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$5,100,000
5 Beds ⋅ 4 Baths ⋅ 621368 MLS
OWNER FINANCING AVAILABLE AT 6% Experience luxury waterfront living in the Florida Keys with this exceptional 5 bedroom, 4 bath estate, ideally positioned at the end of a quiet street with 173 feet of deep-water dockage and an expansive turning basin offering easy maneuverability for large boats, performance boats, and large sportfishing vessels. Offered fully furnished and completely move-in ready, this home is designed for effortless Keys living from day one. Furnishings, décor, and thoughtfully selected finishes complement the home's sophisticated design, while the chef's kitchen features a complete suite of premium Thermador appliances. Built for both luxury and durability, the smart home showcases high-end interior finishes and premium composite exterior materials designed for the coastal environment. Features include a private elevator, programmable smart-home hubs throughout, whole-house surround sound extending to the pool and rooftop, and two laundry rooms, one on each living level. Expansive indoor living areas transition seamlessly outdoors to a private resort-style pool with sun shelf and gazebo. Oversized balconies off the primary suite and kitchen overlook the water, capturing spectacular bay sunsets and views of boats passing through iconic Toilet Seat Cut. The nearly 2,000-square-foot rooftop terrace is a true showpiece, complete with turf, bar, BBQ area, immersive audio, and panoramic views. With direct bay access and a short ride to Tavernier Creek for convenient Atlantic Ocean access, this fully furnished waterfront estate delivers boating, entertaining, luxury, and the Florida Keys lifestyle in one extraordinary package.

265 Pueblo St, Tavernier

$14,000,000
5 Beds ⋅ 4 Baths ⋅ 621096 MLS
The most sought-after bay in all the Florida Keys, and one of the largest properties on it. This true double lot spans 1.3 acres with more than 250' of bayfront facing due west for the perfect nightly sunset. A white sand beach transitions into the clear bay waters, while a protected basin offers a 20,000 lb. lift accommodating up to a 40' boat and a 3,000 lb. skiff lift. Ultra-private, with no neighbors in sight and expansive green lawns throughout. The home is sophisticated yet inviting, with an incredible attention to detail throughout and a distinctive blend of Tuscan Mediterranean architecture and classic Keys styling. Enter through the gates into a private courtyard and open-air atrium with freshwater ponds and fountains. An elevator provides access to the second floor, where a one-of-a-kind living room overlooks the bay with exposed wood beams and tongue-and-groove ceilings. Updated throughout while preserving its original ornate finishes, this level flows from the living and dining rooms into the kitchen with a gas range and dumbwaiter. The bayfront primary suite features an impressive bath with dual vanity areas. Two additional bedrooms share a Jack-and-Jill bath, plus a half bath finishes off the second floor. Halfway down the main staircase is the entrance to one of the favorite rooms in the home: the library. With vaulted ceilings and a fireplace, it is the ultimate setting to work, relax with a good book, or serve as a fifth bedroom. The ground floor offers a separate ensuite guest bedroom, garage with front and rear doors, laundry room with double washers and dryers, and an outdoor kitchen. Outside, a massive 40' x 22' pool features a hot tub and beach-entry shelf. Extensive uplighting and downlighting illuminate the property at night. An additional front lot includes a detached structure currently used as a gym and storage. A once-in-a-lifetime opportunity to own one of Islamorada's most prized bayfront estates.

350 Buttonwood Bight Ln, Tavernier

$5,995,000
5 Beds ⋅ 4 Baths ⋅ 621057 MLS
Welcome to CASA MARE, where contemporary luxury meets the open Atlantic. Built in 2023 by Dellanos Construction of the Keys, this spectacular direct-oceanfront residence offers approximately 3,000 sq. ft. of living space with 5 bedrooms, 4 baths and breathtaking panoramic open-water views from virtually every level. Designed to embrace its extraordinary setting, expansive glass and generous covered terraces create a seamless connection between indoor and outdoor living, with the Atlantic Ocean providing an ever-changing backdrop. Contemporary architectural details include clean modern finishes, warm wood accents and a dramatic floating-style staircase with glass railings. Step outside into your own private oceanfront resort. An impressive infinity-edge pool with in-water seating seemingly blends into the horizon, while a private putting green and low-maintenance outdoor areas provide the perfect setting for entertaining, relaxing and enjoying the Florida Keys lifestyle. Boaters will appreciate the deed-cut boat slip with 17,000-lb. boat lift, offering the rare combination of protected boat storage and immediate access to the open water. Multiple covered outdoor living areas capture panoramic ocean views and tropical breezes, creating exceptional spaces for morning coffee, entertaining friends or simply watching the horizon. With 5 bedrooms, extensive outdoor amenities and an extraordinary direct-oceanfront setting, Casa Mare also offers excellent potential for seasonal rental use. Casa Mare is more than a home--it is a contemporary oceanfront retreat where architecture, boating and the beauty of the Florida Keys come together.

239 Tavernier Dr, Tavernier

$5,499,000
5 Beds ⋅ 5 Baths ⋅ 619946 MLS
Welcome to 142 Guilford Court, a stunning bayfront home located in the highly desirable and sought out neighborhood of Hammer Point. Built in 2021 with solid concrete construction and a concrete roof, this luxury waterfront home was designed for effortless Florida Keys living with panoramic bay views from both the the living spaces and primary bedroom, exceptional outdoor spaces, and high-end finishes throughout. Offered completely turnkey furnished and professionally decorated, this 5-bedroom, 5.5-bathroom residence features approximately 3,500 square feet of interior living space spread across three levels with elevator access to all floors. Every bedroom offers its own private en-suite bathroom, creating the perfect layout for hosting family and guests in comfort and privacy. The open-concept main living area is filled with natural light and framed by expansive impact glass doors overlooking the bay. The chef's kitchen includes premium appliances, quartz countertops, a large butler's closet/pantry, warming drawer, and generous entertaining space that flows seamlessly into indoor and outdoor living areas. Outside, enjoy a resort-style bayfront setting with a concrete dock, sparkling in-ground pool, multiple balconies and patios, fenced yard, covered parking, and breathtaking sunset views over the water. Whether you are looking for a full-time residence, luxury vacation home, or premier Florida Keys waterfront retreat, this property delivers the best of island living. Located in the Tavernier, minutes from Tavernier Creek and many dining venues, 142 Guilford Court is a rare opportunity to own a newer construction bayfront home in the Florida Keys with direct water access and timeless coastal design.

142 Guilford Ct, Tavernier

$27,000,000
5 Beds ⋅ 8 Baths ⋅ 619825 MLS
Set on over 2 acres along prestigious Millionaire's Row in Tavernier, this newly constructed oceanfront estate represents a rare convergence of scale, design, and functionality in the Upper Florida Keys. Encompassing 8,200 square feet of interior living space and over 16,000 square feet total, the residence is thoughtfully designed to accommodate both elevated everyday living and large-scale entertaining.The home features 5 bedrooms, 6 full baths, and 2 half baths, with all bedrooms offering en suite accommodations, custom closet build-outs, and refined finishes throughout. Additional interior spaces include a dedicated office, control room, mud room, and laundry room, providing both comfort and operational efficiency. A private elevator, whole-home sound system, and advanced mechanical infrastructure--including 600-amp service, multiple electrical panels, and five independent AC zones--underscore the property's level of detail and performance. Interior finishes are curated with a modern coastal aesthetic, highlighted by white diamond marble and teak wood flooring & a custom steel roof. The chef's kitchen is outfitted with top-tier Wolf, SubZero, and Cove appliances, including a 60-inch range, dual dishwashers, farmhouse sinks, and custom mahogany countertops--designed to seamlessly blend form and function. Outdoor living is equally exceptional, with 240 feet of oceanfront, anchored by a 120-foot resort-style pool, complete with multiple heating and chilling systems, a gas-heated spa, and full smart control. A fully equipped summer kitchen, cabana bath, and multiple covered entertaining areas create a true indoor-outdoor lifestyle experience. Additional highlights include a 3-car garage and fully equipped workshop with air conditioning, utilities, security systems, and custom lighting. The property is also zoned for weekly rentals, presenting a compelling opportunity for both personal enjoyment and income potential.

88845 Old Hwy, Tavernier

$1,095,000
5 Beds ⋅ 3 Baths ⋅ 619499 MLS
Live the Florida Keys Lifestyle in Your Dream Home Experience the perfect blend of elegance, functionality, and laid-back tropical living in this beautifully designed Florida Keys-style home. The open-concept floor plan creates a seamless flow between the living, dining, kitchen, and loft areas--ideal for both everyday living and entertaining. The spacious primary suite offers a private retreat, complete with a custom ensuite bathroom featuring a luxurious rain shower--perfect for your own spa-like escape. Generously sized guest bedrooms and three full bathrooms ensure comfort and convenience for family and visitors alike. At the heart of the home, the expansive kitchen provides abundant workspace for everything from quick meals to gourmet cooking, all while staying connected to guests in the open living space. Above, a versatile loft adds architectural charm and flexibility--ideal for a home office, media room, or creative studio. Additional highlights include: Separate laundry room for added organization Detached garage with attic storage--perfect for a vehicle, boat, or potential guest conversion Attached storage shed for tools, toys, or future expansion Street-to-street access for easy parking and convenience Plenty of room to design your own private pool and outdoor oasis Enjoy cost savings with insulated glass windows and French doors that fill the home with natural light while enhancing energy efficiency. Step outside and unwind in your private tropical setting--perfect for entertaining, relaxing under the stars, or enjoying quiet moments with friends and family. Ideally located near shopping, dining, schools, and medical facilities, with convenient access to both the bay and ocean via Tavernier Creek. Welcome to your slice of paradise.

106 Gardenia Ave, Tavernier

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