Florida Keys Luxury Homes
The listings below represent the most recent high-end properties available, starting at $3 million. You'll find open water homes, private estates, and waterfront properties from Key Largo to Key West — each offering a different take on island living.
Some of the Best Homes Never Appear on the MLS
Many sellers at this price point prefer privacy and choose not to publicly market their properties. I can help you explore off-market and upcoming listings that align with your goals — especially if you're ready to move when the right home appears.
It's About How You Want to Live
For most buyers in the Florida Keys, the right home isn't just about the specs. Whether the goal is boating access, investment potential, or a private retreat, I help clients find properties that match how they actually plan to use them.
Key Largo: Luxury Closest to Miami
Islamorada and Key West carry the deepest concentration of ultra-high-end estates in the Keys, but Key Largo offers something neither can: waterfront luxury living with the shortest possible drive to Miami. Oceanfront and bayfront estates in communities like Port Largo and Buccaneer Point regularly reach into the multi-million dollar range, appealing to buyers who want the full Keys lifestyle without a long commute to the mainland.
Islamorada: The Heart of Keys Luxury
Islamorada holds some of the deepest luxury inventory in the Keys, with waterfront communities like Venetian Shores and Port Antigua offering open-water estates, private docks, and some of the most sought-after addresses in the Upper Keys.
When you're ready to fine-tune your search or explore homes you won't find here, reach out for a confidential consultation.
Frequently Asked Questions
What qualifies as a luxury home in the Florida Keys?
In the Florida Keys, luxury homes are generally priced at $3 million and above. These include oceanfront estates, bayfront properties, private island retreats, and high-end waterfront homes from Key Largo to Key West.
Are there off-market luxury homes available in the Florida Keys?
Yes. Many high-end sellers prefer privacy and do not publicly list their properties. Working with a local agent who has access to off-market and upcoming listings is often the best way to find them.
What should I consider when buying a luxury home in the Florida Keys?
Beyond price and condition, buyers should evaluate flood zone designation, insurance costs, permitting history, rental restrictions, boating access, and how the property fits their intended lifestyle.
Which areas of the Florida Keys have the most luxury homes?
Islamorada and Key West have the highest concentration of ultra-high-end waterfront estates. Key Largo's luxury market is smaller by comparison, but it holds a distinct advantage for buyers who want Keys luxury living closest to Miami, with oceanfront and bayfront estates that regularly reach into the multi-million dollar range.
Florida Keys Luxury Homes
Looking for a truly unique opportunity in the Florida Keys? Check out these 2 Custom Luxury CBS Pool Homes that are side by side! Live in one, and rent the other, corpor...
- 8 Beds
- 8 Baths
- 621248 MLS
New construction waterfront home with all the bells and whistles. Situated on a large corner lot of nearly 14,000 sq. ft., the property features two electric gated entran...
- 4 Beds
- 5 Baths
- 621244 MLS
Experience Mediterranean elegance and open-water living at this private oceanfront estate, featuring a pool, all set on a gated 10,545 sq. ft. lot in prestigious Key Col...
- 5 Beds
- 6 Baths
- 621235 MLS
Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgett...
- 6 Beds
- 7 Baths
- 621215 MLS
At the very tip of a private peninsula in the heart of the Florida Keys, this stunning Gulffront property delivers the ultimate waterfront lifestyle. Built in 2022, this ...
- 5 Beds
- 5 Baths
- 621212 MLS
This tropical Sombrero Beach 2-Home Compound is set on a spacious 17,600 sq ft fenced lot with Pool, 2 Tikis and located just 2 properties in from the ocean. Fantastic ...
- 5 Beds
- 4 Baths
- 621171 MLS
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...
- 3 Beds
- 3 Baths
- 621153 MLS
Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top di...
- 5 Beds
- 5 Baths
- 621141 MLS
514 Emma is a wonderful single-family home located in Truman Annex. The first floor features a large, updated chef's kitchen with double wall ovens, double refrigerator/f...
- 4 Beds
- 3 Baths
- 621135 MLS
Rare Opportunity: The Only Home For Sale on Crescent Beach, Sunset Key Welcome to 11 Sunset Key Drive -- a fully renovated retreat on the most exclusive private island i...
- 3 Beds
- 3 Baths
- 621128 MLS
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 ...
- 5 Beds
- 3 Baths
- 621117 MLS
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...
- 5 Beds
- 4 Baths
- 621096 MLS
Welcome to CASA MARE, where contemporary luxury meets the open Atlantic. Built in 2023 by Dellanos Construction of the Keys, this spectacular direct-oceanfront residence ...
- 5 Beds
- 4 Baths
- 621057 MLS
Welcome to La Mar-A-Villa on Marina, an exceptional newly built contemporary waterfront residence offering 4,001 sq. ft. of luxury living in the heart of the Florida Keys...
- 5 Beds
- 4 Baths
- 621058 MLS
Welcome to this extraordinary oceanfront estate, gracefully positioned on an oversized 17,900sqft point lot within prestigious Plantation Island, tucked away at the end o...
- 3 Beds
- 4 Baths
- 621038 MLS
Looking for one of the most unique Bayfront Estates in the Florida keys, well you just found it. Just over 3 acres located on the Gulf of America. What makes the property...
- 5 Beds
- 5 Baths
- 621022 MLS
Port Largo Waterfront Paradise Located in one of Key Largo's most desirable neighborhoods, this canal front 4-bedroom, 3.5-bath pool home is truly a boater's dream. Wh...
- 4 Beds
- 4 Baths
- 620996 MLS
Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated archi...
- 4 Beds
- 5 Baths
- 620986 MLS
Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-y...
- 3 Beds
- 4 Baths
- 620985 MLS
Extraordinary opportunity to own one of the Florida Keys' most spectacular oceanfront residences. Set along a breathtaking stretch of pristine shoreline, this remarkable ...
- 5 Beds
- 5 Baths
- 620965 MLS
Spectacular luxury modern home built in 2020, located on a corner lot with over 200 feet of waterfront. This home has four stories, featuring elegant finishes and a gourm...
- 5 Beds
- 4 Baths
- 620964 MLS
NEW CONSTRUCTION | FULLY FURNISHED | 45' BOAT SLIP | OPEN GULF VIEWS Experience elevated Florida Keys living in this newly constructed, fully furnished 5-bedroom, 4-bath ...
- 5 Beds
- 4 Baths
- 620953 MLS
Own an entire private island in the heart of the Florida Keys. Located just ¼ mile offshore from Marathon, East Sister Rock Island offers extraordinary privacy surrounded...
- 4 Beds
- 3 Baths
- 620952 MLS
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 ...
- 4 Beds
- 5 Baths
- 620933 MLS
Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and span...
- 4 Beds
- 4 Baths
- 620913 MLS
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...
- 3 Beds
- 3 Baths
- 620907 MLS
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...
- 4 Beds
- 4 Baths
- 620893 MLS
Set along the Gulf on 2 lots within the sought-after gated Stirrup Key community, this beautifully appointed CBS residence captures panoramic open-water views, unforgetta...
- 3 Beds
- 4 Baths
- 620861 MLS
Embrace the essence of coastal living at this extraordinary bayfront estate, where privacy, comfort, and natural beauty come together on two sun-drenched acres along Flor...
- 10 Beds
- 9 Baths
- 620838 MLS
Crafted for exceptional waterfront living, this custom 6-bedroom, 5.5-bath bayfront estate showcases impeccable craftsmanship, expansive Florida Bay views, seamless indoo...
- 6 Beds
- 6 Baths
- 620837 MLS
A Premier Florida Keys Yacht Property! Positioned on an exceptional point lot at the end of 11th Street in Key Colony Beach, this beautifully renovated waterfront residen...
- 3 Beds
- 2 Baths
- 620786 MLS
A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living....
- 6 Beds
- 7 Baths
- 620770 MLS
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...
- 4 Beds
- 3 Baths
- 620762 MLS
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...
- 5 Beds
- 6 Baths
- 620757 MLS
Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, com...
- 3 Beds
- 3 Baths
- 620747 MLS
Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially se...
- 3 Beds
- 3 Baths
- 620745 MLS
Experience the pinnacle of Florida Keys waterfront living in this exceptional 3-bedroom, 3-bathroom oceanfront estate offering breathtaking open water views, deep-water d...
- 3 Beds
- 3 Baths
- 620742 MLS
Welcome to your Florida Keys waterfront paradise in the highly sought-after Port Largo community of Key Largo. This exceptional 4-bedroom, 3-bathroom home is designed for...
- 4 Beds
- 3 Baths
- 620735 MLS
Welcome to 2000 Manor Lane, an extraordinary coastal retreat positioned on an expansive double lot spanning 15,604 square feet. Offered fully furnished, this impressive ...
- 6 Beds
- 5 Baths
- 620733 MLS
Brand New Luxury Oceanfront Estate | A Boater's, Angler's & Diver's Paradise Experience the ultimate Florida Keys lifestyle from this brand-new luxury oceanfront estat...
- 5 Beds
- 5 Baths
- 620723 MLS
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
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
TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless po...
- 7 Beds
- 5 Baths
- 620661 MLS
Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 s...
- 4 Beds
- 5 Baths
- 620618 MLS
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
Welcome to Palacio Coco Plum. Discover Your Florida Keys Oasis! Spectacular Ocean Front home in Marathon, the heart of the Florida Keys. This stunning property boasts l...
- 5 Beds
- 5 Baths
- 620594 MLS
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
** Seller Financing Available With 50% Down Subject To Acceptable Terms ** Nestled on the private gated island of Sunrise Isles in Marathon, Florida Keys, this 2019 oc...
- 5 Beds
- 5 Baths
- 620585 MLS
A FORTRESS OF LUXURY ON ITS OWN PRIVATE POINT -- KEY COLONY BEACH Built to withstand anything nature delivers, this Mediterranean estate sits on over an acre of private ...
- 5 Beds
- 5 Baths
- 620581 MLS
Welcome to 58244 Overseas Hwy on Grassy Key. This home was built in 2024 to last with superior ICF construction, steel studs, metal roof, impact resistant doors & window...
- 4 Beds
- 3 Baths
- 620562 MLS
Welcome to your private oceanfront retreat, ideally situated on a quiet cul-de-sac in the heart of Tavernier. Set on an expansive 28,705-square-foot lot, this beautifully...
- 3 Beds
- 4 Baths
- 620553 MLS
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
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
Experience the ultimate in modern waterfront luxury with this brand-new concrete masterpiece, thoughtfully designed for both elegance and durability. Boasting 4 bedrooms ...
- 4 Beds
- 4 Baths
- 620542 MLS
Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect ble...
- 2 Beds
- 3 Baths
- 620532 MLS
Don't miss this rare and exceptional opportunity to have your dream waterfront masterpiece begin construction in 2026! Located in the prestigious, gated community of Shar...
- 5 Beds
- 5 Baths
- 620499 MLS
Welcome to Morton Manor, an exceptional gulf-side waterfront estate set on 2.82 private acres where luxury, privacy, and resort-style living come together in this extraor...
- 11 Beds
- 9 Baths
- 620489 MLS
SELLER MOTIVATED Gulf Views with lots of living indoors and out! Looking for a spacious home with 5 bedrooms and 3 baths, a very large pool, easy boating access and 112' ...
- 5 Beds
- 3 Baths
- 620480 MLS
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
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
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
First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's m...
- 5 Beds
- 5 Baths
- 620434 MLS
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
Nestled within the exclusive, gated enclave of Coral Coast, home to just 15 private waterfront estates, this exceptional Bayfront residence offers sweeping views of Flori...
- 5 Beds
- 8 Baths
- 620417 MLS
Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled op...
- 5 Beds
- 4 Baths
- 620413 MLS
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
Experience the rare opportunity to own a brand-new waterfront residence in the heart of Key Colony Beach while still having the ability to personalize the finishes to ref...
- 4 Beds
- 5 Baths
- 620400 MLS
Beyond the gates lies an oceanfront estate whose finest qualities extend far beyond what you have seen! From its protected private marina offering 6 boat slips and fu...
- 7 Beds
- 9 Baths
- 620408 MLS
Where the essence of the Florida Keys meets refined coastal luxury. Widely regarded as one of Key Haven's finest waterfront residences, 94 Driftwood Drive is a rare Gulf-...
- 5 Beds
- 6 Baths
- 620398 MLS
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
First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premi...
- 3 Beds
- 3 Baths
- 620343 MLS
Presenting an extraordinary pre-construction opportunity to own a luxury oceanfront masterpiece, designed and newly constructed in the prestigious enclave of Shipman Poin...
- 4 Beds
- 4 Baths
- 620228 MLS
Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key W...
- 4 Beds
- 5 Baths
- 620222 MLS
Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water ...
- 13 Beds
- 7 Baths
- 620213 MLS
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
Stunning possibilities abound for this home on a double lot on the best street in the much sought after Casa Marina neighborhood in Key West. 1017 Washington Street is a ...
- 4 Beds
- 3 Baths
- 620188 MLS
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 lux...
- 5 Beds
- 4 Baths
- 620179 MLS
Welcome to your slice of paradise in Marathon's highly sought-after ''Behind the Airport'' neighborhood. Live the ultimate Florida Keys lifestyle with unobstructed open w...
- 3 Beds
- 2 Baths
- 620143 MLS
Direct Atlantic oceanfront living with protected canal-side dockage--two features rarely found together in one Florida Keys residence. Situated within an exclusive gat...
- 4 Beds
- 5 Baths
- 620096 MLS
New Construction & Furnished in Key West. Experience timeless Key West charm blended with modern luxury in this stunning property, re-built completely to the historic st...
- 5 Beds
- 7 Baths
- 620098 MLS
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 ...
- 6 Beds
- 9 Baths
- 620077 MLS
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
OCEANFRONT, CBS, POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove,...
- 4 Beds
- 4 Baths
- 620024 MLS
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
Escape to your own private resort in this Mediterranean-inspired waterfront villa on the exclusive Shark Key, a gated island community just 15 minutes from the restaurant...
- 4 Beds
- 4 Baths
- 619993 MLS
Introducing an extraordinary and completely custom Polynesian-inspired estate designed by the owner with finishes imported from all over the world. Perfectly positioned o...
- 5 Beds
- 5 Baths
- 619975 MLS
Newly Built Gulf-front Sanctuary with Panoramic Views, Guest and Pool Houses, Luxe Outdoor Living, and a Deepwater Navigable Dock. Set on 3 secluded acres+/- along one...
- 10 Beds
- 13 Baths
- 619972 MLS
Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off...
- 3 Beds
- 3 Baths
- 619959 MLS
This is set to become one of the most striking homes on Shark Key and it's already underway. A rare opportunity to own a completely brand new waterfront home in one of th...
- 6 Beds
- 7 Baths
- 619953 MLS
Welcome to 142 Guilford Court, a stunning bayfront home located in the highly desirable and sought out neighborhood of Hammer Point. Built in 2021 with solid concrete con...
- 5 Beds
- 5 Baths
- 619946 MLS
Welcome to an elevated expression of island living at 23 Treasure Road in the heart of the Florida Keys. This impeccably maintained waterfront residence showcases breatht...
- 3 Beds
- 3 Baths
- 619918 MLS
Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key offering expansive water views, a white sand beach, and resort-style living....
- 4 Beds
- 4 Baths
- 619913 MLS
CONSTRUCTION COMPLETE! SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys, adjacent to Duck Key. A rare find of just 14 ...
- 5 Beds
- 5 Baths
- 619897 MLS
CONSTRUCTION COMPLETE! MOVE-IN AND RENTAL READY! SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys; adjacent to Duck Ke...
- 5 Beds
- 5 Baths
- 619896 MLS
At the end of prestigious Sunrise Lane, where land meets open water on 3 sides, 3750 Sunrise Lane stands as one of the most extraordinary waterfront offerings in Key West...
- 5 Beds
- 5 Baths
- 619886 MLS
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
Morning Glory - The Dolphin House is one of those rare oceanfront sanctuaries where time softens, stress fades, and every sunrise feels like it was created just for you. ...
- 4 Beds
- 4 Baths
- 619842 MLS
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
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
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
