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

4 Beds ⋅ 6 Baths ⋅ 620394 MLS

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

75090 Overseas Hwy, Islamorada

74980 Overseas Highway Unit 3, Islamorada

$1,890,000

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

5 Beds ⋅ 3 Baths ⋅ 620271 MLS

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

74980 Overseas Highway Unit 3, Islamorada

$7,950,000

Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boater's paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning station, this home is perfectly appointed for waterfront living. Easy ocean access through the nearby Channel 5 Bridge adds to its appeal for avid anglers and adventure seekers alike. Inside, the home features eight spacious bedrooms, each with its own ensuite bath, plus two additional half baths for convenience. The master suite is a private sanctuary with a spa-inspired bath, while the open layout showcases spectacular water views through impact windows and sliding glass doors. An elevator ensures effortless access to all levels, and the wraparound balcony invites you to savor unobstructed panoramas. The gourmet kitchen, complete with high-end stainless steel appliances and gas cooktop, is a chef's delight, complemented by an outdoor kitchen for alfresco entertaining. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

8 Beds ⋅ 10 Baths ⋅ 613653 MLS

Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boater's paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning station, this home is perfectly appointed for waterfront living. Easy ocean access through the nearby Channel 5 Bridge adds to its appeal for avid anglers and adventure seekers alike. Inside, the home features eight spacious bedrooms, each with its own ensuite bath, plus two additional half baths for convenience. The master suite is a private sanctuary with a spa-inspired bath, while the open layout showcases spectacular water views through impact windows and sliding glass doors. An elevator ensures effortless access to all levels, and the wraparound balcony invites you to savor unobstructed panoramas. The gourmet kitchen, complete with high-end stainless steel appliances and gas cooktop, is a chef's delight, complemented by an outdoor kitchen for alfresco entertaining. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

162 Bayview Dr, Islamorada

$10,750,000

Commanding 170 feet of private Florida Bay frontage, and situated on over and acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors providing vast screened porched both upstairs and down. The kitchen anchors the home with gorgeous views and function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amenities continue with a lagoon-style pool, putting green, and ample deepwater dockage with boat lift with Bay to Ocean access in minutes via Channels 2 or 5, offering effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

4 Beds ⋅ 4 Baths ⋅ 616886 MLS

Commanding 170 feet of private Florida Bay frontage, and situated on over and acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors providing vast screened porched both upstairs and down. The kitchen anchors the home with gorgeous views and function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amenities continue with a lagoon-style pool, putting green, and ample deepwater dockage with boat lift with Bay to Ocean access in minutes via Channels 2 or 5, offering effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

75280 Overseas Hwy, Islamorada

$3,100,000

74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence, and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. The existing structure features expansive wraparound windows framing sweeping Atlantic views, plus a top-floor penthouse suite suited for owner occupancy, executive housing, or premium rental use (subject to approvals). The building configuration can also accommodate a rooftop helipad. Commercial Fishing zoning allows for uses such as a destination restaurant, seafood market, marine outfitter, charter or backcountry fishing headquarters, marina-support retail, or other enterprises aligned with the working waterfront. This is a high-visibility, commercial platform where housing, marine access, and US-1 frontage intersect to create compelling long-term value.

3 Beds ⋅ 3 Baths ⋅ 618699 MLS

74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence, and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. The existing structure features expansive wraparound windows framing sweeping Atlantic views, plus a top-floor penthouse suite suited for owner occupancy, executive housing, or premium rental use (subject to approvals). The building configuration can also accommodate a rooftop helipad. Commercial Fishing zoning allows for uses such as a destination restaurant, seafood market, marine outfitter, charter or backcountry fishing headquarters, marina-support retail, or other enterprises aligned with the working waterfront. This is a high-visibility, commercial platform where housing, marine access, and US-1 frontage intersect to create compelling long-term value.

74560 Overseas Hwy, Islamorada

$2,740,000

'Turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of Islamorada' Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully renovated 3-bedroom, 3.5-bath concrete residence delivers the ultimate Florida Keys lifestyle--where luxury, durability, and world-class boating converge. Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. Designed for serious boaters, the property boasts 90 feet of deepwater dockage with immediate access to both the bay and the Atlantic Ocean--no bridges, no delays, just open water within minutes. Inside, the home is completely turnkey, with updated finishes and a seamless indoor-outdoor flow ideal for entertaining or extended stays. Expansive balconies and a large outdoor patio overlook the wide canal, creating a private waterfront setting perfect for sunset dining or relaxing after a day on the water. The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles -- an uncommon convenience in this area. What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle that is seldom available in a single property. Whether you're seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals.

3 Beds ⋅ 4 Baths ⋅ 616500 MLS

'Turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of Islamorada' Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully renovated 3-bedroom, 3.5-bath concrete residence delivers the ultimate Florida Keys lifestyle--where luxury, durability, and world-class boating converge. Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. Designed for serious boaters, the property boasts 90 feet of deepwater dockage with immediate access to both the bay and the Atlantic Ocean--no bridges, no delays, just open water within minutes. Inside, the home is completely turnkey, with updated finishes and a seamless indoor-outdoor flow ideal for entertaining or extended stays. Expansive balconies and a large outdoor patio overlook the wide canal, creating a private waterfront setting perfect for sunset dining or relaxing after a day on the water. The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles -- an uncommon convenience in this area. What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle that is seldom available in a single property. Whether you're seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals.

122 Court Contessa, Islamorada

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