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.
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?
Key Largo, Islamorada, Marathon, and Key West all have significant luxury inventory. Islamorada and Key West tend to attract the highest concentrations of high-end waterfront estates.
Florida Keys Luxury Homes
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
Indulge in the art of refined coastal living in this brand new luxury waterfront residence, where timeless elegance meets modern design across four bedrooms and four and ...
- 4 Beds
- 5 Baths
- 620683 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
A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the histo...
- 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
Experience the PINNACLE of luxury waterfront living at this exceptional oceanfront residence on prestigious Flagship Drive. Completely reimagined with uncompromising atte...
- 4 Beds
- 4 Baths
- 620606 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
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
Nestled on the exclusive private gated island of Sunrise Isles in Marathon, Florida Keys. This magnificent 2019 construction oceanfront estate redefines luxury living. Wi...
- 5 Beds
- 4 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 Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Key...
- 5 Beds
- 4 Baths
- 620578 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
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' of concrete docka...
- 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
- 4 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
BEING SOLD W/ 54 SUNSET RD! MLS#: 620256 - 2 Lots w 200' of w/ crystal clear waterfront on the Bay, ROGO Letter allows for 2 residences to be built on the property. 2...
- 3 Beds
- 2 Baths
- 620255 MLS
Rarely does a Florida Keys property offer the combination of proven vacation rental income, transient rental zoning, private beachfront, and future development flexibilit...
- 4 Beds
- 2 Baths
- 620235 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
An extraordinary opportunity to own one of Key West's most coveted addresses -- iconic Caroline Street in the Historic Seaport, just steps from Duval Street. Fully renova...
- 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
Discover elevated waterfront living in this newly constructed custom two-story concrete residence, offering 4 spacious bedrooms, each with its own private en-suite bath. ...
- 4 Beds
- 4 Baths
- 620205 MLS
Experience luxury waterfront living in this custom-built, new construction two-story concrete home featuring 4 bedrooms and 4 private en-suite baths. Designed for enterta...
- 4 Beds
- 4 Baths
- 620204 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
Experience the rare combination of protected dockage and direct oceanfront living at 128 Sunrise Drive. Situated within an exclusive gated enclave of just 20 lots, this n...
- 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! 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
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 , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, jus...
- 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
A premier transient investment opportunity and a genuinely enchanting way of living meet on Atlantic Boulevard! The Atlantis House is a property with heart and soul. Just...
- 5 Beds
- 4 Baths
- 620001 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
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
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 with expansive water views, white sand beach, and a true resort-style experi...
- 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
Discover Turtle Crawl, the ultimate private sanctuary on the shimmering shores of Long Key -- a rare gated oceanfront estate encompassing nearly one acre of pristine trop...
- 5 Beds
- 5 Baths
- 619817 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
- 619812 MLS
Island living in Prestigious Port Largo, Key Largo's most desirable neighborhood. Set on an oversized 0.33-acre waterfront lot, this pool home offers 50' of dockage with ...
- 4 Beds
- 4 Baths
- 619782 MLS
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
Stunning brand-new custom modern home with just the right amount of Keys flair--where no detail was overlooked from design to layout to finishes. Enter through a priva...
- 5 Beds
- 5 Baths
- 619766 MLS
Stunning brand-new custom modern home with just the right amount of Keys flair--where no detail was overlooked from design to layout to finishes. Enter through a priva...
- 5 Beds
- 5 Baths
- 619767 MLS
TROPICAL ESTATE-Tucked away in the sought after exclusive neighborhood of Key Haven at mile marker 5. Spanning over half an acre this elevated, impact resistant, waterfro...
- 5 Beds
- 5 Baths
- 619762 MLS
Some opportunities require no explanation and this is one of them. A12, A13, and A14 12th Avenue sit side by side on Stock Island's waterfront, combining for 120 feet of ...
- 7 Beds
- 4 Baths
- 619753 MLS
A rare find with beautiful Atlantic ocean view, luxury oceanfront estate where architecture, nature, and experience converge into something truly extraordinary. Bali styl...
- 3 Beds
- 3 Baths
- 619743 MLS
Experience effortless island living in this stunning, recently renovated estate, situated on a rare double lot in the high-and-dry X flood zone. Framed by lush tropical l...
- 4 Beds
- 3 Baths
- 619706 MLS
Experience elevated Florida Keys living at this exceptional waterfront estate in Buccaneer Point. Perfectly positioned on a prime oversized lot, this 5-bedroom, 5-bath re...
- 5 Beds
- 5 Baths
- 619693 MLS
Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural ...
- 3 Beds
- 3 Baths
- 619696 MLS
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
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
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
Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with...
- 3 Beds
- 3 Baths
- 619589 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 Key...
- 4 Beds
- 5 Baths
- 609718 MLS
Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X...
- 4 Beds
- 4 Baths
- 619548 MLS
Your Dream Waterfront Oasis Awaits! Immerse yourself in refined elegance in this 3-bedroom, 4-bathroom sanctuary. The crown jewel of this residence is the unparalleled ca...
- 3 Beds
- 4 Baths
- 619475 MLS
Experience unparalleled luxury and waterfront living in this stunning modern home, built in 2020 and situated on a corner lot with over 200 feet of waterfront property. ...
- 5 Beds
- 3 Baths
- 619474 MLS
Tucked on the private shores and gated community of Tingler Island, this one-of-a-kind dual-waterfront estate is where the Florida Keys lifestyle reaches its fullest expr...
- 3 Beds
- 4 Baths
- 619460 MLS
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
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
Nestled along the Florida Bay in exclusive Buccaneer Point, this exquisite bay front estate offers an unparalleled fusion of opulence, tranquility, and sweeping water vie...
- 5 Beds
- 4 Baths
- 619382 MLS
This 2 bed 2 bath home on the second floor. Recently gone through major renovations from top to bottom- inside out. Open concept with brazilian wood floor, fully furnishe...
- 2 Beds
- 2 Baths
- 619370 MLS
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
