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Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This beautifully remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect combination of luxury, comfort, and island style--all on one level. The open-concept floor plan features a spacious living area ideal for entertaining, a modern kitchen with stainless steel appliances and granite countertops, and three generous bedrooms each with its own bathroom. Built with solid concrete construction, impact windows, and elevated above flood, this home provides durability and peace of mind. Enjoy modern finishes throughout and a large outdoor deck perfect for relaxing or hosting gatherings. Situated on a quiet street with beach access at the end of the road, this home offers both convenience and tranquility. Close to world-class dining, shopping, and some of the best fishing and diving in the Florida Keys. Excellent rental potential--buy one or both adjoining homes for added investment opportunity. 'The adjacent residence offers a rare opportunity to expand into a multi-residence estate or income-producing property.' 'The neighboring home may be acquired to create an exceptional multi-home setting ideal for extended family living or rental income.' 'Purchasing the nearby residence allows for a flexible use property, suitable for private family living or investment purposes.' 'The adjoining property presents a unique opportunity to establish a private multi-home arrangement or enhance rental potential.' 'With the option to acquire the neighboring home, buyers can create a distinctive residential setting with income potential.'Buy both homes and get a $25,000 reduction. Rental Available longterm $6,000 per month

3 Beds ⋅ 3 Baths ⋅ 621912 MLS

Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This beautifully remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect combination of luxury, comfort, and island style--all on one level. The open-concept floor plan features a spacious living area ideal for entertaining, a modern kitchen with stainless steel appliances and granite countertops, and three generous bedrooms each with its own bathroom. Built with solid concrete construction, impact windows, and elevated above flood, this home provides durability and peace of mind. Enjoy modern finishes throughout and a large outdoor deck perfect for relaxing or hosting gatherings. Situated on a quiet street with beach access at the end of the road, this home offers both convenience and tranquility. Close to world-class dining, shopping, and some of the best fishing and diving in the Florida Keys. Excellent rental potential--buy one or both adjoining homes for added investment opportunity. 'The adjacent residence offers a rare opportunity to expand into a multi-residence estate or income-producing property.' 'The neighboring home may be acquired to create an exceptional multi-home setting ideal for extended family living or rental income.' 'Purchasing the nearby residence allows for a flexible use property, suitable for private family living or investment purposes.' 'The adjoining property presents a unique opportunity to establish a private multi-home arrangement or enhance rental potential.' 'With the option to acquire the neighboring home, buyers can create a distinctive residential setting with income potential.'Buy both homes and get a $25,000 reduction. Rental Available longterm $6,000 per month

189 Carroll St, Islamorada

$399,000

Enjoy a tropical retreat at Plantation By The Sea, an oceanfront community in Islamorada. Relax beside the sparkling oceanfront pool or cast a line from the community fishing pier, then head out for waterfront dining, live music, and eclectic local shops. This inviting 2-bedroom, 1.5-bath condo offers a two-level layout with living spaces downstairs and both bedrooms upstairs. Bamboo flooring adds warmth to the living and dining areas and bedrooms. The updated kitchen features white cabinetry and generous counter and storage space. The open living and dining area flows onto a covered balcony nestled among tropical greenery - a pleasant spot for morning coffee or unwinding after a day exploring the island. Both upstairs bedrooms feature sliding glass doors opening to balcony spaces. An updated full bathroom with a tiled walk-in shower, a convenient downstairs half bath, and an in-unit Bosch washer and dryer add everyday comfort. Assigned covered parking and a ground-level storage room provide added convenience. Community amenities also include an oceanfront clubhouse with a kitchen, a pool table, and a ping-pong table - a great place to entertain friends and family. Take in ocean views while working out in the fitness center, or unwind in the men's and women's saunas. Gated entry and kayak and paddleboard storage add to the community's appeal. Nearby Founders Park offers a beach, Olympic-size swimming pool, tennis and pickleball courts, ball fields, and an amphitheater. Whether you're seeking a seasonal getaway or a year-round home, this welcoming condo puts the best of Islamorada within reach.

2 Beds ⋅ 2 Baths ⋅ 621854 MLS

Enjoy a tropical retreat at Plantation By The Sea, an oceanfront community in Islamorada. Relax beside the sparkling oceanfront pool or cast a line from the community fishing pier, then head out for waterfront dining, live music, and eclectic local shops. This inviting 2-bedroom, 1.5-bath condo offers a two-level layout with living spaces downstairs and both bedrooms upstairs. Bamboo flooring adds warmth to the living and dining areas and bedrooms. The updated kitchen features white cabinetry and generous counter and storage space. The open living and dining area flows onto a covered balcony nestled among tropical greenery - a pleasant spot for morning coffee or unwinding after a day exploring the island. Both upstairs bedrooms feature sliding glass doors opening to balcony spaces. An updated full bathroom with a tiled walk-in shower, a convenient downstairs half bath, and an in-unit Bosch washer and dryer add everyday comfort. Assigned covered parking and a ground-level storage room provide added convenience. Community amenities also include an oceanfront clubhouse with a kitchen, a pool table, and a ping-pong table - a great place to entertain friends and family. Take in ocean views while working out in the fitness center, or unwind in the men's and women's saunas. Gated entry and kayak and paddleboard storage add to the community's appeal. Nearby Founders Park offers a beach, Olympic-size swimming pool, tennis and pickleball courts, ball fields, and an amphitheater. Whether you're seeking a seasonal getaway or a year-round home, this welcoming condo puts the best of Islamorada within reach.

87455 Old Hwy Unit APT 234, Islamorada

$3,200,000

Experience the ultimate Florida Keys waterfront lifestyle! Discover this exceptional 4-bedroom, 4-bathroom waterfront residence featuring solid concrete construction, a concrete roof, and a spacious custom-designed kitchen. Enjoy the ultimate boating lifestyle with a private boat lift and direct water access with no bridges. This remarkable property also features a beautiful swimming pool, a spacious garage, an outdoor summer kitchen perfect for entertaining, and breathtaking ocean views from the rooftop. Offering generous living spaces and endless opportunities for boating, fishing, and entertaining, this beautiful Islamorada home combines quality construction, comfort, and coastal elegance. Experience waterfront living at its finest!

4 Beds ⋅ 4 Baths ⋅ 621841 MLS

Experience the ultimate Florida Keys waterfront lifestyle! Discover this exceptional 4-bedroom, 4-bathroom waterfront residence featuring solid concrete construction, a concrete roof, and a spacious custom-designed kitchen. Enjoy the ultimate boating lifestyle with a private boat lift and direct water access with no bridges. This remarkable property also features a beautiful swimming pool, a spacious garage, an outdoor summer kitchen perfect for entertaining, and breathtaking ocean views from the rooftop. Offering generous living spaces and endless opportunities for boating, fishing, and entertaining, this beautiful Islamorada home combines quality construction, comfort, and coastal elegance. Experience waterfront living at its finest!

131 Ojibway Ave, Islamorada

$4,850,000

Discover a rare oceanfront paradise in the Florida Keys, situated on 1.35 acres of private oceanfront property featuring an extraordinary stretch of natural sandy beach, a feature seldom found in the Keys. Perfectly positioned next to iconic Sea Oats Beach, known for its pristine shoreline and seasonal sea turtle nesting, this exceptional estate offers privacy, coastal elegance, and breathtaking turquoise waters, just minutes from Islamorada's renowned dining and shopping. Enter through a private electric gate with ample parking for vehicles, boats, and trailers, plus an oversized three-car garage with pull-through access. An expansive ground-level storage area, currently utilized as a private gym, provides additional space for recreational equipment and boating gear. Built with concrete construction, the residence features impact-resistant windows and doors, along with a 25kW propane generator. Inside, marble floors, granite countertops, stainless steel appliances, a wine refrigerator, built-in ice maker, and spectacular open living spaces create an inviting coastal retreat. Four sets of double sliding impact glass doors frame panoramic ocean views and abundant natural light. The residence features five bedrooms and four full bathrooms, including two guest suites with private baths. The oceanview primary suite offers a walk-in closet, dual vanities, soaking tub, and walk-in shower. Outside, a lagoon-style pool, Jacuzzi, and wraparound balcony create an exceptional setting for entertaining and enjoying the ocean breezes. Offered below its 2026 appraised value, this remarkable oceanfront estate presents a rare opportunity to own 1.35 acres of private oceanfront property with a natural sandy beach, stunning open-water views, and convenient access to Islamorada's restaurants, shopping, and marinas.

5 Beds ⋅ 4 Baths ⋅ 621750 MLS

Discover a rare oceanfront paradise in the Florida Keys, situated on 1.35 acres of private oceanfront property featuring an extraordinary stretch of natural sandy beach, a feature seldom found in the Keys. Perfectly positioned next to iconic Sea Oats Beach, known for its pristine shoreline and seasonal sea turtle nesting, this exceptional estate offers privacy, coastal elegance, and breathtaking turquoise waters, just minutes from Islamorada's renowned dining and shopping. Enter through a private electric gate with ample parking for vehicles, boats, and trailers, plus an oversized three-car garage with pull-through access. An expansive ground-level storage area, currently utilized as a private gym, provides additional space for recreational equipment and boating gear. Built with concrete construction, the residence features impact-resistant windows and doors, along with a 25kW propane generator. Inside, marble floors, granite countertops, stainless steel appliances, a wine refrigerator, built-in ice maker, and spectacular open living spaces create an inviting coastal retreat. Four sets of double sliding impact glass doors frame panoramic ocean views and abundant natural light. The residence features five bedrooms and four full bathrooms, including two guest suites with private baths. The oceanview primary suite offers a walk-in closet, dual vanities, soaking tub, and walk-in shower. Outside, a lagoon-style pool, Jacuzzi, and wraparound balcony create an exceptional setting for entertaining and enjoying the ocean breezes. Offered below its 2026 appraised value, this remarkable oceanfront estate presents a rare opportunity to own 1.35 acres of private oceanfront property with a natural sandy beach, stunning open-water views, and convenient access to Islamorada's restaurants, shopping, and marinas.

74501 Overseas Hwy, Islamorada

$24,995,000

Experience unparalleled oceanfront living at the Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship. Set on just under an acre of pristine coastline, the property offers 19,784 SF of total living and entertaining space, including 10,182 SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors with natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, a Baccarat-inspired grand ballroom, and a custom Glamour Suite. Outdoors, a mosaic pool and spa overlook the Atlantic Ocean, complemented by alfresco dining, a firepit lounge, putting green and multiple terraces with sweeping coastal views. A 300 inch outdoor LED theater and rooftop terrace elevate the experience. A 100ft private dock provides direct ocean access. Approved plans include 6 additional suites, including 2 oceanfront residences, allowing expansion into a multi-structure compound. A rare legacy estate defined by privacy, scale, and presence

7 Beds ⋅ 11 Baths ⋅ 621626 MLS

Experience unparalleled oceanfront living at the Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship. Set on just under an acre of pristine coastline, the property offers 19,784 SF of total living and entertaining space, including 10,182 SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors with natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, a Baccarat-inspired grand ballroom, and a custom Glamour Suite. Outdoors, a mosaic pool and spa overlook the Atlantic Ocean, complemented by alfresco dining, a firepit lounge, putting green and multiple terraces with sweeping coastal views. A 300 inch outdoor LED theater and rooftop terrace elevate the experience. A 100ft private dock provides direct ocean access. Approved plans include 6 additional suites, including 2 oceanfront residences, allowing expansion into a multi-structure compound. A rare legacy estate defined by privacy, scale, and presence

82719 Old Hwy, Islamorada

$3,275,000

Spectacular turnkey luxury meets the ultimate boater's paradise at 59 W Plaza Del Sol, nestled in Islamorada's coveted Port Antigua community! Built with solid concrete construction, this exceptional waterfront residence offers a rare Florida Keys feature: a full lower level, seamlessly connected by an interior staircase. Offering nearly 3,000 SF, 5 bedrooms, and 3 bathrooms, the home provides exceptional flexibility. The lower level features 3 spacious bedrooms, a secondary kitchen, and custom rear deck, while upstairs showcases soaring ceilings, a gourmet kitchen, and 2 additional bedrooms. Completely remodeled from top to bottom with no expense spared! Premium Porcelanosa flooring, custom Hunter Douglas shades, Big Ass Fans, upgraded bathrooms, and a new driveway. Offered fully furnished with luxurious Restoration Hardware pieces, flush-mounted Samsung Frame TVs, and a professional-grade pool table that converts into an expansive dining table. A true boater's and angler's paradise! Enjoy a 75-foot concrete dock with 2 boat lifts and a dedicated fish-cleaning station. Port Antigua's exceptionally wide canals offer quick, direct access to both the Atlantic Ocean and Florida Bay for world-class offshore and backcountry fishing. Cruise straight to Papa Joe's for waterfront dining, with convenient nearby fuel docks, marine services, and boat mechanics. Situated on a generous 7,500 SF lot with ample room for a custom swimming pool and outdoor oasis. Major upgrades include a new metal roof, full impact-resistant windows and doors, 2 new A/C systems, and a garage, and additional storage offering peace of mind. Residents also enjoy exclusive access to Port Antigua's private white-sand beach and community boat ramp. Meticulously renovated, beautifully furnished, and designed for effortless waterfront living, this is an exceptional opportunity to experience the ultimate luxury Florida Keys lifestyle!

5 Beds ⋅ 3 Baths ⋅ 621593 MLS

Spectacular turnkey luxury meets the ultimate boater's paradise at 59 W Plaza Del Sol, nestled in Islamorada's coveted Port Antigua community! Built with solid concrete construction, this exceptional waterfront residence offers a rare Florida Keys feature: a full lower level, seamlessly connected by an interior staircase. Offering nearly 3,000 SF, 5 bedrooms, and 3 bathrooms, the home provides exceptional flexibility. The lower level features 3 spacious bedrooms, a secondary kitchen, and custom rear deck, while upstairs showcases soaring ceilings, a gourmet kitchen, and 2 additional bedrooms. Completely remodeled from top to bottom with no expense spared! Premium Porcelanosa flooring, custom Hunter Douglas shades, Big Ass Fans, upgraded bathrooms, and a new driveway. Offered fully furnished with luxurious Restoration Hardware pieces, flush-mounted Samsung Frame TVs, and a professional-grade pool table that converts into an expansive dining table. A true boater's and angler's paradise! Enjoy a 75-foot concrete dock with 2 boat lifts and a dedicated fish-cleaning station. Port Antigua's exceptionally wide canals offer quick, direct access to both the Atlantic Ocean and Florida Bay for world-class offshore and backcountry fishing. Cruise straight to Papa Joe's for waterfront dining, with convenient nearby fuel docks, marine services, and boat mechanics. Situated on a generous 7,500 SF lot with ample room for a custom swimming pool and outdoor oasis. Major upgrades include a new metal roof, full impact-resistant windows and doors, 2 new A/C systems, and a garage, and additional storage offering peace of mind. Residents also enjoy exclusive access to Port Antigua's private white-sand beach and community boat ramp. Meticulously renovated, beautifully furnished, and designed for effortless waterfront living, this is an exceptional opportunity to experience the ultimate luxury Florida Keys lifestyle!

59 W Plaza Del Sol, Islamorada

$3,900,000

Sunset views in Islamorada's most coveted location: PEN KEY CLUB. From the front doorstep, you can see straight through the house to the sparkling waters of Florida Bay, so the view will take your breath away before you put a foot inside the house! Established in the 1950s, Pen Key Club is a small, private, gated bayfront community on Upper Matecumbe Key, Islamorada's ''downtown'' island. The location is excellent by land and sea. Boating access is exceptional. In fact, it's why the club was founded here. Immediate access to Florida Bay and quick, easy access to the ocean through Whale Harbor Channel. Dockage for boats to 32 feet (plus engines) is available for club members only. Quiet and tucked away, it's close to many of Islamorada's favorite restaurants, including Chef Michael's, Kaiyo and Pierre's, as well as shops and local gathering places like the Cheeca Lodge. Owners share a pool, marina and sunset viewing areas, while the association cares for the landscaping. An onsite property manager receives packages and helps owners with day-to-day needs, making it easy to live here full time or to come and go. Overlooking the marina and bay, this one-level home has high ceilings and two large living areas lined with wide banks of impact glass doors. Expansive bay views extend throughout the main living areas and primary bedroom suite. The large covered patio offers plenty of space for morning coffee, dinner with friends and a front-row seat for the sunset. The comfortable layout puts everything on one floor, with three bedrooms, each with an en suite bath, plus a separate office, laundry room and garage. Concrete construction, impact windows and doors and a metal roof add strength and peace of mind. You really can have it all: big bay views, dockage, excellent boating access and favorite restaurants and shops nearby, with the ease of a single-level home in a peaceful community where living is easy.

3 Beds ⋅ 3 Baths ⋅ 621575 MLS

Sunset views in Islamorada's most coveted location: PEN KEY CLUB. From the front doorstep, you can see straight through the house to the sparkling waters of Florida Bay, so the view will take your breath away before you put a foot inside the house! Established in the 1950s, Pen Key Club is a small, private, gated bayfront community on Upper Matecumbe Key, Islamorada's ''downtown'' island. The location is excellent by land and sea. Boating access is exceptional. In fact, it's why the club was founded here. Immediate access to Florida Bay and quick, easy access to the ocean through Whale Harbor Channel. Dockage for boats to 32 feet (plus engines) is available for club members only. Quiet and tucked away, it's close to many of Islamorada's favorite restaurants, including Chef Michael's, Kaiyo and Pierre's, as well as shops and local gathering places like the Cheeca Lodge. Owners share a pool, marina and sunset viewing areas, while the association cares for the landscaping. An onsite property manager receives packages and helps owners with day-to-day needs, making it easy to live here full time or to come and go. Overlooking the marina and bay, this one-level home has high ceilings and two large living areas lined with wide banks of impact glass doors. Expansive bay views extend throughout the main living areas and primary bedroom suite. The large covered patio offers plenty of space for morning coffee, dinner with friends and a front-row seat for the sunset. The comfortable layout puts everything on one floor, with three bedrooms, each with an en suite bath, plus a separate office, laundry room and garage. Concrete construction, impact windows and doors and a metal roof add strength and peace of mind. You really can have it all: big bay views, dockage, excellent boating access and favorite restaurants and shops nearby, with the ease of a single-level home in a peaceful community where living is easy.

18 Pen, Islamorada

$2,699,000

Location! Location! Location! This incredible custom designed home is located on a quiet lane in the heart of Islamorada, 154 Carroll Street offers privacy, modern construction, and easy access to some of the area's best restaurants, shops, private clubs, and resorts, and beaches. Completed in 2018, the home combines clean coastal design with comfortable and abundant indoor-outdoor living. Mature tropical landscaping creates a private setting around the pool and spa. The handcrafted tiki pavilion is designed for outdoor cooking and entertaining, complete with a mosquito misting system, refrigerator, ice maker, grill, cooktop, all made of marine grade stainless steel, in NatureKast exterior cabinets--an ideal gathering spot for afternoons by the pool, evening entertaining or star gazing in the hot tub. Inside, the two floor cathedral ceilings enhance the interior with bright light, and the open layout features porcelain floors and coastal finishes. Two primary suites offer flexibility, including an upstairs suite with a private balcony and a downstairs suite with an oversized walk-in closet. Additional guest suites and a loft offer plenty of space for family, visitors, or a home office. Built above flood, the home includes impact-rated openings and spray-foam insulation for incredible efficiency. Practical features include a rare attached garage, Tesla charging station, exterior security cameras & wired interior system and a fenced area with room for a boat and trailer. Located within Islamorada's golf cart district, the home makes it easy to leave the car behind and enjoy nearby restaurants, shops, resorts, and local favorites by golf cart, bike, or on foot. Sandy neighborhood beach access at the end of the block puts the Atlantic just a short walk away, while the Islander Resort and the amenities of Upper Matecumbe are close at hand. 154 Carroll Street combines the privacy and features of a new home with a central location designed for tranquil living.

4 Beds ⋅ 4 Baths ⋅ 621562 MLS

Location! Location! Location! This incredible custom designed home is located on a quiet lane in the heart of Islamorada, 154 Carroll Street offers privacy, modern construction, and easy access to some of the area's best restaurants, shops, private clubs, and resorts, and beaches. Completed in 2018, the home combines clean coastal design with comfortable and abundant indoor-outdoor living. Mature tropical landscaping creates a private setting around the pool and spa. The handcrafted tiki pavilion is designed for outdoor cooking and entertaining, complete with a mosquito misting system, refrigerator, ice maker, grill, cooktop, all made of marine grade stainless steel, in NatureKast exterior cabinets--an ideal gathering spot for afternoons by the pool, evening entertaining or star gazing in the hot tub. Inside, the two floor cathedral ceilings enhance the interior with bright light, and the open layout features porcelain floors and coastal finishes. Two primary suites offer flexibility, including an upstairs suite with a private balcony and a downstairs suite with an oversized walk-in closet. Additional guest suites and a loft offer plenty of space for family, visitors, or a home office. Built above flood, the home includes impact-rated openings and spray-foam insulation for incredible efficiency. Practical features include a rare attached garage, Tesla charging station, exterior security cameras & wired interior system and a fenced area with room for a boat and trailer. Located within Islamorada's golf cart district, the home makes it easy to leave the car behind and enjoy nearby restaurants, shops, resorts, and local favorites by golf cart, bike, or on foot. Sandy neighborhood beach access at the end of the block puts the Atlantic just a short walk away, while the Islander Resort and the amenities of Upper Matecumbe are close at hand. 154 Carroll Street combines the privacy and features of a new home with a central location designed for tranquil living.

154 Carroll St, Islamorada

$2,800,000

Welcome to Islamorada, one of the most desirable islands in the Florida Keys, where relaxed island living and life on the water come together. This modern, clean, and beautifully maintained 5-bedroom, 3-bath home sits on a quiet cul-de-sac with a large, fenced yard and plenty of room to enjoy the outdoors. The home offers a flexible layout with 3 bedrooms and 2 baths upstairs, plus a separate 2-bedroom, 1-bath lower level--giving family and guests their own space and privacy. The large kitchen features beautiful Italian finishes and stainless steel appliances, while two A/C systems, hot water on demand, high-impact windows and doors, and a cooled single-car garage add comfort and convenience. Outside is where you'll really enjoy the Keys lifestyle. Take a dip in the saltwater pool and jacuzzi, relax around the outdoor kitchen, or head over to the water and hop in the boat. The property enjoys a very desirable corner location on the canal, with approximately 100 feet of canal frontage, a wide, easy-turnaround canal, and approximately 50+ feet of concrete dock. The location offers quick access to the bay and easy access to the Atlantic through nearby Tavernier Creek. You may even find yourself watching manatees and tarpon swimming right by the property. The yard is fenced and designed for easy living with pea rock and synthetic turf, giving you more time to enjoy the space and less time worrying about maintenance. Whether you're looking for a comfortable full-time home, a place to escape to on weekends, or a property with plenty of room for family and friends, 107 Azalea Street is a place where you can slow down, get on the water, and enjoy everything the Florida Keys have to offer.

5 Beds ⋅ 3 Baths ⋅ 621542 MLS

Welcome to Islamorada, one of the most desirable islands in the Florida Keys, where relaxed island living and life on the water come together. This modern, clean, and beautifully maintained 5-bedroom, 3-bath home sits on a quiet cul-de-sac with a large, fenced yard and plenty of room to enjoy the outdoors. The home offers a flexible layout with 3 bedrooms and 2 baths upstairs, plus a separate 2-bedroom, 1-bath lower level--giving family and guests their own space and privacy. The large kitchen features beautiful Italian finishes and stainless steel appliances, while two A/C systems, hot water on demand, high-impact windows and doors, and a cooled single-car garage add comfort and convenience. Outside is where you'll really enjoy the Keys lifestyle. Take a dip in the saltwater pool and jacuzzi, relax around the outdoor kitchen, or head over to the water and hop in the boat. The property enjoys a very desirable corner location on the canal, with approximately 100 feet of canal frontage, a wide, easy-turnaround canal, and approximately 50+ feet of concrete dock. The location offers quick access to the bay and easy access to the Atlantic through nearby Tavernier Creek. You may even find yourself watching manatees and tarpon swimming right by the property. The yard is fenced and designed for easy living with pea rock and synthetic turf, giving you more time to enjoy the space and less time worrying about maintenance. Whether you're looking for a comfortable full-time home, a place to escape to on weekends, or a property with plenty of room for family and friends, 107 Azalea Street is a place where you can slow down, get on the water, and enjoy everything the Florida Keys have to offer.

107 Azalea St, Islamorada

$4,899,000

Experience turnkey luxury in the renowned Venetian Shores community with this exceptional 4-bedroom, 4-bath concrete waterfront residence, completely rebuilt from top to bottom with designer finishes and thoughtful details throughout. Offered fully furnished and completely outfitted, this home is truly ready to enjoy from day one. Everything is already in place, including linens, bathroom essentials, a fully stocked kitchen, and three mini-bar setups. Currently operating in a highly successful vacation rental program, the property has been thoughtfully designed and equipped for effortless personal use, entertaining, or continued rental operation. The beautifully finished interiors offer a sophisticated coastal feel, while an additional bonus space downstairs provides exceptional flexibility as a potential 5th bedroom, private office, game room, or lounge. Outdoor living is equally impressive. The resort-style pool is both heated and chilled for year-round enjoyment, while extensive landscape and architectural lighting creates an incredible atmosphere after sunset. Under-dock lighting illuminates the water below, perfect for nighttime fish watching and feeding. An outdoor shower provides the ideal place to rinse off after a swim or a long day on the water. Adding even more to the Keys lifestyle, the property includes a customized golf cart, making it easy to cruise through Venetian Shores and enjoy everything this highly sought-after neighborhood has to offer. From the complete rebuild and designer interiors to the turnkey furnishings, flexible living spaces, resort-style outdoor amenities, and established vacation rental operation, every detail of this home has been carefully considered. Simply arrive, unpack, and start enjoying the Florida Keys lifestyle.

4 Beds ⋅ 4 Baths ⋅ 621387 MLS

Experience turnkey luxury in the renowned Venetian Shores community with this exceptional 4-bedroom, 4-bath concrete waterfront residence, completely rebuilt from top to bottom with designer finishes and thoughtful details throughout. Offered fully furnished and completely outfitted, this home is truly ready to enjoy from day one. Everything is already in place, including linens, bathroom essentials, a fully stocked kitchen, and three mini-bar setups. Currently operating in a highly successful vacation rental program, the property has been thoughtfully designed and equipped for effortless personal use, entertaining, or continued rental operation. The beautifully finished interiors offer a sophisticated coastal feel, while an additional bonus space downstairs provides exceptional flexibility as a potential 5th bedroom, private office, game room, or lounge. Outdoor living is equally impressive. The resort-style pool is both heated and chilled for year-round enjoyment, while extensive landscape and architectural lighting creates an incredible atmosphere after sunset. Under-dock lighting illuminates the water below, perfect for nighttime fish watching and feeding. An outdoor shower provides the ideal place to rinse off after a swim or a long day on the water. Adding even more to the Keys lifestyle, the property includes a customized golf cart, making it easy to cruise through Venetian Shores and enjoy everything this highly sought-after neighborhood has to offer. From the complete rebuild and designer interiors to the turnkey furnishings, flexible living spaces, resort-style outdoor amenities, and established vacation rental operation, every detail of this home has been carefully considered. Simply arrive, unpack, and start enjoying the Florida Keys lifestyle.

115 Villa Bella Dr, Islamorada

$3,999,000

Wake up to the sunrise over the Atlantic from this private oceanfront retreat offering two separate residences, a sandy beach, and direct access from Highway to Ocean. This unique property offers a 3BD/3BA main residence plus a separate 1BD/1BA guest house, ideal for extended family, visiting friends, private home, or income producing estate. Enjoy a sandy beach, pool, two beachside tiki huts, observation pier, concrete boat ramp and rock jetties for tide protection, creating the ultimate setting for entertaining and waterfront living. Extensive upgrades include impact windows and doors, metal roof, A/C, stucco, paint, appliances and more. With abundant parking for cars, boats, trailers, toys and guests, there is room for everyone. Just minutes by boat to Alligator Lighthouse and nearby Caloosa Marina for fuel, ice, boat storage and food. A rare opportunity to own a true oceanfront Keys compound with space, privacy and a stunning view!

4 Beds ⋅ 4 Baths ⋅ 621270 MLS

Wake up to the sunrise over the Atlantic from this private oceanfront retreat offering two separate residences, a sandy beach, and direct access from Highway to Ocean. This unique property offers a 3BD/3BA main residence plus a separate 1BD/1BA guest house, ideal for extended family, visiting friends, private home, or income producing estate. Enjoy a sandy beach, pool, two beachside tiki huts, observation pier, concrete boat ramp and rock jetties for tide protection, creating the ultimate setting for entertaining and waterfront living. Extensive upgrades include impact windows and doors, metal roof, A/C, stucco, paint, appliances and more. With abundant parking for cars, boats, trailers, toys and guests, there is room for everyone. Just minutes by boat to Alligator Lighthouse and nearby Caloosa Marina for fuel, ice, boat storage and food. A rare opportunity to own a true oceanfront Keys compound with space, privacy and a stunning view!

75433 Overseas Hwy, Islamorada

$3,700,000

Private. Luxurious. Waterfront. Boater-focused. This is more than a home it is an opportunity to experience the Florida Keys exactly as they were meant to be enjoyed. This stunning 3-bedroom, 3-bath Waterfront - Pool home nestled within a private gated community and offers an exceptional combination of sophisticated upgrades and effortless ocean access. This property is designed with the discerning boater in mind, the property features a large, navigable basin offering easy access to the ocean or the Florida bay through one of the near by cuts making it an ideal home base for fishing, diving, cruising, and exploring the Florida Keys and beyond. With two boat lifts and a floating dock, your vessels are securely accommodated and ready for your next adventure. Inside, the home showcases beautiful luxury upgrades, thoughtfully designed for both elegant entertaining and comfortable island living. Expansive impact windows invite abundant natural light while providing peace of mind. As if this was not enough, this property has a roof top deck where you will have beautiful views of the sunrise sky in the morning and enjoy the sunset sky at night. Whether you're enjoying a quiet morning on the water, entertaining friends and family, or heading out for an offshore adventure, this exceptional property delivers the quintessential Islamorada lifestyle. Boat lift 1 -30,000# can accommodate up to apx. a 42 ft Center Console boat. Lift 2 20,000# can accommodate up to apx. a 36 ft. Center Console boat. There is also a floating dock for additional watercraft. Home was Originally built in 1987 Property appraiser shows Effective Year Built 2018.

3 Beds ⋅ 3 Baths ⋅ 621153 MLS

Private. Luxurious. Waterfront. Boater-focused. This is more than a home it is an opportunity to experience the Florida Keys exactly as they were meant to be enjoyed. This stunning 3-bedroom, 3-bath Waterfront - Pool home nestled within a private gated community and offers an exceptional combination of sophisticated upgrades and effortless ocean access. This property is designed with the discerning boater in mind, the property features a large, navigable basin offering easy access to the ocean or the Florida bay through one of the near by cuts making it an ideal home base for fishing, diving, cruising, and exploring the Florida Keys and beyond. With two boat lifts and a floating dock, your vessels are securely accommodated and ready for your next adventure. Inside, the home showcases beautiful luxury upgrades, thoughtfully designed for both elegant entertaining and comfortable island living. Expansive impact windows invite abundant natural light while providing peace of mind. As if this was not enough, this property has a roof top deck where you will have beautiful views of the sunrise sky in the morning and enjoy the sunset sky at night. Whether you're enjoying a quiet morning on the water, entertaining friends and family, or heading out for an offshore adventure, this exceptional property delivers the quintessential Islamorada lifestyle. Boat lift 1 -30,000# can accommodate up to apx. a 42 ft Center Console boat. Lift 2 20,000# can accommodate up to apx. a 36 ft. Center Console boat. There is also a floating dock for additional watercraft. Home was Originally built in 1987 Property appraiser shows Effective Year Built 2018.

313 North Dr, Islamorada

$6,195,000

Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

4 Beds ⋅ 5 Baths ⋅ 620986 MLS

Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

144 N Rolling Hill Rd, Islamorada

$10,000,000

Extraordinary opportunity to own one of the Florida Keys' most spectacular oceanfront residences. Set along a breathtaking stretch of pristine shoreline, this remarkable estate seamlessly blends exceptional architecture, sophisticated design and an unparalleled waterfront lifestyle. Set on nearly an acre with 100 feet of white-sand Atlantic Ocean frontage, this newly completed renovation by acclaimed D'Asign Source delivers exceptional design, craftsmanship and timeless elegance with breathtaking ocean views from virtually every room. This residence features 5 bedrooms, 4 full bathrooms and 1 half bath, a residential elevator, full-size tennis/pickleball court and spectacular infinity-edge pool with spa. The grand open-concept living space features custom shellstone flooring and seamless indoor-outdoor living. A stunning chef's kitchen is appointed with a complete suite of Miele appliances, including three ovens, two dishwashers, panel-ready refrigerator and freezer, built-in coffee maker and six-burner cooktop with integrated extractor. Additional highlights include a butler's pantry, dedicated laundry room and two expansive bonus rooms ideal for a gym or game room. The top floor offers a luxurious primary suite enhanced by cathedral ceilings, oceanfront terraces and spa-inspired bathroom along with two additional en suite guest rooms. Outdoor living is exceptional, with generous covered entertaining areas, a fully equipped summer kitchen and an infinity pool and spa that appear to merge with the endless turquoise waters of the Atlantic. The gated and fenced grounds provide privacy and include a two-car garage, car lift, whole-house generator and buried propane tank. With WEEKLY rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. This remarkable estate offers a combination of sophisticated luxury, resort-style amenities and unmatched beachfront living in Islamorada

5 Beds ⋅ 5 Baths ⋅ 620965 MLS

Extraordinary opportunity to own one of the Florida Keys' most spectacular oceanfront residences. Set along a breathtaking stretch of pristine shoreline, this remarkable estate seamlessly blends exceptional architecture, sophisticated design and an unparalleled waterfront lifestyle. Set on nearly an acre with 100 feet of white-sand Atlantic Ocean frontage, this newly completed renovation by acclaimed D'Asign Source delivers exceptional design, craftsmanship and timeless elegance with breathtaking ocean views from virtually every room. This residence features 5 bedrooms, 4 full bathrooms and 1 half bath, a residential elevator, full-size tennis/pickleball court and spectacular infinity-edge pool with spa. The grand open-concept living space features custom shellstone flooring and seamless indoor-outdoor living. A stunning chef's kitchen is appointed with a complete suite of Miele appliances, including three ovens, two dishwashers, panel-ready refrigerator and freezer, built-in coffee maker and six-burner cooktop with integrated extractor. Additional highlights include a butler's pantry, dedicated laundry room and two expansive bonus rooms ideal for a gym or game room. The top floor offers a luxurious primary suite enhanced by cathedral ceilings, oceanfront terraces and spa-inspired bathroom along with two additional en suite guest rooms. Outdoor living is exceptional, with generous covered entertaining areas, a fully equipped summer kitchen and an infinity pool and spa that appear to merge with the endless turquoise waters of the Atlantic. The gated and fenced grounds provide privacy and include a two-car garage, car lift, whole-house generator and buried propane tank. With WEEKLY rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. This remarkable estate offers a combination of sophisticated luxury, resort-style amenities and unmatched beachfront living in Islamorada

75751 Overseas Hwy, Islamorada

$780,000

Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, peaceful oceanfront community of just 10 townhomes, you'll have a beach, pool and your own slip for boat up to 30'. Spend the day on the water, relax by the pool or head up to the rooftop deck for ocean breezes & a peekaboo water view. There are four balconies - so you can enjoy some shade at any time of day. Although this seller never rented, the home is eligible for a coveted weekly rental license, giving a new owner the flexibility to enjoy it personally while also taking advantage of the strong Keys vacation rental market. The 2 bedroom, 2.5 bath townhome has a comfortable layout, with a private bath for each bedroom, a half bath on the main living level, and *straight interior* stairs rather than a spiral staircase. It's also refreshingly low maintenance, with concrete construction, a concrete roof, impact windows and doors, and an HOA that takes care of the grounds. Because this is a townhome rather than a condo, owners choose how much insurance to carry, and current insurance costs are surprisingly low. It's even in an X flood zone, so no flood insurance is required. Covered parking and an entry from underneath the home are two more practical touches that make coming and going easy, rain or shine. Trailer/boat storage is allowed under the home. The location works just as well by water as it does by land, with fantastic fishing and diving just steps from home and a great Old Highway location close to Founders Park, restaurants and everything you come to Islamorada to enjoy. Breezy and relaxed when you're here, with the ability to generate income when you're not. It's a rare and excellent combination.. good for your heart and your wallet.

2 Beds ⋅ 3 Baths ⋅ 620945 MLS

Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, peaceful oceanfront community of just 10 townhomes, you'll have a beach, pool and your own slip for boat up to 30'. Spend the day on the water, relax by the pool or head up to the rooftop deck for ocean breezes & a peekaboo water view. There are four balconies - so you can enjoy some shade at any time of day. Although this seller never rented, the home is eligible for a coveted weekly rental license, giving a new owner the flexibility to enjoy it personally while also taking advantage of the strong Keys vacation rental market. The 2 bedroom, 2.5 bath townhome has a comfortable layout, with a private bath for each bedroom, a half bath on the main living level, and *straight interior* stairs rather than a spiral staircase. It's also refreshingly low maintenance, with concrete construction, a concrete roof, impact windows and doors, and an HOA that takes care of the grounds. Because this is a townhome rather than a condo, owners choose how much insurance to carry, and current insurance costs are surprisingly low. It's even in an X flood zone, so no flood insurance is required. Covered parking and an entry from underneath the home are two more practical touches that make coming and going easy, rain or shine. Trailer/boat storage is allowed under the home. The location works just as well by water as it does by land, with fantastic fishing and diving just steps from home and a great Old Highway location close to Founders Park, restaurants and everything you come to Islamorada to enjoy. Breezy and relaxed when you're here, with the ability to generate income when you're not. It's a rare and excellent combination.. good for your heart and your wallet.

136 Aregood Ln, Islamorada

$4,750,000

Villa 1 offers one of the most coveted locations within the exclusive 22-villa community at The Islands of Islamorada. Ideally positioned as the closest oceanfront villa to the private marina, this exceptional residence enjoys some of the community's most impressive ocean views and an incredible connection to the water. 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 ⋅ 620933 MLS

Villa 1 offers one of the most coveted locations within the exclusive 22-villa community at The Islands of Islamorada. Ideally positioned as the closest oceanfront villa to the private marina, this exceptional residence enjoys some of the community's most impressive ocean views and an incredible connection to the water. 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 1, Islamorada

$439,000

Charming concrete bungalow in the heart of Islamorada! Move right into this beautifully updated 1BR/1BA retreat featuring fabulous ocean views from your private rooftop deck. Blending timeless Florida Keys charm with modern finishes, this home offers durable concrete construction with beautiful interior finishes, impact windows, an updated electrical panel, and parking for two vehicles. Relax under the covered Chickee Hut while enjoying spectacular Atlantic sunrises and unforgettable sunset skies. Community amenities include dock privileges, the Atlantic Ocean Jetty Area, a community Chickee Hut, and a low HOA fee of just $149/month, all conveniently located near Snake Creek Marina. Looking for a weekend getaway, vacation rental, or full-time island escape, this is your opportunity to experience the best of Florida Keys living.

1 Beds ⋅ 1 Baths ⋅ 620845 MLS

Charming concrete bungalow in the heart of Islamorada! Move right into this beautifully updated 1BR/1BA retreat featuring fabulous ocean views from your private rooftop deck. Blending timeless Florida Keys charm with modern finishes, this home offers durable concrete construction with beautiful interior finishes, impact windows, an updated electrical panel, and parking for two vehicles. Relax under the covered Chickee Hut while enjoying spectacular Atlantic sunrises and unforgettable sunset skies. Community amenities include dock privileges, the Atlantic Ocean Jetty Area, a community Chickee Hut, and a low HOA fee of just $149/month, all conveniently located near Snake Creek Marina. Looking for a weekend getaway, vacation rental, or full-time island escape, this is your opportunity to experience the best of Florida Keys living.

84961 Old Hwy Unit A1, Islamorada

$4,650,000

Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offering 70 feet of protected dockage, this property is a premier boating opportunity with quick access to the bay and ocean via Snake Creek Bridge. Designed to accommodate family and guests with ease, the oversized home features five spacious bedrooms, four-and-a-half baths, a garage, and an upstairs flex space with a private balcony overlooking the pool and wide canal. Timeless finishes include a charming foyer, rich hardwood flooring throughout, a dedicated office, game room complete with a custom built-in bar, and abundant natural light that enhances every level of the home. Built for both comfort and peace of mind, the residence is equipped with impact-rated doors and windows, a whole-home generator, and a propane tank, providing year-round reliability and resilience. Whether you're entertaining poolside, hosting extended family, or setting out for a day on the water, this exceptional waterfront residence embodies the relaxed luxury and boating lifestyle that define Islamorada.

5 Beds ⋅ 6 Baths ⋅ 620757 MLS

Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offering 70 feet of protected dockage, this property is a premier boating opportunity with quick access to the bay and ocean via Snake Creek Bridge. Designed to accommodate family and guests with ease, the oversized home features five spacious bedrooms, four-and-a-half baths, a garage, and an upstairs flex space with a private balcony overlooking the pool and wide canal. Timeless finishes include a charming foyer, rich hardwood flooring throughout, a dedicated office, game room complete with a custom built-in bar, and abundant natural light that enhances every level of the home. Built for both comfort and peace of mind, the residence is equipped with impact-rated doors and windows, a whole-home generator, and a propane tank, providing year-round reliability and resilience. Whether you're entertaining poolside, hosting extended family, or setting out for a day on the water, this exceptional waterfront residence embodies the relaxed luxury and boating lifestyle that define Islamorada.

109 Valencia Dr, Islamorada

$1,895,000

Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

4 Beds ⋅ 3 Baths ⋅ 620649 MLS

Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

87851 Old Hwy Unit P3, Islamorada

81801 Overseas Highway Unit 715, Islamorada

$549,500

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

1 Beds ⋅ 1 Baths ⋅ 620633 MLS

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 715, Islamorada

81801 Overseas Highway Unit 716, Islamorada

$549,500

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This double queen bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

1 Beds ⋅ 1 Baths ⋅ 620629 MLS

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This double queen bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 716, Islamorada

$3,050,000

Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathrooms with an open living floor plan. The main living level features three bedrooms and two bathrooms, complemented by a spacious living, dining, and kitchen area--ideal for entertaining and relaxed Keys living. The lower level includes two additional bedrooms and one bathroom, all above flood, perfect guest quarters with a full kitchen. Brand new exterior paint! Enjoy 75 feet of deep-water concrete dockage equipped with a 15,000 lb boat lift, providing excellent boating access. The home is solid concrete construction with a metal roof, fenced yard, and plenty of room for a pool. Port Antigua is known for its exceptional amenities, including one of the best private beaches in the Keys and a community boat ramp. With immediate access to Florida Bay and quick proximity to the Atlantic Ocean, this property offers the ultimate Florida Keys lifestyle--boating, water access, and island living at its finest.

5 Beds ⋅ 3 Baths ⋅ 620602 MLS

Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathrooms with an open living floor plan. The main living level features three bedrooms and two bathrooms, complemented by a spacious living, dining, and kitchen area--ideal for entertaining and relaxed Keys living. The lower level includes two additional bedrooms and one bathroom, all above flood, perfect guest quarters with a full kitchen. Brand new exterior paint! Enjoy 75 feet of deep-water concrete dockage equipped with a 15,000 lb boat lift, providing excellent boating access. The home is solid concrete construction with a metal roof, fenced yard, and plenty of room for a pool. Port Antigua is known for its exceptional amenities, including one of the best private beaches in the Keys and a community boat ramp. With immediate access to Florida Bay and quick proximity to the Atlantic Ocean, this property offers the ultimate Florida Keys lifestyle--boating, water access, and island living at its finest.

117 El Capitan Dr, Islamorada

$13,750,000

Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.

5 Beds ⋅ 7 Baths ⋅ 620590 MLS

Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.

19 Avacado St, Islamorada

$4,500,000

An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and quick access to both the Florida Bay and the Atlantic Ocean via Snake Creek. This extraordinary opportunity allows you to complete what was envisioned as one of the Florida Keys' most premier luxury estates. Elevated above flood on **100 feet of canal frontage**, this solid concrete home features a striking concrete roofline and nearly all impact-rated windows and doors already installed, providing an exceptional foundation for your dream home. Designed with **5,559 square feet of air-conditioned living space**, the residence offers an ideal blend of luxury and boating lifestyle. The first level includes **1,467 square feet** of living space, an oversized **897-square-foot garage**, and plans for an expansive entertainment area, fishing gear room, and direct waterfront access. The second level features **2,361 square feet** of living space plus over **1,100 square feet of covered porches**, with plans for three spacious guest suites, each with a private bath, a half bath, laundry room, chef's kitchen, and open-concept living area. The entire third floor is dedicated to the **1,731-square-foot primary retreat**, designed with ocean views, a spa-inspired bath, oversized custom closet, executive office, and private covered porch. An elevator shaft is already in place for easy access to every level. Plans also include a canal-front pool and cabana overlooking Snake Creek Bridge. With a concrete dock, 100 feet of waterfront, deep-water boating, and one of the Keys' finest locations, this property offers the rare opportunity to complete a truly remarkable custom estate while selecting every finish to reflect your own vision. Property is being sold as is. Some images are AI computer generated to show future potential.

3 Beds ⋅ 5 Baths ⋅ 620441 MLS

An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and quick access to both the Florida Bay and the Atlantic Ocean via Snake Creek. This extraordinary opportunity allows you to complete what was envisioned as one of the Florida Keys' most premier luxury estates. Elevated above flood on **100 feet of canal frontage**, this solid concrete home features a striking concrete roofline and nearly all impact-rated windows and doors already installed, providing an exceptional foundation for your dream home. Designed with **5,559 square feet of air-conditioned living space**, the residence offers an ideal blend of luxury and boating lifestyle. The first level includes **1,467 square feet** of living space, an oversized **897-square-foot garage**, and plans for an expansive entertainment area, fishing gear room, and direct waterfront access. The second level features **2,361 square feet** of living space plus over **1,100 square feet of covered porches**, with plans for three spacious guest suites, each with a private bath, a half bath, laundry room, chef's kitchen, and open-concept living area. The entire third floor is dedicated to the **1,731-square-foot primary retreat**, designed with ocean views, a spa-inspired bath, oversized custom closet, executive office, and private covered porch. An elevator shaft is already in place for easy access to every level. Plans also include a canal-front pool and cabana overlooking Snake Creek Bridge. With a concrete dock, 100 feet of waterfront, deep-water boating, and one of the Keys' finest locations, this property offers the rare opportunity to complete a truly remarkable custom estate while selecting every finish to reflect your own vision. Property is being sold as is. Some images are AI computer generated to show future potential.

155 Palo De Oro Dr, Islamorada

$29,000,000

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views. An arcaded hallway with a hand-tiled barrel-vaulted ceiling connects interiors featuring Italian finishes, exquisite marble details, five fireplaces, hand-painted ceiling frescoes, and a one-of-a-kind imported tile roof. Florentine quatrefoil windows, Juliette balconies, wrought-iron railings, copper rain gutters, and hand-carved marble corbels enhance the home's architectural character. The floor plan includes four bedrooms, with three guest suites on the main level and a private third-floor primary retreat featuring two fireplaces, an office, tea room, sitting room, custom walk-in closet, private laundry room, spa-inspired bath, and balconies overlooking the living spaces below. The chef's kitchen is appointed with Viking, Miele, U-Line, and Sub-Zero appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen with a Viking grill, refrigeration, ice maker, bar seating, and covered dining overlooking the pool, beach, and bay. Additional spaces include a formal dining room with a hand-painted ceiling fresco, wellness room, sauna, private theater with wet bar, and a billiards lounge with mahogany coffered ceilings and coconut wood flooring. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep-water dockage, white-sand beach, and crystal-clear waters provide immediate access to world-renowned fishing, diving, snorkeling, and boating. Additional features include an air-conditioned boat room, skiff ramp, 4,000+ SF collector's garage, elevator servicing all 3 levels, Control4 smart home integration, Sonos, and secure walled & gated grounds.

4 Beds ⋅ 6 Baths ⋅ 620394 MLS

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views. An arcaded hallway with a hand-tiled barrel-vaulted ceiling connects interiors featuring Italian finishes, exquisite marble details, five fireplaces, hand-painted ceiling frescoes, and a one-of-a-kind imported tile roof. Florentine quatrefoil windows, Juliette balconies, wrought-iron railings, copper rain gutters, and hand-carved marble corbels enhance the home's architectural character. The floor plan includes four bedrooms, with three guest suites on the main level and a private third-floor primary retreat featuring two fireplaces, an office, tea room, sitting room, custom walk-in closet, private laundry room, spa-inspired bath, and balconies overlooking the living spaces below. The chef's kitchen is appointed with Viking, Miele, U-Line, and Sub-Zero appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen with a Viking grill, refrigeration, ice maker, bar seating, and covered dining overlooking the pool, beach, and bay. Additional spaces include a formal dining room with a hand-painted ceiling fresco, wellness room, sauna, private theater with wet bar, and a billiards lounge with mahogany coffered ceilings and coconut wood flooring. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep-water dockage, white-sand beach, and crystal-clear waters provide immediate access to world-renowned fishing, diving, snorkeling, and boating. Additional features include an air-conditioned boat room, skiff ramp, 4,000+ SF collector's garage, elevator servicing all 3 levels, Control4 smart home integration, Sonos, and secure walled & gated grounds.

75090 Overseas Hwy, Islamorada

$599,000

Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. The main level features an open-concept floor plan with a spacious living area and kitchen, plus full bath, creating an inviting space for entertaining and everyday living. Upstairs, you'll find an expansive primary suite, a generously sized guest bedroom and full bathroom, and a thoughtfully finished loft accessed from the hallway that serves as an ideal bonus sleeping area or home office. Step outside and enjoy the exceptional amenities that make Executive Bay Club one of Islamorada's most sought-after waterfront communities. Residents have access to the newly expanded first-come, first-serve dockage, a bayfront beach area, unforgettable sunsets, and a new heated swimming pool complete with an updated pool deck, clubhouse and bath facilities, pickleball and tennis courts, kayak storage and 24/7 staffed gated entry. Whether you're searching for a full-time residence, vacation retreat, or investment opportunity, this welcoming townhouse offers the ideal blend of island charm to enjoy the Florida Keys lifestyle.

2 Beds ⋅ 2 Baths ⋅ 620393 MLS

Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. The main level features an open-concept floor plan with a spacious living area and kitchen, plus full bath, creating an inviting space for entertaining and everyday living. Upstairs, you'll find an expansive primary suite, a generously sized guest bedroom and full bathroom, and a thoughtfully finished loft accessed from the hallway that serves as an ideal bonus sleeping area or home office. Step outside and enjoy the exceptional amenities that make Executive Bay Club one of Islamorada's most sought-after waterfront communities. Residents have access to the newly expanded first-come, first-serve dockage, a bayfront beach area, unforgettable sunsets, and a new heated swimming pool complete with an updated pool deck, clubhouse and bath facilities, pickleball and tennis courts, kayak storage and 24/7 staffed gated entry. Whether you're searching for a full-time residence, vacation retreat, or investment opportunity, this welcoming townhouse offers the ideal blend of island charm to enjoy the Florida Keys lifestyle.

87200 Overseas Hwy Unit D3, Islamorada

74980 Overseas Highway Unit 3, Islamorada

$1,890,000

Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

5 Beds ⋅ 3 Baths ⋅ 620271 MLS

Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

74980 Overseas Highway Unit 3, Islamorada

88540 Overseas Hwy Unit 101 & Boat Slip 22, Islamorada

$1,100,000

Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND 24,000 lb. Boat Lift in desirable Futura Yacht Club! Located in the heart of Plantation Key in Islamorada, this is one of the most coveted boating locations in the Florida Keys with crystal clear water, spectacular nightly sunsets and easy boating access to both the bay and the ocean! This spacious condo is nicely updated inside and offers a private balcony overlooking the sports courts, grounds and gardens. Owners and renters alike enjoy the abundant community amenities, including an easy boat ramp, onsite boat/trailer storage, a huge pool with poolside club area, kayak storage, tennis and basketball courts and spacious grounds with shady picnic areas. After a day on the water, grab a cocktail and stroll over to the sandy beach area with sunset seating and shaded hammocks to enjoy spectacular Florida Keys sunsets! This first level condo allows for easy access via a single flight of nearby stairs or take the elevator to the lobby. Don't miss this opportunity and make sure you see the property video and 3D tour. Call today to arrange a private showing.

3 Beds ⋅ 2 Baths ⋅ 620148 MLS

Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND 24,000 lb. Boat Lift in desirable Futura Yacht Club! Located in the heart of Plantation Key in Islamorada, this is one of the most coveted boating locations in the Florida Keys with crystal clear water, spectacular nightly sunsets and easy boating access to both the bay and the ocean! This spacious condo is nicely updated inside and offers a private balcony overlooking the sports courts, grounds and gardens. Owners and renters alike enjoy the abundant community amenities, including an easy boat ramp, onsite boat/trailer storage, a huge pool with poolside club area, kayak storage, tennis and basketball courts and spacious grounds with shady picnic areas. After a day on the water, grab a cocktail and stroll over to the sandy beach area with sunset seating and shaded hammocks to enjoy spectacular Florida Keys sunsets! This first level condo allows for easy access via a single flight of nearby stairs or take the elevator to the lobby. Don't miss this opportunity and make sure you see the property video and 3D tour. Call today to arrange a private showing.

88540 Overseas Hwy Unit 101 & Boat Slip 22, Islamorada

81801 Overseas Highway Unit 637, Islamorada

$715,000

Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. Monthly condo insurance is $854 in addition to the monthly association fee.

1 Beds ⋅ 1 Baths ⋅ 619786 MLS

Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. Monthly condo insurance is $854 in addition to the monthly association fee.

81801 Overseas Highway Unit 637, Islamorada

$4,750,000

Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

4 Beds ⋅ 5 Baths ⋅ 619714 MLS

Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

44 W Plaza Del Lago, Islamorada

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