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Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

9 Beds ⋅ 11 Baths ⋅ 621766 MLS

Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

16 Avacado St, 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

79901 Overseas Highway Unit 410, Islamorada

$695,000

Located in the heart of Islamorada, this 2 bedroom, 2 bath condo at The Palms of Islamorada offers beautiful Atlantic Ocean views and a spacious covered porch accessible from both the living room and primary bedroom. The primary suite features an en suite bathroom, while the covered porch provides an inviting outdoor space to enjoy the ocean breeze. Residents can enjoy a variety of resort style amenities within this gated oceanfront community, including a waterfront swimming pool, jacuzzi, tiki hut, fitness facilities, a community room, and covered parking. Situated on Upper Matecumbe Key near Mile Marker 80, The Palms is conveniently located near local favorites such as Lazy Days Restaurant, Papa Joe's, and Bud N' Mary's Marina, along with numerous other dining, shopping, and recreational options. A great opportunity for a primary residence or seasonal getaway in a central Islamorada location.

2 Beds ⋅ 2 Baths ⋅ 621648 MLS

Located in the heart of Islamorada, this 2 bedroom, 2 bath condo at The Palms of Islamorada offers beautiful Atlantic Ocean views and a spacious covered porch accessible from both the living room and primary bedroom. The primary suite features an en suite bathroom, while the covered porch provides an inviting outdoor space to enjoy the ocean breeze. Residents can enjoy a variety of resort style amenities within this gated oceanfront community, including a waterfront swimming pool, jacuzzi, tiki hut, fitness facilities, a community room, and covered parking. Situated on Upper Matecumbe Key near Mile Marker 80, The Palms is conveniently located near local favorites such as Lazy Days Restaurant, Papa Joe's, and Bud N' Mary's Marina, along with numerous other dining, shopping, and recreational options. A great opportunity for a primary residence or seasonal getaway in a central Islamorada location.

79901 Overseas Highway Unit 410, Islamorada

$7,400,000

Discover an extraordinary oceanfront retreat in the Florida Keys, where 1.38 acres of lush tropical grounds, 150 feet of private sandy beachfront, and sweeping Atlantic Ocean views create an exceptional setting for island living. Designed to embrace its spectacular surroundings, this 4,770-square-foot estate offers five bedrooms and five-and-a-half baths, including separate guest quarters for added privacy. Soaring 30-foot ceilings and expansive windows fill the interiors with natural light while showcasing breathtaking ocean views. Elegant furnishings and thoughtfully appointed living spaces complement the home's sophisticated yet relaxed coastal atmosphere. Offered fully furnished and turnkey, the property is ready for immediate enjoyment. Outdoors, a resort-style infinity-edge pool and spa overlook the turquoise Atlantic waters, creating a seamless connection between luxury living and the natural beauty of the Keys. The expansive private beach invites endless days of kayaking, fishing, swimming, or simply relaxing beneath the palms. A spacious two-car garage adds convenience to this exceptional property. With zoning that permits weekly rentals, the estate also presents an attractive opportunity for those seeking a luxury vacation retreat with income-producing potential. Whether envisioned as a private family compound, an unforgettable vacation escape, or a full-time residence, this remarkable estate captures the essence of Florida Keys living--privacy, natural beauty, and effortless oceanfront luxury.

5 Beds ⋅ 6 Baths ⋅ 621646 MLS

Discover an extraordinary oceanfront retreat in the Florida Keys, where 1.38 acres of lush tropical grounds, 150 feet of private sandy beachfront, and sweeping Atlantic Ocean views create an exceptional setting for island living. Designed to embrace its spectacular surroundings, this 4,770-square-foot estate offers five bedrooms and five-and-a-half baths, including separate guest quarters for added privacy. Soaring 30-foot ceilings and expansive windows fill the interiors with natural light while showcasing breathtaking ocean views. Elegant furnishings and thoughtfully appointed living spaces complement the home's sophisticated yet relaxed coastal atmosphere. Offered fully furnished and turnkey, the property is ready for immediate enjoyment. Outdoors, a resort-style infinity-edge pool and spa overlook the turquoise Atlantic waters, creating a seamless connection between luxury living and the natural beauty of the Keys. The expansive private beach invites endless days of kayaking, fishing, swimming, or simply relaxing beneath the palms. A spacious two-car garage adds convenience to this exceptional property. With zoning that permits weekly rentals, the estate also presents an attractive opportunity for those seeking a luxury vacation retreat with income-producing potential. Whether envisioned as a private family compound, an unforgettable vacation escape, or a full-time residence, this remarkable estate captures the essence of Florida Keys living--privacy, natural beauty, and effortless oceanfront luxury.

75931 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

$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

$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

$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

$649,000

Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of beach frontage and a 525' fishing pier. This beautiful one-bedroom King suite, with additional sleeper sofa in the living room and private screened balcony, overlooks the garden and waterfall. This is a luxury, income-producing property. Nightly rentals are allowed, with onsite management, an owner's closet, and owner's use of up to 28 days. The resort offers a 24-hour shuttle, valet parking, concierge service, 5-star fine dining, ballroom, conference room, a spa, fitness center, beach, pools, dock, tiki bars, 9-hole par 3 golf course, Pickle Ball courts, lighted tennis courts, lush gardens, bike path, fishing, diving, snorkeling, water sports and Camp Cheeca for children.

1 Beds ⋅ 1 Baths ⋅ 620677 MLS

Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of beach frontage and a 525' fishing pier. This beautiful one-bedroom King suite, with additional sleeper sofa in the living room and private screened balcony, overlooks the garden and waterfall. This is a luxury, income-producing property. Nightly rentals are allowed, with onsite management, an owner's closet, and owner's use of up to 28 days. The resort offers a 24-hour shuttle, valet parking, concierge service, 5-star fine dining, ballroom, conference room, a spa, fitness center, beach, pools, dock, tiki bars, 9-hole par 3 golf course, Pickle Ball courts, lighted tennis courts, lush gardens, bike path, fishing, diving, snorkeling, water sports and Camp Cheeca for children.

81801 Old Hwy Unit 754, 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

$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

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

$3,800,000

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for 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 ⋅ 619187 MLS

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

82779 Old Hwy Unit 15, Islamorada

$4,000,000

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

4 Beds ⋅ 5 Baths ⋅ 619186 MLS

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

82779 Old Hwy Unit 8, Islamorada

$4,000,000

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

4 Beds ⋅ 5 Baths ⋅ 619185 MLS

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

82779 Old Hwy Unit 7, Islamorada

$14,990,000

Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590 square feet of interior living space & 1,736 square feet of exterior living, with an expansive 230-foot dock. Designed for seamless indoor-outdoor living, the home features a dramatic great room with 23-foot ceilings, panoramic Atlantic exposure, and expansive covered terraces with summer kitchen and outdoor dining areas. A 65-foot heated lagoon-style pool with swim-up bar and fire-pit lounge creates a resort-caliber setting. The chef's kitchen is appointed with Sub-Zero, Wolf, and Thermador appliances. Additional highlights include dual primary suites, private orchid garden, lounge & recreation room, elevator, Sonos surround sound, impact windows and doors, metal roof, double-height garage, water-sports storage room and a full home generator. The essence of beachfront living in Islamorada, combining impressive scale and ultimate privacy. ***A contiguous 0.7-acre lot with development rights for an ancillary building with upstairs storage is available separately.

6 Beds ⋅ 9 Baths ⋅ 618911 MLS

Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590 square feet of interior living space & 1,736 square feet of exterior living, with an expansive 230-foot dock. Designed for seamless indoor-outdoor living, the home features a dramatic great room with 23-foot ceilings, panoramic Atlantic exposure, and expansive covered terraces with summer kitchen and outdoor dining areas. A 65-foot heated lagoon-style pool with swim-up bar and fire-pit lounge creates a resort-caliber setting. The chef's kitchen is appointed with Sub-Zero, Wolf, and Thermador appliances. Additional highlights include dual primary suites, private orchid garden, lounge & recreation room, elevator, Sonos surround sound, impact windows and doors, metal roof, double-height garage, water-sports storage room and a full home generator. The essence of beachfront living in Islamorada, combining impressive scale and ultimate privacy. ***A contiguous 0.7-acre lot with development rights for an ancillary building with upstairs storage is available separately.

88351 Old Hwy, Islamorada

$4,500,000

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chef's kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys' most sought-after locations.

4 Beds ⋅ 4 Baths ⋅ 614893 MLS

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chef's kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys' most sought-after locations.

75761 Overseas Hwy, Islamorada

$5,999,999

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

5 Beds ⋅ 6 Baths ⋅ 618481 MLS

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

137 Sapodilla Dr, Islamorada

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