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Beach Day Every Day! Experience true beachfront living in Islamorada with sweeping Atlantic Ocean views, spectacular sunrises, and a sandy beach right in your backyard. This 6-bedroom, 4-bath home on Lower Matecumbe Key offers a relaxed coastal lifestyle with indoor and outdoor living areas designed to capture the ocean views. The recently remodeled upper-level main living area features a custom kitchen, an updated primary ensuite bath, and impact glass doors opening onto an expansive oceanfront terrace. The ground level provides additional living and entertaining spaces with direct access to the beach. An additional 30' x 20' canal-front parcel is included in the sale. Situated along Sea Oats Beach, a mile-long sea turtle nesting beach, the property is surrounded by the natural beauty of the Florida Keys. Nearby shallow grass flats are renowned for catch-and-release fishing of bonefish and tarpon. Whether enjoyed as a private coastal retreat or a gathering place for family and friends, this distinctive property offers a rare opportunity to own direct Atlantic beachfront in Islamorada.

6 Beds ⋅ 4 Baths ⋅ 622056 MLS

Beach Day Every Day! Experience true beachfront living in Islamorada with sweeping Atlantic Ocean views, spectacular sunrises, and a sandy beach right in your backyard. This 6-bedroom, 4-bath home on Lower Matecumbe Key offers a relaxed coastal lifestyle with indoor and outdoor living areas designed to capture the ocean views. The recently remodeled upper-level main living area features a custom kitchen, an updated primary ensuite bath, and impact glass doors opening onto an expansive oceanfront terrace. The ground level provides additional living and entertaining spaces with direct access to the beach. An additional 30' x 20' canal-front parcel is included in the sale. Situated along Sea Oats Beach, a mile-long sea turtle nesting beach, the property is surrounded by the natural beauty of the Florida Keys. Nearby shallow grass flats are renowned for catch-and-release fishing of bonefish and tarpon. Whether enjoyed as a private coastal retreat or a gathering place for family and friends, this distinctive property offers a rare opportunity to own direct Atlantic beachfront in Islamorada.

74051 Overseas Hwy, Islamorada

$10,950,000

Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

6 Beds ⋅ 8 Baths ⋅ 620680 MLS

Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

77350 Overseas Hwy, Islamorada

$6,150,000

Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the property's thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

6 Beds ⋅ 7 Baths ⋅ 620190 MLS

Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the property's thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

194 Buttonwood Ln, 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

$15,950,000

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants. Agents Welcome

6 Beds ⋅ 8 Baths ⋅ 618816 MLS

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants. Agents Welcome

20 Avacado St, Islamorada

$18,499,000

The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand porte-cochère, the single-level main residence unfolds with soaring ceilings, white oak floors and 12-foot retractable glass walls that dissolve the boundary between interior and oceanfront living. At its center, a chef's kitchen pairs a cascading Calacatta marble island with Thermador appliances and a walk-in pantry, opening seamlessly to expansive living and dining spaces. The main residence includes four bedrooms and six full baths, with an impressive primary suite featuring a fireplace, dual walk-in closets, safe room and spa bath with steam shower. Additional suites offer en suite baths, private balconies and ocean views. A detached two-bedroom, two-bath guest residence brings the estate to six bedrooms while preserving privacy between owners and guests, with substantial grounds offering extraordinary flexibility for the future. Outside, the property assumes the scale of a private resort. Two resort-style pools with spas and sun decks are joined by a summer kitchen, alfresco dining and multiple waterfront terraces. A fitness center with sauna, soundproof theater and golf simulator complete the lifestyle offering. For the yachtsman, the protected deepwater basin accommodates substantial vessels with convenient direct Atlantic access. Built with an uncompromising focus on quality, security and enduring construction, The Oasis is more than an oceanfront residence. It is a legacy-scale Florida Keys estate offering the increasingly rare combination of acreage, significant shoreline, protected deepwater dockage, multiple residences and complete privacy within one extraordinary property.

6 Beds ⋅ 8 Baths ⋅ 615643 MLS

The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand porte-cochère, the single-level main residence unfolds with soaring ceilings, white oak floors and 12-foot retractable glass walls that dissolve the boundary between interior and oceanfront living. At its center, a chef's kitchen pairs a cascading Calacatta marble island with Thermador appliances and a walk-in pantry, opening seamlessly to expansive living and dining spaces. The main residence includes four bedrooms and six full baths, with an impressive primary suite featuring a fireplace, dual walk-in closets, safe room and spa bath with steam shower. Additional suites offer en suite baths, private balconies and ocean views. A detached two-bedroom, two-bath guest residence brings the estate to six bedrooms while preserving privacy between owners and guests, with substantial grounds offering extraordinary flexibility for the future. Outside, the property assumes the scale of a private resort. Two resort-style pools with spas and sun decks are joined by a summer kitchen, alfresco dining and multiple waterfront terraces. A fitness center with sauna, soundproof theater and golf simulator complete the lifestyle offering. For the yachtsman, the protected deepwater basin accommodates substantial vessels with convenient direct Atlantic access. Built with an uncompromising focus on quality, security and enduring construction, The Oasis is more than an oceanfront residence. It is a legacy-scale Florida Keys estate offering the increasingly rare combination of acreage, significant shoreline, protected deepwater dockage, multiple residences and complete privacy within one extraordinary property.

87429 Old Hwy, Islamorada

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