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81906 Overseas Hwy Unit 2, Islamorada
$2,495,000
3 Beds ⋅ 4 Baths ⋅ 617838 MLS
Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, all stainless-steel Bosch appliances, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear--ideal for entertaining or unwinding in complete privacy, while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can hold boats up to 5,000 lbs. Adding to its appeal, 7-day rentals are permitted, making this property a rare and superior investment opportunity in one of Islamorada's most walkable and desirable locations. Ideal for a full-time residence, island getaway, or income-producing asset, this home offers an exceptional blend of luxury, lifestyle, and flexibility. Coral Cove is located in an X flood zone, providing additional peace of mind.

81906 Overseas Hwy Unit 2, Islamorada

11890 1st Ave Unit 2, Marathon
$2,495,000
5 Beds ⋅ 4 Baths ⋅ 618204 MLS
Welcome to The Tides at Vaca Cut #2, a beautifully designed 5-bedroom, 4-bathroom waterfront retreat in one of the Florida Keys' most desirable luxury communities. Offering 2,607 square feet of living space, this newer construction residence (2020) was thoughtfully built and designed by D'Asign Source, a leader in Florida Keys luxury architecture and interiors. Furnished with refined coastal style, the home blends upscale design with relaxed island living. The spacious open-concept living area opens seamlessly to a private pool and hot tub, creating an exceptional outdoor entertainment space framed by sweeping views of the Vaca Cut. Whether enjoying a sunset soak or hosting guests, the outdoor living experience here is second to none. Built with longevity and performance in mind, the home features concrete block construction, impact windows and doors, a metal roof, and double-stacked washers and dryers, making it exceptionally well-suited for high-demand vacation rental use. Boaters will appreciate 36 feet of dockage with immediate access to both the Atlantic Ocean and the Gulf of America, while the constant boat traffic through the cut provides some of the best boat-watching in the Middle Keys. Located in a proven luxury complex with strong rental demand, this turnkey property offers outstanding income potential along with an elevated waterfront lifestyle. Luxury design, prime dockage, and resort-style outdoor living—The Tides at Vaca Cut #2 is an exceptional opportunity to own in one of Marathon's premier waterfront developments.

11890 1st Ave Unit 2, Marathon

515 Caribbean Dr, Key Largo
$2,494,000
5 Beds ⋅ 3 Baths ⋅ 621052 MLS
Waterfront Boater's Paradise in Premier Port Largo Welcome to 515 Caribbean Drive, an exceptional waterfront property in sought-after Port Largo, one of the Upper Keys' premier boating neighborhoods. This solid CBS home, built in 1993, offers 2,748 sq. ft. of living space, 5 bedrooms, 3 baths, serious boating infrastructure, and direct open-ocean access through deep, wide canals. The home features custom cabinetry in the kitchen and baths, a 2019 metal roof, and a 13,000-pound boat lift with functional davits. But the true showstopper is downstairs: an extraordinary 3,144-square-foot climate-controlled garage, offering rare and highly versatile space for boats, vehicles, water toys, equipment, storage, or a workshop. Set on a 12,500-square-foot lot with 100 feet of seawall, this property is designed for the ultimate Keys lifestyle. Deep, wide canals provide an exceptional launch point for boating, fishing, diving, and exploring the Florida Keys and beyond. The location is equally compelling--approximately one hour from Miami, steps from Key Largo Park and Jacobs Aquatic Center, and minutes from excellent restaurants, shopping, and everyday conveniences. For the serious boater or anyone seeking an exceptional waterfront lifestyle, 515 Caribbean Drive offers a rare combination of open-ocean access, substantial climate-controlled garage space, 100 feet of seawall, and outstanding boating infrastructure in one of the Upper Keys' most desirable neighborhoods. Seller financing available with 20% down, 6% interest rate, 5 year balloon!

515 Caribbean Dr, Key Largo

815 39th St, Marathon
$2,490,000
4 Beds ⋅ 4 Baths ⋅ 621438 MLS
Welcome to Emerald Flats, an exclusive gated waterfront community in the heart of Marathon, where sophisticated coastal design and the Florida Keys lifestyle come together effortlessly. Designed & Built by D'Asign Source, this beautifully furnished 4-bedroom, 4-bath residence was completed in 2025 and offers 2,805 square feet of refined living space, thoughtfully designed for both relaxed everyday living and memorable entertaining. High ceilings, abundant natural light, impact-rated windows and doors, and a metal roof complement the home's fresh, modern construction. The interiors are light, airy, and beautifully curated in an elevated coastal palette. At the heart of the home, the designer kitchen pairs quartz countertops, KitchenAid stainless steel appliances, crisp white cabinetry, statement lighting, and an oversized waterfall-edge island with generous seating. A separate bar and entertaining area adds another layer of functionality, while the open-concept layout flows seamlessly into the dining and living spaces. Expansive glass doors invite the outdoors in and open to spacious covered balconies overlooking the Gulf, creating an exceptional setting for morning coffee, sunset cocktails, or simply enjoying the tropical surroundings. The bedrooms are equally inviting, with private balcony access in select rooms and beautifully appointed baths featuring quartz surfaces, glass-enclosed showers, and custom tile details. Boating is an effortless part of the lifestyle with Boat Slip #29 included, measuring approximately 45 feet long by 14.75 feet wide, providing convenient private docking just moments from home. Fully furnished and move-in ready, this exceptional Emerald Flats residence offers the perfect blend of luxury, waterfront living, modern comfort, and easy access to everything that makes Marathon so special. Bring your suitcases, your boat, and start living the Keys lifestyle from day one.

815 39th St, Marathon

114 Sunset Dr, Islamorada
$2,490,000
3 Beds ⋅ 4 Baths ⋅ 618633 MLS
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. Don't miss this delightful waterfront offering in one of the Florida Keys' most desirable boating locations!

114 Sunset Dr, Islamorada

81250 Overseas Highway Unit 2, Islamorada
$2,485,000
3 Beds ⋅ 3 Baths ⋅ 620704 MLS
Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket. This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms, and a tranquil porch ideal for enjoying sunset skies. The top floor is reserved for the expansive master suite, complete with a private balcony and sweeping waterfront views. Tarpon Flats offers an amenity-rich lifestyle tailored to the discerning buyer. Enjoy a waterfront pool and gazebo, private beachfront access, generous dockage for your skiff, a charming greenhouse, and a tennis court with shaded seating for guests. Adding to the ease of ownership, the community provides a full-time concierge service and an on-site handyman, ensuring both comfort and convenience year-round. Sophistication, privacy, and natural beauty converge in this exceptional Islamorada retreat--come discover what makes Tarpon Flats truly one of a kind.

81250 Overseas Highway Unit 2, Islamorada

1212 Olivia St, Key West
$2,475,000
3 Beds ⋅ 2 Baths ⋅ 621462 MLS
Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peaceful neighborhood setting. This is truly a gem waiting to become your tropical island home!

1212 Olivia St, Key West

31473 Warner Rd, Big Pine
$2,450,000
3 Beds ⋅ 4 Baths ⋅ 616722 MLS
Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3BD/4BA pool home offers panoramic water views from every angle, setting the stage for endless sunrises, sunsets, and starry nights. Designed with sophistication and comfort in mind, each bedroom is an ensuite, ensuring privacy and convenience for family and guests. Beyond its beauty, this property is one of the rare few in Monroe County allowing nightly vacation rentals, boasting a highly successful rental history for those seeking both personal enjoyment and income opportunity. Every detail has been thoughtfully curated, impact windows and doors, corian countertops and two on-demand water heaters reflect quality and peace of mind. The boating enthusiast will appreciate one of the few marked channel systems leading directly to the Gulf of Mexico with the Atlantic Ocean just minutes away. Utilize the 220 sq ft extended dock for your vessel to some the best fishing, diving and boating in the continental U.S. Whether lounging poolside, entertaining on the spacious decks or heading out on the water this property offers an unmatched Keys experience. Rare, refined and ready for your investment this is open-water living at its finest.

31473 Warner Rd, Big Pine

154 S Indies Dr, Duck Key
$2,444,000
2 Beds ⋅ 2 Baths ⋅ 618772 MLS
Rare opportunity to secure a prime waterfront homesite on highly desirable Duck Key. This is presenting the perfect canvas to design and build a custom island retreat exactly to your vision. Even better, the property is ROGO exempt, meaning no waiting for a new building permit -- a verified build right is already in place (letter on file). Boaters will appreciate the 82 feet of dockage, deep water dockage and exceptionally quick ocean access. Two davits that are 5,500 lbs each one and a turner on one of them. Center Island is a prime location for privacy on Duck Key. Navigate under the Seaview Bridge and head out through the Headpins for fast access to open water, or take the main channel route for larger sportfishing vessels. Enjoy all the lifestyle perks Duck Key is known for, including nearby dining at Hawks Cay Resort, a welcoming island community. that is golf cart friendly. Fly into Marathon airport with your own plane or Million Air and then drive 15 minutes to your island oasis. Whether you're planning a full-time residence or luxury vacation escape, this is your chance to build your dream home in one of the Florida Keys' most sought-after boating enclaves.

154 S Indies Dr, Duck Key

1511 17th Ter, Key West
$2,434,000
3 Beds ⋅ 4 Baths ⋅ 620092 MLS
Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

1511 17th Ter, Key West

312 E Caribbean Dr, Summerland
$2,400,000
3 Beds ⋅ 2 Baths ⋅ 621795 MLS
OPEN WATER VIEWS. ENDLESS POSSIBILITIES. YOUR SUMMERLAND KEY WATERFRONT RETREAT. Some properties are all about the location - and this is one of them. Set along the open water in sought-after Summerland Key, this well-maintained 3-bedroom, 2-bath concrete home offers incredible unobstructed views, easy boating access, and the opportunity to create your own vision of Florida Keys living. Outside, the open-water setting takes center stage, with expansive views that bring the beauty of the Florida Keys into everyday life. The concrete construction offers a solid foundation, while the fenced property and electric entry gate provide added convenience. From the covered screened balcony upstairs, you can soak in the beauty and catch spectacular sunset views. The existing interior retains its original character, providing a wonderful starting point for buyers ready to reimagine the space and make it their own. Whether your dream is a modern coastal retreat, a relaxed waterfront getaway, or a personal island escape, the possibilities are here. For boaters, waterfront living is about more than a view - it's about getting out on the water and enjoying everything the Keys have to offer. Here, the setting provides the backdrop for days spent exploring, fishing, lobstering, and returning home to spectacular open-water scenery. Straight access to the Atlantic and Gulf waters. Opportunities to secure an open-water property in Summerland Key and transform it to suit your own style are increasingly appealing. Bring your vision, embrace the location, and create something special in the Florida Keys. The views are already here. The next chapter is yours to create.

312 E Caribbean Dr, Summerland

1320 Eliza St, Key West
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 621742 MLS
Welcome to 1320 Eliza Street, a beautiful historic Key West home filled with Old World charm and character. Once serving as a local schoolhouse, this unique property sits on a stunning, tropically landscaped corner lot in a quiet neighborhood, offering the perfect combination of history and privacy in Old Town, Key West. Featuring four (4) bedrooms, two (2) full bathrooms, and two (2) half bathrooms, this home offers plenty of space for family and guests, both indoors and out. A brand-new roof was recently installed, and the home has just been tented, providing added peace of mind. The main residence offers generous living spaces that open beautifully to the lush tropical gardens surrounding the home. The spacious living room flows directly onto a covered porch, allowing you to enjoy the wonderful Key West weather year-round. The chef's kitchen is perfect for preparing everything from a gourmet dinner to a casual meal with family and friends. The first-floor primary bedroom offers plenty of room for a king-size bed, along with a spacious walk-in closet. The second guest bedroom features its own en-suite bathroom and private front porch, giving guests their own special place to relax and enjoy the Key West lifestyle. Upstairs, you'll find a third bedroom along with an oversized walk-in storage area and ample closet space. Step outside and enjoy your own private tropical retreat. Beautiful gardens surround the heated and chilled swimming pool, creating a wonderful setting for entertaining or simply relaxing in the sunshine. Tucked away in the back corner of the property, the separate pool house offers additional privacy and flexibility, making it perfect for guests, a home office, or a quiet getaway. Complete with a half bathroom and outdoor shower, it offers what we like to call a true Key West bathroom! This home is a must see! Schedule your private showing today!

1320 Eliza St, Key West

3206 Riviera Dr, Key West
$2,399,000
3 Beds ⋅ 4 Baths ⋅ 620879 MLS
Waterfront Home in Key West- 60 feet of water frontage, no homes across the canal and a fully gated lot, with your boat behind the house and downtown Key West minutes away. A wall of impact sliding glass doors opens the main living area to the screened patio, the newly renovated pool and the canal beyond. The kitchen has a large center island, premium cabinetry and a dining area that looks out over the pool to the water. Outside is set up for real use: an outdoor kitchen, an outdoor bathroom, shell stone limestone walkways and landscaped grounds. Three bedrooms, two of them en suite, and four full baths. A whole-home generator, two-zone air conditioning, a dedicated laundry room and covered parking. Canal control depth is approx. 3 feet, with approx. 12 feet of bridge clearance at low tide. Move-in ready. Call to see 3206 Riviera Drive in person.

3206 Riviera Dr, Key West

171 Ave D, Marathon
$2,395,000
4 Beds ⋅ 3 Baths ⋅ 621168 MLS
New construction waterfront living in the heart of Coco Plum. This beautifully designed 4-bedroom, 3-bath residence combines modern coastal style, exceptional outdoor living, and direct boating access in one of Marathon's most desirable waterfront neighborhoods. Thoughtfully positioned to take advantage of the setting, the home offers expansive open-water views from nearly every room and a bright, open-concept layout designed for both everyday living and entertaining. The main living level features a spacious living and dining area surrounded by natural light and water views, along with two guest bedrooms and a full bath. Upstairs, two generously sized primary suites each feature private en-suite baths and elevated panoramic views, creating peaceful private retreats above the water. Outdoor living is a true highlight, with three covered terraces spanning both levels, a large resort-style pool, and a convenient poolside prep station with sink and storage. Whether hosting guests, relaxing by the pool, or enjoying a quiet morning overlooking the water, the home is designed to embrace the Florida Keys lifestyle. Boaters will appreciate approximately 50 feet of deep-water dockage with quick ocean access, along with a fish-cleaning station, bait freezer, and covered parking for added convenience. Ideally located near Coco Plum Beach and just minutes from Marathon's dining, shopping, and attractions, this newly constructed waterfront residence offers an exceptional combination of modern comfort, boating access, privacy, and island living, perfect as a full-time residence, vacation retreat, or investment property.

171 Ave D, Marathon

211 S Anglers Dr, Marathon
$2,395,000
4 Beds ⋅ 3 Baths ⋅ 621014 MLS
Fantastic opportunity in Marathon's desirable Sombrero Beach area! Built in 2020, this beautifully designed 4-bedroom, 3-bath waterfront pool home offers 2,464 sq. ft. of comfortable living space and 100ft of dockage for ultimate enjoyment of boating, outdoor living and the easy, island atmosphere you come to the Keys for! Fully furnished and thoughtfully appointed - the open kitchen, dining and living area create an easy gathering space for family and friends, while spacious waterfront balconies on both levels invite you outside to enjoy the views and tropical breezes. On this level you also have a guest bedroom, full bath and separate laundry room for convenience. On the top floor, an ample primary suite offers an en-suite bath, walk in closet & covered balcony. Just down the hall there are 2 more sizable guest bedrooms and a spacious hall bath. Downstairs, the covered entertainment area extends the living space outdoors--perfect for relaxing after a day on the water, entertaining around the pool or simply enjoying life at a slower pace. Store your water toys fishing & boating accessories securely in the garage for easy access. The 10,000sqft lot allows for plenty of parking etc. For the boater, 100 feet of composite dockage along a serene canal provides direct access to open water. And when the beach is calling, beautiful sandy Sombrero Beach is just a short walk away. Central Marathon location is close to shopping, dining, attractions & more. Whether you're searching for a full-time Keys home, a vacation retreat or an investment property, this custom home offers the flexibility to enjoy it your way. Currently operating as an active weekly vacation rental, offering the added ease & opportunity for income when you're not here enjoying it yourself. Come experience the beauty of ocean life - the easy pace, boating and beach days that make living in the heart of the Florida Keys so special.

211 S Anglers Dr, Marathon

319 Grinnell St, Key West
$2,395,000
3 Beds ⋅ 2 Baths ⋅ 618819 MLS
This Income Producing property with future rentals scheduled, 319 Grinnell Street is a captivating residence in the heart of Key West's Historic Seaport, where charm and character abound. This beautifully framed Key West-style home reflects the rich tapestry of the area's history, showcasing classic architecture with inviting porches and intricate details that honor the past. Nestled among a collection of historic homes, 319 Grinnell Street offers a serene escape while remaining close to the vibrant pulse of the seaport. The Historic Seaport is a treasure trove of maritime heritage, featuring streets lined with art galleries, eclectic shops, and gourmet dining options. This lively district, once the center of the island's shipping trade, now celebrates Key West's legacy through its well-preserved structures and vibrant community life. Owning 319 Grinnell Street means immersing yourself in a lifestyle rich with culture and history. Enjoy leisurely strolls along the quaint streets, where the scent of jasmine and the sounds of laughter fill the air. This home is not just a residence; it's an invitation to embrace the unique spirit of Key West, making it a perfect sanctuary for those who value both tradition and modern living. Experience the allure of 319 Grinnell Street, where historic charm meets contemporary comfort in the heart of the enchanting Historic Seaport. Professional Vacation Rental Management is available for this property. Call for a showing today.

319 Grinnell St, Key West

818 39th St, Marathon
$2,390,000
5 Beds ⋅ 4 Baths ⋅ 621439 MLS
Welcome to Emerald Flats, a gated waterfront enclave in the heart of Marathon where refined coastal design meets the Florida Keys lifestyle. Designed & Built by D'Asign Source, this beautifully furnished 5-bedroom, 4-bath residence was completed in 2025 and offers 2,565 square feet of thoughtfully designed living space, with high ceilings, an open-concept layout, impact-rated windows and doors, and a metal roof. Elevated on concrete pilings, the home is designed for both style and durability while creating generous covered space beneath the residence. Inside, the light-filled living areas showcase a sophisticated coastal aesthetic with seamless flow between the kitchen, dining, and gathering spaces. The kitchen is a true centerpiece, featuring quartz countertops, KitchenAid stainless steel appliances, crisp white cabinetry, a striking waterfall-edge island, and generous seating and prep space. Expansive glass doors open to covered balconies, extending the living space outdoors, while a separate bar and entertainment area adds another polished touch for hosting family and friends. Outdoor living is equally impressive, with a private heated pool, tropical landscaping, expansive paver areas, and multiple covered spaces ideal for relaxing or entertaining. Boaters will appreciate the included Boat Slip #30, reported to measure approximately 45 feet long by 14.75 feet wide, offering convenient private docking within the Emerald Flats Marina community. The slip is separately identified by Monroe County as a marina condominium boat-slip parcel. Fully furnished and move-in ready, this home offers an exceptional combination of luxury, boating access, modern construction, and effortless island living in one of Marathon's desirable waterfront communities.

818 39th St, Marathon

1701 Ashby St, Key West
$2,380,000
4 Beds ⋅ 4 Baths ⋅ 621969 MLS
Step inside this beautifully renovated concrete residence, ideally situated in Midtown West, one of Key West's best-kept secrets. Just a quick bike ride from downtown restaurants, live music, and attractions, this fully fenced corner sanctuary has it all. Midtown West offers a relaxed neighborhood atmosphere, where friendly faces & leisurely evening strolls are part of everyday life. Just four blocks away are beaches, the White Street Pier, playgrounds, pickleball/tennis & the popular weekend Artisan Market. With a new roof, impact-rated windows and doors, and an exceptional price per square foot, this home delivers an impressive combination of location, style, value, and uncompromising structural integrity. Spanning an impressive 2,890 square feet, this turn-key residence offers four bedrooms & four full bathrooms, thoughtfully divided between two levels, with two and two on each floor. Expansive foyers on both levels and an enormous dressing room off the primary, offer flex space for reading nooks, fitness or work areas. Large, plentiful closets and a spacious kitchen pantry add to the home's everyday functionality. Modern conveniences include split AC systems, two washer/dryer hook-ups (one for each floor), two tankless, on-demand water heaters, engineered wood flooring, Italian granite countertops, and all-new appliances. Outdoor living is equally appealing, with a private, heat-optional pool featuring a waterfall, a spacious covered lanai for lounging and dining, and multiple decks, including one just off the upstairs primary suite. Built with resilience, this formidable home offers strength, security and privacy but also exudes tropical charm and tranquility. It is a beautiful home, rich in polished details and extra touches. Whether entertaining friends, hosting family or enjoying a quiet evening at home, this home is ideal for every occasion. Additional outdoor storage, irrigation system & off-street parking complete this exceptional Midtown offering.

1701 Ashby St, Key West

3108 Riviera Dr, Key West
$2,380,000
3 Beds ⋅ 2 Baths ⋅ 619644 MLS
Experience the ultimate Key West waterfront lifestyle with this private tropical retreat on the highly coveted Riviera Canal--one of the island's only canals offering direct boating access to world-class fishing and diving. Tucked behind a gated entrance, this beautifully landscaped property welcomes you into a lush, secluded garden setting that feels like your own hidden oasis in the heart of Key West. This meticulously maintained 3-bedroom, 2-bath ground-level pool home blends comfort, style, and functionality. Inside, you'll find elegant travertine flooring throughout, granite countertops, stainless steel appliances, and a wet bar--perfect for entertaining. The thoughtfully designed layout features two separate living areas, with both the main living space and the primary suite opening through hurricane-impact sliding glass doors to the backyard. Step outside to your private resort-style escape, where a stunning in-ground concrete pool overlooks the tranquil canal. Enjoy peaceful water views, frequent visits from manatees, and the natural privacy provided by protected mangroves across the water. The screened, covered lanai creates the perfect setting for outdoor dining and relaxation year-round. Boaters will appreciate the 15,000 lb boat lift, allowing you to go from home to open water in minutes. Additional premium features include a newer generator with large propane tanks, outdoor shower, electric gate, automated irrigation and landscape lighting, covered carport, and secure off-street parking for two vehicles. Located just minutes from Key West International Airport, dining, and local attractions, this exceptional property offers the perfect blend of convenience, privacy, and island luxury. Whether you're seeking a full-time residence or a vacation escape, this waterfront home is a rare opportunity to own a true piece of paradise.

3108 Riviera Dr, Key West

117 La Paloma Rd, Key Largo
$2,350,000
5 Beds ⋅ 5 Baths ⋅ 621107 MLS
Welcome to 4 Palmas -- Your Ultimate Key Largo Retreat! Built in 2016, this custom 5BD/4.5BA waterfront home offers over 5,600 sq. ft. of total indoor-outdoor living! Designed for entertaining, the home features two primary suites (one on each level), 3 living rooms, two bars, an elevator, and 4 private balconies. Step outside to your private tropical oasis complete with a heated pool, expansive sun deck, and covered patio featuring a full outdoor kitchen. Boaters will love the 50 ft. dock on a wide canal with quick ocean and bay access, plus a floating dock for easy launching from you kayak, skiff or jet ski. Whether you're looking for a luxury residence, vacation escape, or premium rental property, 4 Palmas has it all!

117 La Paloma Rd, Key Largo

40 N Bounty Ln, Key Largo
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 620878 MLS
Welcome to one of Buccaneer Point's most extraordinary waterfront estates-a breathtaking modern Balinese-inspired sanctuary where timeless architecture, exceptional craftsmanship, and resort-style living come together in perfect harmony. Situated on an oversized lot with more than 110 feet of waterfront, this custom CBS estate features a concrete roof, standing-seam metal roofing, and over $150,000 in professionally designed tropical landscaping. Dual electric gates welcome you with Royal Palms, Canary Island palms, bamboo, and mature privacy landscaping. Built for both everyday living and entertaining, the home offers expansive waterfront views, premium travertine and wood-look tile flooring, Hunter Douglas motorized shades, and a fully integrated Control4 Smart Home System. The chef's kitchen is equipped with premium JennAir appliances, double convection ovens, an additional wall oven, a six-burner gas range with griddle, pot filler, oversized island, custom cabinetry, and direct access to the waterfront balcony. The outdoor living space is designed for year-round enjoyment with a heated saltwater pool and spa, expansive travertine patio, outdoor kitchen with TV, bar seating, authentic Bakers Pride pizza oven, putting green, waterfront lounge area, cabana bath, covered entertaining space, irrigation system, mosquito misting system, pet run, and fully fenced grounds. Inside, the home offers four spacious bedrooms, including a main-level primary suite with private balcony access and coffee bar. The upper-level owner's retreat features dual walk-in closets, coffee and wine bar, dressing area, steam shower, separate his-and-hers bathrooms, and a private waterfront balcony. A custom wood elevator services every level, leading to a rooftop observation deck with power and water, offering panoramic views of Florida Bay, and some of the best sunsets in the Keys. Combining quality construction, premium amenities & outstanding waterfront location, this is a rare opportunity.

40 N Bounty Ln, Key Largo

127 Seaside Ave, Key Largo
$2,345,000
4 Beds ⋅ 2 Baths ⋅ 617384 MLS
Ocean views, deepwater dockage, dock is being replaced with a lift 9/26, and the rare ability to legally operate nightly rentals - it doesn't get any better! The seller has approval for a 20,000lb boat lift and improvement of the dock. There is also approval for an observation deck into the open ocean. This exceptional oceanfront estate offers a standout turnkey investment opportunity, combining the perfect trifecta for your portfolio: panoramic ocean views, deepwater dockage, and approved nightly rental capability. An ideal family compound and a rare chance to own a fully versatile, income-producing Keys property. Enjoy oceanfront living with two beautifully updated units, each featuring 2 bedrooms and 1 bathroom, separate entrances, and its own oceanfront porch. The property showcases panoramic blue-water views that are simply breathtaking, a rare find for both investors and those seeking a spectacular coastal retreat. Boating enthusiasts will appreciate the 100 feet of concrete dockage with immediate ocean access, along with the unique benefit of ownership of the ocean bottom, offering added value, flexibility, and long-term security. Zoning permits rentals with a minimum stay of just one night, giving you maximum income potential or the option to enjoy it as a private getaway. Whether you're looking to expand your investment portfolio or create your future oceanfront dream home, this home offers unmatched versatility and incredible potential in a beautiful setting. Plenty of parking and room for a pool, expansion or redevelopment! Call today for more details.

127 Seaside Ave, Key Largo

984 Shaw Dr, Key Largo
$2,325,000
3 Beds ⋅ 2 Baths ⋅ 621071 MLS
Located in the desirable Twin Lakes community, this inviting waterfront home offers a wonderful blend of privacy, comfort, and boating convenience. Built in 2001, the upper level features a spacious 3 bedroom, 2 bath split floor plan filled with abundant natural light. The lower level includes a 1 bedroom space, offering added flexibility for guests or home office. Set on a generous 9,937-square-foot lot with 75 feet of waterfront on a wide 70-foot canal, the property is well suited for enjoying the Florida Keys lifestyle. Boaters will appreciate the 20,000-pound boat lift. Outdoor living shines with a swimming pool and spa, plus a gazebo with a bar area ideal for entertaining or relaxing after a day on the water. A concrete privacy wall, electric gated entrance, and covered parking enhance both privacy and convenience. With no neighbor directly across the street, this home offers a uniquely peaceful setting.

984 Shaw Dr, Key Largo

30995 Watson Blvd, Big Pine
$2,300,000
4 Beds ⋅ 3 Baths ⋅ 621731 MLS
Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, durable metal roof, stainless steel appliances, quartz countertops, open-concept living areas, screened porch, private in-ground pool, and covered parking below. Built with modern coastal construction in mind, the CBS structure, impact openings, elevated design, and metal roof provide lasting durability, low-maintenance appeal, and insurance-friendly features for coastal living. The waterfront setting is enhanced by allocated dockage with an approximately 45' access walk leading to a 91' platform, creating a great setup for enjoying boating, kayaking, paddleboarding, and the surrounding water views. Situated on a generous 14,680-square-foot lot with approximately 75' of waterfront frontage, the property captures panoramic Bay/Gulf-front water views and beautiful sunrise exposure. Enjoy boating access via Bogie Channel, with easy access to the backcountry and fast open-water routes to both the Atlantic Ocean and the Gulf. Nearby Looe Key Reef is a favorite destination for snorkeling and scuba diving, with excellent fishing opportunities nearby. Located on the Big Pine Key side of the Bogie Channel Bridge to No Name Key, this setting offers peaceful water views and a unique sense of island privacy. The property can be used as an investment property for vacation rental use, adding flexibility and income appeal. Located near the iconic No Name Pub and surrounded by the natural beauty of Big Pine Key, where Key Deer are a beloved and frequent part of everyday island life. Unlike smaller, more remote keys, Big Pine Key serves as a convenient Lower Keys hub with everyday necessities nearby while still offering the quiet waterfront lifestyle people come to the Keys to enjoy. Construction is complete and ready for immediate occupancy.

30995 Watson Blvd, Big Pine

459 Pattison Dr, Cudjoe
$2,299,995
3 Beds ⋅ 2 Baths ⋅ 621419 MLS
Set on a large, private lot at the corner of two canals, this 3-bedroom, 2-bath, 2,020 sq. ft. waterfront home offers exceptional outdoor living, quick boating access and multiple spaces designed to enjoy the Florida Keys lifestyle. Boaters will enjoy the updated dock and 15K-lb boat lift. The outdoor space is built for entertaining, featuring a waterfront pool with paver decking, a poolside screened lanai, a main-floor screened porch, and an expansive rooftop deck with sweeping ocean views. Inside, the Great Room is filled with natural light, highlighted by an arched window framing views of the pool and canal, with easy access out to the rooftop deck and screened porch. The adjacent kitchen comes fully equipped with granite countertops, stainless steel appliances, and a pantry closet. The main level houses a dedicated guest wing with two bedrooms, one opening to a front porch balcony and the other stepping directly out to the rear screened porch, plus a full guest bathroom with a jetted soaking tub. Upstairs, the top floor serves as a completely private primary suite and second living area. This retreat features a soaking tub, walk-in closet, direct sun deck access showcasing open water views, and steps leading up to the rooftop deck. Additional features include impact-resistant windows and doors, a one-car garage, carport and plenty of storage for your island essentials. The neighborhood also offers the convenience of a full-service marina and waterfront restaurant close to home. With quick open-water access putting world-class fishing, diving and snorkeling within easy reach, this home is perfectly positioned to enjoy the best of the Florida Keys waterfront lifestyle.

459 Pattison Dr, Cudjoe

589 Pirates Rd, Little Torch
$2,299,000
3 Beds ⋅ 4 Baths ⋅ 621868 MLS
Welcome to effortless Keys living! Built in 2017, this beautifully designed 3-bedroom, 3.5-bath CBS canal-front home offers 2,126 sq. ft. of living space, coastal style, privacy, and comfort. With no neighbors directly across the street, enjoy added privacy and openness. Solid CBS construction and impact-resistant windows and doors rated for winds up to 180 mph provide peace of mind. Set on a 50-foot-wide, deep, flow-through canal, the home offers quick, direct access to open water with no bridges. The spacious great room features soaring ceilings, abundant natural light, and a beautiful kitchen with quartz countertops, stainless steel appliances, and elegant finishes. Two ensuite guest bedrooms are on the main living level, while the entire upper level is a private primary retreat with a walk-in closet and bonus den, ideal for an office, workout space, or sitting area. Balconies on multiple levels invite you to enjoy morning coffee, coastal breezes, and stunning sunsets overlooking the salt ponds. A 40-foot concrete dock and 20,000-pound boat lift keep your boat right at home and ready to go. A fish-cleaning station adds convenience after a day on the water, while downstairs enclosed storage provides room for fishing gear, water toys, and Keys essentials. Less than two miles from a public boat ramp, this waterfront home puts world-class fishing, diving, and days on the water within easy reach. Whether it's a morning of fishing, an afternoon of diving, or a sunset cruise, enjoy all the Florida Keys have to offer. With comfort, privacy, and exceptional boating access, this home captures effortless island living!

589 Pirates Rd, Little Torch

272 W Seaview Dr, Duck Key
$2,299,000
3 Beds ⋅ 3 Baths ⋅ 618104 MLS
Welcome to your private island retreat in the heart of Duck Key. Perfectly positioned just a few homes from the Seaview Channel, this exceptional waterfront residence offers instant access to both the Atlantic Ocean and the Gulf of Mexico—an ideal setting for boaters, entertainers, and families alike. This beautifully maintained home features three bedrooms and three baths, including downstairs living space, providing flexible options for guests, extended family, or a private suite. The remodeled kitchen and bathrooms showcase a European design, with wood cabinetry, granite countertops, and refined finishes throughout. Indoor-outdoor living is at the heart of this property. Step outside to a gorgeous pool and Jacuzzi, surrounded by a spacious pool deck with a built-in bar area, perfect for entertaining under the Florida sun. A large screened-in balcony captures beautiful water views in every direction, offering a serene space to relax and unwind. This space could easily be enclosed to add more living space. Additional highlights include a one-car garage, 75 feet of concrete dockage, and a fabulous canal setting just moments from open water. Easy to show and ready to enjoy, this Duck Key home delivers the very best of Keys living—luxury, lifestyle, and location.

272 W Seaview Dr, Duck Key

81250 Overseas Highway Unit 5, Islamorada
$2,290,000
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

1300 Seminary St, Key West
$2,250,000
3 Beds ⋅ 4 Baths ⋅ 621172 MLS
If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborhood. Behind the white picket fence, you will be welcomed to a great room with dramatic ceiling heights, wrapped with sliding glass doorwalls that open to over 500 square feet of covered porches. This home has been very well maintained with several recent updates, including impact windows and doors, pool resurfacing, a new primary A/C unit, deck and interior paint and a charging station for an electric vehicle. A thoughtful floor plan great for entertaining, includes 3bd/3.5ba with the primary suite on the main level. Two additional bedrooms with ensuite baths are private to the upstairs. Built in just 1999 this home is an open palette awaiting your personal selection of cosmetic updates without the unknown obstacles of a historic home. The magic of this home lives in the sprawling backyard wrapped in mature tropical gardens with a large, heated saltwater pool. An excellent opportunity to personalize a well built home that caters to indoor/outdoor living ideal for the year round tropical climate!

1300 Seminary St, Key West

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