Upper Keys Waterfront Condos for Sale - Condominiums, Open Water, Ocean and Bay / Gulf Views

Exquisite Oceanfront at Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada. This MAIN LODGE OCEANFRONT END UNIT condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful King Bedded Oceanview Room. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa, workout facility, and multiple pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted tennis courts and a fitness center. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and shopping. Proximity to Islamoradas famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamoradas most iconic and historic destinations.

Come live your best life - RIGHT ON THE BEACH! Enjoy SUNSETS, big views, DOCKAGE and the ideal Islamorada location. Boaters enjoy immediate BAY access and quick and easy OCEAN access via Snake Creek to the south and Tavernier Creek to the north. Youll be at all your favorite fishing, diving and dining spots in no time at all. Or - stay home and enjoy the beach right outside your door! Beautifully updated and lovely, this furnished bay front townhouse-style condo is directly on the beach and has TWO bedrooms PLUS a sleeping loft and THREE FULL bathrooms! Youll love having space to host your friends and family in the Keys. See every sunset from your own private balcony overlooking the beach and the bay. Enjoy sunsets and full bay views from almost every room. Bring your boat! First come dockage for boats up to 28 at the dock or up to 35 tethered to a piling. Trailer storage for up to three days. Impact windows and doors plus a metal roof add to the strength of the concrete building. Paddle boarding and kayaking is a breeze from this spot - and storage is no problem at all! This unit has a truly surprising amount of indoor and private outdoor storage. 11x14 locked storage area under the unit for all your water toys, plus additional space for your bikes and more gear is just outside the front door. Bring your furry friends! Two pets OK - no weight restriction. J4 has very easy access to the pool, clubhouse and tennis & pickle ball courts. Parking spaces are right outside your door. Founders Park is adjacent to Executive Bay Club with even more tennis, pickle ball, sandy beach, full service marina and more! Spiral stair case provides access to the second floor where youll find two full bedrooms and two full baths.... then it continues on up to the private sleeping loft. A third full bath is on the first level. Come find out why so many people love living on the beach at Executive bay Club.

Enjoy the vibrant coastal lifestyle of Keys living in this desirable BAYFRONT townhome located in sought-after Executive Bay Club in Islamorada! Boasting 2 bedrooms, 2 bathrooms plus a spacious loft, impact windows and doors, along with an open living layout that flows seamlessly through to the outdoor patio offering breathtaking sunsets and unobstructed Florida Bay views. Step out your back door to the sandy beach and dock with 31 boat slips available on a first-come, first-serve basis, along with 6 mooring pilings. Perfectly located to enjoy offshore fishing in the Atlantic Ocean or backcountry fishing in the Florida Bay. The community offers a wealth of resort-style amenities, including a sparkling pool, clubhouse, two tennis/pickleball courts, a sandy beach, kayak and paddleboard storage and a pet-friendly environment. The dock and the walkway to the beach with new sand are recent upgrades. In addition, the pool, bathrooms and clubhouse are all being redone with assessments paid by seller. Secured with a manned/gated entrance. Located just minutes away from 5-star restaurants, breweries, and boutique shops, this townhome offers both luxury and convenience in this prime location.

Welcome to waterfront luxury living at Buttonwood Bay Condominiums. This gated community in Key Largo is built around a deep-water coral rock harbor adjoining the Florida Bay. This residence includes a 29 boat slip conveniently located right outside your back door, providing direct access to the stunning waters of the Florida Keys. Meticulously remodeled with high-end finishes, this unit features two bedrooms, two full baths, and a half guest bath downstairs. New impact glass windows and doors flood the interior with natural light and offer breathtaking views of the marina. The floor-to-ceiling glass accentuates the beauty of the surroundings. Step into a gourmet kitchen adorned with rare blue granite, new cabinets, and state-of-the-art appliances. Community amenities include five tennis and pickleball courts, three heated swimming pools, a well-equipped fitness center, saunas, basketball, a meeting and party venue with kitchen, eight sunset martini docks, and a rare sandy beach! A boaters paradise, Buttonwood Bay also has a Ships Store with fuel pumps, live shrimp, ice, beverages and snacks. Theres a boat launching ramp and on-site storage areas for owners boat trailers. Onsite management, in-house landscape and maintenance staffs, and a 24/7 professional security team provide ease and peace of mind for owners. Experience a lifestyle of relaxation and recreation in this waterfront haven.

Moon Bay in Key Largo is a gated Florida Bay community offering weekly rentals. It is a great investment opportunity for investors or passive income when you are not using it. This corner-end unit offers unparalleled Views. This is an Updated condo that comes completely furnished. Includes a deeded 30 ft. boat slip #63 with a boat lift. Your screened balcony facing the bay gives you a Great Sunset View from this unit. Weekly Rentals, Yes Weekly Rentals ALLOWED!! This unit is licensed for short term rentals. The community just completed all major renovations with in the past 3 years including building roofs, all window and doors upgraded to impact, renovated pool and club house, entire complex painted, the parking lot was repaved, and the elevators were renovated, the HOA is as solid as they come with strong funded reserves! No Worries about assessments in the future and everything is NEW. Come take a tour of the best hidden paradise in Key Largo which offers some of the best diving and fishing! This Unit is Very Well Maintained and Ready for New Owners!

Beautiful 2 bed, 2 bath condo Bay Harbour in Islamorada. This condo boasts a 40 boat slip. Bay Harbour allows 7-day rentals with a license from the Village. Enjoy the pool, hot tub, tennis & pickleball courts, and the many exciting local activities available in the Keys, including fishing charters, boating excursions, snorkeling, and diving adventures.

This is truly a special piece of Paradise. Located in the prestigious Islamorada on the oceanside. Port of Call is low density, small private community, consisting of 5 buildings/10units with many amenities that allows for short term vacation rentals. There is a beautiful beach with shaded tiki hut area, a refreshing pool by the water, as well as boat slips.This updated unit has 2 bedrooms and 2.5 baths. One great feature is the eat in kitchen/dining area set in a sunroom. You have direct ocean views with prevailing breezes and enjoy sunrise from anywhere in the unit. It has two large screened balconies, a spacious roof top sundeck, plus under cover parking. Close to shopping, restaurants, marinas, Founders Park, plus so much more. Two hours to Miami or Key West. Call to see Port of Call today.

Experience stunning bay views and sunsets from this Bayfront condo at Rock Harbor Condominum in Key Largo! This spacious 3-bedroom, 3 Full bath condo offers a large kitchen with wood cabinetry, seamlessly flowing into an open floor plan ideal for entertaining family and friends. Each generously sized bedroom (16 x12+) has a walk-in closet for added convenience and private Bathroom. Relax on the private screened balcony and enjoy the refreshing bay breezes while taking in the expansive water views. Picture waking up every morning to the awe-inspiring beauty of the bay - the perfect start to your day.Rock Harbor Club is a gated, resort-style community surrounded by lush tropical landscaping. Boating enthusiasts will appreciate the easy access, along with optional dry rack storage in-and-out service, and dockage in the sheltered basin. Unwind in the heated and chilled pool, or stay active with a variety of recreational options, including pickleball, tennis, basketball, bocce ball, kayaking, and paddleboarding, all with convenient storage and launch areas.The communitys Bayfront clubhouse offers a range of amenities, from TVs and a fully equipped kitchen to restrooms, showers, saunas, and a gym. Embrace the relaxed Key Largo lifestyle by gathering around the fire pit, lounging on the sandy beach, or enjoying nightly sunsets over the bay. Live the dream and experience the best of Florida Keys living at Rock Harbor Club!

Beautifully completely remodeled townhome in the Boaters paradise. 27 assigned boat slip in your backyard! Travertines floors throughout, new plumbing and electric, SieMatic kitchen cabinets and Liebherr refrigerator. There is nothing that needs to be done! Buttonwood features: on site marina with fuel, bait and tackle shop, 3 heated pools, 3 tennis and 6 pickle ball courts, 2 lots for boat railer storage, beach, new gym, library, club house, on site management and 24-hour manned security including manned security gate. Great location, in close proximity to all amenities but far enough to not be disturbed.

Welcome to Boaters Paradise, featuring a 30 deeded boat slip! Immerse yourself in breathtaking ocean and lagoon views from this stunning 2-bedroom, 2-bathroom unit, which boasts one of the largest open floor plans in the complex at 1,672 sq. ft. This spacious layout provides the perfect backdrop for comfortable living, seamlessly connecting the living, dining, and kitchen areas--ideal for entertaining friends and family.Convenience is key, with an elevator located right outside your front door and a designated parking space directly beneath the unit for easy access. Additionally, a nearby charging station for electric vehicles adds to your comfort.Experience coastal living at its best at Coral Harbour Club, which features a lagoon with a sandy beach, a marina equipped with a boat ramp, fuel, ice, and direct ocean access. Enjoy a wealth of amenities, including tennis courts, bocce ball, an oceanfront pool, pickleball, kayak storage, access to compressed air, and so much more. Embrace a lifestyle filled with relaxation and recreation in this beautiful gated community!

Boaters paradise with resort life living. Enjoy this fully furnished trilevel 3 bed 3 bath townhome with marina and partial ocean view or short term rent it as an investment. Full-service marina, tennis & basketball courts, gym, heated pools (2) with hot spas, clubhouse and picnic areas with bbq grills. Gated entrance with 24/7 security. This unit has been managed by Keys Caribbean, future reservation can be transferred if buyer/s wish to do so.

Discover your retreat in the Landings of Largo! This upgraded 2-bedroom, 2-bath townhouse boasts stunning Florida Bay views, where spectacular sunsets set the stage for unforgettable evenings. Included is a deeded 30-foot boat slip with a 12k lift, perfect for endless boating adventures.Inside, enjoy custom kitchen cabinetry, impact windows, and doors for comfort and peace of mind. Relax on the spacious screened patio or take in breathtaking water views from the pop-out balcony. Beneath the unit, find ample covered parking and additional storage for all your gear.Nestled in a gated community at Mile Marker 98, this property is a haven for families and boating enthusiasts alike. The Landings of Largo features two sparkling pools, a state-of-the-art marina, a private boat ramp, and beautifully maintained grounds that exude tropical charm. With an active community vibe, youll find endless opportunities to connect and enjoy events or peaceful solitude by the water. This pet-friendly sanctuary welcomes two pets of any size, so you can bring your furry friends along to share in the adventure. Whether youre exploring the nearby coral reefs, indulging in world-class fishing, or simply savoring the coastal lifestyle, Landings of Largo offers the perfect setting. Just moments from local dining, shopping, and entertainment, youll enjoy the best of Key Largo living.Your slice of paradise awaits at Landings of Largo--embrace the vibrant lifestyle and create memories to last a lifetime! This Townhouse is SOLD fully furnished~

Fall in love with the breathtaking bayfront views and stunning sunsets from this beautifully remodeled 2-bedroom, 2-bath condo in prestigious Buttonwood Bay! This direct bayfront unit comes with an assigned 36-ft boat slip (36 x 12.75) and offers the ultimate Florida Keys lifestyle with spacious open-concept living and oversized bedrooms. Step inside to enjoy unobstructed bay views the moment you walk through the door, or dine alfresco on your expansive private balcony overlooking crystal-clear waters. The kitchen boasts granite countertops and stainless steel appliances, making it perfect for entertaining. This condo also features a brand-new A/C unit installed in 2025, ensuring year-round comfort in paradise. Buttonwood Bay is renowned for its luxury, five-star resort amenities, including a newly updated clubhouse with a heated pool, state-of-the-art fitness center overlooking the bay, full-service marina with ethanol-free fuel, and a marine store. Additional amenities include three heated pools, a private beach with a floating dock, six pickleball courts, five tennis courts, a basketball court, a childrens library and play area, a boat ramp, trailer storage, and convenient fish-cleaning stations. This condo comes with an assigned parking space conveniently located near the elevator and seven designated guest parking spots for the X Building. The building has a new roof, and a brand-new elevator will be installed soon, offering even more convenience and peace of mind. Situated in the heart of the Upper Keys, Buttonwood Bay provides quick access to nearby restaurants, shops, and Miami, making it the perfect location for your next home or getaway. Bring your golf cart and start living the Keys life today!

Peaceful Palms is a newly-constructed coastal development and spruced weekly vacation rental located in the gated community of Islamorada, Florida. This high-end property includes 15 townhomes, all positioned to offer oceanfront locations and views. Residents can enjoy stunning sights of the Sandbar and Alligator Reef Lighthouse, along with beautiful sunrises. For those interested in boating, there are oceanfront docking facilities available. The development also features an oceanfront pool, making it an ideal spot for a Florida Keys vacation or investment. Each townhome includes three bedrooms, three bathrooms, a spacious garage, and balconies on the second and third floors with oceanfront views. The property is pet-friendly and located near excellent fishing and diving spots. With the possibility of new building permits being limited in the Florida Keys, investing in Peaceful Palms could be a timely opportunity. Currently, the townhomes are available at pre-construction prices.

STRONG RENTAL HISTORY!! Welcome to Luxury Living in this Captivating Penthouse Condominium with Unobstructed Ocean Views in Sea Gulls Development! WEEKLY RENTALS ALLOWED making this an amazing investment opportunity! This remodeled Penthouse unit boasts breathtaking panoramic Atlantic Ocean views and offers an unparalleled lifestyle on the 7th floor. With 3 bedrooms and 2 bathrooms, this residence is the epitome of seaside living. The unit is designed to maximize comfort and style with well-appointed living spaces that seamlessly blend indoor and outdoor living. Enjoy unobstructed ocean views offering a front-row seat to the beauty of the Atlantic featuring two generous balconies providing the perfect setting for savoring the fresh sea breeze and taking in the mesmerizing sunrises. Sea Gulls offers a host of amenities, including a large heated oceanfront swimming pool, a gym and clubhouse. Step onto the large sandy beach just steps away. Secured lobby, ensuring controlled access and two convenient elevators. Nestled in a great location, Sea Gulls provides proximity to 5-star restaurants and shopping. This penthouse is not just a home; its a lifestyle. Immerse yourself in the tranquility of oceanfront living. Dont miss the opportunity to make this beautiful Penthouse your own!

Expansive ocean views! Beautifully updated 2/2 condo with a 35 ft. boat slip and 18,000 lb. boat lift in Islamoradas desirable Ocean Harbour community. Enjoy immediate boating access to the Atlantic Ocean and quick boating access to Florida Bay through nearby Snake Creek channel. Open ocean views throughout from the relaxing screen porch to the large living room, dining area, kitchen and primary bedroom. This unit has been beautifully updated with an open concept kitchen, solid wood cabinets, stainless appliances and granite countertops. Both baths are tastefully updated, and all the doors and windows are impact rated. Ocean Harbour condo is situated on a sprawling 12 acres and the grounds are beautifully manicured and shaded in lush tropical landscaping. In addition to the marina, the community also offers a boat ramp and the rare convenience of onsite boat/trailer storage. There is also a large ocean view pool, ocean view clubhouse, ocean view gym, and ocean-side beach area with tiki huts and lounge chairs for enjoying the ocean breeze. The gated community also offers a covered parking spot and a storage closet for every unit, along with abundant additional open parking, electric car charging station, and tennis courts. This community allows each owner to have two pets (any size). Call today for your private tour of this outstanding Islamorada community.

This exquisite 2-bedroom, 2-bathroom townhouse offers breathtaking views of the florida bay, showcasing stunning sunsets that transform your evenings into a breathtaking spectacle. Just steps from your door lies your private 30-foot deeded boat slip, complete with a 12k boat lift, inviting you to embark on endless aquatic adventures. Fully renovated in 2020, no detail has been overlooked in this sophisticated retreat. The custom kitchen cabinets exude elegance, while bespoke closet systems provide both functionality and style. Enjoy the convenience of ample covered parking, a spacious screened patio for al fresco dining, and additional storage beneath your unit. Impact windows and doors ensure your coastal haven remains secure and serene, while the pop-out balcony bathes the interior in natural light. Situated at Mile Marker 98, Landings of Largo is a gated sanctuary that beckons families and boating enthusiasts alike. The community boasts two inviting pools and a state-of-the-art marina, community boat ramp, along with convenient dry boat and trailer parking, making it effortless to embrace the boating lifestyle amidst the crystal-clear waters of Key Largo. Personal watercrafts allowed. This pet-friendly haven welcomes two pets of any size, allowing you to share your seaside sanctuary with your furry companions. Please note, short-term rentals are not permitted, ensuring the tranquility and charm of this remarkable community remain intact. Step aboard and immerse yourself in the luxurious lifestyle that awaits you at Landings of Largo, where cherished memories and a vibrant coastal community come together in perfect harmony.

Bay Harbour condos, located at MM 74.5 on Lower Matecumbe is a very desirable community. BAY HARBOUR ALLOWS 7-DAY RENTALS. Transient Rental License can be obtained from the Village of Islamorada that allows weekly rentals which are restricted in most communities in Islamorada and indeed all of Monroe County. This 2,000 sq. ft three-bedroom, two and a half bathrooms has a view of the sunrise on the Atlantic Ocean. A 30 boat slip is included which allows quick access to Florida Bay and a short ride will bring you to the ocean through channel 2 or channel 5. This gated community boasts a fantastic pool and hot tub along with a gym, clubhouse and tennis courts. Landscaping and maintenance of the property is professionally directed by the on-site property manager. This unit is equipped with propane gas range. Floor plan dimensions in photos are very close estimates. Buyer to verify.

Ideal location in the desirable Bay Harbour community. Convenient access to Florida Bay and the Atlantic Ocean. Community amenities include a pool, hot tub, gym, and clubhouse. Perfect for year-round living or as a vacation rental as Bay Harbour allows 7-day rentals with a Village Vacation Rental License. This condo has a 16,000# boat lift in the designated boat slip.

A Boaters Dream! Deepwater dockage on the oceanside of desirable Upper Matecumbe Key! Beautiful Beacon Reef condo complex has a newly renovated pier with available shore power can fit up to 35 boat. Unit 405 is one of the rarely available units that come with deeded covered parking spacious enough for a boat & trailer as well as your car or truck. Immaculate and cared for, Unit 405 has had the same owner since 94. Features include amazing open water ocean views from covered balcony and primary bedroom. Kitchen has been updated with stainless steel appliances and custom cabinetry. Primary bathroom has been updated with added closet space. All windows are impact. The Beacon Reef complex is expertly and exquisitely maintained top to bottom with a long list of First class amenities such as resort style tropical landscaping with shady palm trees, lush green grass & a sandy beach w/ lounge chairs. Zero entry, large walk-in pool. Chickee hut and multiple BBQs for entertaining. . Private sauna & gym overlooking the ocean. Club house with kitchen available to homeowners for private functions. A great investment as monthly rentals are allowed upon approval.