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$5,999,000
5 Beds ⋅ 7 Baths ⋅ 620457 MLS
Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf of thoughtfully designed living space, set just 2 lots from the bay and across from a tranquil mangrove preserve that enhances both privacy and natural beauty. Boaters will love the setup - 100' of dockage with 2 elevator boat lifts (20,000lb and 15,000lb), plus easy access to Everglades National Park and the Atlantic Ocean through the 65' Channel 5 Bridge. Inside, the home feels open, bright, and refined. There are 5 ensuite bedrooms and 2 half baths, each bedroom featuring its own ductless A/C along with the central system. The primary suite includes a cozy sitting area, his-and-hers closets, and partial bay views. A secondary primary suite opens directly to the pool deck, offering privacy for guests or family. The top level centers around a stunning great room with vaulted ceilings, fireplace, and a chef's kitchen with high-end appliances - the perfect setting for entertaining. On the lower level, a relaxed family room with fireplace and wet bar creates another comfortable gathering space. Additional features include laundry on both floors, an elevator, 2-car garage, and gated circular drive. Out back, the saltwater pool, outdoor kitchen, and sound system create a true resort-style atmosphere. The east-facing orientation means warm morning sunshine, shady afternoons, and gentle ocean breezes. With CBS construction, metal roof, whole house generator and impact windows and doors, this home blends luxury, comfort, and peace of mind. This is waterfront living for those who value both elegance and ease - the Keys lifestyle at its finest.

430 Palm Dr, Islamorada
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 620190 MLS
Welcome to 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 chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's 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 property's 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. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

194 Buttonwood Ln, Islamorada
$2,300,000
605436 MLS
WELCOME TO 'SEA WINDS'! IT'S TIME TO BUILD YOUR DREAM HOME! This outstanding property is ready for your personal building plans and has an active permit in the Village of Islamorada. Located in Safety Harbor, one of the most desirable neighborhoods in The Sports Fishing Capital of the World. The oversized lot is 11,373 sf with a boat ramp, 30 ft. of dock that can be expanded, and 88.5ft of seawall in place. The very desirable location allows for a larger boat with direct bay access and quick ocean access with plenty of turn around space in the deep water canal type setting offering at least 5ft. of draft. Lower Matecumbe offers outstanding off shore and back country fishing 8 miles away from most of the charter boat fishing fleet. Across the street are Bay Front Multi-Million Dollar homes allowing you to build up to 38ft in height to capture the outstanding bay views in your brand new home. Don't miss the opportunity to own one of the last buildable lots in the Village of Islamorada with a permit in place! The documents tab outlines the outstanding features of this amazing property!

445 Palm Dr, Islamorada
$4,700,000
4 Beds ⋅ 4 Baths ⋅ 617501 MLS
Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm. Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access. Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic. Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.

166 Bayview Dr, Islamorada
$5,600,000
6 Beds ⋅ 8 Baths ⋅ 613346 MLS
Welcome to Mykonos Villa, a luxurious 6-bedroom, 7.5-bathroom estate in Islamorada, FL. This home features an open layout with natural light, sleek finishes, and refined design. The gourmet kitchen, with a La Cornue stove, high-end appliances, and custom cabinetry, flows seamlessly into the living and dining areas, perfect for entertaining. A smart home system manages temperature, security, and pool features. Each bedroom includes a private en-suite bathroom. The master suite offers breathtaking views, a private balcony, spa-inspired bathroom, and spacious walk-in closet. Outdoors, enjoy a pool, hot tub, kitchen, 100 feet of private dockage, two boat lifts, and a fish cleaning station. Mykonos Villa—Live where the ocean greets luxury, and paradise is your everyday address.

400 Palm Dr, Islamorada
$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
$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
$3,950,000
4 Beds ⋅ 3 Baths ⋅ 617856 MLS
Panoramic Bay and Sunset Views! Breathtaking Bayfront Home in Safety Harbor. Experience the stunning beauty of panoramic bay views from this exquisite bayfront home in the premier Safety Harbor neighborhood on Lower Matecumbe. This home is in pristine condition and features an irreplaceable cut-in boat slip with a composite dock on the bay ensuring that your views are not obstructed, and providing immediate bay access and quick ocean access via the two bridges at Channels 2 and 5. Inside, you'll find four spacious bedrooms and three bathrooms, perfect for comfortable living. An enclosed garage for all of your fishing and diving gear. The home is equipped with a new whole house generator, ensuring uninterrupted power. Step outside and immerse yourself in resort-style living with a luxurious pool and spa, lush low maintenance landscaping, perfect for relaxation and entertaining. Enjoy breathtaking sunsets year-round from your own private oasis either at the tiki bar, the dock, or one of the two bayfront screened porches. Don't miss the opportunity to own this exceptional bayfront home in Safety Harbor. Schedule your private showing today!

182 Bayview Dr, Islamorada
$3,900,000
4 Beds ⋅ 3 Baths ⋅ 614036 MLS
ACTIVE POOL PERMIT! A truly spectacular waterfront home with 150 feet of prime bay frontage, offering breathtaking views of some of the clearest waters in the Florida Keys. This property has undergone a complete top-to-bottom renovation with exceptional attention to detail. Solid concrete bunker with a concrete roof and impact windows & doors. Boaters will appreciate the deep-water dockage, accommodating nearly any vessel, with easy ocean access through Channel 5. The main living area upstairs features three bedrooms, two bathrooms, and a beautifully designed kitchen with high-end appliances—all framed by stunning turquoise water views from nearly every room. Downstairs, a separate guest suite includes a private bedroom, bathroom, living room, and kitchen, perfect for visitors or additional living space. A pool permit is already in place, or you can take a refreshing swim right in the bay. This home is truly one-of-a-kind—don't miss the chance to own a special piece of paradise!

442 Palm Dr, Islamorada
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 617822 MLS
VA Assumable! Experience refined waterfront living in the Florida Keys, where luxury meets effortless access to world-class boating and fishing. This exceptional canal-front residence is thoughtfully designed for discerning buyers who value privacy, convenience, and a true connection to the water. A private dock with newly added 15,000 lb boat lift provides seamless access to open water, allowing you to leave your backyard and reach premier fishing grounds in minutes. A utility elevator lift enhances everyday comfort, making it easy to move gear, provisions, and luggage between levels with ease. Outdoor living is elevated for both entertaining and function. A custom storage shed equipped with an ice machine and two deep freezers caters perfectly to avid anglers and boating enthusiasts, offering an ideal setup for bait, ice, and fresh catch storage—an uncommon and highly desirable feature in the Keys. Inside, the home offers a bright, coastal interior that complements the surrounding water views, creating a calm and inviting retreat. Designed for both full-time living and elegant escapes, the residence balances relaxed island style with upscale practicality. Whether hosting sunset gatherings, heading offshore at first light, or enjoying quiet evenings by the water, this property delivers a lifestyle defined by ease, sophistication, and the unparalleled beauty of the Florida Keys. An exceptional opportunity for those seeking a premier waterfront home that supports both luxury living and an active boating lifestyle.

439 Palm Drive Dr, Islamorada
$725,000
605576 MLS
Introducing an exceptional opportunity that beckons all who crave the allure of waterfront living: an impressive 11,520 square foot lot in the prestigious Safety Harbor subdivision. Nestled within Lower Matecumbe in the Village of Islamorada, this property boasts 120 feet of canal frontage. Located in Safety Harbor subdivision, this parcel of land presents a unique canvas upon which to build your dream home. The lot offers ample space for you to bring your vision to life. One of the standout features of this property is its remarkable 120 feet of canal frontage. The canal provides direct access to the inviting waters, allowing you to embark on aquatic adventures right from your own backyard. Indulge in boating, kayaking, or paddleboarding at your leisure, immersing yourself in the stunning natural surroundings that the Keys are renowned for. It's important to note that permits are neither included nor applied for.

Bayview Dr, Islamorada