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Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full residences, a separate garage/media house and a move-in ready package of extras unlike any other property in the Keys. This remarkable compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through a private gate to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, the new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. The welcome package also includes a newer 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two full homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property encompasses 2 acres of upland, 1.2 acres of baybottom, a separate buildable lot, plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private retreat.

6 Beds ⋅ 9 Baths ⋅ 620077 MLS

Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full residences, a separate garage/media house and a move-in ready package of extras unlike any other property in the Keys. This remarkable compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through a private gate to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, the new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. The welcome package also includes a newer 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two full homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property encompasses 2 acres of upland, 1.2 acres of baybottom, a separate buildable lot, plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private retreat.

139 Gimpy Gulch Dr, Islamorada

$11,500,000

LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering deep-water dockage with a 20,000 lb boat lift, a white sandy beach and stunning unobstructed panoramic views of the Florida Bay located in desirable Lower Matecumbe. Spanning nearly 6,000 square feet of extraordinary living space with 7 bedrooms and 7 bathrooms. Thoughtfully designed for ultimate comfort, this estate features two separate guest wings, each offering three private bedroom suites, ideal for family, guests or an unparalleled private retreat. The gourmet chef's kitchen, perfect for entertaining, leads to an expansive and inviting great room, elegant tray ceilings, designer finishes, and sophisticated architectural details throughout. A private elevator offers effortless access between levels. Step outside to your own tropical sanctuary, where a stunning pool deck overlooks the sparkling waters of Florida Bay. Lush tropical landscaping provides privacy, while spacious covered terraces provide the perfect backdrop for unforgettable sunsets and year-round outdoor living. With WEEKLY rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. Experience the Florida Keys lifestyle in one of Lower Matecumbe's most exclusive waterfront settings. SELLER FINANCING AN OPTION WITH 50% DOWN.

7 Beds ⋅ 7 Baths ⋅ 619776 MLS

LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering deep-water dockage with a 20,000 lb boat lift, a white sandy beach and stunning unobstructed panoramic views of the Florida Bay located in desirable Lower Matecumbe. Spanning nearly 6,000 square feet of extraordinary living space with 7 bedrooms and 7 bathrooms. Thoughtfully designed for ultimate comfort, this estate features two separate guest wings, each offering three private bedroom suites, ideal for family, guests or an unparalleled private retreat. The gourmet chef's kitchen, perfect for entertaining, leads to an expansive and inviting great room, elegant tray ceilings, designer finishes, and sophisticated architectural details throughout. A private elevator offers effortless access between levels. Step outside to your own tropical sanctuary, where a stunning pool deck overlooks the sparkling waters of Florida Bay. Lush tropical landscaping provides privacy, while spacious covered terraces provide the perfect backdrop for unforgettable sunsets and year-round outdoor living. With WEEKLY rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. Experience the Florida Keys lifestyle in one of Lower Matecumbe's most exclusive waterfront settings. SELLER FINANCING AN OPTION WITH 50% DOWN.

75840 Overseas Hwy, Islamorada

$11,500,000

A rare architectural masterpiece by renowned architect Max Strang, this modern coastal estate in Port Antigua, Islamorada, redefines luxury waterfront living. Set on a private sandy beach, the residence offers 5 bedrooms, 6 full baths and 2 half baths across 6,367 SF of interior space and 10,483 total SF. Strang's signature tropical modernist design showcases natural materials, clean lines, and expansive glass walls framing panoramic ocean views. Amenities include a gym, golf simulator room, movie theater living area and a spectacular summer kitchen for entertaining. Outdoor living shines with a resort-style pool, spacious terraces and direct beach access. Every detail embodies refined elegance, relaxed sophistication and the timeless allure of Islamorada's coastal beauty. Being offered fully furnished.

5 Beds ⋅ 8 Baths ⋅ 617575 MLS

A rare architectural masterpiece by renowned architect Max Strang, this modern coastal estate in Port Antigua, Islamorada, redefines luxury waterfront living. Set on a private sandy beach, the residence offers 5 bedrooms, 6 full baths and 2 half baths across 6,367 SF of interior space and 10,483 total SF. Strang's signature tropical modernist design showcases natural materials, clean lines, and expansive glass walls framing panoramic ocean views. Amenities include a gym, golf simulator room, movie theater living area and a spectacular summer kitchen for entertaining. Outdoor living shines with a resort-style pool, spacious terraces and direct beach access. Every detail embodies refined elegance, relaxed sophistication and the timeless allure of Islamorada's coastal beauty. Being offered fully furnished.

236 Costa Bravo Dr, Islamorada

$10,000,000

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.

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

$7,600,000

Discover paradise in Islamorada, with beautiful ocean views, protected canal dockage, and resort-style amenities that you'll never want to leave! Blending luxury living with the Florida Keys lifestyle, this home is designed with both entertaining and relaxation in mind. You'll find modern touches throughout this fully-furnished 4 bed, 5 bath home with an abundance of natural light enhancing it's coastal charm. The main level showcases ocean views from the large kitchen, living and dining areas, a French door sunroom and a massive elevated patio for seamless indoor/outdoor entertaining. Head downstairs and bring your resort experience to life. Relax under the poolside beach cabana, complete with an outdoor kitchen and furnished interior bonus room with a full bath connected by interior stairs or elevator. Sunbathe on your sandy beach complemented by a well-manicured backyard with privacy landscaping, mangroves, palm trees and a turf lawn. Take a dip in the resort-style pool/spa, play a little putt-putt golf, or use the access steps to the canal and explore the oceanside bonefish flat. Located in the heart of the sportfishing capital of the world, this home has the avid fishermen and watersport enthusiasts covered. With 200' of waterfrontage and 90' of dockage, safely secure your boats on the 40,000# or 15,000# lifts in the deep protected canal. Within minutes you could head offshore chasing big game fish or run bayside to fish the backcountry or explore the Everglades park. Just steps away from your dock is a dedicated tackle room complete with a chest freezer, commercial ice machine, rigging bench, rod racks and tool storage. Accompanied by an oversized 2 car garage, you'll have plenty of room to store all your toys and cars. Concrete construction, newer Interlock Aluminum Slate Roofing and equipped with impact windows & doors, this home was built to withstand anything. Start living your dream today in this true Florida Keys retreat on beautiful Lower Matecumbe.

4 Beds ⋅ 5 Baths ⋅ 619928 MLS

Discover paradise in Islamorada, with beautiful ocean views, protected canal dockage, and resort-style amenities that you'll never want to leave! Blending luxury living with the Florida Keys lifestyle, this home is designed with both entertaining and relaxation in mind. You'll find modern touches throughout this fully-furnished 4 bed, 5 bath home with an abundance of natural light enhancing it's coastal charm. The main level showcases ocean views from the large kitchen, living and dining areas, a French door sunroom and a massive elevated patio for seamless indoor/outdoor entertaining. Head downstairs and bring your resort experience to life. Relax under the poolside beach cabana, complete with an outdoor kitchen and furnished interior bonus room with a full bath connected by interior stairs or elevator. Sunbathe on your sandy beach complemented by a well-manicured backyard with privacy landscaping, mangroves, palm trees and a turf lawn. Take a dip in the resort-style pool/spa, play a little putt-putt golf, or use the access steps to the canal and explore the oceanside bonefish flat. Located in the heart of the sportfishing capital of the world, this home has the avid fishermen and watersport enthusiasts covered. With 200' of waterfrontage and 90' of dockage, safely secure your boats on the 40,000# or 15,000# lifts in the deep protected canal. Within minutes you could head offshore chasing big game fish or run bayside to fish the backcountry or explore the Everglades park. Just steps away from your dock is a dedicated tackle room complete with a chest freezer, commercial ice machine, rigging bench, rod racks and tool storage. Accompanied by an oversized 2 car garage, you'll have plenty of room to store all your toys and cars. Concrete construction, newer Interlock Aluminum Slate Roofing and equipped with impact windows & doors, this home was built to withstand anything. Start living your dream today in this true Florida Keys retreat on beautiful Lower Matecumbe.

91 Iroquois Dr, Islamorada

$6,500,000

The prettiest, most perfect Keys home you ever did see. Discover one of the most beautifully updated homes in the Florida Keys, set on two spacious lots on Sapodilla Drive. This exceptional property has been completely reimagined with high-quality upgrades throughout, including a brand-new metal roof, a stunning pool and spa, and a private dock with boat lift offering protected dockage and peaceful bay views. Thoughtfully designed for both everyday living and entertaining, the home features tasteful, modern finishes and a striking shell stone privacy wall that enhances its sense of seclusion. Positioned at the end of the street, the setting offers rare privacy and a quiet, tucked-away feel. Two garages provide ample room for vehicles, watercraft, and gear, making this property as practical as it is refined. A truly turnkey home with standout features in a highly desirable location.

3 Beds ⋅ 3 Baths ⋅ 619209 MLS

The prettiest, most perfect Keys home you ever did see. Discover one of the most beautifully updated homes in the Florida Keys, set on two spacious lots on Sapodilla Drive. This exceptional property has been completely reimagined with high-quality upgrades throughout, including a brand-new metal roof, a stunning pool and spa, and a private dock with boat lift offering protected dockage and peaceful bay views. Thoughtfully designed for both everyday living and entertaining, the home features tasteful, modern finishes and a striking shell stone privacy wall that enhances its sense of seclusion. Positioned at the end of the street, the setting offers rare privacy and a quiet, tucked-away feel. Two garages provide ample room for vehicles, watercraft, and gear, making this property as practical as it is refined. A truly turnkey home with standout features in a highly desirable location.

158 Sapodilla Dr, Islamorada

$5,550,000

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.

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

$5,475,000

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.

5 Beds ⋅ 7 Baths ⋅ 614879 MLS

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.

75851 Overseas Hwy, Islamorada

$5,400,000

Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built in 2014, this concrete fortress is storm-resilient and also offers a host of sustainability features including a whole-house solar array. Situated on a peninsula with 250+ feet of crystal-clear open waterfront, the gated estate provides unparalleled privacy. 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 Islamorada's 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.

3 Beds ⋅ 3 Baths ⋅ 617408 MLS

Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built in 2014, this concrete fortress is storm-resilient and also offers a host of sustainability features including a whole-house solar array. Situated on a peninsula with 250+ feet of crystal-clear open waterfront, the gated estate provides unparalleled privacy. 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 Islamorada's 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.

100 List St, Islamorada

$5,325,000

Discover Serenity Cove: Where Privacy Meets the Ease of Keys Living Serenity Cove is a distinctive waterfront estate that offers an exceptional blend of privacy, space, and comfort along the calm waters of Florida Bay. Set on nearly 1.75 acres stretching from the main highway to the bay, this custom designed property invites you to enjoy the easy, relaxed lifestyle that has made the Florida Keys famous. From first light to sunset, Serenity Cove captures the spirit of the Keys. Wake up to water views, prepare your favorite meals in a chef inspired kitchen, and spend days boating, fishing, or swimming directly from your own dock. Evenings can be enjoyed watching beautiful sunsets on the private beach watching the sky change colors over the bay. This property is ideal for those who appreciate a quiet setting and an easy flow between indoor comfort and outdoor adventure. Its thoughtful design and quality finishes reflect craftsmanship and care, while the expansive grounds provide room to relax, gather, or simply take in the natural beauty around you. Convenient access to Islamorada's dining, shopping, and services completes the picture—making Serenity Cove not just a house, but a lifestyle destination in the Florida Keys.

4 Beds ⋅ 4 Baths ⋅ 617285 MLS

Discover Serenity Cove: Where Privacy Meets the Ease of Keys Living Serenity Cove is a distinctive waterfront estate that offers an exceptional blend of privacy, space, and comfort along the calm waters of Florida Bay. Set on nearly 1.75 acres stretching from the main highway to the bay, this custom designed property invites you to enjoy the easy, relaxed lifestyle that has made the Florida Keys famous. From first light to sunset, Serenity Cove captures the spirit of the Keys. Wake up to water views, prepare your favorite meals in a chef inspired kitchen, and spend days boating, fishing, or swimming directly from your own dock. Evenings can be enjoyed watching beautiful sunsets on the private beach watching the sky change colors over the bay. This property is ideal for those who appreciate a quiet setting and an easy flow between indoor comfort and outdoor adventure. Its thoughtful design and quality finishes reflect craftsmanship and care, while the expansive grounds provide room to relax, gather, or simply take in the natural beauty around you. Convenient access to Islamorada's dining, shopping, and services completes the picture—making Serenity Cove not just a house, but a lifestyle destination in the Florida Keys.

75560 Overseas Hwy, Islamorada

$4,250,000

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 offers 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 salt 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 warranty 2. New Dock and Stair Brick Pavers 3. New third-floor Impact Windows 4. Two New third-floor Impact French Doors 5. Two New third-floor electric Rolladen Hurricane Shutters 6. Swimming poll resurfacing with new glass edge surround 7. Dock has a 220-volt pedestal to service dock-side marine electric needs

6 Beds ⋅ 5 Baths ⋅ 617415 MLS

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 offers 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 salt 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 warranty 2. New Dock and Stair Brick Pavers 3. New third-floor Impact Windows 4. Two New third-floor Impact French Doors 5. Two New third-floor electric Rolladen Hurricane Shutters 6. Swimming poll resurfacing with new glass edge surround 7. Dock has a 220-volt pedestal to service dock-side marine electric needs

153 Stromboli Dr, Islamorada

$4,200,000

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.

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

$4,000,000

Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with an active permit and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

618904 MLS

Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with an active permit and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

75750 Overseas Hwy, Islamorada

$3,815,000

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

4 Beds ⋅ 5 Baths ⋅ 618400 MLS

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 14, Islamorada

$3,800,000

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. *Some interior photos are from comparable villas within the property and not exact villa listed.

4 Beds ⋅ 5 Baths ⋅ 619832 MLS

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. *Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 16, Islamorada

$3,700,000

Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.

5 Beds ⋅ 4 Baths ⋅ 620430 MLS

Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.

87445 Old Hwy, Islamorada

$3,600,000

Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dock—your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area—ideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

5 Beds ⋅ 3 Baths ⋅ 618165 MLS

Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dock—your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area—ideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

87950 Overseas Hwy, Islamorada

$3,510,000

Welcome to Casa Tranquila in the highly desirable Venetian Shores neighborhood of Islamorada, where boating convenience meets tropical serenity. With 105 feet of dockage just one home from Snake Creek, this property offers immediate access to both the bay and the ocean--perfect for effortless days on the water. A brick-pavered driveway leads to a welcoming foyer and interior staircase, guiding you to the light-filled main living level. Here, an open floor plan creates an inviting space for gathering. The well-appointed kitchen features stainless steel appliances and flows effortlessly into the dining and living areas, making entertaining both easy and enjoyable. Just off the dining space, a convenient dry bar provides the perfect spot for preparing cocktails and serving guests. Two sets of sliding glass doors extend the living area onto a spacious screened terrace--ideal for enjoying breezes and waterfront views. This level also offers two comfortable bedrooms, two full baths, and a dedicated laundry room for added convenience. The private third-floor primary suite is a true retreat, complete with an ensuite bath and an expansive open terrace overlooking the water--your own peaceful escape for sunrise coffee or evening relaxation. Surrounded by lush, mature landscaping--including ponytail palms, queen palms, ginger, and fishtail palms--the property feels like a secluded tropical oasis. The backyard is designed for both relaxation and entertaining, featuring a heated saltwater pool with spa and waterfall, a charming tiki hut with lighting and fan, and fruit-bearing key lime and mango trees that enhance the island ambiance. With its prime location, thoughtful layout, and beautifully curated indoor and outdoor spaces, this home captures the essence of the Islamorada lifestyle--elegant, inviting, and effortlessly connected to the water.

3 Beds ⋅ 3 Baths ⋅ 619454 MLS

Welcome to Casa Tranquila in the highly desirable Venetian Shores neighborhood of Islamorada, where boating convenience meets tropical serenity. With 105 feet of dockage just one home from Snake Creek, this property offers immediate access to both the bay and the ocean--perfect for effortless days on the water. A brick-pavered driveway leads to a welcoming foyer and interior staircase, guiding you to the light-filled main living level. Here, an open floor plan creates an inviting space for gathering. The well-appointed kitchen features stainless steel appliances and flows effortlessly into the dining and living areas, making entertaining both easy and enjoyable. Just off the dining space, a convenient dry bar provides the perfect spot for preparing cocktails and serving guests. Two sets of sliding glass doors extend the living area onto a spacious screened terrace--ideal for enjoying breezes and waterfront views. This level also offers two comfortable bedrooms, two full baths, and a dedicated laundry room for added convenience. The private third-floor primary suite is a true retreat, complete with an ensuite bath and an expansive open terrace overlooking the water--your own peaceful escape for sunrise coffee or evening relaxation. Surrounded by lush, mature landscaping--including ponytail palms, queen palms, ginger, and fishtail palms--the property feels like a secluded tropical oasis. The backyard is designed for both relaxation and entertaining, featuring a heated saltwater pool with spa and waterfall, a charming tiki hut with lighting and fan, and fruit-bearing key lime and mango trees that enhance the island ambiance. With its prime location, thoughtful layout, and beautifully curated indoor and outdoor spaces, this home captures the essence of the Islamorada lifestyle--elegant, inviting, and effortlessly connected to the water.

131 Bayview Isle Dr, Islamorada

$3,350,000

Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open plan connects casual dining, island seating, and a gourmet kitchen outfitted with Sub-Zero and Wolf appliances, Caesar-stone counters, and abundant storage. Oversized covered terrace expand your living space outdoors, where multiple seating areas, TV, a fireplace, and an infrared/gas grill create the ultimate setting for entertaining against the ocean backdrop. The master suite features king-sized accommodations, terrace access, and a spa-inspired ensuite with a luxurious tub and glass shower. Three additional guest suites, 2 with king beds and private balconies, 1 with two twin beds and all with en-suite baths that provide comfort and privacy. This exclusive enclave sits between the Atlantic Ocean and Florida Bay on Islamorada's most vibrant island, Upper Matecumbe Key. Maison's private grounds include over 350 feet of natural sand beach, a 155-foot day pier, lavish 86-foot lagoon-style pool, heated jacuzzi, and space for every water activity. Details such as porcelain tile, U-Line beverage center, Lynx grill, Kohler fixtures, built-in closets, and energy-efficient construction reflect luxury and comfort at every turn. Owning at Maison Residences gives you the rare flexibility to enjoy your home while also generating income. With 7-day minimum rentals approved, you can use your residence as a private retreat and still take advantage of strong demand for luxury short-term stays in Islamorada. This makes Unit 201 not only a lifestyle purchase with world-class boating, fishing, diving, and snorkeling, but also a smart investment opportunity!

4 Beds ⋅ 5 Baths ⋅ 616523 MLS

Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open plan connects casual dining, island seating, and a gourmet kitchen outfitted with Sub-Zero and Wolf appliances, Caesar-stone counters, and abundant storage. Oversized covered terrace expand your living space outdoors, where multiple seating areas, TV, a fireplace, and an infrared/gas grill create the ultimate setting for entertaining against the ocean backdrop. The master suite features king-sized accommodations, terrace access, and a spa-inspired ensuite with a luxurious tub and glass shower. Three additional guest suites, 2 with king beds and private balconies, 1 with two twin beds and all with en-suite baths that provide comfort and privacy. This exclusive enclave sits between the Atlantic Ocean and Florida Bay on Islamorada's most vibrant island, Upper Matecumbe Key. Maison's private grounds include over 350 feet of natural sand beach, a 155-foot day pier, lavish 86-foot lagoon-style pool, heated jacuzzi, and space for every water activity. Details such as porcelain tile, U-Line beverage center, Lynx grill, Kohler fixtures, built-in closets, and energy-efficient construction reflect luxury and comfort at every turn. Owning at Maison Residences gives you the rare flexibility to enjoy your home while also generating income. With 7-day minimum rentals approved, you can use your residence as a private retreat and still take advantage of strong demand for luxury short-term stays in Islamorada. This makes Unit 201 not only a lifestyle purchase with world-class boating, fishing, diving, and snorkeling, but also a smart investment opportunity!

80639 Old Hwy Unit 201, Islamorada

$3,250,000

TURN KEY Canal-Front Islamorada Home with Pool, Dock & Private Beach Access Luxury canal-front home in Islamorada offering spacious living, refined coastal design, and exceptional outdoor amenities. This meticulously maintained residence features a flexible split floor plan with a main-level living area, wet bar, bedroom, and full bath overlooking the outdoor kitchen and resort-style pool. Upstairs includes 3 additional bedrooms, 2.5 baths, an open living area, pristine kitchen, and walk-in laundry room/office. The fenced backyard is designed for easy living with turf, low-maintenance landscaping, and privacy! Concrete dock with 20,000 lb boat lift and space for multiple boats. Owners also enjoy access to the private White Marlin homeowners beach and close proximity to area amenities. The perfect Florida Keys getaway with strong monthly rental income potential! A rare opportunity for turnkey waterfront living in the heart of Islamorada.

4 Beds ⋅ 4 Baths ⋅ 618873 MLS

TURN KEY Canal-Front Islamorada Home with Pool, Dock & Private Beach Access Luxury canal-front home in Islamorada offering spacious living, refined coastal design, and exceptional outdoor amenities. This meticulously maintained residence features a flexible split floor plan with a main-level living area, wet bar, bedroom, and full bath overlooking the outdoor kitchen and resort-style pool. Upstairs includes 3 additional bedrooms, 2.5 baths, an open living area, pristine kitchen, and walk-in laundry room/office. The fenced backyard is designed for easy living with turf, low-maintenance landscaping, and privacy! Concrete dock with 20,000 lb boat lift and space for multiple boats. Owners also enjoy access to the private White Marlin homeowners beach and close proximity to area amenities. The perfect Florida Keys getaway with strong monthly rental income potential! A rare opportunity for turnkey waterfront living in the heart of Islamorada.

145 Venetian Dr, Islamorada

$3,220,000

Stunning Plantation Key canal front pool home! This exceptional all-concrete residence boasts a rare layout with five bedrooms, five full baths, and one-half bathroom, perfect for family living and entertaining. The chef's kitchen is a true standout, featuring a sprawling granite island, top of the line appliances, and abundant cabinet space, making it a culinary dream. A gorgeous exotic wood staircase leads you through the home's three magnificent levels, starting from the welcoming entryway and ascending to the stunning primary suite on the third floor. The suite is an oasis of tranquility, with ample space and stunning views of the surrounding beauty.Enjoy the marble floors as you make your way to the private concrete rooftop deck, where you can soak in breathtaking panoramic ocean views. On the first level, enjoy the cozy theater room for movie nights, a legal one bedroom, one bathroom guest suite offering privacy and comfort, and a tackle room ideal for storing fishing gear and outdoor equipment. The home is designed for peace of mind, elevated above potential flooding, and offers ample storage space throughout. Adventure awaits just minutes away in Tavernier Creek, providing quick access to both the Atlantic Ocean and Florida Bay for fishing enthusiasts or anyone who loves water. The exterior features a heated and chilled swimming pool, outdoor entertainment area, and a 24,000-pound boat lift, making this home the ultimate in luxury coastal living.

5 Beds ⋅ 6 Baths ⋅ 619367 MLS

Stunning Plantation Key canal front pool home! This exceptional all-concrete residence boasts a rare layout with five bedrooms, five full baths, and one-half bathroom, perfect for family living and entertaining. The chef's kitchen is a true standout, featuring a sprawling granite island, top of the line appliances, and abundant cabinet space, making it a culinary dream. A gorgeous exotic wood staircase leads you through the home's three magnificent levels, starting from the welcoming entryway and ascending to the stunning primary suite on the third floor. The suite is an oasis of tranquility, with ample space and stunning views of the surrounding beauty.Enjoy the marble floors as you make your way to the private concrete rooftop deck, where you can soak in breathtaking panoramic ocean views. On the first level, enjoy the cozy theater room for movie nights, a legal one bedroom, one bathroom guest suite offering privacy and comfort, and a tackle room ideal for storing fishing gear and outdoor equipment. The home is designed for peace of mind, elevated above potential flooding, and offers ample storage space throughout. Adventure awaits just minutes away in Tavernier Creek, providing quick access to both the Atlantic Ocean and Florida Bay for fishing enthusiasts or anyone who loves water. The exterior features a heated and chilled swimming pool, outdoor entertainment area, and a 24,000-pound boat lift, making this home the ultimate in luxury coastal living.

141 Canal St, Islamorada

$3,200,000

5 Beds ⋅ 4 Baths ⋅ 620230 MLS

139 Tequesta St, Islamorada

$3,150,000

Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling approximately 1,500 square feet, and 2 bedrooms and 1 bathroom downstairs totaling approximately 1,140 square feet. The private resort-style backyard features a heated pool with sun shelf, hot tub, expansive patio, hammock lounge, and mature palms creating a true tropical setting. Enjoy deep-water canal frontage with 70 feet of dockage and two boat lifts rated at approximately 15,000 pounds and 20,000 pounds, providing exceptional boating capacity. Located on one of Venetian Shores' desirable 100-foot-wide canals, the property offers generous maneuvering space and convenient access to both the Atlantic Ocean and Florida Bay through nearby Snake Creek, making offshore fishing and backcountry boating easily accessible within minutes. The custom tiki pavilion includes a full outdoor kitchen with built-in grill, refrigeration, sink, bar seating, mounted TV, and generous space for hosting gatherings year-round. Inside, the bright open-concept living area showcases vaulted ceilings with exposed beams, abundant natural light, and French doors that create seamless indoor-outdoor flow to the balcony overlooking the canal. The primary suite offers balcony access, dual vanities, soaking tub, glass-enclosed shower, and walk-in closet. A gated brick driveway provides generous parking, and the home is offered furnished for immediate enjoyment or continued use as a full-time residence, seasonal escape, or investment opportunity. This Venetian Shores waterfront property delivers the location, spacious layout, wide canal setting, and boating infrastructure buyers are searching for in the Florida Keys.

5 Beds ⋅ 3 Baths ⋅ 618653 MLS

Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling approximately 1,500 square feet, and 2 bedrooms and 1 bathroom downstairs totaling approximately 1,140 square feet. The private resort-style backyard features a heated pool with sun shelf, hot tub, expansive patio, hammock lounge, and mature palms creating a true tropical setting. Enjoy deep-water canal frontage with 70 feet of dockage and two boat lifts rated at approximately 15,000 pounds and 20,000 pounds, providing exceptional boating capacity. Located on one of Venetian Shores' desirable 100-foot-wide canals, the property offers generous maneuvering space and convenient access to both the Atlantic Ocean and Florida Bay through nearby Snake Creek, making offshore fishing and backcountry boating easily accessible within minutes. The custom tiki pavilion includes a full outdoor kitchen with built-in grill, refrigeration, sink, bar seating, mounted TV, and generous space for hosting gatherings year-round. Inside, the bright open-concept living area showcases vaulted ceilings with exposed beams, abundant natural light, and French doors that create seamless indoor-outdoor flow to the balcony overlooking the canal. The primary suite offers balcony access, dual vanities, soaking tub, glass-enclosed shower, and walk-in closet. A gated brick driveway provides generous parking, and the home is offered furnished for immediate enjoyment or continued use as a full-time residence, seasonal escape, or investment opportunity. This Venetian Shores waterfront property delivers the location, spacious layout, wide canal setting, and boating infrastructure buyers are searching for in the Florida Keys.

105 Palo De Oro Dr, Islamorada

$3,067,500

Venetian Shores Has It All! Welcome to your slice of paradise in the heart of Islamorada's most sought-after boating community. This beautiful 4 bedroom, 3 bath coastal retreat is designed for both relaxation and entertainment, featuring 70 feet of deep-water dockage along a 100-foot wide canal - just seconds from open water via Snake Creek. Step inside the front door to access the elevator and interior stairs. Upstairs, the main living area offers 2 bedrooms and 2 baths, a wide open floor plan, and a gourmet kitchen with a large center island, granite countertops, stainless steel appliances, and a dedicated workstation. Enjoy sunset cocktails from the screened canal-side terrace, accessed via impact-rated sliding glass doors. Downstairs, the ground level is a haven for guests and fun - featuring a pool table, a comfortable tv area, 2 more bedrooms and a full bath, laundry room, and garage for all your gear. The backyard is pure Keys magic - complete with a heated pool, tiki hut, hot tub and an expansive deck for sunbathing or relaxing in the shade. Boaters will love the 70 ft concrete dock with a 15,000 lb boat lift, 50 amp shore power and fish cleaning station. This home checks every box for the ultimate island lifestyle - whether you're heading east to the Atlantic or west to Florida Bay's backcountry to enjoy fishing and breathtaking sunsets. Live the dream in Venetian Shores - where the boating is easy and the living is even better.

4 Beds ⋅ 3 Baths ⋅ 616450 MLS

Venetian Shores Has It All! Welcome to your slice of paradise in the heart of Islamorada's most sought-after boating community. This beautiful 4 bedroom, 3 bath coastal retreat is designed for both relaxation and entertainment, featuring 70 feet of deep-water dockage along a 100-foot wide canal - just seconds from open water via Snake Creek. Step inside the front door to access the elevator and interior stairs. Upstairs, the main living area offers 2 bedrooms and 2 baths, a wide open floor plan, and a gourmet kitchen with a large center island, granite countertops, stainless steel appliances, and a dedicated workstation. Enjoy sunset cocktails from the screened canal-side terrace, accessed via impact-rated sliding glass doors. Downstairs, the ground level is a haven for guests and fun - featuring a pool table, a comfortable tv area, 2 more bedrooms and a full bath, laundry room, and garage for all your gear. The backyard is pure Keys magic - complete with a heated pool, tiki hut, hot tub and an expansive deck for sunbathing or relaxing in the shade. Boaters will love the 70 ft concrete dock with a 15,000 lb boat lift, 50 amp shore power and fish cleaning station. This home checks every box for the ultimate island lifestyle - whether you're heading east to the Atlantic or west to Florida Bay's backcountry to enjoy fishing and breathtaking sunsets. Live the dream in Venetian Shores - where the boating is easy and the living is even better.

136 Giardino Dr, Islamorada

$3,003,000

The Ospreys are back! Welcome to The Osprey's Nest; your perch by the Ocean in one of Islamorada's most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20' dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive. Listing includes canal parcel with dock across the street RE#00389220-000100

4 Beds ⋅ 3 Baths ⋅ 612438 MLS

The Ospreys are back! Welcome to The Osprey's Nest; your perch by the Ocean in one of Islamorada's most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20' dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive. Listing includes canal parcel with dock across the street RE#00389220-000100

133 Sunset Dr, Islamorada

$3,000,000

Direct Oceanfront Home with deeded boat slip in desirable Anglers Reef. This rarely available 2000 sq ft 4 bedroom, 3 bath home has endless views of the ocean from every room. Like watching the sun rise, this home also features an additional 800 sq ft of decking to enjoy the ocean views while sipping your coffee. Upgrades include impact windows & doors, a metal roof, Anglers Reef is a private gated community with 52 homes. Amenities include a marina, community pool on the Ocean, 2 sandy beaches & quaint streets to take walks.

4 Beds ⋅ 3 Baths ⋅ 621702 MLS

Direct Oceanfront Home with deeded boat slip in desirable Anglers Reef. This rarely available 2000 sq ft 4 bedroom, 3 bath home has endless views of the ocean from every room. Like watching the sun rise, this home also features an additional 800 sq ft of decking to enjoy the ocean views while sipping your coffee. Upgrades include impact windows & doors, a metal roof, Anglers Reef is a private gated community with 52 homes. Amenities include a marina, community pool on the Ocean, 2 sandy beaches & quaint streets to take walks.

152 Anglers Way, Islamorada

$3,000,000

Tucked away on a quiet cul-de-sac in the highly sought-after Port Antigua neighborhood, this beautifully updated waterfront home is designed for effortless Florida Keys living. With an impressive 145 feet of dockage, a 15,000 pound boat lift, sparkling pool, and quick access to the water, it's the perfect setting for boating, fishing, and entertaining. Inside, vaulted ceilings and an open floor plan create a bright, airy atmosphere, while two expansive 10 foot sliding glass doors seamlessly connect the living space to the waterfront terrace overlooking the pool and canal. The stunning kitchen serves as the heart of the home, featuring stainless steel appliances, a waterfall-edge island with seating for five, and plenty of space for gathering with family and friends. A separate laundry room and pantry add convenience and functionality. The spacious primary suite enjoys peaceful water views and features an en-suite bath with a double vanity and separate shower. Two generously sized guest bedrooms and a well-appointed guest bath provide comfortable accommodations for family and friends. Downstairs, a versatile bonus room offers additional space for a home office, gym, hobby room, or overflow guests. Impact windows and doors, along with a durable metal roof, provide peace of mind, allowing you to focus on enjoying the laid-back waterfront lifestyle that makes the Keys so special. Whether you're heading out for a day on the water, relaxing poolside, or enjoying sunset breezes from the terrace, this exceptional Port Antigua property is ready to become your island retreat.

3 Beds ⋅ 2 Baths ⋅ 620319 MLS

Tucked away on a quiet cul-de-sac in the highly sought-after Port Antigua neighborhood, this beautifully updated waterfront home is designed for effortless Florida Keys living. With an impressive 145 feet of dockage, a 15,000 pound boat lift, sparkling pool, and quick access to the water, it's the perfect setting for boating, fishing, and entertaining. Inside, vaulted ceilings and an open floor plan create a bright, airy atmosphere, while two expansive 10 foot sliding glass doors seamlessly connect the living space to the waterfront terrace overlooking the pool and canal. The stunning kitchen serves as the heart of the home, featuring stainless steel appliances, a waterfall-edge island with seating for five, and plenty of space for gathering with family and friends. A separate laundry room and pantry add convenience and functionality. The spacious primary suite enjoys peaceful water views and features an en-suite bath with a double vanity and separate shower. Two generously sized guest bedrooms and a well-appointed guest bath provide comfortable accommodations for family and friends. Downstairs, a versatile bonus room offers additional space for a home office, gym, hobby room, or overflow guests. Impact windows and doors, along with a durable metal roof, provide peace of mind, allowing you to focus on enjoying the laid-back waterfront lifestyle that makes the Keys so special. Whether you're heading out for a day on the water, relaxing poolside, or enjoying sunset breezes from the terrace, this exceptional Port Antigua property is ready to become your island retreat.

125 Porto Vista Ct, Islamorada

$2,800,000

Welcome to your Venetian Shores retreat, where relaxed coastal living meets effortless waterfront luxury. This completely updated pool home is designed for easy living and unforgettable entertaining, with an open floor plan, beautiful finishes, and seamless indoor-outdoor flow. The heart of the home is a spacious kitchen with a generous island, opening to the living area and a wall of sliding glass doors. Step outside to a covered terrace overlooking the resort-style pool and waterfront, with plenty of pool deck for soaking up the sun and a shaded poolside area for lingering over long lunches or evening cocktails. Boaters will love the 70 feet of dockage, complete with a 20,000-pound boat lift. Venetian Shores is known for its 100-foot-wide canals and exceptional boating access, with a quick route to the ocean or bay through Snake Creek. Built with CBS construction and a concrete roof, the home offers an elevator plus both interior and exterior stair access between floors. Upstairs, you'll find the main living area and two bedrooms and two baths, while the downstairs offers an additional bedroom and bath. A bonus room, ample storage, and cabana bath add flexibility and convenience. With its resort-style pool, generous waterfront, easy boating access, and beautifully updated interiors, this is the kind of home that makes everyday life feel like a vacation, casual, polished, and unmistakably coastal.

3 Beds ⋅ 3 Baths ⋅ 620907 MLS

Welcome to your Venetian Shores retreat, where relaxed coastal living meets effortless waterfront luxury. This completely updated pool home is designed for easy living and unforgettable entertaining, with an open floor plan, beautiful finishes, and seamless indoor-outdoor flow. The heart of the home is a spacious kitchen with a generous island, opening to the living area and a wall of sliding glass doors. Step outside to a covered terrace overlooking the resort-style pool and waterfront, with plenty of pool deck for soaking up the sun and a shaded poolside area for lingering over long lunches or evening cocktails. Boaters will love the 70 feet of dockage, complete with a 20,000-pound boat lift. Venetian Shores is known for its 100-foot-wide canals and exceptional boating access, with a quick route to the ocean or bay through Snake Creek. Built with CBS construction and a concrete roof, the home offers an elevator plus both interior and exterior stair access between floors. Upstairs, you'll find the main living area and two bedrooms and two baths, while the downstairs offers an additional bedroom and bath. A bonus room, ample storage, and cabana bath add flexibility and convenience. With its resort-style pool, generous waterfront, easy boating access, and beautifully updated interiors, this is the kind of home that makes everyday life feel like a vacation, casual, polished, and unmistakably coastal.

121 Severino Dr, Islamorada

$2,700,000

Paradise found--experience the best of Florida Keys waterfront living in this beautifully updated, lushly landscaped lakefront home offering exceptional privacy and tranquil water views. Boaters will appreciate easy access from the lake to the bay and direct ocean access through nearby Tavernier Creek. Inside, soaring ceilings and impact-rated windows and doors fill the home with natural light, creating a bright, open atmosphere. The spacious great room flows onto an expansive waterfront deck just steps from the lake--perfect for relaxing or entertaining. The chef's kitchen features maple cabinetry, granite countertops, Thermador refrigerator and oven, Bosch dishwasher, commercial ice maker with filtration, and a GE Profile wine cooler. The oversized island showcases etched glass panels depicting an underwater seascape, illuminated with remote-controlled LED lighting. The main level includes two guest bedrooms and two updated bathrooms, including one ensuite. A custom tamarind wood serpentine staircase leads to the private third-floor primary suite with beautiful water views. The primary bath offers a whirlpool tub, walk-in steam shower, and skylights. Additional features include an oversized two-car garage with 12-foot ceilings and ample storage, plus a large ground-level storage area currently configured as a guest apartment with a permitted full bath. Outdoors, enjoy a secluded heated pool surrounded by tropical landscaping and a 60-foot concrete dock finished with durable IPE (Brazilian walnut). With no neighbors behind, on one side, or across the water, this property offers rare privacy and quick access to both Florida Bay and the Atlantic Ocean--capturing the essence of relaxed Keys living.

3 Beds ⋅ 4 Baths ⋅ 619060 MLS

Paradise found--experience the best of Florida Keys waterfront living in this beautifully updated, lushly landscaped lakefront home offering exceptional privacy and tranquil water views. Boaters will appreciate easy access from the lake to the bay and direct ocean access through nearby Tavernier Creek. Inside, soaring ceilings and impact-rated windows and doors fill the home with natural light, creating a bright, open atmosphere. The spacious great room flows onto an expansive waterfront deck just steps from the lake--perfect for relaxing or entertaining. The chef's kitchen features maple cabinetry, granite countertops, Thermador refrigerator and oven, Bosch dishwasher, commercial ice maker with filtration, and a GE Profile wine cooler. The oversized island showcases etched glass panels depicting an underwater seascape, illuminated with remote-controlled LED lighting. The main level includes two guest bedrooms and two updated bathrooms, including one ensuite. A custom tamarind wood serpentine staircase leads to the private third-floor primary suite with beautiful water views. The primary bath offers a whirlpool tub, walk-in steam shower, and skylights. Additional features include an oversized two-car garage with 12-foot ceilings and ample storage, plus a large ground-level storage area currently configured as a guest apartment with a permitted full bath. Outdoors, enjoy a secluded heated pool surrounded by tropical landscaping and a 60-foot concrete dock finished with durable IPE (Brazilian walnut). With no neighbors behind, on one side, or across the water, this property offers rare privacy and quick access to both Florida Bay and the Atlantic Ocean--capturing the essence of relaxed Keys living.

151 Lake Rd, Islamorada

$2,600,000

Pickle Ball Estate is a stunning new luxury retreat in the heart of Islamorada, masterfully crafted by 4 Keys Construction. This brand-new four-bedroom, five-bathroom residence is a true standout, blending refined coastal design with resort-style living. Designed for both relaxation and entertainment, the home features a private pickleball court, making it a rare and exciting find in the Florida Keys. Spacious interiors, high-end finishes, and thoughtful craftsmanship throughout reflect 4 Keys Construction's latest masterpiece, including a gourmet kitchen equipped with premium Miele appliances. Ideally located, Pickle Ball Estate offers access to a community boat ramp, perfect for days on the water, and is just minutes from Founders Park, where you can enjoy beaches, events, sports facilities, and family-friendly amenities. Whether you are seeking a primary residence, a vacation home, or an investment property, Pickle Ball Estate delivers the ultimate Islamorada lifestyle with luxury, recreation, and island living at its finest.

4 Beds ⋅ 5 Baths ⋅ 618956 MLS

Pickle Ball Estate is a stunning new luxury retreat in the heart of Islamorada, masterfully crafted by 4 Keys Construction. This brand-new four-bedroom, five-bathroom residence is a true standout, blending refined coastal design with resort-style living. Designed for both relaxation and entertainment, the home features a private pickleball court, making it a rare and exciting find in the Florida Keys. Spacious interiors, high-end finishes, and thoughtful craftsmanship throughout reflect 4 Keys Construction's latest masterpiece, including a gourmet kitchen equipped with premium Miele appliances. Ideally located, Pickle Ball Estate offers access to a community boat ramp, perfect for days on the water, and is just minutes from Founders Park, where you can enjoy beaches, events, sports facilities, and family-friendly amenities. Whether you are seeking a primary residence, a vacation home, or an investment property, Pickle Ball Estate delivers the ultimate Islamorada lifestyle with luxury, recreation, and island living at its finest.

114 Royal Ln, Islamorada

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