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$13,000,000
5 Beds 5 Baths 619817 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 tropical beauty and a powdery white-sand beach. This exclusive 5-bedroom, 5-bath residence invites you to embrace a lifestyle defined by serenity, wellness, and effortless connection to the sea. Spanning over 5,000 square feet of elevated concrete construction, the home captures breathtaking panoramic Atlantic views from nearly every room. Soaring cathedral ceilings and an open-concept design create a sense of boundless space, bathed in natural light. Four spacious bedrooms on the main level offer refined comfort, while the second-floor entertainment lounge and widow's walk reveal mesmerizing vistas of both the Ocean and Gulf -- a true testament to the beauty of the Keys. Outdoors, your private resort oasis awaits. A 40-foot resort-style pool glistens amidst swaying palms, framed by an expansive covered veranda perfect for alfresco dining, yoga at sunrise, or sunset cocktails by the sea. Begin your morning with gentle stretches on the sand as the ocean breeze flows around you, or indulge in a private seaside massage beneath the palms for the ultimate relaxation. The soft, white-sand beach invites laughter and family fun -- building sandcastles, paddleboarding together, or exploring the turquoise waters from your private dock with a 16,000 lb lift and 4-ft draft. Perfectly positioned between Islamorada and Marathon, this Long Key jewel offers the rare combination of tranquility and convenience. Whether hosting a sunset soirée, sharing quality time with loved ones, or escaping into a moment of stillness by the sea, Turtle Crawl embodies the ultimate Florida Keys lifestyle -- luxurious, rejuvenating, and deeply connected to nature. Experience the essence of oceanfront living in the heart of the Florida Keys. Call to arrange your private showing!

65760 Overseas Hwy, Layton

$12,500,000
6 Beds 7 Baths 620770 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. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

32 Sunset, Key West

$12,500,000
5 Beds 6 Baths 620398 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-front home in a premier neighborhood just minutes from the energy and culture of Key West offering a lifestyle defined by serenity, sophistication, and seamless access to world-class cuisine and adventure. Framed by spectacular water views from every room, the architecture embraces its setting with an effortless elegance. A mesmerizing infinity-edge pool and spa appear to merge with the open sea, creating a private resort experience at the water's edge. Inside, the chef's kitchen commands attention with state-of-the-art appliances and a dramatic solid-walnut entertainment island--an exquisite centerpiece for gatherings both intimate and grand. 5 bedrooms and 5.5 baths, including primary suites on both levels, this home is thoughtfully designed for comfort, privacy, and elevated living. Hardwood floors, impact-glass windows, and an oversized 2-car garage with direct dock access and room for a boat trailer reflect attention to detail. Flexible spaces accommodate a gym, studio, or entertainment room, while a meticulously organized storage area supports both home and pool systems with precision. For the boating and water-sport enthusiast, a dedicated equipment room provides direct access to the oceanfront dock and boat lift, placing the Key's endless waterways at your doorstep. A custom iron staircase rising from the first to the third floor serves as a sculptural showpiece with its ocean-inspired artistry echoing the coastal surroundings. This is more than a home-it is a statement of lifestyle, where tranquility and sophistication meet the unmistakable allure of the Florida Keys.

94 Driftwood Dr, Key Haven

$12,500,000
6 Beds 7 Baths 619953 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 the Florida Keys' most exclusive gated communities. Positioned on Sea Lore Lane, this 18,750 sq ft waterfront lot offers more than 90 feet of pristine shoreline and uninterrupted open water views. Designed by Artibus Design, the residence is currently under construction and envisioned as a nearly 6,000 sq ft modern coastal showpiece with 6 bedrooms and 6.5 bathrooms. Every inch of this home is being thoughtfully built for modern waterfront living, combining bold architecture, expansive walls of glass, elevated finishes, and seamless indoor outdoor flow throughout. This is the appeal of brand new construction in the Keys. Fresh design. Modern materials. Current building standards. A home created for the way buyers want to live today. Inside, expansive open living spaces, gallery style proportions, striking focal points, an indoor gym, and a large entertainment room create a setting that feels both sophisticated and inviting. Outside, a resort style waterfront environment takes center stage with a pool, expansive covered outdoor living spaces, and a large three car garage beneath the home, all designed to maximize the incredible setting and open water views. For a limited time, a buyer has the rare opportunity to step in and customize finishes and details, helping shape the final vision while avoiding the years of planning, approvals, and uncertainty that can come with building in the Florida Keys. With construction already in progress, this is an opportunity to secure one of the most exciting new builds coming to Shark Key before completion. This is more than new construction. It's the opportunity to own one of the island's most exciting new waterfront homes and create something truly exceptional in the Florida Keys.

31 Sea Lore Ln, Shark Key

$12,450,000
22 Beds 21 Baths 620702 MLS
Located on approximately 2 acres of upland and nearly one acre of bay bottom, this 21-room boutique hotel offers direct access to Florida Bay and stunning waterfront living in South Key Largo. Stretching from the Overseas Highway to the pristine waters of Florida Bay, the property is a true hidden gem. Family-owned, well maintained, and one of the Upper Keys' rarest bay front hospitality investment opportunities. Enjoy protected dockage with direct bay access, a private sandy beach, a concrete boat ramp, a heated and chilled swimming pool, outdoor grilling areas, and multiple tiki huts. Guests also benefit from spectacular year-round sunset views, creating a memorable Keys experience. 10 guest rooms have been tastefully renovated with a modern coastal design, while the remaining rooms have been refreshed with new paint and updated furnishings, delivering immediate rental income with strong upside potential to further increase revenue and value. Ideally located near dining, shopping, and the area's most popular attractions, this exceptional property offers a variety of possibilities: continue operating as a cherished boutique hotel, reposition to enhance performance, or redevelop into an even more valuable waterfront destination. A truly rare, turnkey investment with tremendous upside in one of the Florida Keys' most desirable locations.

97850 Overseas Hwy, Key Largo

$12,450,000
5 Beds 7 Baths 618181 MLS
Welcome to Villa Splendida in exclusive Duck Key, Florida. This custom built estate has been curated from the gated entrances to the 180' of protected ocean front dockage. Featuring a classic Mediterranean styling the spacious grounds host a variety of mature tropical plantings, fruit trees, and ease of maintenance turf throughout. The home itself is spacious and comfortable allowing elegant flow throughout the property. Enter to soaring 2-story grand room with open floor plan into the dining and chefs kitchen with walk-in pantry, Wolf and Subzero appliances, a first level guest suite, undersea themed theater room, laundry, powder room and open water views and poolside access from all rooms. The second level hosts two guest suites, a mezzanine with sweeping views of the lower level and open ocean, and a sumptuous primary suite with expanded ensuite, walk-in closet and private oceanfront balcony. There is also a separate attached guest cottage complete with laundry. The elevated patio incorporates a custom beach entry pool with infinity edge waterfall, spa, outdoor kitchen and space perfect for entertaining or just lounging at your own private oceanfront resort. Just steps from the pool is 180' of protected dockage complete with a 57k lb boat lift and jet ski lift platform that will hold up to 6 jet skis. Additional amenities include: a custom sound system throughout the entire property inside and out, large capacity ice machine, 4+ car garages, fully fenced and gated for privacy, mature landscaping and lighting, multiple laundry facilities, and full under house access and storage. Call today for more information and to schedule a private tour of this one-of-a-kind Duck Key estate.

301 Ixora St, Duck

$12,250,000
617400 MLS
Offering Overview This sale includes a rare combination of income-producing assets, valuable licenses, and entitlements in the Florida Keys, at appraised value consisting of: • 25 Transient Rental Licenses - Currently in use and potentially available to be moved to another qualifying development, subject to all applicable approvals. • 150-Seat Restaurant - Established food & beverage venue with a newer tiki structure, ideal for waterfront or resort-style dining. • 5COP Quota Liquor License available separately - A valuable, transferable 5COP license allowing for the sale of beer, wine, and spirits for on-premises consumption, providing significant upside for the restaurant and bar operation which also allows for packaged Liquor sales. • 25-Room Hotel - Turnkey lodging operation benefiting from the transient licenses and strong Florida Keys tourism demand. • Dive Shop & Vessel - A popular, well-respected Florida Keys dive operation, including a 49-passenger coast guard approved Vessel with its own 2cop bar license allowing for wine and beer sales, retail/gear component, and a established customer base.

27340 Overseas Hwy, Ramrod

$11,750,000
7 Beds 9 Baths 620408 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 fully integrated smart-home technology to its rooftop observation deck, private sandy shoreline, and resort-caliber outdoor living, every element has been designed to deliver an exceptional waterfront lifestyle. Welcome to 16 Seaside Avenue. This extraordinary 7-bedroom, 7 full and 2 half-bath residence offers luxurious living designed for effortless entertaining and multi-generational enjoyment. From the moment the private gates open, a fully integrated smart home system seamlessly controls the estate--from the front entrance and security system to interior lighting, climate, surround sound, and even the dock lighting--creating a level of convenience rarely found in waterfront homes. A commercial elevator services all three levels, while a whole-house generator provides peace of mind year-round. With everyday living in mind, the home features 2 dedicated laundry rooms for the upmost functionality. Every bedroom serves as a private retreat, complete with its own spa-inspired ensuite bathroom, spacious walk-in closet, and custom built-in closet system. Expansive open living areas are filled with natural light and thoughtfully designed to maximize breathtaking Atlantic Ocean views. Outdoor living rivals that of a private resort. The spectacular oceanfront pool, spa and waterfall, covered gazebo, outdoor kitchen, and integrated indoor and outdoor surround sound create the perfect setting for entertaining. A private sandy beach and pier provide an idyllic place to enjoy spectacular sunrises over the Atlantic, while the rooftop observation deck captures sweeping panoramic ocean views of both the ocean and bay. Best of all this property offers the ability for short term 7-Day rentals! This is a rare opportunity to own an estate designed to deliver the very best of the Florida Keys!

16 Seaside Ave, Key Largo

$11,700,000
6 Beds 8 Baths 620680 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 serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

77350 Overseas Hwy, Islamorada

$11,000,000
18 Beds 21 Baths 615103 MLS
Welcome to an unparalleled collection of THREE designer residences on one of the most exclusive waterfront parcels in the Florida Keys. Located just steps from Coco Plum Beach and the Atlantic Ocean, this rare investment opportunity is the ultimate blend of luxury, lifestyle, and income potential. Professional Designed and built by D'Asign Source in 2019, each residence is a testament to timeless architecture, sophisticated interiors, and exceptional craftsmanship. Each of the three homes spans off 4,066 square feet and features 6 spacious bedrooms and 6.5 bathrooms with custom millwork and designer fixtures. The interiors are professionally furnished with a curated blend of comfort and elegance, complemented by expansive ceiling heights, open-concept living areas and balconies throughout. Designed with privacy in mind, each home includes its own private pool, tiki hut, and a dock offering deepwater and direct ocean access. Impact windows and doors provide storm security and peace of mind, while each home offers three (3) air conditioning units to ensures optimal climate control on each level. Boating an abundance of storage on each level, an oversized laundry room, walk in pantry and en- suite accompanying each room. Whether you envision a serene family compound, a luxury short-term rental business, or an exclusive corporate retreat, this property offers incredible versatility and value. Zoned for weekly rentals, the income potential is substantial, making this one of the most attractive investment opportunities in the Florida Keys.

2394 Coco Plum Dr, Marathon

$11,000,000
18 Beds 21 Baths 615102 MLS
Welcome to an unparalleled collection of THREE designer residences on one of the most exclusive waterfront parcels in the Florida Keys. Located just steps from Coco Plum Beach and the Atlantic Ocean, this rare investment opportunity is the ultimate blend of luxury, lifestyle, and income potential. Professional Designed and built by D'Asign Source in 2019, each residence is a testament to timeless architecture, sophisticated interiors, and exceptional craftsmanship. Each of the three homes spans off 4,066 square feet and features 6 spacious bedrooms and 6.5 bathrooms with custom millwork and designer fixtures. The interiors are professionally furnished with a curated blend of comfort and elegance, complemented by expansive ceiling heights, open-concept living areas and balconies throughout. Designed with privacy in mind, each home includes its own private pool, tiki hut, and a dock offering deepwater and direct ocean access. Impact windows and doors provide storm security and peace of mind, while each home offers three (3) air conditioning units to ensures optimal climate control on each level. Boating an abundance of storage on each level, an oversized laundry room, walk in pantry and en- suite accompanying each room. Whether you envision a serene family compound, a luxury short-term rental business, or an exclusive corporate retreat, this property offers incredible versatility and value. Zoned for weekly rentals, the income potential is substantial, making this one of the most attractive investment opportunities in the Florida Keys.

2394 Coco Plum Dr, Marathon

$11,000,000
4 Beds 4 Baths 616886 MLS
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 the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors providing vast screened porched both upstairs and down. The kitchen anchors the home with gorgeous views and function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amenities continue with a lagoon-style pool, putting green, and ample deepwater dockage with boat lift with Bay to Ocean access in minutes via Channels 2 or 5, offering effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

75280 Overseas Hwy, Islamorada

$10,999,999
6 Beds 6 Baths 617713 MLS
Introducing 57 Garden Cove Drive, a rare opportunity to own a private, resort-style Key Largo waterfront compound set on nearly 26,000 square feet of land, now OFFERED TOGETHER with an additional adjacent vacant residential parcel, creating exceptional flexibility for future expansion or development. Thoughtfully designed to capture both scale and functionality, the residence features 6 bedrooms & 6 bathrooms, complemented by a private elevator for seamless access throughout. Expansive interiors are filled with natural light, effortlessly connecting indoor living spaces to the surrounding tropical landscape. For boating enthusiasts, the property offers 100FT of premium dockage delivering immediate & unrestricted access to open water -- a rare & highly desirable feature in the Keys. Beyond its lifestyle appeal, the property stands out as a proven income-producing asset. With 7-day short-term rental approval, it is currently operating as a successful vacation rental and wedding venue, supported by an exceptional rental history -- offering both immediate revenue & long-term investment potential. The true differentiator lies in the land and flexibility. With the inclusion of the adjacent parcel, the property presents a unique opportunity to further enhance the estate -- whether through additional structures, expanded amenities, or the creation of a fully realized private resort-style compound. Framed by swaying palms & open water views, this is more than a home -- it is a turnkey lifestyle investment with development upside, positioned in one of the most desirable waterfront enclaves in the Florida Keys.

57 Garden Cove Dr, Key Largo

$10,900,000
6 Beds 5 Baths 618449 MLS
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. Offering 220+ linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels included in this sale, opening options in the future for the fortunate owner that resides here. Completely renovated in 2020, the home presents a clean, contemporary aesthetic with Viking appliances, bespoke finishes, and a subtle, neutral palette inspired by the flowing surrounding turquoise waters. A custom saltwater pool equipped with both heater and chiller provides year-round enjoyment for everyone. This Safety Harbor residence delivers both elegance and function for the discerning boater or sunset lover. Impeccably maintained and move-in ready, it offers a rare combination of low-maintenance living, thoughtful design, quiet living and enduring appeal in the Florida Keys. Private showings available by appointment.

186 & 165 Bayview Dr, Islamorada

$10,500,000
618462 MLS
Manatee Bay Club Marina - Rare Investment Opportunity in the Florida Keys Located on the iconic 18-Mile Stretch entering Key Largo at the Miami-Dade/Monroe County line, Manatee Bay Club is a private, gated marina condominium association offering a truly unique investment opportunity. This offering includes 56 boat slips (2,309 linear feet) within a 94-slip marina that is exceptionally well maintained and financially strong, with healthy reserve funding in place. The marina features aluminum docks, pool, beach, laundry facilities and a floating bathhouse. The Marina is configured with 7 finger piers and 1 dock that parallels US1. . A Dock and G Dock are included in this sale, with A Dock also conveying a large upland area, presenting the rare possibility to create a private, secluded enclave within the community. Other docks in this sale are scattered throughout the community in varying lengths. Beautiful buttonwood landscaping enhances the natural surroundings and creates a distinctive, tranquil ambiance rarely found in marina properties. This is more than just a marina--it is also a strong income-producing rental asset. Most slips are leased on 6-month terms, attracting Miami boaters who enjoy weekend trips to the Keys, as well as seasonal snowbirds escaping northern winters. Financials are available for qualified investors. For those seeking a well-run, income-generating marina in a prime Florida Keys location, Manatee Bay Club stands out as a hidden gem. Showings are easy to schedule--don't miss this exceptional opportunity. Please see site plan and highlight areas for sale. SEE DOCUMENT TAB FOR SITE PLAN

100 Morris Ln Unit 56 Slips, Key Largo

$10,499,000
6 Beds 8 Baths 617664 MLS
Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key! This extraordinary new construction stunner is engineered as a rare modern fortress— built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set on prime open water with sweeping panoramic views, this property delivers the rare combination of minimalist modernism, structural integrity, and luxury resort-style design. The residence showcases a dramatic full flat rooftop deck spanning the entire top of the main home, offering uninterrupted 360° ocean sunrise and sunset views - private viewing platform unlike anything else in the Lower Keys. Inside, a breathtaking 19-ft double-volume open living area is wrapped in walls of glass, flooding the space with natural light. Sleek interior glass railings, porcelain floors, and refined finishes create a sophisticated aesthetic. Stunning chef's kitchen appointed with quartzite countertops, Monogram appliances, a bespoke bar, and a stone wine-display feature, all designed for high-end entertaining. The main residence features four luxurious private suites, each oriented to capture open-water views with direct access to generous covered terraces. A rare architectural highlight is the elevated above-flood concrete garage with soaring ceilings, loft storage space, dual cisterns, and luxury living quarters above, with kitchenette, washer/dryer, full bath, and a versatile flex room ideal for a bedroom, gym or office. A dedicated cabana bath opens directly to the pool. Outdoor living is elevated with a stunning pool and spa, outdoor shower, landscape lighting, and expansive covered entertaining and parking. A 230-ft dock is included in the sale. A statement of power, design, and luxury—brand new, turnkey, and crafted for the UHNW buyer seeking an exceptional coastal masterpiece!

1041 E Buttonwood Dr, Sugarloaf

$9,999,000
5 Beds 5 Baths 620581 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 point, surrounded by water on three sides. Engineered like a true hurricane shelter -- steel and poured concrete construction rated for 200mph winds, Andersen Hurricane-impact windows throughout, and a full security system -- this is a home that lets you enjoy paradise without ever worrying about the forecast. Behind that fortress strength is pure luxury. Sun-soaked stucco, soaring arches, wrought iron details, and Italian marble floors create timeless old-world elegance, while walls of windows frame turquoise water from nearly every room. A canal runs along one side, with a dock for water toys that can be extended for larger vessels. The opposite side opens to protected Vaca Cut, complete with a 25,000 lb boat lift and quick access to open ocean. Outside, a glistening pool and waterfall spa shimmer in iridescent blue tile, surrounded by deck and covered patio space built for grand-scale entertaining -- comfortably hosting 100+ guests -- with an outdoor kitchen perfect for dining as dolphins play offshore. Inside, the chef's kitchen boasts double ovens, granite counters, and top-of-the-line appliances, opening to sun-filled living and dining rooms. The main level also offers a den/bedroom, laundry, air-conditioned 2 car garage space (currently office, playroom, storage), and two finished baths. A marble staircase, lit by picture windows and trimmed in custom wrought iron, leads to a second-floor landing with sweeping views. The Master Suite delivers sunset views from bed or balcony, a spa bath with honey onyx double vanity and mosaic shower, and a custom walk-in closet. Three additional en suite bedrooms with walk-in closets complete the upper level. Storm-proof strength. Old-world soul. Resort-style luxury. Fully furnished -- just bring your bathing suit.

390 13th St, Key Colony

$9,999,000
5 Beds 5 Baths 619975 MLS
Introducing an extraordinary and completely custom Polynesian-inspired estate designed by the owner with finishes imported from all over the world. Perfectly positioned on the most premier lot within the exclusive gated enclave of Shark Key, offering an exceptional blend of privacy and waterfront luxury. Set on a sprawling 1.56-acre lot with an impressive 850 feet of water frontage, this custom residence spans approximately 4,622 sq. ft. and captures breathtaking open water views and unforgettable sunset skies. A long private driveway sets a dramatic tone on arrival, winding through lush grounds and passing the tennis court before revealing the home in complete privacy and anticipation. Inside, a grand entry leads into the Chef's Kitchen and Great Room boasting 180 degree water views. Soaring cathedral ceilings, rich mahogany woodwork, and exposed beams create a warm yet striking architectural statement. Walls of glass doors frame open water views and open seamlessly to the expansive wraparound deck, perfect for entertaining or enjoying iconic Keys sunsets. The thoughtfully designed layout separates the North and South wings, connected by a striking mahogany-wrapped hallway that enhances flow and elegance. The main wing is home to all Living Areas and the Primary Suite featuring soaring ceilings, his & her dressing areas and bath featuring imported tile and water views. The South wing offers exceptional flexibility with a second living area and 4 Bedrooms creating a private retreat for family and visitors. A winding staircase leads to a second-floor guest suite with elevated open water views and serene privacy. Intricate coastal tilework throughout and the custom emerald tile roof reinforces the island aesthetic, while impact windows provide durability and peace of mind. Outdoor living is truly exceptional, featuring a wraparound deck, resort-style pool, multiple tiki huts, and a waterfront lounging area ideal for entertaining or relaxing.

87 Cannon Royal Dr, Shark Key

$9,888,000
3 Beds 2 Baths 619724 MLS
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now-- an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, -- this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

1430 Vernon Ave, Key West

$9,700,000
4 Beds 7 Baths 617714 MLS
This custom-built, elevated two-story estate sits on a 7,300 SF point lot at the coveted tip of Adam's Cut Waterway, with 167 feet of waterfront offering panoramic views that open directly to Largo Sound with ocean access. More than a home, it is an unparalleled opportunity to own an iconic piece of Keys history—an architecturally significant retreat built to exceptional standards of strength, beauty, and design. Spanning 3,723 SF, the 4BR/5+2BA residence features a triple-poured concrete roof, 8 inches of concrete between floors, Italian La Finestra impact windows and doors, whole-house sound system, interior elevator, Shell Reef honed limestone floors, and concealed-hinge custom doors. The main level showcases a stunning light-filled living room framed by floor-to-ceiling windows, a remote-controlled drop-down TV, stone accent wall, and sleek wet bar—all opening to the expansive wraparound terrace overlooking Adam's Cut. An open dining area complements the chef's kitchen with a backlit polished Plume Quartz waterfall island, JennAir gas cooktop, integrated refrigeration, and Liebherr wine cooler. This floor includes three bedrooms, including a junior suite with private balcony and spa-style bath, plus a designer powder room, laundry room, and two additional ensuite guest rooms. The private principal suite spans the second floor, featuring a high-pitched ceiling, midnight bar, elevated bed platform, flexible additional room, and a spa-inspired bath. It opens to a private terrace with a rooftop infinity pool, swim-up bar, and jacuzzi for a true resort experience. Ground-level highlights include a grand covered terrace w/summer kitchen, Lynx grill, salt-chlorinated pool, teak ceilings, standalone bar, and cabana bath. A hidden gem is the brick-lined, temperature-controlled 200-bottle wine cellar w/ a decanting area. A 77' private dock w/ permitting in progress for a 30,000 lb boatlift, swim platform, and sunning areas complete this extraordinary Keys masterpie

180 Pompano Dr, Key Largo

$9,500,000
7 Beds 4 Baths 579482 MLS
Beautiful adjoining oceanfront gated estates available individually or together. Each parcel has a single family residence with vacation rental income potential and are zoned Suburban Commercial for development opportunities..*UPDATE: There are 50 TDRs (TREs) available, preliminarily reviewed by Monroe County and transferable to these parcels for higher development potential! This unique wooded acreage has a deep basin and channel for ocean access, with dolphin piling boat slips and boat ramp. Single Family Residences with ROGO exemptions for remodel/rebuild possibilities. Highest approval rate via Monroe County is for MIXED-USE COMMERCIAL development. (The 6.1 acre parcel may be sold together with contiguous 3.2 acre parcel@95325 Overseas Hwy, AK#1592986,RE#00483360 000000 13 62 38 PT TR 5&6 SOUTHCLIFF ESTS PB2-45 & PT GOV LOT 1 & ADJ BAY for grand total of 9.36 acres, includes 1137 sf 1970 2/1 cbs home, metal roof.) *Includes data for both parcels and for taxes. This is a duplicate listing. Broker part owner/family owned.

95351 Overseas Hwy, Key Largo

$9,500,000
6 Beds 11 Baths 610645 MLS
Casa Mañana Shores, located in the heart of Marathon, is a developer's dream or a private owner's potential paradise. This secured gulf front estate offers 3.86 acres of land and is surrounded by an eight foot concrete wall with three gated entrances. The property boasts approximately 540 linear feet of Highway frontage and 695 linear feet of water frontage. It offers 218 feet of concrete dockage, including a cut-in protected boat slip. There is even room for a helicopter landing pad. This unique property is zoned mixed-use commercial and comes with one commercial transferable building right. It is currently a private residence with a separate garage and workshop. The 10,852 square foot mansion is solid concrete construction with concrete pilings and copper pipes. It has ten bedrooms, six and a half bathrooms, and a sauna, game room and great room. Repairs are needed, and the interior needs substantial updating. An attached partially screened enclosure holds an impressive 12 ft deep swimming pool that measures 25 x 50 ft. The garage/workshop is a separate structure with two rooms with mini split air conditioning. The existing structures could be demolished for those with a vision, leaving you with a 3.86 acre blank canvas in the center of town. Its versatile designation offers multiple possibilities for residential and/or commercial use. Over the years it has previously housed a motel with a marina, a 19-unit trailer park, and a restaurant. This property lends itself to a variety of development or rehabilitation possibilites to create the vision of your dreams!

6500-6600 Overseas Hwy, Marathon

$9,500,000
6 Beds 11 Baths 610643 MLS
Casa Mañana Shores, located in the heart of Marathon, is a developer's dream or a private owner's potential paradise. This secured gulf front estate offers 3.86 acres of land and is surrounded by an eight foot concrete wall with three gated entrances. The property boasts approximately 540 linear feet of Highway frontage and 695 linear feet of water frontage. It offers 218 feet of concrete seawall, including a cut-in protected boat slip. There is even room for a helicopter landing pad to be installed. This unique property is zoned mixed-use commercial and comes with one commercial transferable building right. It is currently a private residence with a separate garage and workshop. The 10,852 square foot mansion is solid concrete construction. It has ten bedrooms, six and a half bathrooms, a sauna, game room and great room. Repairs are needed, and the interior needs significant updating. An attached partially screened enclosure holds an impressive 12 ft deep swimming pool that measures 25 x 50 ft. The garage/workshop is a separate structure with two rooms with a mini split air conditioner. The existing structures could be demolished for those with a vision, leaving you with a 3.86 acre blank canvas in the center of town. Its versatile zoning designation offers multiple possibilities for residential and/or commercial use. Over the years it has previously housed a motel with a marina, a 19-unit trailer park, and a restaurant. This property presents the opportunity to create the ultimate secluded retreat of your dreams!

6500-6600 Overseas Hwy, Marathon

$9,499,000
608897 MLS
Nestled along the serene waterfront, these two picturesque parcels offer an unparalleled opportunity to indulge in the quintessential Florida Keys lifestyle. These two expansive plots of land incl. bay bottom present the perfect canvas for your dream waterfront retreat and /or commercial ventures. The Northern parcel consists of about 1,400 ft. of native shoreline, providing ample space for waterfront activities such as swimming, fishing, kayaking, and paddleboarding with deep water on one side and shallow bay bottom on the other side. Spanning 2.03 acres of Mixed Use upland and a total of 45 acres, including bay bottom. Potential uses on the Northern parcel could be Commercial retail, restaurant uses, or any combination thereof, imagine a floating restaurant, small marina, Commercial recreation uses including amusement or sea life park, opening doors to community-centric projects that serve the needs of locals and visitors alike. The off shore island along the channel offers great camp sites. With Mixed Use zoning in place, commercial fishing docks are permitted, providing an excellent opportunity for entrepreneurs in the fishing industry to establish a thriving business. The Southern parcel consists of about 40 acres of mangrove forest, beach berms, hammocks, and trails with approx. 6 acres of upland. So many possibilities. Build your own Equestrian Estate, ''The Southernmost stables''. This property would be an excellent place to host large events like concerts, weddings, farm to table / wine tastings, or possibly therapeutic programs or retreats. Beautiful beach areas. Easy to get to, as the island has access to the mainland via a ½ mile land bridge. The property is also located next to one of the largest mega yacht marinas and close to two upscale hotels. The Southern parcel of Cow Key can be purchased by itself. See MLS #601994. Buyer to verify all information and uses.

7000 5th St, Stock Island

$8,995,000
6 Beds 5 Baths 617329 MLS
Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach — a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and diving. A protected 6-boat basin with room for extra boats is the centerpiece of the waterfront, complete with 25K and 16K lifts, a boat ramp, sandy beach, lookout point, and composite observation deck. After a day on the water, unwind in the lagoon-style saltwater pool with heater, chiller, and custom water features. The expansive tiki bar includes TVs, True refrigerator/freezer drawers, and an ice machine—perfect for effortless outdoor entertaining. Additional features include a firepit, private sandy beach, and a full outdoor kitchen equipped with built-in BBQ, Viking appliances, and True refrigeration. The upper level offers a bright and open Great Room with sweeping ocean views, a spacious dining area, and a chef's kitchen with stainless appliances. Two covered verandas provide ideal spaces for taking in the breezes and panoramic vistas. The primary suite features an office, en suite bath, walk-in closet with laundry, sunroom, and loft. Two additional upstairs guest rooms comfortably accommodate visitors, while the separate downstairs living area offers three more guest bedrooms for privacy and flexibility. Designed for hosting and convenience, the home is equipped with a Sonos sound system, property-wide Wi-Fi, abundant storage, a two-car garage with fishing lockers, and generous parking along a winding paver driveway. Lush, mature landscaping surrounds the property, creating a serene and secluded Sugarloaf Key retreat. Call for more information today!

16750 Old State Road 4a, Sugarloaf

$8,900,000
620210 MLS
4.75-Acre INDUSTRIAL property consisting of approximately 21,738 square feet of warehouse space situated on fully fenced land in Homestead, Florida. Constructed with durable Twin-T concrete roofing and CBS block walls & commerical truck scale, this facility is designed to support a wide range of industrial operations including warehousing, distribution, logistics, manufacturing, moving and storage, and fleet-based businesses. Strategically located within the Urban Development Boundary (UDB), the property offers excellent accessibility and operational flexibility. The site features approximately 328 feet of frontage on Redland Road (SW 187 Avenue) and extends approximately 632 feet in depth, providing ample space for outdoor storage, vehicle parking, equipment staging, and container storage.

150 Sw 14th Ave, Homestead

$8,750,000
618856 MLS
Waterfront motel and marina property in Marathon offered with thirteen transferable transient building rights, highway frontage, and redevelopment potential. Sea Cove is located on Overseas Highway with approximately 200 feet of US-1 frontage, more than two acres of buildable uplands, and additional bay bottom ownership. The property has a long history of marina and lodging use and includes an existing boat ramp with direct boating access. The site has historically supported motel operations, marina services, and small retail activity. The offering includes the real estate together with thirteen transferable transient building rights that allow nightly rental use within the City of Marathon, subject to zoning and City approval if relocated. Previous planning and engineering work studied redevelopment of the site as a marina focused project. Concept plans illustrate a dry boat storage structure of approximately 33,000 square feet accommodating roughly 150 dry racks together with approximately 30 wet slips. Prior discussions have also included extended dockage approaching 550 feet and potential marina services including fueling facilities, subject to required approvals. The site includes significant waterfront area together with bay bottom ownership that has historically supported dockage and marina activity. Showings by appointment only. Please do not visit the property or speak with employees without listing agent present.

12685 Overseas Hwy, Marathon

$8,590,000
8 Beds 10 Baths 613653 MLS
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 point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boater's paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning station, this home is perfectly appointed for waterfront living. Easy ocean access through the nearby Channel 5 Bridge adds to its appeal for avid anglers and adventure seekers alike. Inside, the home features eight spacious bedrooms, each with its own ensuite bath, plus two additional half baths for convenience. The master suite is a private sanctuary with a spa-inspired bath, while the open layout showcases spectacular water views through impact windows and sliding glass doors. An elevator ensures effortless access to all levels, and the wraparound balcony invites you to savor unobstructed panoramas. The gourmet kitchen, complete with high-end stainless steel appliances and gas cooktop, is a chef's delight, complemented by an outdoor kitchen for alfresco entertaining. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

162 Bayview Dr, Islamorada