Islamorada Homes for Sale, Single Family Houses, MLS Home Listings

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout.Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation.On the main floor, the gourmet kitchen is a chefs dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock.This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating open water views and is situated on 1.3 acres of land. Complete with three bedrooms and two bathrooms, this ground-level, and updated residence is the perfect place to entertain while basking in all of the beauty the Keys offers. Zoned residential estate, this income-producing home qualifies for weekly rentals, which provides ample opportunities for a discerning buyer.

This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this residence offers ample space for family and guests. Enjoy stunning ocean views from various vantage points within the home, enhancing the comfort and breathtaking natural beauty. The observation dock provides a perfect spot for relaxation, while the saltwater pool equipped with heater/chiller, ensures year-round enjoyment. Added features are quartz countertops, top-of-the-line appliances and the Residential Estate zoning allows weekly vacation rentals with a high-income stream.This combination of amenities creates an inviting atmosphere that reflects the privacy and charm of the Florida Keys lifestyle.

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chefs kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys most sought-after locations.

Exquisite Tri-Level Waterfront Estate in Islamorada!Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence boasts an open-concept floor plan with soaring ceilings, a fireplace and a grand living area.Enjoy seamless indoor-outdoor living with an expansive wraparound veranda, perfect for soaking in the breeze and relaxing water views. The beautifully landscaped 10,000sqft lot provides privacy and tranquility, while the swimming pool offers the ultimate relaxation.For boating enthusiasts, this property is a dream come true! Featuring 100 of deep-water concrete dockage equipped with a 20,000lb catamaran width elevator boat lift and a 5500lb set of davits you will enjoy immediate access to both the Atlantic Ocean and Florida Bay for excellent offshore and backcountry fishing. A two-car garage with a new A/C unit, plus additional covered carport parking, ensures ample space for vehicles and storage along with a beautifully paved driveway.Come experience the best of the Florida Keys lifestyle in this exceptional waterfront retreat!Updates....1. NEW 2-car Air Conditioning Split with 10-year warranty2. New Dock and Stair Brick Pavers3. New third-floor Impact Windows4. Two New third-floor Impact French Doors5. Two New third-floor electric Rolladen Hurricane Shutters6. Swimming poll resurfacing with new glass edge surround7. Dock has a 220-volt pedestal to service dock-side marine electric needs

Welcome to your private tropical retreat in the heart of Islamorada, Florida Keys. This stunning gated oceanfront estate showcases unparalleled beauty with a private walk-in sandy beach, offering direct access to crystal-clear waters. Designed for both relaxation and recreation, the property features 5 spacious bedrooms, 6.5 luxurious bathrooms, a resort-style pool, a pickleball court, and a putting green, all set amidst lush, tranquil landscaping.Wake up to spectacular ocean views from nearly every room, and enjoy the serenity of your tropical surroundings. This property is offered turn-key, fully furnished and equipped, making it an ideal primary residence, second home, or lucrative vacation rental opportunity in one of the Keys most desirable locations.Your dream oceanfront lifestyle awaits in Islamorada -- where every day feels like a vacation.

$400,000 PRICE REDUCTION !! ... Welcome to Serenity Cove, a remarkable, comfortably luxurious estate set along the shores of the Florida Bay. This custom-designed property, stretching from the highway to the bay is almost 1.75 acres. It is perfect for those who value peace, relaxation, and the simple joys of what the Florida Keys has to offer.This home offers four bedrooms and four bathrooms and 110 of dock with multiple slips accommodating up to a 45 boat with 5 draft and 16k lift. This home has been thoughtfully designed with tasteful moldings, and warm, inviting finishes. The kitchen, is equipped with top-tier appliances, custom cabinetry, and a roomy island - perfect for those who love to cook and entertain. It smoothly transitions into the formal dining room, making it an ideal space for both quiet family dinners and larger celebrations.The second-floor suite, with its spacious layout, welcoming fireplace, and private balcony, is the ultimate retreat. The en-suite bathroom, has a dual vanity, a claw-foot soaking tub, and a walk-in shower, guarantees moments of relaxation.The first floor offers a smart design with separate living areas and bedrooms. The 1st floor suite includes a steam shower and a reinforced safe room that doubles as a walk-in closet. The additional two bedrooms and a den with surround sound and a wet bar are comfortably located on the opposite side of the home.Enjoy quiet moments on the covered patio or engage in lively gatherings around the spacious poolside patio, which leads directly to the sandy beach for amazing sunsets. Here, youll find ample seating, a fire pit, a Boat House and steps leading to the basin for swimming and exploring the Bays unique ecosystem.Serenity Cove is comfortably tucked away from the hustle of US1, offering a sense of privacy and security, while maintaining easy access to schools, shopping, dining that make Islamorada so desirable.

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

Seeking privacy, luxury AND convenience? This custom bayfront estate built by the current owner in 2014 offers it all! Situated on a peninsula with 250+ feet of crystal-clear open water frontage, this one-of-a-kind Keys home is located in the heart of Islamorada within walking distance of all your favorite local dining spots. As you enter the gated estate, you are welcomed home by unparalleled privacy and seclusion. This open water home has no neighbors looking through side yards and of course, no neighbors across a canal. Designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and open water views, this luxurious home also boasts marble floors throughout and a gorgeous floating staircase. Begin your day by stepping out of your bedroom to your private bayfront terrace and into a stunning second floor Infinity Edge pool, complete with a heater/chiller. In the evening, experience the brilliance of Islamoradas sunsets from every room, the rooftop or outdoor lanais, which provide a grand total of almost 6,000 sf of combined indoor and outdoor living space. Floor-to-ceiling sliding glass doors disappear into pockets, bringing the indoors out and the outdoors in. Just one step outside the main kitchen is a full outdoor kitchen and bayside dining, al fresco. For stargazing, venture up to the rooftop deck for a breathtaking front row seat. Ready to get on the water? Your boats will comfortably berth on the 100 deep water dock with two lifts and are kept safe by built-in storm protection. Other functional luxuries include an elevator, an enormous three-car 2,200 sf garage with workshop/storage, camera/security system and mature landscaping with fruit trees. A fourth bedroom with bath can be easily added without modifying the structure at a reasonable cost. With all living space above flood and built to withstand sustained 200 mph winds, this concrete home has accordion shutters over impact for ultimate storm resiliency. Call today!

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.

Introducing 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chefs kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breathtaking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the homes exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the propertys thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. A true statement of coastal luxury--this is Florida living at its finest.

Southern Shore - A Modern Coastal Masterpiece Nestled in an exclusive oceanfront setting, Southern Shore is a premier coastal residence offering an unobstructed, 180-degree panorama of the Atlantic Ocean. This exceptional, all-concrete estate spans 3,790 square feet of meticulously designed indoor living space, complemented by 2,580 square feet of expansive terraces for seamless outdoor living. Inside, the home features four luxurious en-suite bedrooms, offering breathtaking ocean views. The chef-inspired kitchen is outfitted with custom floor-to-ceiling cabinetry, sleek quartz countertops, and top-of-the-line appliances. State-of-the-art smart home technology, custom-built closets, and the convenience of an elevator elevate both form and function in this sophisticated residence. The interior spaces reflect a perfect balance of elegance and comfort. With floor-to-ceiling windows throughout, the home captures the essence of the tropical lifestyle, offering stunning vistas of the ocean from nearly every room--living areas, kitchen, and bedrooms alike. The outdoor spaces of this estate are designed to host gatherings in style, featuring a rooftop deck, multiple terraces, and a luxurious pool and spa area with an outdoor shower. For boat enthusiasts there is a 12K lift boat and letter from the Village Planning and Building Department allowing a 24K 4 post lift. All protected by a gated entry. Located within the serene Plantation Key community, this property also includes a misting system and occupies an expansive lot with direct ocean access. This is the ultimate tropical sanctuary for those seeking a premier location with unparalleled views, superior construction, and a full suite of luxurious amenities. Note: The owner is a licensed Florida real estate agent. For additional details, please refer to the full property description available in the document tab.

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

Experience the pinnacle of luxury waterfront living in this extraordinary custom contemporary estate, ideally positioned in the heart of Islamoradas premier community of Venetian Shores. Newly constructed, the residence radiates modern coastal elegance and features impeccable attention to detail. A total of five spacious bedrooms and five en-suite bathrooms are thoughtfully laid out, complemented by a half bath and separate cabana-style guest quarters, creating an ideal retreat for family and visitors.Located on the bayside, the estate offers 100 feet of deep-water dockage, complete with a cut-in boat slip, 2 boat lifts & a float-on double jet ski lift. With direct access to the Gulf and Atlantic through world-famous Snake Creek, the location is a dream for avid boaters and luxury seekers.Inside, soaring tray ceilings, marble tiled floors, a private elevator, and a grand staircase elevate the living experience. The open-concept layout seamlessly connects the kitchen, dining, and living areas for effortless flow. The chefs kitchen features premium appliances including a Dacor gas cooktop, a walk-in pantry w/custom shelving, a prep island, and an expansive bar-height island for gathering. A private, elevated two-story guest wing includes a spacious bedroom & bath, as well as a billiard/game room w/full bath. The third-floor owners suite offers a sanctuary, highlighted by dual walk-in closets, a circular soaking tub, oversized shower, and separate water closet. Finally, there is a 3 car garage for all your cars & water toys.Outdoor living is just as impressive with multiple balconies overlooking tropical landscaping & wide canal. A heated pool/spa anchors the expansive outdoor area with outdoor kitchen, covered dining & lounging areas, a fire pit, hammock, sandy yard, palms, plume grass & lemon trees. This estate is a rare offering that perfectly blends refined style, tropical comfort, and unparalleled boating access, the very essence of luxury Keys living.

Youre not just buying a home--youre embracing an unparalleled waterfront lifestyle! This exquisite six-bedroom, four-bathroom residence, featuring two primary suites, is situated on a highly sought-after corner lot with breathtaking water views from every room. Boating enthusiasts will love the 220+/- ft. of concrete dock, offering ample space to park yachts and welcome guests arriving by boat, complete with three boat lifts for ultimate convenience.Completely gut-renovated down to the studs in 2020, this custom home feels brand new, boasting a cool, neutral color palette that mirrors the surrounding turquoise waters while maintaining a warm and inviting ambiance. Owners have meticulously kept the property in pristine condition. A local realtor recently said it was the cleanest house shes been in in decades! Energy efficiency and low maintenance further accentuates effortless luxury living.Step outside to enjoy a custom saltwater pool, built in 2021, featuring both a heater and a chiller for year-round relaxation. With direct Bay-to-Ocean access via Channel 5 Bridge, this location is a dream for boaters. Inside, Viking appliances and countless upgrades and custom touches elevate this homes elegance and functionality creating a wow factor throughout the stunning home.Opportunities like this are rare in the Florida Keys. Start living the dream in the most desirable area in the Florida Keys! Dont wait - schedule a showing today!

Set on 1.38 acres of pristine oceanfront in the Florida Keys, this private estate offers the perfect blend of luxury, serenity, and tropical beauty. With an enormous 150-foot private beach, this stunning 4,770-square-foot residence presents an unparalleled opportunity to experience the magic of oceanfront living.The home features five bedrooms and five and a half baths, including separate guest quarters for added privacy. Towering 30-foot ceilings create a grand, open atmosphere, while expansive windows frame breathtaking views of the Atlantic Ocean. Offered turnkey, this estate is move-in ready, with exquisite furnishings that complement its elegant design.Step outside to a resort-style infinity-edge pool with spa. A spacious two-car garage provides convenience, while the estates zoning allows for weekly rentals, making it a remarkable investment opportunity.This property is more than just a home--its a tropical oasis where you can kayak, fish, or build sandcastles right from your backyard. Whether you seek a family getaway or a primary residence, this estate offers the best of both worlds: a tranquil retreat surrounded by nature yet still within the comforts of the United States.

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

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 boaters 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 chefs 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

Discover the unparalleled beauty and tranquility of this Bayfront Estate, nestled on the pristine shores of Lower Matecumbe in the Florida Keys. Surrounded by lush, meticulously landscaped grounds, this exceptional property offers direct waterfront on the crystal clear waters of the Gulf. Experience breathtaking sunsets over the horizon, world-class tarpon fishing just steps away, and private dockage with ample space for multiple boats.Unwind in the stunning infinity pool, blending seamlessly with the serene surroundings. This is a rare opportunity where every moment feels like a dream!Developed with two buildings, splitting the living between the two making this unique design quite special. Embrace this exciting design or modify and create your own design. Blending the two buildings brings all living together. Other treasures of this estate property include a 2 car garage, separate guest suite, expansive indoor outdoor entertaining overlooking the bay, separate concrete building for versatile use, boat lift, boat ramp, German inspired fireplace, electric gate, sprawling green space, and so much more.Owner is ready to sell. What an opportunity!