing Rd, Tavernier image
154 Redwing Rd, Tavernier $3,750,000

Experience the ultimate Florida Keys waterfront lifestyle in this exceptional BayFront retreat located in the prestigious Sunshine Estates community on Plantation Key. Si...

  • 4 Beds
  • 5 Baths
  • 620543 MLS
239 Plantation Ave, Tavernier image
239 Plantation Ave, Tavernier $2,499,000

Welcome to your slice of paradise in the village of Islamorada! This solid concrete waterfront home was completely updated in 2007 including seawall, all plumbing and ele...

  • 3 Beds
  • 3 Baths
  • 620442 MLS
430 Palm Dr, Islamorada image
430 Palm Dr, Islamorada $5,999,000

Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf ...

  • 5 Beds
  • 7 Baths
  • 620457 MLS
195 Ojibway Ave, Tavernier image
195 Ojibway Ave, Tavernier $5,950,000

Introducing an extraordinary, newly constructed waterfront estate that must be experienced in person. Perfectly positioned on a generous 13,200 sq ft double lot with 120 ...

  • 4 Beds
  • 4 Baths
  • 620455 MLS
155 Palo De Oro Dr, Islamorada image
155 Palo De Oro Dr, Islamorada $4,900,000

An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and qu...

  • 3 Beds
  • 5 Baths
  • 620441 MLS
87445 Old Hwy, Islamorada image
87445 Old Hwy, Islamorada $3,995,000

Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vaca...

  • 5 Beds
  • 4 Baths
  • 620430 MLS
109 Giardino Dr, Islamorada image
109 Giardino Dr, Islamorada $3,875,000

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...

  • 4 Beds
  • 3 Baths
  • 620412 MLS
111 Spoonbill Rd, Tavernier image
111 Spoonbill Rd, Tavernier $2,999,000

Updated canal front pool home located in a desirable neighborhood with quick and easy access to the bay or ocean via Tavernier Creek, a boaters dream. It features a 3 be...

  • 3 Beds
  • 4 Baths
  • 620411 MLS
182 Airstream Ln, Tavernier image
182 Airstream Ln, Tavernier $1,250,000

Welcome to stunning Florida Bay views and breathtaking sunsets in the heart of Plantation Key! This beautifully remodeled and fully furnished modular home offers the perf...

  • 2 Beds
  • 2 Baths
  • 620396 MLS
75090 Overseas Hwy, Islamorada image
75090 Overseas Hwy, Islamorada $29,000,000

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre ...

  • 4 Beds
  • 6 Baths
  • 620394 MLS
140 Iroquois Dr, Islamorada image
140 Iroquois Dr, Islamorada $1,495,000

Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of ...

  • 3 Beds
  • 3 Baths
  • 620353 MLS
127 & 121 Monroe Dr Unit 1-3, Tavernier image
127 & 121 Monroe Dr Unit 1-3, Tavernier $2,399,000

Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily l...

  • 4 Beds
  • 4 Baths
  • 620278 MLS
194 Buttonwood Ln, Islamorada image
194 Buttonwood Ln, Islamorada $6,150,000

Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence s...

  • 6 Beds
  • 7 Baths
  • 620190 MLS
113 Villa Bella Dr, Islamorada image
113 Villa Bella Dr, Islamorada $2,695,000

Welcome to one of Islamorada's finest homes! Located in Venetian Shores the premier boating community of Islamorada. One of only two streets in the neighborhood with curb...

  • 5 Beds
  • 3 Baths
  • 620127 MLS
139 Gimpy Gulch Dr, Islamorada image
139 Gimpy Gulch Dr, Islamorada $14,900,000

Yes, you can have it all! Tucked away behind mature tropical landscaping and stretching across an expanse of more than 250 feet of sandy bayfront shoreline, 139 Gimpy Gul...

  • 6 Beds
  • 9 Baths
  • 620077 MLS
89401 Old Hwy, Tavernier image
89401 Old Hwy, Tavernier $13,500,000 ▼

Private Helicopter Estate in the Florida Keys. Behind private gates on prestigious Million Air Row, this exceptional oceanfront estate spans nearly 2.5 acres and offer...

  • 8 Beds
  • 8 Baths
  • 620067 MLS
84961 Old Hwy Unit LOT 27, Islamorada image
84961 Old Hwy Unit LOT 27, Islamorada $899,000

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...

  • 1 Beds
  • 1 Baths
  • 620039 MLS
89505 Old Hwy, Tavernier image
89505 Old Hwy, Tavernier $26,400,000

Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind g...

  • 7 Beds
  • 10 Baths
  • 620022 MLS
316 Woods Ave, Islamorada image
316 Woods Ave, Islamorada $2,400,000

Welcome to your own private slice of Islamorada paradise! This canal-front home offers easy access to Florida Bay along with stunning lake views and unforgettable sunsets...

  • 4 Beds
  • 4 Baths
  • 620004 MLS
125 Gardenia St Unit 125, Tavernier image
125 Gardenia St Unit 125, Tavernier $1,750,000

Experience luxury waterfront living in the heart of the Florida Keys! 4 bedrooms and 2 bathrooms. This stunning modern home offers sleek finishes, breathtaking canal view...

  • 4 Beds
  • 2 Baths
  • 619976 MLS
154 Milano Dr, Islamorada image
154 Milano Dr, Islamorada $3,000,000 ▼

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 ...

  • 2 Beds
  • 2 Baths
  • 619931 MLS
75071 Overseas Hwy, Islamorada image
75071 Overseas Hwy, Islamorada $3,199,000

Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscap...

  • 3 Beds
  • 2 Baths
  • 619869 MLS
88835 & 88845 Old Hwy, Tavernier image
88835 & 88845 Old Hwy, Tavernier $40,000,000

A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatche...

  • 8 Beds
  • 11 Baths
  • 619826 MLS
88845 Old Hwy, Tavernier image
88845 Old Hwy, Tavernier $27,000,000

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 functio...

  • 5 Beds
  • 8 Baths
  • 619825 MLS
88835 Old Hwy, Tavernier image
88835 Old Hwy, Tavernier $15,000,000

An exceptional opportunity on coveted Millionaire's Row in Tavernier, 88835 Old Highway offers over 3 acres of oceanfront property paired with a rare additional acre feat...

  • 3 Beds
  • 3 Baths
  • 619824 MLS
75840 Overseas Hwy, Islamorada image
75840 Overseas Hwy, Islamorada $13,500,000 ▼

LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pri...

  • 7 Beds
  • 7 Baths
  • 619776 MLS
189 Ocean Dr, Tavernier image
189 Ocean Dr, Tavernier $2,299,000

Fantastic oceanside canal home offering peek-a-boo ocean views from both the front and backyard. Enjoy a straight shot to the Atlantic Ocean, perfect for world-class fish...

  • 5 Beds
  • 4 Baths
  • 619737 MLS
74049 Overseas Hwy, Islamorada image
74049 Overseas Hwy, Islamorada $3,999,999

Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represen...

  • 4 Beds
  • 4 Baths
  • 619687 MLS
1101 Mastic St, Islamorada image
1101 Mastic St, Islamorada $6,999,000 ▼

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its f...

  • 8 Beds
  • 6 Baths
  • 619673 MLS
132 Gardenia St, Tavernier image
132 Gardenia St, Tavernier $1,200,000

Everything you need and nothing you don't. This ground-level 3-bedroom, 3-bathroom home offers an easy, functional layout with that unmistakable Florida Keys feel the mom...

  • 3 Beds
  • 3 Baths
  • 619593 MLS
88747 Old Hwy, Islamorada image
88747 Old Hwy, Islamorada $8,000,000

Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ult...

  • 3 Beds
  • 3 Baths
  • 619592 MLS
169 Venetian Way, Islamorada image
169 Venetian Way, Islamorada $1,650,000 ▼

Experience Coastal Luxury and privacy with this exceptional 5 bedroom, 3 bath home on two lots!! Over 2900 sq. ft. of thoughtfully designed living space. Constructed of...

  • 5 Beds
  • 3 Baths
  • 619545 MLS
131 Bayview Isle Dr, Islamorada image
131 Bayview Isle Dr, Islamorada $3,900,000 ▼

Welcome to Casa Tranquila in the highly desirable Venetian Shores neighborhood of Islamorada, where boating convenience meets tropical serenity. With 105 feet of dockage ...

  • 3 Beds
  • 3 Baths
  • 619454 MLS
265 Pueblo St, Tavernier image
265 Pueblo St, Tavernier $6,600,000

Experience the pinnacle of luxury waterfront living in the Florida Keys with this exceptional estate, perfectly positioned at the end of a quiet street with 173 feet of d...

  • 5 Beds
  • 4 Baths
  • 619405 MLS
141 Canal St, Islamorada image
141 Canal St, Islamorada $3,499,000 ▼

Stunning Plantation Key canal front pool home! This exceptional all-concrete residence boasts a rare layout with five bedrooms, five full baths, and one-half bathroom, pe...

  • 5 Beds
  • 6 Baths
  • 619367 MLS
124 Venetian Way, Islamorada image
124 Venetian Way, Islamorada $1,599,000

Island Living in Prestigious Venetian Shores! Welcome to this newly custom-built 4bd/3ba residence ideally positioned on a tranquil plugged canal in one of the most soug...

  • 4 Beds
  • 3 Baths
  • 619331 MLS
113 San Juan Dr Unit & Boat Slip, Islamorada image
113 San Juan Dr Unit & Boat Slip, Islamorada $1,695,000 ▼

Desirable Venetian Shores 3 bedroom / 2 bath home just steps to your boat slip! Enjoy a direct sight line view of your boat and surround yourself with peaceful water view...

  • 3 Beds
  • 2 Baths
  • 619311 MLS
82719 Old Hwy, Islamorada image
82719 Old Hwy, Islamorada $24,995,000

Experience unparalleled oceanfront living at the Chateau on the Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal livin...

  • 7 Beds
  • 11 Baths
  • 619281 MLS
82779 Old Hwy Unit 15, Islamorada image
82779 Old Hwy Unit 15, Islamorada $3,800,000

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort con...

  • 4 Beds
  • 5 Baths
  • 619187 MLS
82779 Old Hwy Unit 8, Islamorada image
82779 Old Hwy Unit 8, Islamorada $3,800,000

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort con...

  • 4 Beds
  • 5 Baths
  • 619186 MLS
82779 Old Hwy Unit 7, Islamorada image
82779 Old Hwy Unit 7, Islamorada $3,800,000

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort con...

  • 4 Beds
  • 5 Baths
  • 619185 MLS
149 Lake Rd, Tavernier image
149 Lake Rd, Tavernier $2,750,000 ▼

Don't let the address fool you, this home has easy bay access! Welcome to relaxed waterfront living in the Village of Islamorada, where open water views and nightly suns...

  • 3 Beds
  • 2 Baths
  • 619095 MLS
136 San Remo Dr, Islamorada image
136 San Remo Dr, Islamorada $4,445,000 ▼

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 nea...

  • 8 Beds
  • 4 Baths
  • 619083 MLS
200 Plantation Dr, Tavernier image
200 Plantation Dr, Tavernier $2,100,000 ▼

Located just off the ocean off Tavernier Creek, this premier location rarely comes available. Gorgeous views and breezes! Concrete home with concrete roof, inground pool...

  • 4 Beds
  • 2 Baths
  • 619079 MLS
77340 Overseas Hwy, Islamorada image
77340 Overseas Hwy, Islamorada $3,999,999

Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys resident...

  • 2 Beds
  • 2 Baths
  • 619064 MLS
319 Woods Ave, Tavernier image
319 Woods Ave, Tavernier $1,090,000 ▼

Charming 2-bedroom, 2-bath ground-level canal-front home located in a highly desirable Florida Keys neighborhood. The home features a split floor plan with a one-bedro...

  • 2 Beds
  • 2 Baths
  • 618962 MLS
75131 Overseas Hwy, Islamorada image
75131 Overseas Hwy, Islamorada $4,500,000

Beautiful 100' of oceanfront property on Lower Matecumbe Key. This offering consists of a 100' lot with a triplex apartment building (3 TDRs),.This gives you lots of poss...

  • 3 Baths
  • 618928 MLS
150 List St, Islamorada image
150 List St, Islamorada $4,900,000

Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet...

  • 1 Beds
  • 1 Baths
  • 618918 MLS
88351 Old Hwy, Islamorada image
88351 Old Hwy, Islamorada $15,990,000

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 yo...

  • 6 Beds
  • 9 Baths
  • 618911 MLS
105 Palo De Oro Dr, Islamorada image
105 Palo De Oro Dr, Islamorada $3,995,000

Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence d...

  • 5 Beds
  • 3 Baths
  • 618653 MLS
20 Avacado St, Islamorada image
20 Avacado St, Islamorada $15,950,000

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Hig...

  • 6 Beds
  • 8 Baths
  • 618816 MLS
87950 Overseas Hwy, Islamorada image
87950 Overseas Hwy, Islamorada $3,800,000

Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop str...

  • 5 Beds
  • 3 Baths
  • 618165 MLS
75761 Overseas Hwy, Islamorada image
75761 Overseas Hwy, Islamorada $4,999,900

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid conc...

  • 4 Beds
  • 4 Baths
  • 614893 MLS
75131 Overseas Hwy, Islamorada image
75131 Overseas Hwy, Islamorada $6,495,000

Beautiful 200' of oceanfront property on Lower Matecumbe Key. This offering consists of one 100' lot, vacant with TDR & contiguously, a 100' lot with a triplex apartment ...

  • 3 Beds
  • 3 Baths
  • 608546 MLS
185 Ojibway Ave, Tavernier image
185 Ojibway Ave, Tavernier $1,895,000 ▼

Bay views with a canal front price! This beautifully coastal modern renovated property is located on the main free flowing canal in the desirable community of Indian Wate...

  • 3 Beds
  • 2 Baths
  • 618096 MLS
79775 Overseas Hwy, Islamorada image
79775 Overseas Hwy, Islamorada $29,500,000

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...

  • 6 Beds
  • 6 Baths
  • 618152 MLS
159 Iroquois Dr, Islamorada image
159 Iroquois Dr, Islamorada $1,675,000 ▼

Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach n...

  • 3 Beds
  • 3 Baths
  • 618050 MLS
88 W Plaza Del Lago, Islamorada image
88 W Plaza Del Lago, Islamorada $4,750,000 ▼

Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime water...

  • 5 Beds
  • 5 Baths
  • 615676 MLS
82749 Old Hwy, Islamorada image
82749 Old Hwy, Islamorada $6,900,000 ▲

Welcome to Casa Mar Azul, a one-of-a-kind oceanfront estate located along the iconic Old Highway in Islamorada — a rare offering with 200 feet of oceanfront shoreline, a ...

  • 3 Beds
  • 3 Baths
  • 616520 MLS
121 Lisbon Ct, Islamorada image
121 Lisbon Ct, Islamorada $2,075,000 ▼

What does everyone dream of? The smallest house in the best neighborhood -- and this one delivers. Welcome to easy, breezy living in Port Antigua, where charm, quality, a...

  • 2 Beds
  • 2 Baths
  • 618666 MLS
171 Kahiki Dr, Tavernier image
171 Kahiki Dr, Tavernier $4,799,000 ▼

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 p...

  • 3 Beds
  • 3 Baths
  • 618338 MLS
75055 Overseas Hwy, Islamorada image
75055 Overseas Hwy, Islamorada $2,790,000 ▼

Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views ...

  • 3 Beds
  • 2 Baths
  • 617520 MLS
166 Bayview Dr, Islamorada image
166 Bayview Dr, Islamorada $4,700,000 ▼

Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers...

  • 4 Beds
  • 4 Baths
  • 617501 MLS
81486 Overseas Hwy, Islamorada image
81486 Overseas Hwy, Islamorada $22,500,000

Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on...

  • 7 Beds
  • 9 Baths
  • 618525 MLS
84961 Old Hwy Unit 18, Islamorada image
84961 Old Hwy Unit 18, Islamorada $999,000

Beautiful Atlantic Ocean views surround this newer concrete home featuring an open-concept floor plan with 2 bedrooms and 2 bathrooms. Tastefully furnished with a coastal...

  • 2 Beds
  • 2 Baths
  • 618847 MLS
186 & 165 Bayview Dr, Islamorada image
186 & 165 Bayview Dr, Islamorada $10,900,000

A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over ½ acre lot with panoramic water views from every room. Offerin...

  • 6 Beds
  • 5 Baths
  • 618449 MLS
162 Bayview Dr, Islamorada image
162 Bayview Dr, Islamorada $8,590,000 ▼

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 po...

  • 8 Beds
  • 10 Baths
  • 613653 MLS
75280 Overseas Hwy, Islamorada image
75280 Overseas Hwy, Islamorada $11,000,000

Commanding 170 feet of private Florida Bay frontage, and situated on over and acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures...

  • 4 Beds
  • 4 Baths
  • 616886 MLS
109 Columbus Dr, Islamorada image
109 Columbus Dr, Islamorada $6,700,000

Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of ...

  • 4 Beds
  • 5 Baths
  • 616619 MLS
81906 Overseas Hwy Unit 2, Islamorada image
81906 Overseas Hwy Unit 2, Islamorada $2,495,000

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 re...

  • 3 Beds
  • 4 Baths
  • 617838 MLS
117 Leoni Dr, Islamorada image
117 Leoni Dr, Islamorada $4,600,000 ▼

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake ...

  • 5 Beds
  • 6 Baths
  • 617341 MLS
228 Tide Ave, Tavernier image
228 Tide Ave, Tavernier $6,975,000 ▼

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, an...

  • 4 Beds
  • 5 Baths
  • 618703 MLS
87895 Old Hwy, Islamorada image
87895 Old Hwy, Islamorada $24,995,000

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 ...

  • 5 Beds
  • 8 Baths
  • 617705 MLS
109 Milano Dr, Islamorada image
109 Milano Dr, Islamorada $2,500,000 ▼

Located in the highly desirable Venetian Shores neighborhood in Islamorada, this canal front home offers 70 feet of dockage with a brand new concrete dock and seawall, ma...

  • 3 Beds
  • 3 Baths
  • 618461 MLS
87429 Old Hwy, Islamorada image
87429 Old Hwy, Islamorada $18,999,000 ▼

A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a...

  • 6 Beds
  • 8 Baths
  • 615643 MLS
76412 Overseas Hwy, Islamorada image
76412 Overseas Hwy, Islamorada $2,300,000

Make all of your Florida Keys fantasies come true at Fantasy Harbor! We're willing to bet you never even knew this gated community on Islamorada's Lower Matecumbe existed...

  • 3 Beds
  • 3 Baths
  • 611841 MLS
81906 Overseas Hwy Unit 3, Islamorada image
81906 Overseas Hwy Unit 3, Islamorada $2,649,000

Welcome to Coral Cove Residence 3, perfectly positioned in the heart of Islamorada. This turn-key, thoughtfully designed three-bedroom, three-and-a-half-bath residence wa...

  • 3 Beds
  • 4 Baths
  • 617758 MLS
115 Azalea St, Tavernier image
115 Azalea St, Tavernier $2,220,000

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 privat...

  • 5 Beds
  • 3 Baths
  • 617279 MLS
137 Sapodilla Dr, Islamorada image
137 Sapodilla Dr, Islamorada $6,150,000 ▼

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boa...

  • 5 Beds
  • 6 Baths
  • 618481 MLS
142 Gulfview Dr, Islamorada image
142 Gulfview Dr, Islamorada $1,075,000

ACTIVE BUILDING AND DOCK PERMITS. BUILD RIGHT AWAY. Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. ...

  • 3 Beds
  • 4 Baths
  • 617029 MLS
316 North Dr, Islamorada image
316 North Dr, Islamorada $2,400,000 ▼

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 ''Plant...

  • 3 Beds
  • 4 Baths
  • 616205 MLS
80201 Overseas Hwy, Islamorada image
80201 Overseas Hwy, Islamorada $7,400,000 ▼

Experience Islamorada living at its absolute finest with this remodeled oceanfront estate. Situated on 200 feet of sandy waterfront with unobstructed views of the Atlanti...

  • 5 Beds
  • 6 Baths
  • 616417 MLS
251 Azalea St, Tavernier image
251 Azalea St, Tavernier $1,390,000 ▼

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, ...

  • 2 Beds
  • 2 Baths
  • 616971 MLS
181 Nautilus Dr, Islamorada image
181 Nautilus Dr, Islamorada $5,999,999

Brand new 2026 coastal luxury in Islamorada's White Marlin Beach. 181 Nautilus Dr offers the ultimate Keys lifestyle with 5 bedrooms, 5.5 baths, and 5,320 SF of living ar...

  • 5 Beds
  • 6 Baths
  • 618158 MLS
241 Tollgate Blvd, Islamorada image
241 Tollgate Blvd, Islamorada $4,249,000 ▼

Near-new luxury home in coveted Toll Gate Shores, Islamorada, Florida. Near perfection, describes this newly constructed 3-bedroom, 3-bath residence offering single-lev...

  • 3 Beds
  • 3 Baths
  • 618244 MLS
122 Court Contessa, Islamorada image
122 Court Contessa, Islamorada $2,750,000 ▼

'Turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of Islamorada' Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Isla...

  • 3 Beds
  • 3 Baths
  • 616500 MLS
88547 Old Hwy, Tavernier image
88547 Old Hwy, Tavernier $6,500,000 ▼

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires' Row... Islamorada's premier address. New dock with two boat lifts (16,000 lb. and 10,000 lb.)...

  • 4 Beds
  • 3 Baths
  • 610778 MLS
216 Sonny Rd, Tavernier image
216 Sonny Rd, Tavernier $2,200,000 ▼

Offered for the first time in its history, this exceptional corner-lot waterfront residence has been meticulously cared for by its original owners and presents a rare opp...

  • 3 Beds
  • 2 Baths
  • 618660 MLS
150 Azalea St, Tavernier image
150 Azalea St, Tavernier $1,849,000 ▼

Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp &...

  • 4 Beds
  • 2 Baths
  • 617994 MLS
114 Spoonbill Rd, Tavernier image
114 Spoonbill Rd, Tavernier $2,199,000 ▼

Newly renovated 3-bedroom, 2-bath canal-front CBS home with direct bay access. The interior has been fully updated with tasteful coastal finishes, along with new impact w...

  • 3 Beds
  • 2 Baths
  • 617796 MLS
144 N Rolling Hill Rd, Tavernier image
144 N Rolling Hill Rd, Tavernier $6,450,000 ▼

This luxury bayfront home in the Florida Keys offers discriminant buyers a complete coastal lifestyle package with year-round sunset views, hurricane-rated construction, ...

  • 4 Beds
  • 5 Baths
  • 617522 MLS

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