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$3,900,000
4Beds
4.5Baths
2,807Sqft
Key Largo, Florida, 33037, United States
Welcome to The Lookout, a premiere four-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in the heart of Key Largo. Centrally located to all that Key Largo has to offer, yet discreetly set within a private, gated community, this residence offers a rare balance of accessibility and seclusion.
Homes and Land
$3,900,000
48 E Playa Largo Boulevard
4Beds
4.5Baths
2,807Sqft
Key Largo, Florida, 33037, United States
Welcome to The Lookout, a premiere four-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in the heart of Key Largo. Centrally located to all that Key Largo has to offer, yet discreetly set within a private, gated community, this residence offers a rare balance of accessibility and seclusion. Built to the highest structural standards to withstand coastal conditions, the home reflects a commitment to longevity, performance, and refined design.The residence is offered fully furnished with a designer-grade interior package, delivering a cohesive, turnkey experience. Clean architectural lines, premium materials, and thoughtfully curated interiors define the living spaces, while expansive ocean-facing terraces extend the homes livability outdoors. Open-concept living and dining areas are designed for both everyday use and entertaining, with each bedroom suite offering privacy and comfort.Owners enjoy exclusive access to a private clubhouse, resort-style pool, and landscaped grounds. Directly across the street, Playa Largo Resort & Spa, Autograph Collection provides full access to world-class dining, spa services, beach amenities, and water-based activities, enhancing both lifestyle and rental appeal. The community is intentionally limited in scale, preserving a residential atmosphere while benefiting from resort infrastructure just moments away.A defining attribute of this offering is the flexibility of ownership and rental strategy. New owners may elect to participate in the Playa rental management program with full resort privileges or self-manage and rent independently, providing uncommon control over use and income. With nightly rentals permitted, this premier oceanfront residence is equally suited as a refined weekend retreat, a rental income opportunity, or a long-term hold in one of the Florida Keys most established resort communities. Quiet, secure, and impeccably positioned.
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Homes and Land
$3,900,000
48 E Playa Largo Boulevard
4Beds
4.5Baths
2,807Sqft
$3,900,000
Key Largo, Florida, 33037, United States
$4,500,000
4Beds
4.5Baths
3,756Sqft
Key Largo, Florida, 33037, United States
Mahogany Bay in Key Largo is comprised of 4 Balinese style homes located on almost 5 beautiful acres on the Florida Bay. This Bali inspired home commands privacy along with spectacular water and sunset views from the great room, gorgeous kitchen, large open terraces, and the primary suite with a private terrace. There are 2 additional guest suites.
Homes and Land
$4,500,000
101954 Overseas Highway
4Beds
4.5Baths
3,756Sqft
Key Largo, Florida, 33037, United States
Mahogany Bay in Key Largo is comprised of 4 Balinese style homes located on almost 5 beautiful acres on the Florida Bay. This Bali inspired home commands privacy along with spectacular water and sunset views from the great room, gorgeous kitchen, large open terraces, and the primary suite with a private terrace. There are 2 additional guest suites. The interior features an open floor plan with 9 ceilings, impact resistant doors and windows, high end stainless appliances, custom millwork, quartz countertops, marble and wood flooring, spa-like bathrooms, and 8 interior wood doors. This homes exterior features include a private heated pool with spa, covered area for parking, and additional poolside seating for entertaining, privacy landscaping, metal roofing, garage, and plenty of parking in the area behind the home. This special property also includes a separate one bedroom, one bath guest cottage complete with living area, kitchenette, and an expansive porch all appointed with the same design and custom finishes as the main house.
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Homes and Land
$4,500,000
101954 Overseas Highway
4Beds
4.5Baths
3,756Sqft
$4,500,000
Key Largo, Florida, 33037, United States
$10,900,000
6Beds
4.5Baths
4,394Sqft
Lower Matecumbe, Florida, 33036, United States
A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over 1/2 acre lot with panoramic water views from every room. Offering 220 linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge.
Homes and Land
$10,900,000
186 & 165 Bayview Drive
6Beds
4.5Baths
4,394Sqft
Lower Matecumbe, Florida, 33036, United States
A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over 1/2 acre lot with panoramic water views from every room. Offering 220 linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels included in this sale, opening options in the future for the fortunate owner that resides here. Completely renovated in 2020, the home presents a clean, contemporary aesthetic with Viking appliances, bespoke finishes, and a subtle, neutral palette inspired by the flowing surrounding turquoise waters. A custom saltwater pool equipped with both heater and chiller provides year-round enjoyment for everyone. This Safety Harbor residence delivers both elegance and function for the discerning boater or sunset lover. Impeccably maintained and move-in ready, it offers a rare combination of low-maintenance living, thoughtful design, quiet living and enduring appeal in the Florida Keys.Private showings available by appointment.
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Homes and Land
$10,900,000
186 & 165 Bayview Drive
6Beds
4.5Baths
4,394Sqft
$10,900,000
Lower Matecumbe, Florida, 33036, United States
$3,800,000
4Beds
4.5Baths
2,574Sqft
Upper Matecumbe Key Islamorada, Florida, 33036, United States
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios.
Homes and Land
$3,800,000
82779 Old Highway
4Beds
4.5Baths
2,574Sqft
Upper Matecumbe Key Islamorada, Florida, 33036, United States
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime.Some interior photos are from comparable villas within the property and not exact villa listed.
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Homes and Land
$3,800,000
82779 Old Highway
4Beds
4.5Baths
2,574Sqft
$3,800,000
Upper Matecumbe Key Islamorada, Florida, 33036, United States
$3,100,000
3Beds
3.5Baths
1,488Sqft
Lower Matecumbe, Florida, 33036, United States
Artfully updated canal-front pool home on beloved Sunset Drive! This delightful residence was recently remodeled from top to bottom by a local and renowned builder and features a bright open floor plan, modern kitchen with stainless steel appliances, and coastal-inspired finishes throughout. Bonus pre-firm 1BA/1BA downstairs.
Homes and Land
$3,100,000
114 Sunset Drive
3Beds
3.5Baths
1,488Sqft
Lower Matecumbe, Florida, 33036, United States
Artfully updated canal-front pool home on beloved Sunset Drive! This delightful residence was recently remodeled from top to bottom by a local and renowned builder and features a bright open floor plan, modern kitchen with stainless steel appliances, and coastal-inspired finishes throughout. Bonus pre-firm 1BA/1BA downstairs. The exterior offers a private pool, spacious lounging areas, and substantial dockage suitable for a large vessel, providing immediate access to open water. Clean lines, natural light, and thoughtful updates create a move-in-ready retreat to relax and absorb the peacefulness of island life. Dont miss this delightful waterfront offering in one of the Florida Keys most desirable boating locations!
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Homes and Land
$3,100,000
114 Sunset Drive
3Beds
3.5Baths
1,488Sqft
$3,100,000
Lower Matecumbe, Florida, 33036, United States
$6,490,000
5Beds
5.5Baths
5,456Sqft
Lower Matecumbe, Florida, 33036, United States
Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you.
Homes and Land
$6,490,000
137 Sapodilla Drive
5Beds
5.5Baths
5,456Sqft
Lower Matecumbe, Florida, 33036, United States
Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you.The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chefs kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views.The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.
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Homes and Land
$6,490,000
137 Sapodilla Drive
5Beds
5.5Baths
5,456Sqft
$6,490,000
Lower Matecumbe, Florida, 33036, United States
$2,890,000
3Beds
2Baths
1,400Sqft
Lower Matecumbe, Florida, 33036, United States
Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch, lower level covered patio, living room and 2 of the 3 bedrooms.Fully remodeled in 2021, this charming get-away has been entirely refreshed with new everything...
Homes and Land
$2,890,000
75055 Overseas Highway
3Beds
2Baths
1,400Sqft
Lower Matecumbe, Florida, 33036, United States
Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch, lower level covered patio, living room and 2 of the 3 bedrooms.Fully remodeled in 2021, this charming get-away has been entirely refreshed with new everything...including impact windows and doors, metal roof, flooring, new appliances, central air, pool equipment and electric gate. Furnishings and finishes reflect the coastal cottage style creating the epitome of relaxation and embodying the Florida Keys lifestyle.
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Homes and Land
$2,890,000
75055 Overseas Highway
3Beds
2Baths
1,400Sqft
$2,890,000
Lower Matecumbe, Florida, 33036, United States
$7,795,000
5Beds
5Baths
3,841Sqft
Plantation Key, Florida, 33070, United States
San Roc is a stunning, gated oceanfront estate set on 2.34 lush tropical acres with 130 feet of direct ocean frontage. This exceptional new-construction residence, completed in 2024, offers 3,841 square feet of elegant living space. Enter the property through a private gate and a winding, tree lined drive. The main home features four bedrooms, four bathrooms, and a separate guest ensuite.
Homes and Land
$7,795,000
89701 Old Highway
5Beds
5Baths
3,841Sqft
Plantation Key, Florida, 33070, United States
San Roc is a stunning, gated oceanfront estate set on 2.34 lush tropical acres with 130 feet of direct ocean frontage. This exceptional new-construction residence, completed in 2024, offers 3,841 square feet of elegant living space. Enter the property through a private gate and a winding, tree lined drive. The main home features four bedrooms, four bathrooms, and a separate guest ensuite.Inside, a chefs kitchen awaits, complete with Brazilian quartzite countertops and premium appliances. The open floor plan takes full advantage of panoramic ocean views, filling each room with natural light.Step outside to your private oasis, where a sparkling pool beckons, framed by gently swaying palms and an expansive terrace overlooking the water. The boat basin, separate dock and private channel provide deep-water dockage to this property. The outdoor area is a true extension of the homes refined indoor spaces. The estate is complete with an oversized two-car garage. San Roc stands out as a rare offering where every detail celebrates the ultimate in privacy, style, and oceanfront living.
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Homes and Land
$7,795,000
89701 Old Highway
5Beds
5Baths
3,841Sqft
$7,795,000
Plantation Key, Florida, 33070, United States
$3,995,000
5Beds
4Baths
4,014Sqft
Plantation Key, Florida, 33036, United States
This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.
Homes and Land
$3,995,000
87445 Old Highway
5Beds
4Baths
4,014Sqft
Plantation Key, Florida, 33036, United States
This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this residence offers ample space for family and guests. Enjoy stunning ocean views from various vantage points within the home, enhancing the comfort and breathtaking natural beauty. The observation dock provides a perfect spot for relaxation, while the saltwater pool equipped with heater/chiller, ensures year-round enjoyment. Added features are quartz countertops, top-of-the-line appliances , impact resistant windows ,and the Residential Estate zoning allows weekly vacation rentals with a high-income stream.This combination of amenities creates an inviting atmosphere that reflects the privacy and charm of the Florida Keys lifestyle.
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Homes and Land
$3,995,000
87445 Old Highway
5Beds
4Baths
4,014Sqft
$3,995,000
Plantation Key, Florida, 33036, United States
$3,095,000
4Beds
2Baths
2,426Sqft
Key West, Florida, 33040, United States
This is a rare find on the Riviera Canal in Key West.
Homes and Land
$3,095,000
3720 Flagler Avenue
4Beds
2Baths
2,426Sqft
Key West, Florida, 33040, United States
This is a rare find on the Riviera Canal in Key West. This tranquil oasis offers unparalleled waterfront experience in one of the most coveted locations in Key West where every day feels like a vacation! Newly built in 2016 to the highest hurricane proof standards, this one-of-a-kind four-bedroom, two-bath haven is more than just a home--its a boaters dream, a sunseekers paradise, and the ultimate in indoor-outdoor luxury living. Offered turn key!Imagine waking up each morning in the heart of this island gem, with 80 feet of wide canal frontage just outside your door, complete with a 20,000 lb boat lift and davit ready for your larger vessel. Whether youre setting sail for a day on the water or simply soaking up the tropical vibes, this home puts you right where the action is.The split floor plan gives everyone their own space to unwind, while the open-concept living area beckons you to gather and celebrate the good life. With wall-to-wall sliding glass impact doors and travertine floors throughout, your living space seamlessly merges with the outdoors, bringing in natural light and the gentle breezes. Step into your own private oasis! A sparkling pool, surrounded by meticulously maintained landscaping, is the perfect spot for a lazy afternoon dip. Prefer a sunset barbecue? Your covered outdoor dining and lounge area sits on sleek travertine floors, with plenty of space to relax rain or shine.The kitchen is a showstopper, featuring quartz countertops, custom cabinetry, and stainless-steel appliances, perfect for whipping up fresh seafood feasts or hosting cocktails at the bar with a view of the pool. The primary bedroom is the ultimate retreat, with its own seating area and French doors that open right onto the pool deck. Additional features include a whole-house Generac generator, impact and soundproof windows and doors throughout, and a gated circular driveway that offers complete privacy.
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Homes and Land
$3,095,000
3720 Flagler Avenue
4Beds
2Baths
2,426Sqft
$3,095,000
Key West, Florida, 33040, United States
$4,695,000
4Beds
4Baths
4,176Sqft
Shark Key, Florida, 33040, United States
Tucked behind swaying palms and lush tropical landscaping, this elegant waterfront estate captures the very best of Florida Keys living. From breathtaking sunset views to exceptional outdoor spaces, every moment here feels like a true escape.Whether you are relaxing on your private beach or entertaining poolside, the setting is unforgettable.
Homes and Land
$4,695,000
24 Cannon Royal Drive
4Beds
4Baths
4,176Sqft
Shark Key, Florida, 33040, United States
Tucked behind swaying palms and lush tropical landscaping, this elegant waterfront estate captures the very best of Florida Keys living. From breathtaking sunset views to exceptional outdoor spaces, every moment here feels like a true escape.Whether you are relaxing on your private beach or entertaining poolside, the setting is unforgettable. It is the kind of home that reminds you exactly why you chose island life.Inside, sun filled living spaces open to sweeping Gulf views and an abundance of natural light. The gourmet kitchen is beautifully appointed with custom cabinetry, high end appliances, and an oversized island designed for gathering, hosting, and everyday living.Upstairs, the primary suite is a retreat of its own, offering panoramic water views and a spacious walk in closet. Three additional bedrooms are located on the upper level, while a fifth bedroom and full bath on the main level provide flexibility for guests or extended stays.Designed for seamless indoor-outdoor living, the home flows effortlessly to a private deck, sparkling pool, and observation dock. It is a front row seat to some of the most spectacular sunsets in the Keys.Additional highlights include a copper patina roof, a three-car covered carport, full house generator, generous storage, and a wave runner lift.Located within the prestigious gated community of Shark Key, just minutes from Key West, residents enjoy resort style amenities including a clubhouse, inland swimming lagoon and beach, as well as pickleball and tennis courts.24 Cannon Royal Drive is more than a home. It is a lifestyle defined by privacy, beauty, and the magic of the Florida Keys.
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Homes and Land
$4,695,000
24 Cannon Royal Drive
4Beds
4Baths
4,176Sqft
$4,695,000
Shark Key, Florida, 33040, United States
$25,000,000
Key Haven, Florida, 33040, United States
Introducing Enchanted Island, an unparalleled private island located 1.5 miles from Key West accessible via its own private highway exit from US 1. This rare real estate jewel offers an exclusive escape like no other.Presently zoned for sub urban residential use, the island permits the construction of up to two homes.
Homes and Land
$25,000,000
1 Seppala Way
Key Haven, Florida, 33040, United States
Introducing Enchanted Island, an unparalleled private island located 1.5 miles from Key West accessible via its own private highway exit from US 1. This rare real estate jewel offers an exclusive escape like no other.Presently zoned for sub urban residential use, the island permits the construction of up to two homes. Elevated 15 feet to meet construction codes and with building permits already secured, Enchanted Island is posed for your development aspirations. Additionally, the seller has completed engineered architectural plans for a 7,437 SF home. For those with a vision grander in scale, the option of rezoning and securing permits for up to ten homes exists, providing endless possibilities for your imagination. Enchanted Island boasts all essential utilities, including a new 1000A 120/240V power service, underwater sewer and power lines, and AT&T fiber connectivity. With building permits in hand, your journey from blueprint to building can commence without delay.Spanning an impressive 4 acres, Enchanted Island offers both tranquility and unique features, such as a private ocean reef and partial dredging, ideal for potential boat dock installation. In addition to its private highway access, the island has a history with helicopter use, hinting at the potential for establishing a heliport to further enhance its exclusivity and convenience for the distinguished few who will call it home or their luxury getaway.Enchanted Island seamlessly combines isolation with connectivity, offering a lifestyle statement for the discerning few. This exotic haven envisioned for the elite seeking not just a residence but a statement of lifestyle, stands ready to fulfill visions of grandeur against the breathtaking backdrop of the Florida Keys.Seize the unparalleled opportunity to turn your dream of island living into your reality with Enchanted Island.
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