Welcome to Southwinds, your exclusive oceanfront oasis in the heart of Lower Matecumbe, Islamorada. This stunning 5-bedroom, 6.5-bath CBS home embodies luxury and tropical living. Spanning nearly 4,000 sq. ft., Southwinds offers breathtaking ocean views, with floor-to-ceiling impact windows that flood the interior with natural light, seamlessly connecting you to the stunning beauty of the Atlantic. One of the standout features of Southwinds is its 100' natural sandy beach, a rare find in Keys oceanfront homes.  Stroll the 150' foot pier which features water, electric and a fish cleaning station.  Read a book or enjoy your favorite beverage under the tiki.  The pool features a spillover edge, bubbler, sun shelf and hot tub.  The grand outdoor Mahogany bar is ideal for entertaining against the backdrop for the ocean breezes. A private pickleball court offers hours of fun and fitness for you and your guests, right in your own backyard. Paired with a putting green, this home provides a truly unique lifestyle experience that caters to the active, outdoor enthusiast.The home features a large kitchen with a pass-thru, an induction range, wine and beverage coolers, and two sets of washers and dryers for ultimate convenience. The third-floor wet bar and expansive open balconies offer additional space to enjoy the spectacular views. The gated property also features landscape lighting, an irrigation system, a spacious garage, and storage room.Southwinds is a sanctuary for those seeking a private retreat or a valuable investment. Whether you're in search of a second home or a high-performing rental property, this residence offers everything you could desire. Zoning allows for weekly vacation rentals, Southwinds presents an ideal opportunity for generating rental income.

Welcome to this charming Old Florida-style cottage, an ideal weekend retreat nestled on Lower Matecumbe Key in Islamorada! This property is set on nearly half an acre, boasting an impressive 100 ft of private beach frontage directly on the crystal-clear ocean. This cottage is a perfect fixer-upper opportunity, offering you the chance to renovate and personalize the existing structure or build your dream home on this stunning piece of prime real estate. Step inside to discover two spacious bedrooms and two full bathrooms. The interior features beautiful beamed and tongue-and-groove ceilings, adding a touch of character and warmth to the space. Imagine starting your mornings with a cup of coffee or unwinding in the evenings with a glass of wine, all while enjoying breathtaking views of the magnificent Atlantic Ocean. The gentle ocean breezes create a serene atmosphere, perfect for quiet contemplation and entertaining friends and family. With its prime location and charming features, this cottage is a rare find that invites you to embrace the laid-back Florida Keys lifestyle. Don't miss your chance to make this idyllic getaway your own!

Fabulous Plantation Beach lot only 3 lots from the bayfront Homeowner's Park!  This lot is currently #30 in BPAS system.  Plantation Beach is a lovely neighborhood with bayfront and non waterfront homes.  The Homeowner's Park is on the bay and features a boat ramp, jetty into the bay, roped off swimming area, volleyball court and kayak and paddleball racks.  There is plenty of parking for your truck and trailer once you put your boat in the water.  Make this your home in the Florida Keys!

Fabulous top floor location with spectacular ocean views!  This spacious condo has tile floors throughout and a lovely open terrace to enjoy the ocean view and breezes.  Both bedrooms are spacious and the primary bedroom opens to the oceanfront terrace.  The Palms of Islamorada is conveniently located close to the downtown Islamorada area. You are only minutes from enjoying shopping in the boutiques and galleries and eating in numerous restaurants that are very close by. The Palms has an oceanfront pool, hot tub, assigned parking with plenty of guest parking, 2 gyms as well as kayak and paddleboard storage.  A fantastic view of Alligator Lighthouse is included  at no extra cost.

Plantation by the Sea!!! Recently remodeled 2 bedroom 2 bath in the Heart of World Famous Islamorada! This tastefully remodeled unit has new kitchen, appliances, bathrooms, flooring, textured walls and ceiling and a new AC unit. Oceanfront heated pool, long fishing dock with plenty of fish! Fitness room, large fully equipped oceanfront clubhouse/ game room, sunbathing area, private storage and assigned covered parking. This oceanfront condominium is within walking distance to Founders Park, shopping and restaurants... all in the heart of World Famous Islamorada! Enjoy the spectacular Atlantic Ocean views everyday, as you enjoy this vacation lifestyle from Plantation by the Sea. Please allow 24 hours notice to show.

Experience the ultimate Florida Keys lifestyle in this spacious 2-bedroom, 3-bath condo located in the highly sought-after, gated Executive Bay Club. With manned security for added peace of mind, this unit offers a versatile sleeping loft and a cozy office/sleeping nook, providing ample space for family and guests.The bright kitchen boasts granite countertops, stainless steel appliances, and a tankless hot water system. The master bedroom features its own private bathroom, while both bedrooms include plantation shutters for added privacy and style. You will enjoy this unit's close location to the pool and sandy beach, as well as easy access to community amenities like the clubhouse, dockage, and tennis and basketball courts--all just steps away from Founders Park, where local festivals and events take place throughout the year. Pet owners will appreciate that the community allows 2 approved pets, making it a perfect fit for animal lovers. Don't miss this fantastic opportunity--ask about the rental income potential!

RARE OPPORTUNITY to own an oceanfront home in the prestigious Anglers Reef development in Islamorada. Deeded boat slip accommodating up to a 31 ft boat included in offering. A beautiful 2-bedroom, 2.5-bath, 2-story home with 2 porches and a balcony overlooking the Atlantic Ocean. Located in the gated community of Anglers Reef on Windley Key approximately half way between Miami and Key West. This property contains 2 large bedroom suites with bathrooms on the 2nd floor. A living room, kitchen, dining room and powder room on the main level. Looks out on the community pool and marina (see included video). Upgrades include impact windows/doors, metal roof, composite decks/railings, granite counter tops with wood cabinets, tile floors downstairs and bamboo floors upstairs, shutters/blinds, brand new dishwasher and refrigerator. The community features 2 sandy beaches, pool, gated entry, marina, kayaks and paddle boards. Perfect home for primary residence, vacation family home or investment property. Call today for a showing

Building Permit in hand! | Rendering Video: https://www.youtube.com/watch?v=3tuEiLlpmng |                       Lot Video: https://youtu.be/evRl11NXQuQ | This remarkable oceanfront property offers unobstructed views of the open Atlantic with year-round, breathtaking sunrises and broad views from East to Southwest. The building permit for a single family residence is in hand and can be revised to build the house of your dreams on this large 23,238+- sq. ft. lot plus bay bottom. A permit for observation dock and tiki hut platform has been applied for, mangrove height reduction permit is in hand. Enjoy direct ocean access and quick bay access through Snake Creek in the sport fishing capital of the world. Islamorada offers some the best restaurants in the Upper Keys and you are within walking distance to Founders Park's shallow water beach, sand volleyball court and playgrounds for children.The area offers nearby boat slips and dry docks to store your boat or you may use any of the nearby boat ramps.  Zoning on this property allows for weekly vacation rentals, making it an invaluable investment.Enjoy endless ocean views and breezes from this truly spectacular property. Please note that video shown does not reflect approved plans.Approved building plans do not reflect rendered photos and rendered video.

Experience waterfront living at its finest in this ground-floor condo located in the coveted Coral Harbour Club Condo (CHC). This spacious unit features an open floor plan with 3 bedrooms and 2 bathrooms, complemented by a large wraparound terrace and garden area. It also has exclusive rights of use to 1 of the 7 boat slips ( 6-30' & 1- 50')with direct ocean access.  The common areas of CHC offer breathtaking views of the Atlantic Ocean, clubhouse, resort-style oceanfront pool, Tiki Hut/BBQ area, tennis courts and protected marina with convenient facilities such as a fuel pump & fish cleaning stations.Discover the epitome of refined living & luxurious amenities.

Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with a TDR and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

MOTIVATED SELLER! 'Coconut Cottage'&#8239;beckons you to the quintessence of tropical living in Islamorada. This oceanfront haven boasts a&#8239;90ft sandy beach, a private boat basin, and an inviting waterfront pool, creating an idyllic backdrop for both relaxation and adventure. The main residence, featuring&#8239;four bedrooms and three bathrooms, exudes vintage Florida elegance, complemented by a&#8239;screened-in porch&#8239;where one can savor the panoramic ocean vistas and gentle sea breezes. A separate&#8239;one-bedroom, one-bathroom guest cottage&#8239;offers additional privacy and comfort, making it ideal for hosting friends or family. Constructed with durability in mind, both homes feature&#8239;concrete walls and metal roofing, ensuring a sanctuary that stands the test of time. The property's lush tropical landscaping and gated entry promise a secluded retreat, fully fenced to ensure your exclusive slice of paradise remains undisturbed. Ample parking accommodates a fleet of cars, boats, and trailers, while a dedicated storage shed keeps your water toys and fishing gear organized. Coconut Cottage isn't just a residence; it's a lifestyle choice for those who dream of a&#8239;natural tropical setting. Envision your special day at this perfect wedding venue, where a&#8239;7-day rental policy&#8239;aligns seamlessly with celebrations and gatherings. With a charming boutique hotel nearby, your guests will enjoy the convenience and luxury that this unique property affords. Discover the rare gem that is Coconut Cottage, a treasure nestled in one of Islamorada's most sought-after locations, where every day feels like a blissful escape from the ordinary.

Nestled in the panoramic setting of Islamorada, Florida, the brand new construction at 87895 Old Hwy offers a premium blend of luxury, privacy, and elegant island living. Sprawled over two acres on the azure Atlantic, this opulent abode stretches a massive 9,011 sq ft under air, extending to over 15,000 sq ft under roof. The expansive property includes five spacious bedrooms, five state-of-the-art baths, along with three additional half baths. The home features Thermador /Uline appliances including ice makers & upgraded eco-insulated commercial CGI windows and doors, an additional investment of $200k over the original allowance, that enhance the comfort and luxury of the interiors. Experience unmatched waterfront vistas with the house's 160 ft concrete jetty wrapped in a retaining wall and an 80 ft dock with electric and water facilities. Preserve your luxury vessels on the 20k 4 post elevator lift, adding convenience to lifestyle. The residence also includes an exercise room w/ possible conversion to 6th bedroom, theater room w/ possible conversion to 7th bedroom , office/den, & a laundry room on each level. An elevator ensures smooth movement across the floors. Indulge in outdoor living with the private pool, jacuzzi & around 1735 sqft of porches for lavish entertainment & serene lounging.The property comes protected by a concrete retention wall along the entire perimeter of the shoreline, ensuring complete tranquility. A private gated entrance exudes grandeur while providing security. This estate is zoned (Residential Estate), allowing the owner to apply for vacation rentals, if desired. Currently under construction with an estimated completion date in February or March 2024, the property is perfect for those seeking a custom luxury experience. Enjoy a world-class island living experience in this architecturally significant estate filled with premium luxuries nestled right on the turquoise-blue waters of the Atlantic. Agents please check agent remarks

Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Now being offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; a timeless 4 bedroom main house, an expansive 4 bedroom guest house and a lovely 2 bedroom caretaker's cottage. This tropical and tranquil estate has nearly 8.5 acres of upland plus 7.98 acres of ocean bottom plus ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes.  Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals.

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