Islamorada Waterfront Homes on the Bay / Gulf Side of the Island For Sale

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.

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!

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!

Welcome to BAYVIEW HIDEAWAY a generously sized, COMPLETELY RENOVATED home with top-tier finishes showcasing stunning Florida bay views of calm waters and vibrant nightly sunsets, combining tropical charm with modern luxury--ideal for those in search of a tranquil getaway in an unforgettable PRIVATE setting. Situated on TWO SEPARATE LOTS-each with its own parcel ID--the buildable bayfront lot has endless potential. The price per square foot reflects this extraordinary opportunity. The property features 220+/- FT. OF CONCRETE DOCK, an additional 200+/-ft. of water frontage, THREE BOAT LIFTS, helicopter access, a NEW PRIVATE POOL, and SIX BEDROOMS EACH WITH WATER VIEWS. Ideally located in Islamorada just north of the Channel 5 Bridge with its 65 clearance and 30 minutes from Marathon executive airport, it offers nearly IMMEDIATE ACCESS to the ocean or Intracoastal Waterway, world-class offshore and backcountry fishing, reef diving, and an array of nearby attractions, outdoor activities, and dining--striking a perfect balance of seclusion and accessibility ideal for any boater, angler or water enthusiast!

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly 4 acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The homes architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. Spanning over 6,900 square feet, the interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A bonus, versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio. This downtown Islamorada estate in an incomparable location; walking distance to shopping, dining, and local culture, also has appeal that extends to those with a passion for the great outdoors. Two protected docking basins and boat lift, sandy lounging beach, expansive outdoor lanai and outdoor kitchen offers the ideal space for entertaining or enjoying a quiet evening watching the sunset. Fly the seaplane in or land the helicopter. Premier boating access just moments away from the Intracoastal waterway and Ocean channels. Serenity Cay is not just a home, its an experience.

Spectacular 1.65-Acre Bayfront Estate in Islamorada, Florida Keys |
8 Bedrooms | 9.5 Bathrooms | 10,228 Total Sq Ft | 150 Waterfront | Dockage | Pool | BeachWelcome to a rare offering in the heart of the Florida Keys--this 1.65-acre gated bayfront compound in Islamorada combines timeless island luxury with modern amenities and endless water views. With 150 feet of private waterfront, dockage, boat ramp, private beach, two pools, and lush, mature tropical landscaping, this estate is a true Keys sanctuary.The 7,562 sq ft main residence boasts 5 spacious bedrooms, 5.5 bathrooms, an office, and exquisite finishes throughout. The gourmet kitchen features marble and dolomite countertops, a custom mosaic tile backsplash, built-in Miele coffee system, wine dispenser, 36 Wolf gas cooktop, four Sub-Zero refrigerators, and two laundry rooms. A stunning 180-bottle glass wine cellar, handmade wood bar with wood sink, Sonos sound system, and living room with blackout shades to enhance the entertaining potential.Additional highlights include an elevator, Lutron lighting system, Toto toilets, expansive covered porches with panoramic open bay views, an outdoor kitchen complete with Italian brick pizza oven, Evo flat grill, and smoker, as well as a tackle room and 4-car garage.The 2,666 sq ft guest house offers a private gated drive, 3 bedrooms, 4 bathrooms, a private pool, and a fully equipped kitchen with JennAir appliances, making it ideal for hosting guests or extended family in complete privacy.With two gated driveways, serene lawns, and a high-end tropical ambiance, this estate seamlessly blends privacy, prestige, and paradise.A one-of-a-kind legacy property - experience the ultimate Florida Keys lifestyle.