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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

$5,325,000

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

$4,200,000

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

$3,950,000

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!

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

$3,525,000

SELLERS SAY WE'RE READY TO SELL! Introducing the Sea Pearl: a rare and refined coastal masterpiece nestled just four parcels from the Gulf. This ultra-modern smart home constructed in 2016 redefines luxury Keys living, offering five spacious bedrooms, five and a half bathrooms, and over 4,100 square feet of meticulously designed and furnished interior space. Boaters will delight in 70 feet of concrete dockage with water and electric, 15,000 lb boat lift, and panoramic sunset views over a protected nature preserve across the canal—ensuring privacy and tranquility that can never be built upon. This concrete haven is fully equipped with a whole-home generator, Control4 smart system (for AC, music, lights, alarm, security cameras, TV's and more), impact windows/doors, metal roof, and a sleek glass elevator connecting all three levels. Nearly 1,500 square feet of open-air porches and patios invite you to unwind and soak in the Gulf breezes. Step inside the ground level to a welcoming foyer that opens to a sitting area, custom wet bar, Angler's room, and guest ensuite bedroom. Just beyond, enjoy a resort-style pool and built-in spa surrounded by shell stone decking that stays cool even in the summer heat. On the second level, a show-stopping modern kitchen features custom cabinetry, Brittanica Cambria quartz countertops, expansive island with waterfall edge, seating for 8, GE Monogram appliances, Viking 6-burner induction cooktop, and wine cooler—perfect for entertaining. This level also offers three additional bedrooms, including a Jack-and-Jill suite, full laundry, and half bath. The entire top floor is reserved for the primary suite: a true sanctuary with sweeping water views and open air porch, spa-like bathroom with soaking tub, glass shower, bidet, and a custom walk-in closet. With optional White Marlin Beach access, this home is the epitome of modern island elegance—where every detail has been curated for comfort, style, and the ultimate Florida Keys lifestyl

5 Beds ⋅ 6 Baths ⋅ 614792 MLS

SELLERS SAY WE'RE READY TO SELL! Introducing the Sea Pearl: a rare and refined coastal masterpiece nestled just four parcels from the Gulf. This ultra-modern smart home constructed in 2016 redefines luxury Keys living, offering five spacious bedrooms, five and a half bathrooms, and over 4,100 square feet of meticulously designed and furnished interior space. Boaters will delight in 70 feet of concrete dockage with water and electric, 15,000 lb boat lift, and panoramic sunset views over a protected nature preserve across the canal—ensuring privacy and tranquility that can never be built upon. This concrete haven is fully equipped with a whole-home generator, Control4 smart system (for AC, music, lights, alarm, security cameras, TV's and more), impact windows/doors, metal roof, and a sleek glass elevator connecting all three levels. Nearly 1,500 square feet of open-air porches and patios invite you to unwind and soak in the Gulf breezes. Step inside the ground level to a welcoming foyer that opens to a sitting area, custom wet bar, Angler's room, and guest ensuite bedroom. Just beyond, enjoy a resort-style pool and built-in spa surrounded by shell stone decking that stays cool even in the summer heat. On the second level, a show-stopping modern kitchen features custom cabinetry, Brittanica Cambria quartz countertops, expansive island with waterfall edge, seating for 8, GE Monogram appliances, Viking 6-burner induction cooktop, and wine cooler—perfect for entertaining. This level also offers three additional bedrooms, including a Jack-and-Jill suite, full laundry, and half bath. The entire top floor is reserved for the primary suite: a true sanctuary with sweeping water views and open air porch, spa-like bathroom with soaking tub, glass shower, bidet, and a custom walk-in closet. With optional White Marlin Beach access, this home is the epitome of modern island elegance—where every detail has been curated for comfort, style, and the ultimate Florida Keys lifestyl

172 Venetian Dr, 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

$3,205,000

Exquisite Canal Front Retreat in Prestigious Port Antigua, Islamorada Welcome to your dream waterfront oasis in the highly coveted Port Antigua community of Islamorada. This meticulously remodeled 5-bedroom, 3-bath (3 Up / 2 Down) residence embodies luxury coastal living with 100 feet of premier dockage, offering effortless access to Florida Bay, Channel 2, and Channel 5, placing the Atlantic Ocean just minutes away. This turnkey masterpiece has been completely redesigned and built with high-end finishes and state-of-the-art craftsmanship. On the exterior you have board & batten downstairs and hardy board upstairs. Step inside to soaring high ceilings, driftwood tile flooring with clean lines, hurricane-impact windows and doors that flood the home with natural light while framing breathtaking sunrise views. The gourmet designer kitchen is a chef's delight, featuring sleek stainless steel appliances, a professional-grade hood, wet bar with wine cooler and custom cabinetry, creating an elegant and functional space for entertaining. Each bathroom is a statement of sophistication, boasting exquisite decorator designs, while built-in custom closets and all-new interior finishes enhance the home's refined aesthetic. The outdoor living spaces are just as impressive, this oversized pie-shaped lot on the canal is a rare find, ensuring privacy and abundant space for waterside relaxation. There is room for a pool and all the poolside entertaining space one could yearn for. Residents of Port Antigua enjoy exclusive community amenities, including a private beach with tiki huts and BBQ grills, a boat ramp, and access to the Port Antigua sandbar, where endless days of sun-soaked adventure await. Whether you're seeking the perfect boater's paradise, a serene Florida Keys retreat, or an entertainer's dream, this exceptional home offers it all. Experience waterfront luxury at its finest - schedule your private showing today!

5 Beds ⋅ 3 Baths ⋅ 614184 MLS

Exquisite Canal Front Retreat in Prestigious Port Antigua, Islamorada Welcome to your dream waterfront oasis in the highly coveted Port Antigua community of Islamorada. This meticulously remodeled 5-bedroom, 3-bath (3 Up / 2 Down) residence embodies luxury coastal living with 100 feet of premier dockage, offering effortless access to Florida Bay, Channel 2, and Channel 5, placing the Atlantic Ocean just minutes away. This turnkey masterpiece has been completely redesigned and built with high-end finishes and state-of-the-art craftsmanship. On the exterior you have board & batten downstairs and hardy board upstairs. Step inside to soaring high ceilings, driftwood tile flooring with clean lines, hurricane-impact windows and doors that flood the home with natural light while framing breathtaking sunrise views. The gourmet designer kitchen is a chef's delight, featuring sleek stainless steel appliances, a professional-grade hood, wet bar with wine cooler and custom cabinetry, creating an elegant and functional space for entertaining. Each bathroom is a statement of sophistication, boasting exquisite decorator designs, while built-in custom closets and all-new interior finishes enhance the home's refined aesthetic. The outdoor living spaces are just as impressive, this oversized pie-shaped lot on the canal is a rare find, ensuring privacy and abundant space for waterside relaxation. There is room for a pool and all the poolside entertaining space one could yearn for. Residents of Port Antigua enjoy exclusive community amenities, including a private beach with tiki huts and BBQ grills, a boat ramp, and access to the Port Antigua sandbar, where endless days of sun-soaked adventure await. Whether you're seeking the perfect boater's paradise, a serene Florida Keys retreat, or an entertainer's dream, this exceptional home offers it all. Experience waterfront luxury at its finest - schedule your private showing today!

230 Biscayne Blvd, 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

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

$2,900,000

Welcome to 109 Sapodilla Dr., Islamorada, FL This waterfront gem is nestled on the serene Sandy Cove Basin, offering a rare blend of privacy and deep-water access in a protected lagoon. This home is built entirely of concrete, including the roof, providing unmatched durability and peace of mind. Thoughtfully remodeled with a keen eye for detail, the residence effortlessly combines modern elegance with coastal charm. The oversized lot is beautifully landscaped, creating a tranquil oasis that's perfect for outdoor living. Boating enthusiasts will appreciate the private dock and boat ramp, providing seamless access to the open waters. Relax in the sparkling pool and jacuzzi, soaking in the Florida sunshine. A two-car garage adds convenience and ample storage, making this home as functional as it is luxurious. Whether you're seeking a permanent residence or a weekend retreat, 109 Sapodilla Dr. offers the best of Florida Keys living.

4 Beds ⋅ 4 Baths ⋅ 616038 MLS

Welcome to 109 Sapodilla Dr., Islamorada, FL This waterfront gem is nestled on the serene Sandy Cove Basin, offering a rare blend of privacy and deep-water access in a protected lagoon. This home is built entirely of concrete, including the roof, providing unmatched durability and peace of mind. Thoughtfully remodeled with a keen eye for detail, the residence effortlessly combines modern elegance with coastal charm. The oversized lot is beautifully landscaped, creating a tranquil oasis that's perfect for outdoor living. Boating enthusiasts will appreciate the private dock and boat ramp, providing seamless access to the open waters. Relax in the sparkling pool and jacuzzi, soaking in the Florida sunshine. A two-car garage adds convenience and ample storage, making this home as functional as it is luxurious. Whether you're seeking a permanent residence or a weekend retreat, 109 Sapodilla Dr. offers the best of Florida Keys living.

109 Sapodilla Dr, Islamorada

$2,500,000

Stunning canal-front home at the rare T-junction of two crystal-clear waterways in Port Antigua—one of Islamorada's most sought-after communities. This fully updated 4 bed, 3 bath pool home is offered turnkey and ready for immediate enjoyment. Upstairs features an open split floor plan with two spacious ensuite bedrooms, new porcelain wood-look tile throughout, fresh paint, all-new LED lighting, and a sleek kitchen with quartz countertops. The living area opens to a screened balcony overlooking your private dock and wide water views. Downstairs offers a beautifully renovated 2 bed, 1 bath guest suite with its own kitchenette—ideal for visitors or extended family. Enjoy a brand-new pool with fountain, a stylish louvered pergola for sunbathing or shade, a wraparound porch, and a screened upper balcony. Dual A/C units and water heaters add comfort and convenience. Port Antigua residents enjoy a private white sand beach, boat ramp, and direct ocean access—making this a must-see waterfront retreat.

4 Beds ⋅ 3 Baths ⋅ 615116 MLS

Stunning canal-front home at the rare T-junction of two crystal-clear waterways in Port Antigua—one of Islamorada's most sought-after communities. This fully updated 4 bed, 3 bath pool home is offered turnkey and ready for immediate enjoyment. Upstairs features an open split floor plan with two spacious ensuite bedrooms, new porcelain wood-look tile throughout, fresh paint, all-new LED lighting, and a sleek kitchen with quartz countertops. The living area opens to a screened balcony overlooking your private dock and wide water views. Downstairs offers a beautifully renovated 2 bed, 1 bath guest suite with its own kitchenette—ideal for visitors or extended family. Enjoy a brand-new pool with fountain, a stylish louvered pergola for sunbathing or shade, a wraparound porch, and a screened upper balcony. Dual A/C units and water heaters add comfort and convenience. Port Antigua residents enjoy a private white sand beach, boat ramp, and direct ocean access—making this a must-see waterfront retreat.

141 El Capitan Dr, Islamorada

$2,300,000

Thanksgiving Special reduced to $2,699,000! Gobble Gobble Gobble it up while its still available!4 bedrooms 3.5 bath gorgeous waterfront home in Islamorada's Port Antigua awaits a new owner! Dramatic main living area with cathedral ceiling, freshly painted, recent new roof, impact windows, roll down shuttered second level outside balcony for entertaining, top of the line kitchen with Miele and Sub Zero appliances and Faber exhaust island stove, exquisite baths, wine cooler, ice machine (negotiable) grand staircase entry way, alarm system, wired for stereo inside and out, covered parking, room for pool, great entertainment and storage area on ground level along with spacious tackle and storage. Tropical fruit trees, shady side of the canal in a superior neighborhood offering park, ramp and private homeowner's beach. 27000lbs elevator lift for your big boat. Currently configured for a 42 Freeman Catamaran. Easy to show. Contact agent for appointment.

4 Beds ⋅ 4 Baths ⋅ 609856 MLS

Thanksgiving Special reduced to $2,699,000! Gobble Gobble Gobble it up while its still available!4 bedrooms 3.5 bath gorgeous waterfront home in Islamorada's Port Antigua awaits a new owner! Dramatic main living area with cathedral ceiling, freshly painted, recent new roof, impact windows, roll down shuttered second level outside balcony for entertaining, top of the line kitchen with Miele and Sub Zero appliances and Faber exhaust island stove, exquisite baths, wine cooler, ice machine (negotiable) grand staircase entry way, alarm system, wired for stereo inside and out, covered parking, room for pool, great entertainment and storage area on ground level along with spacious tackle and storage. Tropical fruit trees, shady side of the canal in a superior neighborhood offering park, ramp and private homeowner's beach. 27000lbs elevator lift for your big boat. Currently configured for a 42 Freeman Catamaran. Easy to show. Contact agent for appointment.

72 W Plaza Granada, Islamorada

$2,241,000

Welcome to your slice of paradise in Port Antigua, one of Islamorada's most sought-after neighborhoods! This beautifully maintained 3-bedroom, 2-bath home combines coastal charm with modern comfort, offering everything you need to enjoy the Florida Keys lifestyle. Step inside to find an inviting entrance foyer leading to the main living area. On the main living level you'll enjoy an open floor plan perfect for entertaining, featuring a large living area surrounded by impact windows and doors, the kitchen with stainless steel appliances, a pantry, and a laundry room with additional storage. Two comfortable guest bedrooms and a guest bath complete this level, providing plenty of space for family and friends. The interior staircase connects all levels seamlessly, culminating in a private third-floor primary suite complete with a covered terrace—the perfect spot to unwind and take in the tropical breeze. Downstairs, enjoy a fantastic entertaining area featuring a built-in grill, garage, and carport for plenty of parking and storage. For the boating enthusiast, this property provides quick access to the clear waters of Florida Bay and beyond and offers 60 feet of concrete dockage and two boat lifts. As a resident of Port Antigua, you'll have access to one of the most beautiful private homeowners' beaches in the Keys, complete with tiki huts, picnic areas, and a community boat ramp. Whether you're looking for a full-time residence or a weekend getaway, this home offers the ultimate blend of comfort, privacy, and Keys lifestyle.

3 Beds ⋅ 2 Baths ⋅ 617106 MLS

Welcome to your slice of paradise in Port Antigua, one of Islamorada's most sought-after neighborhoods! This beautifully maintained 3-bedroom, 2-bath home combines coastal charm with modern comfort, offering everything you need to enjoy the Florida Keys lifestyle. Step inside to find an inviting entrance foyer leading to the main living area. On the main living level you'll enjoy an open floor plan perfect for entertaining, featuring a large living area surrounded by impact windows and doors, the kitchen with stainless steel appliances, a pantry, and a laundry room with additional storage. Two comfortable guest bedrooms and a guest bath complete this level, providing plenty of space for family and friends. The interior staircase connects all levels seamlessly, culminating in a private third-floor primary suite complete with a covered terrace—the perfect spot to unwind and take in the tropical breeze. Downstairs, enjoy a fantastic entertaining area featuring a built-in grill, garage, and carport for plenty of parking and storage. For the boating enthusiast, this property provides quick access to the clear waters of Florida Bay and beyond and offers 60 feet of concrete dockage and two boat lifts. As a resident of Port Antigua, you'll have access to one of the most beautiful private homeowners' beaches in the Keys, complete with tiki huts, picnic areas, and a community boat ramp. Whether you're looking for a full-time residence or a weekend getaway, this home offers the ultimate blend of comfort, privacy, and Keys lifestyle.

104 W Plaza Granada, Islamorada

$2,200,000

Welcome to Port Antigua! This beautiful Key West-style home in Port Antigua boasts an open floor plan with a spacious kitchen featuring a large center island. The main living area on the second floor includes three bedrooms and two bathrooms, while the first floor offers an entertainment room that could serve as a fourth bedroom. Two sets of sliding glass doors lead to a screened-in porch overlooking the canal, perfect for enjoying the waterfront views. The home is equipped with high-impact-resistant windows and doors for added security and energy efficiency. Boaters will appreciate the 45-foot concrete dock with a 15,000 lb-rated boat lift, making it easy to enjoy life on the water. As part of Port Antigua's Homeowners Association, residents have exclusive access to a private beach with breathtaking year-round sunsets. This is a fantastic opportunity to embrace the Keys lifestyle—don't miss out!

3 Beds ⋅ 2 Baths ⋅ 614307 MLS

Welcome to Port Antigua! This beautiful Key West-style home in Port Antigua boasts an open floor plan with a spacious kitchen featuring a large center island. The main living area on the second floor includes three bedrooms and two bathrooms, while the first floor offers an entertainment room that could serve as a fourth bedroom. Two sets of sliding glass doors lead to a screened-in porch overlooking the canal, perfect for enjoying the waterfront views. The home is equipped with high-impact-resistant windows and doors for added security and energy efficiency. Boaters will appreciate the 45-foot concrete dock with a 15,000 lb-rated boat lift, making it easy to enjoy life on the water. As part of Port Antigua's Homeowners Association, residents have exclusive access to a private beach with breathtaking year-round sunsets. This is a fantastic opportunity to embrace the Keys lifestyle—don't miss out!

189 Gulfview Dr, Islamorada

$2,200,000

Welcome to your coastal retreat in the coveted White Marlin Beach neighborhood—where relaxed Keys living meets timeless elegance. This beautifully updated canalfront home offers 1,911 sq. ft. of light-filled living space upstairs, complemented by a large open terrace perfect for morning coffee, sunset cocktails, or relaxing with family and friends. Upstairs, an open floor plan seamlessly connects the living, dining, and kitchen areas, creating an inviting flow ideal for both everyday living and hosting. A spacious primary bedroom suite and two guest bedrooms provide comfort and privacy. Downstairs, a generous bonus area with a full bath offers a place to relax after a day on the water. Outside, enjoy the true Keys lifestyle with a sparkling pool, expansive pool deck, ample parking, two carports, and dockage just steps from your door. As a resident of White Marlin Beach, you'll also enjoy access to the neighborhood's beloved homeowners' park, featuring a beautiful sandy beach, charming tiki huts, and BBQ grills—an ideal setting for gatherings with friends and neighbors. This is coastal living at its finest: elegant yet welcoming, perfectly designed for making memories on and off the water.

3 Beds ⋅ 3 Baths ⋅ 618348 MLS

Welcome to your coastal retreat in the coveted White Marlin Beach neighborhood—where relaxed Keys living meets timeless elegance. This beautifully updated canalfront home offers 1,911 sq. ft. of light-filled living space upstairs, complemented by a large open terrace perfect for morning coffee, sunset cocktails, or relaxing with family and friends. Upstairs, an open floor plan seamlessly connects the living, dining, and kitchen areas, creating an inviting flow ideal for both everyday living and hosting. A spacious primary bedroom suite and two guest bedrooms provide comfort and privacy. Downstairs, a generous bonus area with a full bath offers a place to relax after a day on the water. Outside, enjoy the true Keys lifestyle with a sparkling pool, expansive pool deck, ample parking, two carports, and dockage just steps from your door. As a resident of White Marlin Beach, you'll also enjoy access to the neighborhood's beloved homeowners' park, featuring a beautiful sandy beach, charming tiki huts, and BBQ grills—an ideal setting for gatherings with friends and neighbors. This is coastal living at its finest: elegant yet welcoming, perfectly designed for making memories on and off the water.

193 Nautilus Dr, Islamorada

$2,050,000

Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

3 Beds ⋅ 3 Baths ⋅ 619722 MLS

Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

137 Cortez Dr, Islamorada

$2,000,000

Tucked away on a peaceful, hidden boat basin, this diamond in the rough embraces natural privacy from its setting within a broad expanse of native surroundings. Clear waters, endless skies, and unforgettable sunsets. With +/-135 feet of concrete seawall on a private basin, this property offers exceptional space for boating, water-sports, or simply soaking in the tranquil beauty of the Florida Keys. Resting on a rare double lot totaling +/-18,975 square feet, the home provides an incredible sense of privacy and potential. The generous property size allows for lush landscaping, outdoor entertaining, and ample room to expand or design your dream retreat by the water's edge. Inside, the living space unfolds across three levels. A spacious double garage anchors the ground floor, while the second level features the main living area and a guest bedroom with water views. The top floor is dedicated to the primary suite—a private sanctuary with broad views of the basin, frequented by manatees and tarpon. This weekend escape can be your canvas for a future Keys masterpiece, in perfect harmony with nature.

2 Beds ⋅ 2 Baths ⋅ 617174 MLS

Tucked away on a peaceful, hidden boat basin, this diamond in the rough embraces natural privacy from its setting within a broad expanse of native surroundings. Clear waters, endless skies, and unforgettable sunsets. With +/-135 feet of concrete seawall on a private basin, this property offers exceptional space for boating, water-sports, or simply soaking in the tranquil beauty of the Florida Keys. Resting on a rare double lot totaling +/-18,975 square feet, the home provides an incredible sense of privacy and potential. The generous property size allows for lush landscaping, outdoor entertaining, and ample room to expand or design your dream retreat by the water's edge. Inside, the living space unfolds across three levels. A spacious double garage anchors the ground floor, while the second level features the main living area and a guest bedroom with water views. The top floor is dedicated to the primary suite—a private sanctuary with broad views of the basin, frequented by manatees and tarpon. This weekend escape can be your canvas for a future Keys masterpiece, in perfect harmony with nature.

76434 Overseas Hwy, Islamorada

$1,960,000

Beautifully updated coastal home in the prestigious private beach community of Port Antigua, Islamorada. This move-in-ready home is the best value currently available in one of the most sought-after neighborhoods, offering unmatched tranquility and access to one of the finest private sandy beach communities in the Keys. Thoughtfully renovated interior featuring an open-concept layout, modern finishes, and impact-resistant windows and doors throughout, providing peace of mind and storm protection. The bright living space seamlessly transitions into a stylish kitchen featuring quartz countertops, stainless steel appliances, and modern cabinets—ideal for relaxed entertaining. The outdoor covered space offers ample room for lounging, grilling, or simply enjoying the laid-back Keys lifestyle.

3 Beds ⋅ 2 Baths ⋅ 616627 MLS

Beautifully updated coastal home in the prestigious private beach community of Port Antigua, Islamorada. This move-in-ready home is the best value currently available in one of the most sought-after neighborhoods, offering unmatched tranquility and access to one of the finest private sandy beach communities in the Keys. Thoughtfully renovated interior featuring an open-concept layout, modern finishes, and impact-resistant windows and doors throughout, providing peace of mind and storm protection. The bright living space seamlessly transitions into a stylish kitchen featuring quartz countertops, stainless steel appliances, and modern cabinets—ideal for relaxed entertaining. The outdoor covered space offers ample room for lounging, grilling, or simply enjoying the laid-back Keys lifestyle.

64 W Plaza Del Sol, Islamorada

$1,950,000

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.

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

$1,600,000

This property was originally commercial and was changed by the Village of Islamorada without notifying the owner. A land use attorney is workiing on fixing the issue so it can be commercial again. Right now the land was changed to native residential. This property is 3.2 Acres, with 1 of those acres being hardwood so it cannot be built on. 2 acres have been scarified and was being used as tennis courts with a club house on it.

1 Beds ⋅ 3 Baths ⋅ 616210 MLS

This property was originally commercial and was changed by the Village of Islamorada without notifying the owner. A land use attorney is workiing on fixing the issue so it can be commercial again. Right now the land was changed to native residential. This property is 3.2 Acres, with 1 of those acres being hardwood so it cannot be built on. 2 acres have been scarified and was being used as tennis courts with a club house on it.

76800 Overseas Hwy, Islamorada

$1,490,000

Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of newly decked dockage along the tranquil ''Sleepy Lagoon'', this exceptional property combines relaxed island living with effortless boating access to both the ocean and bay. The light-filled second floor features an open-concept living, dining, and kitchen area with soaring cathedral ceilings and new vinyl flooring throughout. The recently remodeled kitchen showcases new cabinetry, stainless steel appliances, and an inviting layout ideal for entertaining. Two bright bedrooms with laminate flooring are located on this level, including a spacious primary with en-suite bath. Step outside onto the expansive second-floor balcony and enjoy breathtaking lagoon views while watching manatees glide by and fish jump in the tranquil waters below. The first floor offers additional flexible living space with an open bedroom/living area and full bath, featuring sliding glass doors that lead directly to the tropical backyard, pool, and dock. Designed for comfort and convenience, this fully turnkey home includes well-maintained accordion shutters on all non-impact windows, generous storage space for water toys and gardening equipment, and a securely anchored storage shed. Outdoor living is truly exceptional. Relax beneath the airy chickee hut, cool off in the in-ground pool after a day on the water, or entertain family and friends with freshly grilled BBQ favorites in the private backyard oasis. Additional features include a JetDock, fish cleaning station, spacious outdoor shower, fenced backyard for pets, and ample parking for boats, trailers, RVs, and recreational equipment. Residents may enjoy access to a beautiful sandy beach within the subdivision through a voluntary HOA membership. The beach is a protected turtle nesting habitat.

3 Beds ⋅ 3 Baths ⋅ 620353 MLS

Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of newly decked dockage along the tranquil ''Sleepy Lagoon'', this exceptional property combines relaxed island living with effortless boating access to both the ocean and bay. The light-filled second floor features an open-concept living, dining, and kitchen area with soaring cathedral ceilings and new vinyl flooring throughout. The recently remodeled kitchen showcases new cabinetry, stainless steel appliances, and an inviting layout ideal for entertaining. Two bright bedrooms with laminate flooring are located on this level, including a spacious primary with en-suite bath. Step outside onto the expansive second-floor balcony and enjoy breathtaking lagoon views while watching manatees glide by and fish jump in the tranquil waters below. The first floor offers additional flexible living space with an open bedroom/living area and full bath, featuring sliding glass doors that lead directly to the tropical backyard, pool, and dock. Designed for comfort and convenience, this fully turnkey home includes well-maintained accordion shutters on all non-impact windows, generous storage space for water toys and gardening equipment, and a securely anchored storage shed. Outdoor living is truly exceptional. Relax beneath the airy chickee hut, cool off in the in-ground pool after a day on the water, or entertain family and friends with freshly grilled BBQ favorites in the private backyard oasis. Additional features include a JetDock, fish cleaning station, spacious outdoor shower, fenced backyard for pets, and ample parking for boats, trailers, RVs, and recreational equipment. Residents may enjoy access to a beautiful sandy beach within the subdivision through a voluntary HOA membership. The beach is a protected turtle nesting habitat.

140 Iroquois Dr, Islamorada

$1,450,000

Seller will consider seller financing. Florida Keys waterfront home, offered fully furnished, no homeowners association, 1,786 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed & elevated in 2021. Boaters paradise w/75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift. There is also a private neighborhood concrete boat ramp that can be used. Canal depth is estimated 10-12 FT. Unique layout offers 2 bedrooms & 2 baths on the second floor with full kitchen & spacious living room area, washer & dryer. First floor offers 1 bedroom & 1 bath, washer & dryer, full kitchen (separate living units). New roof/hurricane impact windows. Easy storage space. Ample parking.

3 Beds ⋅ 3 Baths ⋅ 616594 MLS

Seller will consider seller financing. Florida Keys waterfront home, offered fully furnished, no homeowners association, 1,786 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed & elevated in 2021. Boaters paradise w/75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift. There is also a private neighborhood concrete boat ramp that can be used. Canal depth is estimated 10-12 FT. Unique layout offers 2 bedrooms & 2 baths on the second floor with full kitchen & spacious living room area, washer & dryer. First floor offers 1 bedroom & 1 bath, washer & dryer, full kitchen (separate living units). New roof/hurricane impact windows. Easy storage space. Ample parking.

126 Columbus Dr, Islamorada

101 Gulfview Dr Unit 204 & 30' boat slip with lift, Islamorada

$1,300,000

Experience luxury island living in the heart of Islamorada at Bay Harbour, one of the Florida Keys' most desirable waterfront communities. Unit 204 offers breathtaking ocean and lagoon water views and an exceptional blend of elegance, comfort, and investment potential. This spacious 3-bedroom, 2.5-bath residence has been fully remodeled and impeccably maintained, featuring beautiful high-end finishes throughout and a stunning designer kitchen perfect for entertaining. The oversized primary suite offers a true retreat with a spacious bedroom and a beautifully appointed spa-inspired primary bathroom. Offered 100% turnkey, this residence is ready for immediate enjoyment or income production, with the flexibility of 7-day rentals and a strong established, impressive rental history. Boaters will appreciate the assigned boat slip and private 20,000-pound boat lift, providing easy access to some of the best fishing and boating in the Florida Keys. Bay Harbour is known for its upscale amenities, prime location, and relaxed coastal lifestyle, making this an exceptional opportunity for both personal enjoyment and investment.

3 Beds ⋅ 3 Baths ⋅ 619919 MLS

Experience luxury island living in the heart of Islamorada at Bay Harbour, one of the Florida Keys' most desirable waterfront communities. Unit 204 offers breathtaking ocean and lagoon water views and an exceptional blend of elegance, comfort, and investment potential. This spacious 3-bedroom, 2.5-bath residence has been fully remodeled and impeccably maintained, featuring beautiful high-end finishes throughout and a stunning designer kitchen perfect for entertaining. The oversized primary suite offers a true retreat with a spacious bedroom and a beautifully appointed spa-inspired primary bathroom. Offered 100% turnkey, this residence is ready for immediate enjoyment or income production, with the flexibility of 7-day rentals and a strong established, impressive rental history. Boaters will appreciate the assigned boat slip and private 20,000-pound boat lift, providing easy access to some of the best fishing and boating in the Florida Keys. Bay Harbour is known for its upscale amenities, prime location, and relaxed coastal lifestyle, making this an exceptional opportunity for both personal enjoyment and investment.

101 Gulfview Dr Unit 204 & 30' boat slip with lift, Islamorada

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