Islamorada spans five islands in the Upper Florida Keys — Plantation Key, Windley Key, Upper Matecumbe, Lower Matecumbe, and Tea Table Key — running from roughly Mile Marker 90 down to MM 74. Known as the Sport Fishing Capital of the World, it draws buyers looking for oceanfront estates, canalfront homes with Atlantic and Florida Bay access, and a village character unlike anywhere else in the Keys.
Current Islamorada Market Stats


Read my most recent Florida Keys Real Estate Market Report for 2026
Browse listings by neighborhood below. Data pulls directly from the Florida Keys MLS and updates every 5 minutes.
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Wake up to the sunrise over the Atlantic from this private oceanfront retreat offering two separate residences, a sandy beach, and direct access from Highway to Ocean. T...
RARELY AVAILABLE AT FUTURA YACHT CLUB! This beautifully remodeled end-unit townhome offers an exceptional Florida Keys lifestyle, complete with two side-by-side deeded bo...
Exceptional Brand New Waterfront Home in a prime Plantation Key location. This striking three-level contemporary residence offers 60 feet of protected deep-water dockage...
This home is special and just waiting for the next family to make memories here. Tucked among lush tropical landscaping, this inviting Islamorada home offers the perfect...
Welcome to your Florida Keys retreat at Summer Sea! Enjoy bay views from your private open deck area. This 2-bedroom, 1.5-bath condo offers updates throughout and coastal...
CBS home on a large lot in Islamorada's desirable Edenaire! This concrete 2 bedroom, 2 bath house has a metal roof, impact windows and doors, and is in an X flood zone. H...
Private. Luxurious. Waterfront. Boater-focused. This is more than a home it is an opportunity to experience the Florida Keys exactly as they were meant to be enjoyed. T...
Welcome to your private island home retreat, The Belle House. Highlighted on the Netflix series Bloodline as the home of Kevin & Belle Rayburn. Set on an expansive half-a...
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...
OCEAN ACCESS WATERFRONT OPPORTUNITY IN VENETIAN SHORES! Immaculate 2-story CBS concrete home offering the ultimate Florida Keys lifestyle! Situated on a 100' wide deep-wa...
THIS UPDATED BEAUTY LOCATED IN RENOWNED VENETIAN SHORES IS A TRUE MUST SEE!! LOCATED IN ONE OF VENETIAN SHORES MOST EXCLUSIVE LOCATIONS GIARDINO DRIVE. UPSTAIRS: THREE ...
OCEANFRONT PENTHOUSE -- STRONG RENTAL INCOME. Welcome to PH701 at Sea Gulls, a rare and incredibly unique 3-bed, 2-bath oceanfront penthouse. With over 2,100 sq ft of liv...
This waterfront home offers 36 feet of dockage and a beautifully renovated interior designed for effortless Keys living. Thoughtfully updated and tastefully decorated, th...
The most sought-after bay in all the Florida Keys, and one of the largest properties on it. This true double lot spans 1.3 acres with more than 250' of bayfront facing du...
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 ...
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...
A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout livi...
BEAUTIFUL CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000! LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY IN THE HIGHLY DESIRABLE PLANTATION BY THE SEA ON THE OCE...
Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated archi...
Canal front living, right where you want it. Set along one of Islamorada's most popular canals, this turnkey 3-bedroom, 3-bath home offers a waterfront setup that makes l...
Extraordinary opportunity to own one of the Florida Keys' most spectacular oceanfront residences. Set along a breathtaking stretch of pristine shoreline, this remarkable ...
BEAUTIFUL PLANTATION KEY COLONY 2BR-2BA CBS Block Construction with a Brand New Metal Roof, featuring a PRIVATE COMMUNITY BOAT RAMP with a Low Voluntary $250 Yearly Fee a...
Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, ...
Villa 1 offers one of the most coveted locations within the exclusive 22-villa community at The Islands of Islamorada. Ideally positioned as the closest oceanfront villa ...
Welcome to your Venetian Shores retreat, where relaxed coastal living meets effortless waterfront luxury. This completely updated pool home is designed for easy living an...
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...
ONE OF THE LOWEST PRICED HOMES IN THE VILLAGE OF ISLAMORADA! Charming Home in a desirable Plantation Key Subdivision! This well-maintained Sheffield Steel home offers e...
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 d...
Welcome to Summer Seas, a desirable waterfront community in the heart of the Florida Keys! This beautifully maintained 2-bedroom, 1.5-bath condominium offers the perfect ...
This exceptional waterfront estate situated on two lots and on a deep water canal with a 50ft dock is situated in the heart of Plantation Key. The property features a gra...
Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offer...
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...
More Space Than the Tax Records Reflect! This charming Tavernier home offers much more than meets the eye. While the tax records reflect a 2-bedroom home, the enclosed...
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...
Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islam...
Turn key furnished condo in Islamorada! This beautifully appointed 2 bedroom, 2 bath condo features an open floor plan, abundant natural light and a rare balcony. Remodel...
Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan wi...
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the h...
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the h...
Gorgeous 3 bedroom 2 bathroom home on a spacious corner lot, with plenty of room for boats and RVs. Updated and remodeled bathrooms, open concept kitchen, laundry room an...
Waterfront 3/3 Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedr...
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 Futura Yacht Club! Your island getaway awaits in this highly desirable Plantation Key community. Unit 304 is a 2 bed, 2 bath, beautifully maintained con...
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...
Rare Mixed-Use Opportunity with Spectacular Ocean Views in Islamorada MM 74.5. Endless possibilities await at this highly visible, commercially zoned property located ...
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...
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 ...
Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. ...
Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily l...
Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly s...
Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situate...
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...
Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND 24,000 lb. Boat Lift in desirable Futura Yacht Club! Located in the heart of Plantation Key in ...
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...
ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this charming home is perfectly situated in the heart o...
Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full ...
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...
Located in Plantation by the Sea, this Islamorada townhouse offers 2 bedrooms, 1.5 bathrooms, covered parking, and a storage unit in a gated oceanfront complex. Inside, ...
Rare opportunity to own a half-acre corner parcel in the heart of Plantation Key. With an existing structure already in place, the property offers the flexibility for an ...
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...
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 ...
Welcome to Summer Sea Condominium Apt 424, a beautifully remodeled and fully furnished bayfront residence in the heart of Islamorada. This turnkey, 2-bedroom, 2-full bath...
Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscap...
Experience all that Islamorada has to offer from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms...
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...
Spacious 4 bed, 3 bath home in the desirable Indian Mound neighborhood on Plantation Key. Sitting on two lots totaling about 11,000 sq ft, there's plenty of privacy and e...
Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca h...
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...
Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story ...
Welcome to Sand Pebbles -- Islamorada's Hidden Gem. Located in the heart of the Village of Islamorada, this spacious 2-bedroom, 2-bathroom condo at the boutique community...
Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its f...
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...
Fully furnished turn key townhome in Islamorada at Las Maravillas is available, one of only 10 private residences on the bayside on Lower Matecumbe in the Village. Docka...
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...
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-ins...
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...
Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just...
Live the Florida Keys Lifestyle in Your Dream Home Experience the perfect blend of elegance, functionality, and laid-back tropical living in this beautifully designed ...
'Blue Haven' is a beautifully renovated elevated 2-story residence in the heart of Islamorada, offering the ideal blend of modern upgrades and relaxed Florida Keys living...
TOP FLOOR oceanfront living awaits in this beautifully updated 2-bedroom, 2-bath condo located in desirable Sea Gulls development in Plantation Key. Enjoy breathtaking At...
Welcome to your Keys get-a-away! Snuggled in the heart of Plantation Key colony, right at the entrance of the village of Islamorada: your island dreams, weekend oasis, or...
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...
Attention Investors! Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Sportfishing Capital of the World''. This spacious Two Queen b...
Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setti...
This island resort style unit offers stations for dockage up to 25-foot boats, trailer storage and boat ramp. There is a pool for the development, pickle ball and tenn...
Elevated direct oceanfront living from a 5th-floor 2 bedroom 2 bath residence in Sea Gulls on Plantation Key in Islamorada. This all concrete building offers peace of min...

Jim Signor: 305-394-4449