Florida Keys LUXURY Homes for Sale, Single Family Houses, Florida Keys Real Estate

Welcome to 30 Ocean Front Drive... a one acre open water estate with floor-to-ceiling panoramic ocean views from wall to wall! The 3/2 main home is meticulously updated and the 1/1.5 guest house addition opens to an infinity edge pool with swim-up bar and integrated full outdoor kitchen, all under an expansive gazebo. The one-of-a-kind pool also offers zero-entry, a tanning platform plus a separate swim-out, and it is also lap length in between. The guest house features bi-fold NanaWall glass doors to welcome in expansive ocean views and an indoor/outdoor Bang Olufsen stereo system for entertaining. The concrete home itself offers an elevator to all interior levels plus an exterior stop on the pool deck, impact windows/doors, Pedini kitchen, Miele appliances, marine-grade Carrier a/c systems, quartz counters, landscape lighting, lush tropical landscaping and more. One car garage and two carports. Privately gated double lot with 193 ft. on the ocean and a boat ramp. All updates and addition by DAsign Source. Must see!

With its special transient license, The Royal Compound is currently generating $500,000 a year from first-class guests who will accept only the best in vacation homes. Whats interesting is that most of the rental income comes from monthly rentals, so you can expect almost as much income without a transient license. This extraordinary home is situated on one of the largest lots (14,183 SF) in Truman Annex and is being offered as the ultimate turnkey property. There are a total of 5 bedrooms and 4 bathrooms: 3 bedrooms and 2 bathrooms in the main house and two 1 bedroom, 1 bathroom private cottages. This expansive property includes a covered seating and dining area under the gazebo, which overlooks the resort-style heated pool and outdoor kitchen. The value of this home is not only its privacy with exotic landscaping, but its ability to generate income when you are away. Schedule your private showing of The Royal Compound to appreciate the uniqueness of this one-of-a-kind property!

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 ultimate getaway for relaxation and adventure.Unwind in the oversized heated pool or customized hot tub after a day of sun and fun. The Tiki Hut provides convenient storage for all your water toys, making your boating and beach days effortless. Enjoy practicing your swing on the private putting golf course, all while surrounded by breathtaking ocean scenery.With a lucrative 7-day rental option and an easily obtainable license, this gem is perfect for both personal enjoyment and investment. Dont miss your chance to own this slice of paradise--schedule a viewing today!

Welcome to luxury living at its finest! This custom-built Mediterranean Villa is situated in the exclusive, gated community of Shark Key--one of the most coveted waterfront enclaves in the Florida Keys. Offering unparalleled privacy and security, this prestigious neighborhood is a haven for discerning homeowners. Spanning 5,180 square feet of meticulously designed living space, this four-bedroom, five-bathroom residence also features an office and a game area. The home boasts an airy, open floor plan with exquisite finishes and architectural details that exude elegance. The heart of the home is the spacious living room, where soaring ceilings and breathtaking open-water views set the stage for unforgettable gatherings. Adjacent, the gourmet chefs kitchen is a culinary dream, equipped with a top-of-the-line Viking six-burner gas range, ample pantry space & laundry, and a dining area that comfortably seats ten. Sliding doors lead to an expansive deck overlooking the pool and tranquil waters, perfect for enjoying sunsets or relaxing by the fireplace. Second Floor Retreat The primary suite is a serene sanctuary accessed through double doors, featuring a large bedroom & bath ensuite, a his & her walk-in closet, a sitting area with a wet bar, enjoy sweeping open water views on the outside deck. Two additional bedrooms, each with en-suite baths, are complemented by two outside lofts and central sitting area, ideal for unwinding while overlooking the lagoon and grounds. Distinctive Features Borano custom mahogany impact double front doors Elevator-ready design with dedicated areas on each floor, Chair lift from ground level to the first floor, a First floor bedroom suite with en-suite bath and sitting area, Two one-car garages with separate entries, Impact windows and doors throughout, Wet bar in the game room, First floor full guest bathroom for convenience. Funished with Exclusions.Amenities; Inland swimming lagoon & Beach, Tennis & Pickleball court, & Club House

Step into Luxury Living at Its Finest..Welcome to this magnificent custom-built home nestled within the prestigious gated community of Shark Key, one of the Florida Keys most coveted waterfront enclaves. Offering unparalleled security with 24-hour surveillance, Shark Key provides a serene and secure haven for discerning homeowners.This elegant residence spans 3,875 square feet of meticulously crafted living space and features four bedrooms that exude sophistication and style at every turn. Experience a bright, open floor plan adorned with exquisite finishes and architectural details, seamlessly blending indoor and outdoor living.Automated window treatments and a Uro-Wall that folds inviting the outdoors in, transforming the spacious living area into an extension of the lush outdoor oasis. The covered lanai is an entertainers dream, showcasing a luxurious heated infinity pool and spa with a waterfall, all overlooking the breathtaking blue waters of the Gulf of Mexico.Gourmet Chefs Kitchen..
The gourmet kitchen is a culinary masterpiece, equipped with top-of-the-line Wolf and Miele appliances. A large island with seating for four serves as the centerpiece, perfect for hosting family and friends. Adjacent to the kitchen, the dining area offers stunning open water views, while the nearby bar room features a wine EuroCave, ice drawer & refrigerator drawer, and convenient access to the lanai and pool area.Primary Suite Retreat..
Escape to the second-floor with two master suites the primary master suite, a private sanctuary with a spa-like ensuite bath, expansive walk-in closet, and a tranquil sitting area ideal for watching sunsets over the Gulf. The thoughtfully placed laundry room is conveniently nearby.Additional Features
..This home also includes parking beneath the residence and ample storage space, ensuring both functionality and convenience.

Nestled on a lushly landscaped, gated point lot, this elegant Oceanfront Duck Key Estate epitomizes resort-style seaside living. Offering sprawling dockage with enviable boating, custom 2021 pool, and sandy beach, your ideal Florida Keys lifestyle awaits! Fully renovated in 2020, every detail has been considered in this intuitively designed retreat; with expertly curated aesthetics blending relaxed sophistication with the surrounding turquoise waters, beckoning the outdoors in. Upon entry, the massive great room boasts cathedral tongue and groove ceilings and sweeping views of Toms Harbour. Entertain for the masses with a breezy open concept floor plan and an expertly-appointed Chefs Kitchen in the heart of the home. Premium Viking appliances, granite countertops, custom cabinetry, and sprawling island with seating allows for cultivating culinary masterpieces with ease. Wake to endless turquoise water views in the primary suite, which features private balcony, hidden TV lift, custom walk-in closet, and opulent en suite bath with dolomite stone shower. Visitors will enjoy elevated accommodation in either of two generous guest bedrooms, also complete with Ocean Views! Additional interior upgrades include a multi-use laundry room with office and pantry space, and two climate-controlled attics. Built to withstand the elements with impact resistant doors and windows. Enjoy year-round alfresco living from an expansive covered veranda. Downstairs, this exceptional property caters to outdoor entertaining with a backyard oasis complete with in-ground, concrete, saltwater pool and spa with heater, chiller, and custom lighting. Steps from the pool, a 56 dock with 20K and 10K lifts, allows for frequent boating. This unparalleled property also offers a sandy beach, private lagoon, and low-maintenance turf yard. Providing abundant privacy and incomparable Sunrises and Sunsets, this exquisite coastal estate offers a refined Florida Keys lifestyle where relaxation meets luxury.

Discover unparalleled privacy and tranquility in this one-of-a-kind oceanfront estate, a true sanctuary nestled amidst the untouched beauty of the Florida Keys. Tucked behind a private gate, the estate begins with a scenic drive through acres of pristine, preserved nature, leading to your own private island. This secluded haven, like no other in the Florida Keys, was once a source of inspiration for Budd Post--the visionary engineer behind the legendary Card Sound Road. It offers an extraordinary blend of history, natural beauty, and modern luxury.Surrounded by breathtaking 360-degree views, the propertys expansive decks and waterfront tiki hut provide unmatched solitude and serenity. Here, you can reflect on days spent exploring the unspoiled waters of the Florida Keys, far removed from the bustle of everyday life.Crafted to perfection, the estates concrete construction ensures strength and resilience while maintaining an air of timeless elegance. Inside, cathedral ceilings and a grand limestone fireplace create a warm and sophisticated ambiance. The dining room, framed by panoramic ocean views, offers an intimate setting for unforgettable gatherings. Three en-suite bedrooms promise unmatched comfort and privacy, making the home as functional as it is exquisite.Boasting over 130 feet of concrete dockage, the estate is a boaters dream, offering the perfect gateway to explore the azure waters that surround you. Whether pursuing nautical adventures or savoring the peace of waterfront living, this property delivers an exceptional experience.This private haven is truly like no other in the Florida Keys--a rare gem where luxury, seclusion, and nature converge. Every corner of this secluded retreat invites you to embrace the unparalleled charm of coastal living in an enchanting and one-of-a-kind setting.

Beautiful 300 of oceanfront property on Lower Matecumbe Key. This offering consists of two 100 lots, vacant & contiguous, a 100 lot with a triplex apartment building, and 2 additional Transferable Development Rights. This gives you endless possibilities for redevelopment of the property. The two vacant lots have an additional 200 of bay bottom. Fantastic 180 ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property.Recap: 300 of oceanfront made up of 2 vacant lots, 1 lot with 3 apartments, bay bottom on the vacant lots, and 2 additional transferable building rights.Note: One of the owners is a State of Florida Real Estate Licensee

Prime Old Town Key West Gem - 326 Caroline St. Welcome to 326 Caroline Street, a historic estate in the heart of Old Town Key West. Located in the prestigious Truman Annex and directly across the street from the Truman Little White House, this property offers a rare blend of history, privacy, and tranquility just steps from Duval Street. Set on over 13,000 square feet of lush tropical landscaping, the estate includes a three-bedroom, three-bathroom main house and a two-story guesthouse connected by a covered deck. Enjoy hardwood floors, crown moldings, and an updated kitchen with custom cabinetry and KitchenAid appliances, top of the line Mitsubishi Central HVAC system and many other luxurious custom finishes. The property features a large garage for two vehicles, plus gated parking for two more--an exceptional find in Old Town. Originally located across the street, the main home was moved to its corner location in 1990, adding a unique historical touch.With spacious decks, sunshine on your pool and lush landscaping, this serene retreat is perfect for relaxing or entertaining. Dont miss this opportunity to own a piece of Key West paradise--schedule your private showing today!

Stunning Sugarloaf Beach estate, with Open Water Views, infinity pool, and private, wide sandy beach, surrounded by nature! Currently utilized as a successful vacation rental, where nightly rentals are allowed, this sprawling 4,509 Sq. Ft. floor plan features 4 bedrooms, 3.5 bathrooms, office, media room, and attached 4+ car garage, just outside the magic of Key West! The great room shows off soaring cathedral ceilings, Open Water Views through impact sliding glass doors, and access to an expansive covered veranda for year-round indoor-outdoor entertaining! Spend the day lounging on 120 of private beach, or cool off in the infinity pool, complete with spa and coral rock deck, just steps from the sand. A convenient poolside outdoor wet bar offers added convenience with beverage cooler, sink, and ice machine! An added bonus is the full cabana bathroom accessed from the pool deck, ideal for rinsing away salt and sand. Entertain for the masses with an expansive Chefs Kitchen, boasting loads of storage, premium appliances, spacious island with additional prep sink, and peninsula with counter seating. The spacious dining area is provides room for enjoying lavish meals with guests or dine al fresco on the massive covered veranda with peaceful turquoise Ocean Views! After a day in the sunshine, retire to a luxurious primary suite with a massive walk-in closet, private balcony with Ocean Views, and an opulent en suite, complete with infinity edge soaking tub, walk-in steam shower, additional laundry room, and wet bar with mini fridge! Enjoy peace and privacy on this lushly landscaped lot, nestled within coveted Sugarloaf Beach, well-established and abundantly exclusive, with proximity to fabulous dining, and nightlife in Key West! This exceptional Sugarloaf Key retreat wont last long!

Sunset Haven This absolutely delightful and serene Florida bayfront beauty will take your breath away the moment you walk in. Delightful double primary ensuite layout and open porches and patios galore adorn this fresh feeling home. 180 degree open water views complete nightly with painted sky sunsets and the best boating proximity; just a stones throw to the Intracoastal waterway and both Tavernier Creek and Snake Creek for easy Bay to Ocean access. 108 of protected dockage with ramp, boat lift and tiki, ample parking and plenty of room for a pool if you need one.

Beautiful adjoining oceanfront gated estates available individually or together for a reduced price! Each parcel has a single family residence with vacationrental income potential and are zoned Suburban Commercial for development opportunities.*UPDATE: There are 50 TDRs (TREs) available, reviewed by Monroe County and transferable to these parcels for higher development potential! This unique wooded acreage has a deepbasin and channel for ocean access, with dolphin piling boat slips and boat ramp. Single Family Residences with ROGO exemptionsfor remodel/rebuild possibilities. Highest approval rate via Monroe County is for MIXED-USE COMMERCIAL development. (The 6.1acre parcel may be sold together with contiguous 3.2 acre parcel@95325 Overseas Hwy, AK#1592986,RE#00483360 000000 13 6238 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 cbshome, metal roof.) This is a duplicate listing. Broker part owner/family owned.

Experience unparalleled island living on Sunset Key, an exclusive island community located in the heart of Key West Harbor. Accessible 24 hours a day via a dedicated island ferry, this extraordinary home offers the ultimate blend of privacy, luxury, and convenience. All this just a four minute boat ride from the vibrant streets of Key West.This bright and airy 4-bedroom residence is designed to capture breathtaking open ocean views. Large windows bathe the home in natural light, creating an inviting and serene atmosphere. The heart of the home is a fabulous chefs kitchen equipped with top-of-the-line appliances, perfect for creating culinary masterpieces while taking in the views of the sparkling water.Step outside to your beach-front oasis, where you can unwind and enjoy the gentle sea breeze or take in a spectacular sunset over the Gulf of Mexico. On the island, a wealth of world-class amenities awaits, including a gourmet restaurant, a rejuvenating spa, tennis courts, and more, ensuring your every need is met in this tropical paradise.With unparalleled luxury, exceptional views, and exclusive island living, this property offers the perfect retreat in one of the most sought-after destinations in the world.

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost comfort. Located in a serene cove with a pristine natural beach, the home features floor-to-ceiling windows that offer stunning 180-degree panoramic views of the ocean. Every corner is meticulously designed with tasteful decor, exuding elegance while providing a personal, comfortable atmosphere. The property is in downtown Islamorada, Florida Keys, and includes a private beachfront terrace, a third-story private balcony, and a tranquil pool with a tiki hut, making it ideal for relaxation and entertaining. The outdoor spaces feature a cozy firepit, offering the perfect setting for intimate gatherings with the sound of the waves as a backdrop. As a vacation rental, this residence is a lucrative investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.

Perched on the prestigious Millionaires Row and enveloped by lush tropical greenery, this extraordinary estate boasts two spectacular homes on one expansive lot, offering a rare blend of luxury and exclusivity in Old Town Key West. With six lavish ensuite bedrooms and a serene pool, this property is a true masterpiece.The main residence, meticulously restored, exudes timeless charm while seamlessly integrating modern opulence. Off-street parking for two and a newly constructed guest house elevate this homes grandeur. Upon entry, youll be greeted by an airy living space featuring rich Dade County pine walls that lead to a 12-person dining room, perfect for hosting elegant gatherings.The kitchen is a chefs delight, adorned with bespoke cabinetry, sculpted marble countertops, and state-of-the-art Sub-Zero & Wolf appliances, including a wine cooler and coffee center. Elegant French doors open to a wrap-around porch that blends indoor and outdoor living.On the main floor, a versatile ensuite bedroom can double as a welcoming den. Upstairs, three additional ensuite bedrooms offer breathtaking views of the lush foliage, each adorned with vaulted ceilings and luxurious finishes. The primary suite is a haven of comfort, featuring a retractable window, custom closets, and a lavish bath with timeless marble, dual sinks, and a walk-in shower.The guest house is a marvel of design, with soaring vaulted ceilings, exposed cross beams, and a charming sleeping loft. It includes two ensuite bedrooms, a full kitchen fitted with Miele appliances, custom tiling, and a stylish island for casual dining. Every detail, from the reclaimed river wood floors to the impact windows and doors, exudes luxury. Separating the two homes is a Craig Reynolds-designed tropical paradise, complete with a saline pool and cascading waterfall. The outdoor space is thoughtfully finished with an outdoor shower and private half bath. 1109 Fleming Street is the epitome of refined island living.

Nestled on the exclusive, gated island of Sunrise Isles in Marathon, Florida Keys, this magnificent new construction oceanfront estate redefines luxury living. With only 20 residences on this private island, youll experience a rare blend of privacy and community, surrounded by the serene beauty of the Keys. This exquisite 5-bedroom, 4-bathroom residence spans 3,415 square feet of meticulously crafted living space, designed to capture stunning ocean views from every angle.Set on over 20,000 square feet of prime waterfront land, the property features 110 feet of sandy beach oceanfront shoreline and an additional 110 feet of protected dockage outfitted with a 20,000LB lift along a private canal ideal for boating enthusiasts seeking convenient, safe access to open waters. The open-concept floor plan seamlessly connects a gourmet kitchen, spacious dining, and living areas, with floor-to-ceiling windows that flood the home with natural light and offer unobstructed views of the Atlantic.Outdoor amenities include a resort-style pool with water features and a relaxing jacuzzi, creating a true island oasis for entertaining or unwinding. Each bedroom is designed with an en-suite bathroom for the utmost privacy, while the primary suite serves as a luxurious retreat with panoramic views, a spa-inspired bathroom, and a custom walk-in closet.This one-of-a-kind property in Sunrise Isles is the ultimate Florida Keys sanctuary, where privacy, luxury, and coastal beauty come together in perfect harmony. Just 1/2 mile from stunning Sombrero Beach. Shopping, dining, and Marathon Airport private airstrip within a few miles of the home. Dont miss the rare opportunity to own your piece of paradise in the beautiful Florida KeysModel home available for preview showings. Take advantage and choose your finishes and decors prior to completion. Seldom are new construction residences offered in the Florida Keys, reach out for a private model home tour and additional details.

This Key Haven Estate rests on over 15,000 square feet of land with more than 260 linear feet of water access all while boasting over 6500 square feet of the finest living accommodations in the Florida Keys. The main Home has 5 Bedrooms and 4 and 1/2 bathrooms, the guest house has 3 bedrooms and 3 bathrooms. 39 Evergreen has the finest finishings all encased in 11 inches of solid concrete using insulated concrete forms and solid poured floors and stairs. Utilizing this type of Construction not only provides tremendous safety and privacy but allows for the impact glass windows and doors to be protected by hidden European style roll down shutters. The home has a vast 60 long pool with multiple levels, waterfalls and 6 seats to the swim up bar in the custom gazebo, perfect for entertaining, or when you are finished in the homes Private 400+ Square foot Gym. This home can accommodate over 9 vehicles in its 3800 Square Foot garage and has a Generator and Fire Suppression system for additional safety and security.

This distinguished estate, erected in 1904, proudly stands as the revered historic landmark known as Building 11, The Smithery within the esteemed confines of the Truman Annex--an exclusive gated community formerly part of the United States Naval Station, Key West. This exceptional offering epitomizes expert restoration, boasting lofty ceilings, majestic 22 brick exterior walls, and imposing wooden beams that seamlessly marry historic allure with contemporary finesse upon an expansive, idyllic plot. A quintet of majestic arched French doors adorns the facade, beckoning vistas of the verdant tropical surroundings. The ground level unfolds with sweeping travertine floors adorned with artisanal fixtures, housing a gracious great room with a bespoke bar, a gourmet kitchen, an elegant dining area, and additional living space. Nestled on this level, a guest suite seamlessly extends to the inviting poolside retreat, graced with a cascading waterfall and tranquil stone deck. Ascending to the upper level reveals an enchanting realm, where the primary and guest suites are interconnected by a captivating gallery bridge, each enveloped in luxurious amenities and adorned with custom built-ins, sumptuous hardwood flooring, and exquisite lighting fixtures. Lavish bathrooms, featuring opulent upgrades, adorn both wings, ensuring unparalleled comfort and refinement. Exquisitely maintained, this abode has garnered the admiration of a select few, its architectural brilliance cherished by those fortunate enough to experience its splendor. The expansive carport, a newly fashioned storage enclave echoing the original architectural charm--further enhances the allure of this hidden treasure. Nestled amidst illustrious neighbors, including Trumans Little White House this jewel epitomizes one of the most coveted addresses within the Florida Keys, offering a lifestyle of unrivaled sophistication and allure.

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. New dock with two boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for great income potential. The sandy backyard is shaded by palms and the large pool is fenced for privacy. The winding drive from the gate to the home is dotted with seating spots for enjoying the wildlife and tropical foliage. There is also a separate storage room and workshop downstairs, a gardening shed and landscape lighting along the driveway. Call today!

Welcome to Southwinds, your exclusive oceanfront oasis in the heart of Lower Matecumbe, Islamorada. This stunning 5-bedroom, 6.5-bath CBS home embodies luxury and tropical living. Spanning nearly 4,000 sq. ft., Southwinds offers breathtaking ocean views, with floor-to-ceiling impact windows that flood the interior with natural light, seamlessly connecting you to the stunning beauty of the Atlantic. One of the standout features of Southwinds is its 100 natural sandy beach, a rare find in Keys oceanfront homes. Stroll the 150 foot pier which features water, electric and a fish cleaning station. Read a book or enjoy your favorite beverage under the tiki. The pool features a spillover edge, bubbler, sun shelf and hot tub. The grand outdoor Mahogany bar is ideal for entertaining against the backdrop for the ocean breezes. A private pickleball court offers hours of fun and fitness for you and your guests, right in your own backyard. Paired with a putting green, this home provides a truly unique lifestyle experience that caters to the active, outdoor enthusiast.The home features a large kitchen with a pass-thru, an induction range, wine and beverage coolers, and two sets of washers and dryers for ultimate convenience. The third-floor wet bar and expansive open balconies offer additional space to enjoy the spectacular views. The gated property also features landscape lighting, an irrigation system, a spacious garage, and storage room.Southwinds is a sanctuary for those seeking a private retreat or a valuable investment. Whether youre in search of a second home or a high-performing rental property, this residence offers everything you could desire. Zoning allows for weekly vacation rentals, Southwinds presents an ideal opportunity for generating rental income.