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.
Islamorada waterfront homes include canalfront, bayfront, and oceanfront properties across Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key.
Islamorada, known as the Village of Islands, encompasses Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key.
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.
Listings are pulled directly from the Florida Keys MLS and updated every five minutes.
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...
Coastal Luxury. Endless Lifestyle. A rare opportunity to own an extraordinary Plantation Key waterfront estate where captivating ocean views, 140 feet of protected docka...
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...
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...
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...
Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathr...
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...
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...
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...
Experience the ultimate Florida Keys waterfront lifestyle in this exceptional BayFront retreat located in the prestigious Sunshine Estates community on Plantation Key. Si...
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...
Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf ...
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 ...
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...
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...
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...
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...
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...
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 ...
Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of ...
Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily l...
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...
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...
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...
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...
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...
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...
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...
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...
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 ...
Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscap...
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...
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...
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...
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...
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...
Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represen...
Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its f...
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...
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...
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...
Welcome to Casa Tranquila in the highly desirable Venetian Shores neighborhood of Islamorada, where boating convenience meets tropical serenity. With 105 feet of dockage ...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys resident...
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...
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...
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...
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...
Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence d...
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...
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...
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...
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 ...
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...
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...
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...
Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime water...
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 ...
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...
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...
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 ...
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...
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...
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...
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...
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...
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...
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 ...
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...
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 ...
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...
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 ...
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...
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...
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...
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...
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...
Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boa...
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. ...
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...
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...
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, ...
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...
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...
'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...
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.)...
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...
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 &...
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...
This luxury bayfront home in the Florida Keys offers discriminant buyers a complete coastal lifestyle package with year-round sunset views, hurricane-rated construction, ...

Jim Signor: 305-394-4449