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ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this charming 1-bedroom, 1-bath trailer offers the perfect opportunity to enjoy the laid-back Florida Keys lifestyle. Ideally situated in the heart of Islamorada, this property offers a relaxed island atmosphere with the convenience of being just minutes from renowned waterfront restaurants, local breweries, boutique shopping, and the many attractions that make Islamorada so desirable. Step outside and enjoy the island breeze, or take advantage of the community's wonderful oceanfront amenities, including a chickee hut, oceanfront jetty, and dock privileges. Relax under the chickee hut while taking in beautiful sunrises and breathtaking sunsets over the water. Low monthly HOA fees of just $149 include common area and road maintenance. Don't miss this opportunity to own your own slice of paradise in the Sport Fishing Capital of the World and experience everything that makes the Florida Keys so special! YOU OWN THE LAND.

1 Beds ⋅ 1 Baths ⋅ 621872 MLS

ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this charming 1-bedroom, 1-bath trailer offers the perfect opportunity to enjoy the laid-back Florida Keys lifestyle. Ideally situated in the heart of Islamorada, this property offers a relaxed island atmosphere with the convenience of being just minutes from renowned waterfront restaurants, local breweries, boutique shopping, and the many attractions that make Islamorada so desirable. Step outside and enjoy the island breeze, or take advantage of the community's wonderful oceanfront amenities, including a chickee hut, oceanfront jetty, and dock privileges. Relax under the chickee hut while taking in beautiful sunrises and breathtaking sunsets over the water. Low monthly HOA fees of just $149 include common area and road maintenance. Don't miss this opportunity to own your own slice of paradise in the Sport Fishing Capital of the World and experience everything that makes the Florida Keys so special! YOU OWN THE LAND.

84961 Old Hwy Unit 28, 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

79901 Overseas Highway Unit 217, Islamorada

$399,000

Discover this 1 bedroom / 1 bath condo at The Palms of Islamorada, ideally located in the heart of Islamorada on Upper Matecumbe Key. Offering 827sf of living space, this condo features a spacious open porch, covered parking, and convenient kayak and paddleboard storage. The Palms is a gated oceanfront community situated directly on the Atlantic Ocean, with views of Alligator Lighthouse. Residents enjoy a variety of amenities, including a waterfront swimming pool, jacuzzi, tiki hut for entertaining and grilling, fitness facilities, and a community room. Conveniently located near Mile Marker 80, The Palms is adjacent to Lazy Days Restaurant and just minutes from local favorites such as Papa Joe's and Bud N' Mary's Marina. Nearby marinas offer boat storage options, while numerous restaurants, shops, and recreational activities are just a short distance away. Whether you're looking for a primary residence or a seasonal getaway, this condo offers a wonderful opportunity to enjoy the Florida Keys lifestyle in a central Islamorada location.

1 Beds ⋅ 1 Baths ⋅ 621774 MLS

Discover this 1 bedroom / 1 bath condo at The Palms of Islamorada, ideally located in the heart of Islamorada on Upper Matecumbe Key. Offering 827sf of living space, this condo features a spacious open porch, covered parking, and convenient kayak and paddleboard storage. The Palms is a gated oceanfront community situated directly on the Atlantic Ocean, with views of Alligator Lighthouse. Residents enjoy a variety of amenities, including a waterfront swimming pool, jacuzzi, tiki hut for entertaining and grilling, fitness facilities, and a community room. Conveniently located near Mile Marker 80, The Palms is adjacent to Lazy Days Restaurant and just minutes from local favorites such as Papa Joe's and Bud N' Mary's Marina. Nearby marinas offer boat storage options, while numerous restaurants, shops, and recreational activities are just a short distance away. Whether you're looking for a primary residence or a seasonal getaway, this condo offers a wonderful opportunity to enjoy the Florida Keys lifestyle in a central Islamorada location.

79901 Overseas Highway Unit 217, Islamorada

$23,500,000

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

$400,000

Opportunity awaits to bring your vision to life! This 14,300-square-foot parcel encompasses approximately one-third of an acre, with 130 feet of frontage and 110 feet of depth. Situated on the bayside of Plantation Key in the established High Point neighborhood, this oversized Florida Keys vacant land opportunity offers the space to envision your own island retreat. Partially cleared and fenced, the property is conveniently located near schools, restaurants, shopping, boating, fishing, and all that Islamorada has to offer. Preliminary communications with the Village of Islamorada Building and Planning Departments indicate that the parcel is buildable; however, no formal building approval or permits are currently in place. No protected species restrictions or conservation easements are currently known. Buyers are to independently verify all.

621733 MLS

Opportunity awaits to bring your vision to life! This 14,300-square-foot parcel encompasses approximately one-third of an acre, with 130 feet of frontage and 110 feet of depth. Situated on the bayside of Plantation Key in the established High Point neighborhood, this oversized Florida Keys vacant land opportunity offers the space to envision your own island retreat. Partially cleared and fenced, the property is conveniently located near schools, restaurants, shopping, boating, fishing, and all that Islamorada has to offer. Preliminary communications with the Village of Islamorada Building and Planning Departments indicate that the parcel is buildable; however, no formal building approval or permits are currently in place. No protected species restrictions or conservation easements are currently known. Buyers are to independently verify all.

High Point Rd, 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

$1,700,000

Beautiful 2BR/2.5BA home in Anglers Reef, Islamorada's upscale gated oceanfront community. Features a 31' deeded BOAT SLIP with direct Atlantic access and no bridges, making it ideal for boating and fishing enthusiasts. Offered turnkey furnished with hardwood floors, granite countertops, stainless steel appliances, impact windows and doors, 2 private carports, two bedroom balconies, a front porch, and a rear porch. Enjoy a private community beach, pool, and oceanfront marina. Approved for weekly vacation rentals, offering an excellent investment opportunity or the perfect Florida Keys retreat!

2 Beds ⋅ 3 Baths ⋅ 621627 MLS

Beautiful 2BR/2.5BA home in Anglers Reef, Islamorada's upscale gated oceanfront community. Features a 31' deeded BOAT SLIP with direct Atlantic access and no bridges, making it ideal for boating and fishing enthusiasts. Offered turnkey furnished with hardwood floors, granite countertops, stainless steel appliances, impact windows and doors, 2 private carports, two bedroom balconies, a front porch, and a rear porch. Enjoy a private community beach, pool, and oceanfront marina. Approved for weekly vacation rentals, offering an excellent investment opportunity or the perfect Florida Keys retreat!

133 Anglers Way, Islamorada

$735,000

Solid Concrete Home on Plantation Key! Live the Islamorada lifestyle from this solid concrete home in a desirable Plantation Key subdivision. The home is ground level and built above flood. It offers 4 bedrooms, 3 bathrooms, a comfortable living area, and a large dining room for entertaining family and friends. Out back, a spacious, fully fenced yard has plenty of room for a pool, a garden, or simply relaxing outdoors. Owners can use the neighborhood HOA park, its boat ramp for direct bay access, with the ocean a short run away and short term dockage. Founders Park is just minutes away, with a swimming pool, sandy beach, boat ramp, playground, dog park, and tennis and pickleball courts. Acclaimed restaurants, shopping, schools, and the hospital are all close by. This home puts you in the middle of everything Islamorada has to offer. Orange Lane is a great fit for investors, renovators, or buyers who want to build equity.

4 Beds ⋅ 3 Baths ⋅ 621604 MLS

Solid Concrete Home on Plantation Key! Live the Islamorada lifestyle from this solid concrete home in a desirable Plantation Key subdivision. The home is ground level and built above flood. It offers 4 bedrooms, 3 bathrooms, a comfortable living area, and a large dining room for entertaining family and friends. Out back, a spacious, fully fenced yard has plenty of room for a pool, a garden, or simply relaxing outdoors. Owners can use the neighborhood HOA park, its boat ramp for direct bay access, with the ocean a short run away and short term dockage. Founders Park is just minutes away, with a swimming pool, sandy beach, boat ramp, playground, dog park, and tennis and pickleball courts. Acclaimed restaurants, shopping, schools, and the hospital are all close by. This home puts you in the middle of everything Islamorada has to offer. Orange Lane is a great fit for investors, renovators, or buyers who want to build equity.

101 Orange Ln, 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

$2,195,000

Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.

3 Beds ⋅ 4 Baths ⋅ 621487 MLS

Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.

33 Pen, Islamorada

$760,000

Charming CBS home located in Plantation Key Colony, situated on a corner lot and in an X flood zone. Offering over 1,300sf of living space, this 2 bedroom / 2 bath home features a spacious, open floor plan ideal for everyday living and entertaining. The generous kitchen offers abundant cabinetry and counter space and flows seamlessly into the main living area. Both bathrooms have been tastefully updated, and the interior has been freshly painted. Tile flooring throughout, recessed lighting, coastal colors, and a metal roof add to the home's appeal. Outside, enjoy a fenced yard, room for a pool, and ample off-street parking. The neighborhood offers a homeowners park with a boat ramp, providing convenient water access to enjoy the Florida Keys lifestyle. Conveniently located close to schools, shopping, dining, and local amenities, this inviting home is ready to enjoy.

2 Beds ⋅ 2 Baths ⋅ 621446 MLS

Charming CBS home located in Plantation Key Colony, situated on a corner lot and in an X flood zone. Offering over 1,300sf of living space, this 2 bedroom / 2 bath home features a spacious, open floor plan ideal for everyday living and entertaining. The generous kitchen offers abundant cabinetry and counter space and flows seamlessly into the main living area. Both bathrooms have been tastefully updated, and the interior has been freshly painted. Tile flooring throughout, recessed lighting, coastal colors, and a metal roof add to the home's appeal. Outside, enjoy a fenced yard, room for a pool, and ample off-street parking. The neighborhood offers a homeowners park with a boat ramp, providing convenient water access to enjoy the Florida Keys lifestyle. Conveniently located close to schools, shopping, dining, and local amenities, this inviting home is ready to enjoy.

202 Hibiscus St, Islamorada

$1,495,000

Stunning new custom pool home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space. Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features a spacious open-concept layout ideal for both everyday living and entertaining. Soaring 10-foot vaulted ceilings and oversized 8-foot doors define the home's modern architectural style. Additional highlights include a two-car garage, swimming pool, low-maintenance turf, and quality construction that sets a new standard for homes in the area. Located in desirable downtown Islamorada, you're close to popular restaurants, shopping, a grocery store, and a beloved brewery. With new construction permits currently suspended in Islamorada, opportunities like this are becoming increasingly rare. Don't miss your chance to own one of the last newly built homes in this prime location - this property truly checks all the boxes.

4 Beds ⋅ 3 Baths ⋅ 621431 MLS

Stunning new custom pool home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space. Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features a spacious open-concept layout ideal for both everyday living and entertaining. Soaring 10-foot vaulted ceilings and oversized 8-foot doors define the home's modern architectural style. Additional highlights include a two-car garage, swimming pool, low-maintenance turf, and quality construction that sets a new standard for homes in the area. Located in desirable downtown Islamorada, you're close to popular restaurants, shopping, a grocery store, and a beloved brewery. With new construction permits currently suspended in Islamorada, opportunities like this are becoming increasingly rare. Don't miss your chance to own one of the last newly built homes in this prime location - this property truly checks all the boxes.

36 Park Rd, Islamorada

$3,500,000

A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada.

621407 MLS

A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada.

Overseas Highway, Islamorada

$1,199,999

Experience the Florida Keys lifestyle at Anglers Reef, Islamorada's upscale gated oceanfront community. This beautifully appointed 2 bedroom, 2.5 bath home features a covered carport & four inviting porches, perfect for enjoying the tropical surroundings. Inside, you'll find Brazilian cherry hardwood floors, a spacious kitchen with granite countertops, stainless steel appliances, two breakfast bars, & abundant cabinetry. Additional features include a durable metal roof & impact windows & doors. Vacation rentals are permitted, making this an excellent opportunity for both personal enjoyment & investment. The home has been part of a successful rental program for many years & enjoys an established following of returning guests. Anglers Reef offers resort style amenities including two sandy beaches, an oceanfront swimming pool, & a private marina directly on the Atlantic Ocean. Enjoy your own Islamorada vacation retreat while generating rental income when you're away. A rare opportunity to own in one of Islamorada's most desirable oceanfront communities. Schedule your private showing today!

2 Beds ⋅ 3 Baths ⋅ 621401 MLS

Experience the Florida Keys lifestyle at Anglers Reef, Islamorada's upscale gated oceanfront community. This beautifully appointed 2 bedroom, 2.5 bath home features a covered carport & four inviting porches, perfect for enjoying the tropical surroundings. Inside, you'll find Brazilian cherry hardwood floors, a spacious kitchen with granite countertops, stainless steel appliances, two breakfast bars, & abundant cabinetry. Additional features include a durable metal roof & impact windows & doors. Vacation rentals are permitted, making this an excellent opportunity for both personal enjoyment & investment. The home has been part of a successful rental program for many years & enjoys an established following of returning guests. Anglers Reef offers resort style amenities including two sandy beaches, an oceanfront swimming pool, & a private marina directly on the Atlantic Ocean. Enjoy your own Islamorada vacation retreat while generating rental income when you're away. A rare opportunity to own in one of Islamorada's most desirable oceanfront communities. Schedule your private showing today!

111 Anglers Way, Islamorada

$2,950,000

RARE OPPORTUNITY IN CORAL COVE! Welcome to Island Hopper, an award-winning tropical plantation-style home in one of Islamorada's most private gated communities. Set on an oversized double lot, this beautifully updated 4-bedroom, 3-bath home offers 3,550 sq. ft. of living space plus 1,200 sq. ft. of covered outdoor living. A spectacular wraparound porch, soaring windows, and abundant natural light capture the relaxed elegance of Keys living. The private top-floor primary suite features a walk-in closet, Jacuzzi tub, and adjoining office. Recent upgrades include impact windows and doors, four new A/C units, approximately 5,000 sq. ft. of new marble pavers, 7,500 sq. ft. of new turf, and lush tropical landscaping with mature orchids and privacy hedging. Enjoy the privacy of a dry-lot home with the benefits of waterfront living. Coral Cove's amenities include community boat dockage with water and power, fish-cleaning station, oceanfront pool, and tiki huts. Four covered parking spaces plus dedicated golf-cart parking complete the property. Ideally located in the heart of Islamorada, within walking distance of restaurants, shopping, and entertainment. With only 9 homes in Coral Cove, opportunities to own in this special community are exceptionally rare.

4 Beds ⋅ 3 Baths ⋅ 621398 MLS

RARE OPPORTUNITY IN CORAL COVE! Welcome to Island Hopper, an award-winning tropical plantation-style home in one of Islamorada's most private gated communities. Set on an oversized double lot, this beautifully updated 4-bedroom, 3-bath home offers 3,550 sq. ft. of living space plus 1,200 sq. ft. of covered outdoor living. A spectacular wraparound porch, soaring windows, and abundant natural light capture the relaxed elegance of Keys living. The private top-floor primary suite features a walk-in closet, Jacuzzi tub, and adjoining office. Recent upgrades include impact windows and doors, four new A/C units, approximately 5,000 sq. ft. of new marble pavers, 7,500 sq. ft. of new turf, and lush tropical landscaping with mature orchids and privacy hedging. Enjoy the privacy of a dry-lot home with the benefits of waterfront living. Coral Cove's amenities include community boat dockage with water and power, fish-cleaning station, oceanfront pool, and tiki huts. Four covered parking spaces plus dedicated golf-cart parking complete the property. Ideally located in the heart of Islamorada, within walking distance of restaurants, shopping, and entertainment. With only 9 homes in Coral Cove, opportunities to own in this special community are exceptionally rare.

80902 Old Hwy, Islamorada

$2,790,000

Wake up to endless ocean views and the effortless simplicity of life on the beach. This pristine three-bedroom, two-bath oceanfront retreat offers a private, gated setting with a pool, spacious covered patio, and beautiful beach and ocean views from the upper porch, lower-level patio, living area, and two of the three bedrooms. Fully remodeled in 2021, this charming getaway was thoughtfully refreshed throughout, including impact windows and doors, a metal roof, new flooring, appliances, central air conditioning, pool equipment, and an electric entry gate. Coastal cottage-inspired furnishings and finishes create a casual, welcoming atmosphere designed for effortless island living. From mornings overlooking the ocean to afternoons by the pool, this beautifully maintained home captures the relaxed simplicity of the Florida Keys lifestyle.

3 Beds ⋅ 2 Baths ⋅ 621394 MLS

Wake up to endless ocean views and the effortless simplicity of life on the beach. This pristine three-bedroom, two-bath oceanfront retreat offers a private, gated setting with a pool, spacious covered patio, and beautiful beach and ocean views from the upper porch, lower-level patio, living area, and two of the three bedrooms. Fully remodeled in 2021, this charming getaway was thoughtfully refreshed throughout, including impact windows and doors, a metal roof, new flooring, appliances, central air conditioning, pool equipment, and an electric entry gate. Coastal cottage-inspired furnishings and finishes create a casual, welcoming atmosphere designed for effortless island living. From mornings overlooking the ocean to afternoons by the pool, this beautifully maintained home captures the relaxed simplicity of the Florida Keys lifestyle.

75055 Overseas Hwy, 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

$3,999,999

Welcome to your Port Antigua coastal contemporary home. 101 Buena Vista Court is a beautiful canal front home blending distinctive architectural character with the comforts of modern island living. Thoughtfully designed to take full advantage of its tropical surroundings, this home offers beautiful views, generous outdoor living spaces, and a rooftop terrace where you can settle in as the sun begins to set, every evening a painted sky, reminding you why you've ended up in the Florida Keys. Inside, the home offers an effortless combination of space, light and functionality. An elevator provides convenient access between levels, a dedicated workshop and ample space for all of your gear to make everyday island living easy. For the boating enthusiast, the property offers two boat lifts and the kind of waterfront access that makes spontaneous days on the water part of the lifestyle. Port Antigua is a neighborhood where everyone still waves at each other, the community is welcoming and it's always a joy to return home here. Having access to the private beach with grills, tiki huts, and a private boat ramp are just some of the many reasons people love to be in Port Antigua

4 Beds ⋅ 4 Baths ⋅ 621350 MLS

Welcome to your Port Antigua coastal contemporary home. 101 Buena Vista Court is a beautiful canal front home blending distinctive architectural character with the comforts of modern island living. Thoughtfully designed to take full advantage of its tropical surroundings, this home offers beautiful views, generous outdoor living spaces, and a rooftop terrace where you can settle in as the sun begins to set, every evening a painted sky, reminding you why you've ended up in the Florida Keys. Inside, the home offers an effortless combination of space, light and functionality. An elevator provides convenient access between levels, a dedicated workshop and ample space for all of your gear to make everyday island living easy. For the boating enthusiast, the property offers two boat lifts and the kind of waterfront access that makes spontaneous days on the water part of the lifestyle. Port Antigua is a neighborhood where everyone still waves at each other, the community is welcoming and it's always a joy to return home here. Having access to the private beach with grills, tiki huts, and a private boat ramp are just some of the many reasons people love to be in Port Antigua

101 Buena Vista Ct, Islamorada

$1,950,000

Perfect fishing retreat/home. A boater's and angler's paradise in Venetian Shores! This 3-bedroom, 2-bath home at 161 Palermo Drive offers deep water and immediate access to the bay and ocean. Enjoy an open floor plan and screened porch, plus concrete construction, a concrete roof, impact windows & doors. A lift makes carrying heavy items upstairs easier. A spacious downstairs rec room with storage, covered parking, and a separate A/C shed for your fishing gear make it easy to enjoy life on the water.

3 Beds ⋅ 2 Baths ⋅ 621340 MLS

Perfect fishing retreat/home. A boater's and angler's paradise in Venetian Shores! This 3-bedroom, 2-bath home at 161 Palermo Drive offers deep water and immediate access to the bay and ocean. Enjoy an open floor plan and screened porch, plus concrete construction, a concrete roof, impact windows & doors. A lift makes carrying heavy items upstairs easier. A spacious downstairs rec room with storage, covered parking, and a separate A/C shed for your fishing gear make it easy to enjoy life on the water.

161 Palermo Dr, Islamorada

$699,000

Looking for a private 3-bedroom condo with dockage that feels like home? Coral Harbour Club's distinctive open-sided building design provides windows on multiple exposures--including in the kitchen and in every bedroom and bath--filling the home with natural light and tropical views. Shared community boat slips and an excellent on-site marina make boating part of everyday life, with fuel and ice available on the property. Head out for fishing, diving, sandbar days or exploring the Florida Keys, then return to your peaceful retreat. Unlike most waterfront condos squeezed onto a narrow strip of shoreline, Coral Harbour Club spans approximately 14 lush acres with mature landscaping and remarkably spacious, private grounds. Two pets any size are welcome, with shaded walks and access to the Atlantic. Nearby covered parking provides convenient access to the building's central elevator up to the third floor, which is shared with only four other residences. Inside, this spacious split-plan condo has been thoughtfully updated for timeless Keys living. The kitchen features a classic Tuscan-style renovation with newer appliances, while both baths have been updated in elegant island style. One bedroom currently serves as a custom built-in office and can easily convert back. Additional features include new central A/C, full-size washer and dryer, generous closets and additional hall storage. A large wrap-around screened porch extends from both side bedrooms across the living area--perfect for morning coffee or unwinding after a day on the water. Impact windows and doors offer peace of mind, while accordion shutters protect the porch while you're away. Amenities include an oceanfront pool, expansive clubhouse, saltwater lagoon with sandy beach, tennis, pickleball and bocce ball courts, and extensive waterfront grounds with shady seating spots for enjoying shimmering sunrises and ever-changing ocean views.

3 Beds ⋅ 2 Baths ⋅ 621332 MLS

Looking for a private 3-bedroom condo with dockage that feels like home? Coral Harbour Club's distinctive open-sided building design provides windows on multiple exposures--including in the kitchen and in every bedroom and bath--filling the home with natural light and tropical views. Shared community boat slips and an excellent on-site marina make boating part of everyday life, with fuel and ice available on the property. Head out for fishing, diving, sandbar days or exploring the Florida Keys, then return to your peaceful retreat. Unlike most waterfront condos squeezed onto a narrow strip of shoreline, Coral Harbour Club spans approximately 14 lush acres with mature landscaping and remarkably spacious, private grounds. Two pets any size are welcome, with shaded walks and access to the Atlantic. Nearby covered parking provides convenient access to the building's central elevator up to the third floor, which is shared with only four other residences. Inside, this spacious split-plan condo has been thoughtfully updated for timeless Keys living. The kitchen features a classic Tuscan-style renovation with newer appliances, while both baths have been updated in elegant island style. One bedroom currently serves as a custom built-in office and can easily convert back. Additional features include new central A/C, full-size washer and dryer, generous closets and additional hall storage. A large wrap-around screened porch extends from both side bedrooms across the living area--perfect for morning coffee or unwinding after a day on the water. Impact windows and doors offer peace of mind, while accordion shutters protect the porch while you're away. Amenities include an oceanfront pool, expansive clubhouse, saltwater lagoon with sandy beach, tennis, pickleball and bocce ball courts, and extensive waterfront grounds with shady seating spots for enjoying shimmering sunrises and ever-changing ocean views.

88181 Old Hwy Unit APT G31, Islamorada

81250 Overseas Highway Unit 5, Islamorada

$2,290,000

Only sophistication and class represented in Islamorada's most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off it's manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maid's quarters with more amazing views from the private balcony. If amenities are what you're after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

4 Beds ⋅ 3 Baths ⋅ 621329 MLS

Only sophistication and class represented in Islamorada's most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off it's manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maid's quarters with more amazing views from the private balcony. If amenities are what you're after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

81250 Overseas Highway Unit 5, Islamorada

$3,900,000

Rare opportunity in downtown Islamorada. This is a development dream property on three quarter of an acre with six transient units,one market rate unit plus a commercial restaurant. Lots of options for redevelopment from restaurant with employee housing to a small boutique hotel with its own eatery. License for more than 200 seats with indoor and outdoor dining and plenty of parking ,opportunities like this in the heart of Islamorada are not available often. This is a must see and won't last .

7 Beds ⋅ 7 Baths ⋅ 621298 MLS

Rare opportunity in downtown Islamorada. This is a development dream property on three quarter of an acre with six transient units,one market rate unit plus a commercial restaurant. Lots of options for redevelopment from restaurant with employee housing to a small boutique hotel with its own eatery. License for more than 200 seats with indoor and outdoor dining and plenty of parking ,opportunities like this in the heart of Islamorada are not available often. This is a must see and won't last .

80939 Overseas Hwy, 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

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