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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

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

2623 Gulfview Dr, Key West
$2,400,000
3 Beds ⋅ 3 Baths ⋅ 621218 MLS
Welcome to your waterfront escape in Key West. Located within a gated community, Gulfview Pointe offers the perfect blend of island charm, comfort, and an exceptional waterfront lifestyle and just minutes from world-famous Duval Street and all that Key West has to offer. This move-in-ready 3-bedroom, 2.5-bath home welcomes you with classic Key West architecture, lush tropical surroundings, and inviting indoor and outdoor living spaces. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Step outside to your own private tropical retreat, where a sparkling pool surrounded by composite decking creates the perfect setting for relaxing, entertaining, and enjoying the year-round Florida Keys sunshine. Beyond the pool, your private dock opens the door to endless adventures. Spend the afternoon fishing, set out on your personal watercraft, paddleboard or kayak, or simply unwind and watch another spectacular Key West sunset from your own backyard. A covered carport and the privacy of a gated community complete this island home. Whether you're searching for a full-time residence, your own Key West getaway, or investment opportunity with luxury vacation rental potential in this highly sought-after community, Gulfview Pointe offers an exceptional opportunity. Opportunities like this don't come around often--invest in your dream home and start living the Key West waterfront lifestyle you've been dreaming of. Call today to schedule your private showing!

2623 Gulfview Dr, Key West

1502 Shaw Dr, Key Largo
$2,400,000
3 Beds ⋅ 3 Baths ⋅ 621111 MLS
**SELLER FINANCING AVAILABLE** WELCOME TO THIS EXCEPTIONAL FULLY REMODELED WATERFRONT HOME, WHERE MODERN LUXURY MEETS FUNCTIONALITY. NO DETAIL WAS OVERLOOKED AND NO EXPENSE WAS SPARED IN TRANSFORMING THIS PROPERTY INTO A TRUE WATERFRONT SHOWPIECE. THE OVERSIZED, LOW-MAINTENANCE LOT IS SECURELY ENCLOSED BY A 6-FOOT METAL GATE AND OFFERS PAVED PARKING FOR 10+ VEHICLES. THE BEAUTIFULLY FINISHED YARD FEATURES PREMIUM ASTRO TURF, A BRAND-NEW POOL WITH WATER HEATER, AND A 2024 CONCRETE DOCK WITH A NEW 20,000-LB BOAT LIFT AND NEW OUTDOOR KITCHEN. THE SOLID-CONCRETE HOME, INCLUDING THE ROOF, HAS BEEN COMPLETELY UPDATED WITH BRAND-NEW IMPACT WINDOWS AND DOORS, PLUMBING, ELECTRICAL, AND HIGH-END FINISHES THROUGHOUT. CUSTOM BUILT-INS IN EVERY CLOSET PROVIDE EXCEPTIONAL STORAGE AND FUNCTIONALITY. EVERYTHING HAS BEEN THOUGHTFULLY DESIGNED. TO COMPLETE THIS IMPRESSIVE WATERFRONT PROPERTY. THIS IS A RARE OPPORTUNITY TO OWN A TURNKEY WATERFRONT HOME WITH PREMIUM UPGRADES THROUGHOUT.

1502 Shaw Dr, Key Largo

316 North Dr, Islamorada
$2,400,000
3 Beds ⋅ 4 Baths ⋅ 621073 MLS
Simply the best location, exclusive & extremely private. This is a rare find and a single-family home that's rarely available. It's tucked away in the prestigious ''Plantation Lake Estates,'' a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach, tennis courts, a full-service marina, a dog park, sports fields, and Olympic-size lap pools. This home boasts a stunning great room with a gorgeous coral fireplace and soaring wood beam ceilings. They all overlook the glistening Atlantic Ocean, providing priceless views and sunrises. The home has a metal roof, a modern kitchen, updated baths, and impact windows and doors. The exterior has been reinforced with rebar and stucco. There are three inviting bedrooms, including a third-floor master en-suite with a private porch. A large ''rec room'' with a cabana kitchen is perfect for indoor-outdoor entertaining. You'll have world-class fishing and diving right in your own backyard.

316 North Dr, Islamorada

3206 Riviera Dr, Key West
$2,399,000
3 Beds ⋅ 4 Baths ⋅ 620879 MLS
Experience the best of waterfront living at 3206 Riviera Drive, a beautifully updated canal-front home offering 60 feet of waterfront, exceptional privacy, and direct access to the Key West boating lifestyle. With no homes across the canal, the property enjoys peaceful water views and a uniquely private setting. Designed for both everyday living and entertaining, the open-concept interior is filled with natural light and seamlessly connects to the outdoors through a wall of impact-rated sliding glass doors. The chef's kitchen features premium cabinetry, a large center island, and a waterfront dining area overlooking the pool and canal. The home offers three spacious bedrooms, including two en-suite bedrooms, three full bathrooms, a dedicated laundry room, two-zone air conditioning, and a whole-home generator. Outside, the tropical backyard is built for enjoying the Keys. Relax by the newly renovated heated pool, entertain from the outdoor kitchen, unwind on the screened patio, or enjoy the convenience of an outdoor bathroom. Shell stone limestone walkways, lush landscaping, covered parking, and a fully gated lot complete this private waterfront retreat. Offering the perfect combination of luxury, comfort, and functionality, 3206 Riviera Drive is move-in ready and seller financing may be available.

3206 Riviera Dr, Key West

229 Pescayo Ave, Marathon
$2,399,000
4 Beds ⋅ 5 Baths ⋅ 619881 MLS
Looking for the best of both worlds? Enjoy your vacation home and let it pay for its self when your not. Since January 2024, 229 Pescayo has hosted 113 stays across 860 guest nights and generated $512,831 in accommodation revenue. An incredible 88% occupancy rate 4.96 / 5.0 guest rating Fully furnished, income-generating from day one -- zero ramp-up period This isn't a fixer-upper with 'potential.' It's a proven, cash-flowing short-term rental with the reviews, occupancy, and forward bookings to prove it -- built in 2023 and already established as one of the area's busiest vacation rentals. Why It Performs: Every finish was chosen to drive nightly rate and occupancy, not just curb appeal. Boaters and premium-amenity guests are the target market, and the property is built to convert them into repeat bookings: 72' of deep-water dockage, water & electric at dock, outdoor lighting Less than 10 minutes to open water & Vaca Cut for Gulf access Heated pool with paver decking Covered entertaining area + large covered upper terrace for shaded, salt-air living 240V EV charger 800 sq ft storage enclosure Aluminum gated vehicle access + security cameras The Property: Double doors open into an open-concept kitchen and living space -- quartz countertops, tile backsplash, built-in wine cooler, and tile flooring throughout. Four master suites, each with a private bath, plus an additional half bath for guests. Sold fully furnished -- dishes, linens, smart TVs, all of it. Bottom Line: No lease-up, no renovation, no guesswork on rates. Bring your boat -- the income is already running.

229 Pescayo Ave, Marathon

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
Introducing 319 Grinnell Street, 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

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

205 S Point Dr, Sugarloaf
$2,375,000
5 Beds ⋅ 4 Baths ⋅ 617951 MLS
Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views. The primary suite is a private sanctuary, highlighted by a wall of windows that greets each morning with sweeping vistas of the open Atlantic—an ever-changing canvas of blues that defines life in the Florida Keys. Throughout the home, wall-to-wall water views create a seamless connection between indoor comfort and the surrounding seascape, offering multiple spaces to relax, entertain, and soak in the coastal atmosphere. Set on an impressive 12,500-square-foot lot, the property provides ample room for outdoor living, recreation, and plenty of room for a pool. Boaters will appreciate the 120-foot concrete seawall with davits, delivering effortless access to world-class fishing, diving, and the iconic Lower Keys sandbars. The elevated design allows the entire lower level to transform into an expansive open-air lounge and entertainment area, complemented by a generous storage room for all your boating and island gear, plus abundant parking. Located in one of the Lower Keys' most sought-after neighborhoods, this peaceful waterfront escape is just 15 minutes from Key West, offering the perfect balance of privacy and convenience. Schedule your private showing today—available in person or via live video—and discover the essence of luxury island living.

205 S Point Dr, Sugarloaf

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

280 14th St, Key Colony
$2,350,000
3 Beds ⋅ 2 Baths ⋅ 621083 MLS
Some homes give you a place to live. KoKomo gives you a lifestyle, an investment opportunity, and a reason to look forward to every sunrise. What if your next home felt like a vacation--and could produce income when you're away? Welcome to KoKomo at 280 14th Street, a waterfront retreat on one of Key Colony Beach's quieter residential streets. Imagine beginning your morning with coffee on the expansive wraparound screened porch, feeling the island breeze, and deciding whether the day calls for fishing, diving, cruising--or relaxing beside your private pool. This inviting 3-bedroom, 2-bath single-family home features: • An open floor plan with vaulted ceilings • Direct porch access from every bedroom • Private pool and spacious waterfront setting • Two-car garage • Versatile bonus/flex space • Approximately 37 feet of dockage • Fish-cleaning station and bait freezer • Proven vacation-rental history dating to 2003 For boaters, the location makes every day on the water easier. Enjoy quick access through Vaca Cut to the Gulf, while the open Atlantic is also only minutes away. You'll be close to golf, pickleball, tennis, Sunset Park, the marina, restaurants, and the Cabana Club--yet comfortably removed from the busier areas of the island. Continue operating KoKomo as an income-producing vacation rental, enjoy it seasonally, or make it your full-time waterfront home. Key Colony Beach permits vacation rentals with a seven-night minimum stay, offering valuable flexibility for future ownership. Can you picture yourself here?

280 14th St, Key Colony

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

287 & 289 Golf Club Dr, Key West
$2,350,000
6 Beds ⋅ 6 Baths ⋅ 620852 MLS
Set within the exclusive enclave of The Sanctuary at Key West Golf Club, this rare offering presents two distinct residences united as one extraordinary parcel -- a configuration unlike anything currently available on the Key West market. Verandas and porches wrap the property, framing sweeping views of the lake and the emerald fairways of the 17th hole, while tiled floors flow throughout both residences, blurring the line between the two homes and the tropical air outside. At the heart of it all, a resort-caliber pool measuring an impressive 12 x 30 feet anchors a 1,500 square foot outdoor terrace, where long tables are set for twelve or more, indoors and out, beneath the Key West sky. With 6 bedrooms and 5.5 bathrooms spread across 2,840 square feet, this dual-residence estate is purpose-built for the multigenerational family, offering the rare gift of togetherness paired with independence -- separate structures for separate households, united by a single spectacular pool deck built for gathering. For the discerning second-home buyer or investor, the dual-dwelling design opens the door to flexible living arrangements or income-generating potential, a configuration increasingly coveted in today's Key West market. This is more than a home -- it is a once-in-a-lifetime opportunity to establish a family legacy on one of Key West's most coveted golf course settings. Here, generations will gather beneath the verandas, celebrate over long tables set for twelve, and watch the sun set over the 17th green. This is Key West living, reimagined for the modern family -- and passed down for generations to come.

287 & 289 Golf Club Dr, Key West

272 W Seaview Dr, Duck Key
$2,350,000
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

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 ⋅ 614697 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

581 12th St, Key Colony
$2,299,000
4 Beds ⋅ 2 Baths ⋅ 621230 MLS
Set along the water in sought-after Key Colony Beach, this 4-bedroom, 2-bath home captures everything buyers love about the Florida Keys--boating, a private pool, generous outdoor living space, and a strong history as a successful vacation rental. Inside, the layout is comfortable and inviting, with an open kitchen featuring abundant cabinetry, expansive countertops, and bar seating that flows naturally into the dining and living areas. Four bedrooms provide plenty of room for family and guests, while the primary suite enjoys its own bath and access to a covered outdoor deck. A dedicated laundry area adds everyday convenience. The outdoor spaces are the real highlight. The waterfront backyard is designed for the Keys lifestyle, with a private swimming pool, spacious pool deck, covered entertaining area, outdoor shower, tropical landscaping, and plenty of room to relax after a day on the water. The property also offers substantial canal frontage with a seawall, dockage, and a boat lift, creating an easy setup for boaters. From here, enjoy convenient access toward both the Gulf and Atlantic for fishing, diving, snorkeling, and days on the water. Back at home, cool off in the pool, lounge along the canal, or gather beneath the covered lower-level entertaining space. Additional features include a metal roof, covered parking and storage areas, mature tropical landscaping, and multiple outdoor spaces that make the home especially well suited for full-time living, a family getaway, or continued vacation rental use. With its 4-bedroom layout, private pool, dockage, boat lift, outdoor shower, and established rental history, this waterfront home offers a wonderful opportunity to enjoy the best of Key Colony Beach.

581 12th St, Key Colony

1400 W 63rd St, Marathon
$2,299,000
2 Beds ⋅ 3 Baths ⋅ 620384 MLS
Enjoy endless ocean views from this charming Florida Keys waterfront retreat. Sitting on the edge of the Atlantic just one house in from open water, this stilted 2-bedroom, 2.5-bath CBS home also offers possible 3-bedroom flexibility and is a true boater's dream with 85 feet of waterfront frontage, concrete seawall, a 13,500 lb boat lift, deep-water dockage, and instant access to the Atlantic. The channel is slightly right as soon as you come out of the canal, placing you just minutes from Sombrero Light and some of the best boating, fishing, and diving the Keys have to offer. The home features a spacious, light-filled layout with a large living area, generous waterside windows, and sliding glass doors that frame the ocean views and open to east-facing covered porches on two levels. Inside, you'll find a comfortable eat-in kitchen with stainless steel appliances, abundant natural light, generous storage, walk-in closets, and impact windows and doors for added peace of mind. Outdoor living is the highlight, with a new waterfront pool and hot tub, expansive deck, large waterside porch, fenced yard, tropical landscaping, and multiple spaces to relax, dine, entertain, or simply take in the ocean breeze. Additional features include a garage, CBS construction, metal roof, travertine-paved driveway, inviting covered patio areas, and a large front yard offering flexibility for additional parking, boat/RV storage, or future use. The home is also available furnished, offering added convenience for those ready to start enjoying the Keys lifestyle right away. With open water just moments away, this Marathon property offers the perfect blend of boating, ocean views, poolside relaxation, and laid-back Keys living. This one is a must-see to truly appreciate.

1400 W 63rd St, Marathon

181 12th St, Key Colony
$2,299,000
3 Beds ⋅ 2 Baths ⋅ 620280 MLS
Welcome to modern coastal living in the gem of the Florida Keys, Key Colony Beach. This fully remodeled pool home has a clean, contemporary feel and an easy, open layout that appeals to buyers who want something truly move-in ready. Sitting on a rare 16,725 sq ft lot - about twice the size of the typical lot here - and on the sought-after west side of KCB, there's plenty of room for multiple cars, trailers, and even an RV. This solid CBS stilt home is wrapped in lush landscaping and fruit trees, giving it a private, tropical vibe. Inside, cathedral ceilings make the 1,775 sq ft, 3-bed, 2-bath floor plan feel even larger. Nesting sliders open to a big screened porch, a great outdoor kitchen, and several spots to lounge by the pool, so indoor and outdoor living flow together naturally. Sunset Beach Park is a short stroll away when you want postcard-worthy sunsets, and the 50' concrete dock with 50-amp power and water puts you minutes from the Vaca sandbar and to the Bay via Vaca Cut, making it easy to head out for fishing, diving, or snorkeling. With a pool you can heat or chill for year-round use and 7-day rentals allowed, this property works for a personal getaway as is also a high-demand vacation rental investment property. It's not just a Keys home--it's the turnkey lifestyle buyers are looking for in Key Colony Beach!

181 12th St, Key Colony