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$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
$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
$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
$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
$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
$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
$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
$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
$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
$3,995,000
4Beds
4Baths
2,669Sqft
Key Largo, Florida, 33037, United States
This resort-style oceanfront home is the perfect vacation home or primary residence, offering unparalleled views of the Atlantic Ocean along with a heated pool and hot tub, beach area with wood fire pit, propane tiki torches, pavilion, and deep water dockage with a boat lift. The spacious interior features 4 bedrooms and 4 bathrooms across three levels.
Homes and Land
$3,995,000
802 Bonito Lane
4Beds
4Baths
2,669Sqft
Key Largo, Florida, 33037, United States
This resort-style oceanfront home is the perfect vacation home or primary residence, offering unparalleled views of the Atlantic Ocean along with a heated pool and hot tub, beach area with wood fire pit, propane tiki torches, pavilion, and deep water dockage with a boat lift. The spacious interior features 4 bedrooms and 4 bathrooms across three levels. The main living area on the second floor includes high wood ceilings, panoramic ocean views, an oceanfront balcony, and a bedroom with an adjacent bathroom. The third floor is dedicated to the primary suite, complete with a private balcony for a birds-eye view. The ground level includes two additional bedrooms with en-suites and a large laundry room. Additional highlights include a garage for boating and dive gear, impact windows and doors, gated entry, paver driveway, and parking for multiple vehicles. Located at mile marker 95 in Key Largo, enjoy world-class fishing and diving right from your backyard.
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Homes and Land
$3,995,000
802 Bonito Lane
4Beds
4Baths
2,669Sqft
$3,995,000
Key Largo, Florida, 33037, United States
$4,695,000
3Beds
3Baths
1,973Sqft
Lower Matecumbe, Florida, 33036, United States
Near-new luxury home in coveted Toll Gate Shores, Islamorada, Florida. Near perfection, describes this newly constructed 3-bedroom, 3-bath residence offering single-level living with elevator access in the highly sought-after waterfront Keys community. Completed in 2024/2025 by renowned local contractor CBT Construction, the home blends modern luxury with a relaxed tropical elegance.
Homes and Land
$4,695,000
241 Tollgate Boulevard
3Beds
3Baths
1,973Sqft
Lower Matecumbe, Florida, 33036, United States
Near-new luxury home in coveted Toll Gate Shores, Islamorada, Florida. Near perfection, describes this newly constructed 3-bedroom, 3-bath residence offering single-level living with elevator access in the highly sought-after waterfront Keys community. Completed in 2024/2025 by renowned local contractor CBT Construction, the home blends modern luxury with a relaxed tropical elegance. The state-of-the-art kitchen is designed to impress as well as maintain functionality. The kitchen features quartz finishes, top-quality appliances, a professional gas range and oven, ice maker, and expansive cabinetry and counter space. This kitchen is ideal for entertaining, gathering, and everyday living especially if you have more than one chef in the house! A generous counter bar provides additional seating for guests and spectators alike. Three exceptionally spacious bedrooms create a comfortable retreat, with two offering ensuite baths, all complementing the homes gracious island-inspired design. The ground floor enclosure has approximately 900sq ft of additional useable space for enjoyment hobby and workshop and garage areas. Exact square footage not warranted.Boating enthusiasts will appreciate protected yacht dockage on Hurricane Creek, complete with a 15,000 lb boat lift and approximately 5-6 feet of controlled depth, depending on tide. Additional highlights include a swimming pool, whole-home generator, and private access to the owners neighborhood park. Owner occupied--advance notice is appreciated. Schedule your private showing today.
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Homes and Land
$4,695,000
241 Tollgate Boulevard
3Beds
3Baths
1,973Sqft
$4,695,000
Lower Matecumbe, Florida, 33036, United States
$2,800,000
3Beds
3Baths
2,049Sqft
Key West, Florida, 33040, United States
Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.
Homes and Land
$2,800,000
508 Grinnell Street
3Beds
3Baths
2,049Sqft
Key West, Florida, 33040, United States
Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.
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Homes and Land
$2,800,000
508 Grinnell Street
3Beds
3Baths
2,049Sqft
$2,800,000
Key West, Florida, 33040, United States
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