Florida Keys Waterfront Condos on the Bay / Gulf Side of the Island For Sale

Welcome to Waterfront Living at Buttonwood Bay in Key Largo!Experience stunning sunsets and the ultimate boaters paradise from this beautifully situated residence in the highly sought-after Buttonwood Bay community. Enjoy your own private waterfront patio just steps from a protected 33 dockage, perfect for effortless boating access. Spread across 42 acres of tropical beauty, Buttonwood Bay features a deep-water coral rock harbor with direct access to the Florida Bay and nearby Atlantic Ocean. Step inside to a comfortable open living floor plan offering 2 bedrooms and 1.5 bathrooms, blending comfort and style in a relaxed setting. Enjoy resort-style amenities including a full-service marina and boat ramp, on-site Ships Store with everything from snacks and drinks to bait, ice, fuel and owners parking for trailers, three heated pools, five tennis and pickle ball courts, fitness center with waterfront marina views, saunas, a basketball court, clubhouse, sandy beach, 24-house security and staffed gatehouse. Whether youre looking for a full-time residence or the perfect weekend escape, this is your chance to embrace the Florida Keys lifestyle. Buttonwood Bay isnt just a location--its a way of life.

KEY WEST mid town open water 2/2 gem boasting an open floor plan offered turnkey with new furnishings and a deeded 12 X 24 gulf side boat dock. Hilton Haven is a unique neighborhood located mid island on a strip of land that offers a mixed use of waterfront properties on each side. This 8 unit condominium complex is at the end enjoying peace and quiet and also has its own private white sand beach and waterfront pool. Many extras to be enjoyed including tile floors throughout, 2 balconies offer both waterfront and sunset views and an abundance of closet space plus a designated generous storage room for all of your beach/water toys. Property was recently enrolled in a professional monthly vacation rental program. All of this within the city limits of Key West where you will find both nightlife, easy airport access and all of your shopping needs a bike ride or short drive away.

Beautiful 2 bed, 2 bath condo Bay Harbour in Islamorada. This condo boasts a 30 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.

Waterfront Corner Gem with Boat Slip at Your Back Door!Live the dream in this meticulously maintained and beautifully updated 2-bedroom, 2.5-bath corner unit in the sought-after Buttonwood Bay community. Your 36 boat slip is just steps from your back door, offering unbeatable convenience for avid boaters--no need to haul gear or walk across the complex. Its true waterfront living at its finest.This turn-key home is move-in ready and features thoughtful upgrades throughout, including impact windows and doors, granite countertops, tiled floors, two spacious walk-in showers, and built-in dressers. Enclosed balconies create a light-filled, open feel while maximizing living space and showcasing tranquil water views.Nestled in the heart of Key Largo, Buttonwood Bay is a 42-acre gated paradise with direct access to Florida Bay and the Intracoastal Waterway. Enjoy world-class amenities: three heated pools, five tennis courts, a fitness center with saunas, a clubhouse with full kitchen and game room, basketball courts, and eight spectacular sunset martini docks. The community also features a rare sandy beach, full-service marina with fuel, snacks, and ice, a boat ramp, trailer storage, and a 24-hour manned gate for peace of mind.With corner-unit privacy, a generous side yard, and a boat slip right outside your back door, this home delivers the ultimate Florida Keys lifestyle. Paradise is calling--dont let this one slip away!

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~

Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathroom condo, an exceptional opportunity for a personal coastal escape or a versatile vacation rental. Fully furnished with modern decor, high-end appliances, and meticulous craftsmanship, this turnkey property is poised to impress from the moment you step in. Conveniently located at the entrance to the island of Key West, it offers seamless access to a wealth of shops, dining, entertainment, and recreation options, delivering convenience and enjoyment at every turn. With its streamlined rental setup, this condo is perfect for buyers seeking potential income or for those desiring an upscale island retreat all to themselves with all the amenities one could possibly ask for. Property has two restaurants, a bar, covered parking, mini marina dockage for boating while visiting and a fitness center all on site. Experience the best of refined island living!

Remarkable Waterfront Retreat- 32 Hilton Haven #9, Key West, FLWelcome to an exclusive waterfront sanctuary in the private community of Bay Villas in Hilton Haven. This beautiful 2 bedroom, 2.5 bath residence offers direct water views making it a rare gem in Key West.The primary suite boasts panoramic water views and balcony. The peaceful setting is just minutes from Old Town Key West, This home is ideal for those seeking the ultimate island lifestyle, Whether as a full-time residence, vacation getaway or investment opportunity, 32 Hilton Haven #9 is a rare find . Schedule your private showing today...

The LOWEST PRICED UNIT AT INDIGO REEF ON THE MARKET! Freshly painted inside & out & READY TO ENJOY THE ULTIMATE Keys Lifestyle! Located in INDIGO REEF, a luxurious town-house style community situated directly on the Gulf of Mexico just minutes from the heart of Marathon, yet quiet & tucked away from it all. With over 10 Acres of private land and gated, Villa 24 boasts incredible OPEN WATER views, vaulted ceilings in the main bedroom, quick and easy ocean access through the Vaca cut and an OPEN concept floor plan. This 3 bed/2.5 bath 1600 Sqft. townhome comes with a deeded 35 ft boat slip located just steps away from the unit. Indigo Reef community offers a spacious HEATED resort style pool with plenty of cushioned lounge chairs, Ice machine, Kayak storage, professional GYM room and ample owners storage located in the temperature controlled HOA building with room for bikes and fishing gear. This home also comes with its own covered parking spot just steps from the front HOA building where more parking can be found along with additional storage on top. Villa 24 comes fully furnished and is a weekly vacation rental. Enjoy nightly sunsets while sipping a Key lime margarita from your GULF VIEW unit! You will LOVE sitting under your covered porch while you gaze over the gorgeous BLUE tones of the Gulf & relax after a successful day out on the water. This villa was recently modernized and freshly painted inside and out. Other notable features include, tile flooring throughout, GRANITE counter tops & STAINLESS steel appliances. SOLD FURNISHED & TURN KEY, ready for you to rent, relax & enjoy the Margarita~ville / Keys lifestyle all year long. Call today to make this home your island dream getaway!

Year to day as of May 31, 2025 gross income $95K!!! Tranquility and stunning Bay views await! Welcome to Tranquility Bay Resort, located in the heart of Marathon, offering resort-style amenities and outstanding rental capabilities. A rare opportunity for a corner unit, this 3-bedroom, 2.5-bath gulf front townhome is uniquely situated at the quiet, northern end of the resort, yet convenient to all of the fabulous amenities. A perfect blend of luxury and investment with no rental restrictions and a strong rental history.Step inside and be greeted by stunning open bay views from your private porch! Enjoy the extra light from additional windows afforded by the end location. This home comes fully equipped with dishes, linens, furniture, and more, making it truly turnkey. The inviting main level features a spacious living and dining area, a fully equipped kitchen, a half bath, and a balcony that leads directly to the water. Upstairs, the primary suite includes an en-suite bath and a large porch with breathtaking water views, while two additional guest bedrooms, a full bath, and a laundry area complete the second floor.Resort amenities include two pools, a sandy beach, watersports, top rated Butterfly Cafe restaurant, a Tiki Bar, and putting greens, making Tranquility Bay a top destination for visitors. Centrally located in the heart of the Florida Keys, this property is a strong income producer, recognized with multiple TripAdvisor awards.Dont let the sun set on this exceptional investment and vacation home opportunity at one of the Florida Keys most successful & sought-after resorts!

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!

Luxury Waterfront Living with Premier Boating Access at Seawatch Condominium. A beautiful 3-bedroom, 2-bathroom residence in this exclusive community. This beautifully appointed condo offers a spacious open floor plan, an upgraded kitchen with granite countertops, Primary bath is upgraded with two individual vanities and large walk in shower. Guest bathroom is upgraded with tile and granite countertops. A large screened-in porch totaling 400 sq ft perfect for enjoying the tropical breeze. For boating enthusiasts, this property is a dream come true. The unit includes a deeded 30-foot boat slip, providing incredibly easy access to both the Atlantic Ocean and the Gulf of Mexico through Vaca Cut channel. Whether youre heading offshore for world-class fishing or exploring the backcountry waters of the bay, navigating between the two is effortless from this prime location. Additionally, the community offers boat barn storage that can house your boat, trailer and other storage items for added convenience. Each unit is assigned a covered parking space. The gated community of Seawatch Condo sits on 17 acres and boasts resort-style amenities, including tennis and pickleball courts, workout room, large pool and spa, and an inviting veranda room for social gatherings. The meticulously maintained grounds create a serene, private atmosphere, making this a perfect retreat for full-time residents or seasonal homeowners. Rental Restrictions: No rentals are allowed for the first two years of ownership; after that, a minimum rental period of 30 days applies. If youre seeking the ultimate Florida Keys lifestyle, complete with luxury, comfort, and unparalleled boating access, look no further. Schedule your private tour today!

OPEN WATER VIEWS and BREATHTAKING SUNSETS from this Gulfpointe townhome! Enjoy happy hour on the balcony and look for the green flash! Located in a tucked-away community directly of the Gulf of Mexico. Open the impact sliding glass doors on two sides of this corner unit and feel the sea breezes. Move in ready! This spacious two bedroom, two and a half bath condo has new air conditioning, new dishwasher, new bait chest freezer, and granite countertops. The common area amenities include a beautiful pool with a new heater and chiller! Newer impact windows, sliders and front door, metal roof and exterior paint. The community dock can accommodate boats up to 36 feet. Dockage is on a first come, first serve basis with owners having priority. Covered designated parking for three vehicles. Wrap-around balconies on both the main floor and upper floor with stunning Gulf views and the Vaca Cut Channel. The condo complex recently passed State of Florida certification requirements. Spalling repairs completed and no pending assessments. Weekly rental option. B&BATVAI

Welcome to a breathtaking beach house in Tranquility Bay Resort, where luxury meets profitability. This 3-bedroom, 3-bathroom waterfront townhome offers the perfect blend of a tropical escape and an income-producing investment.Nestled in an idyllic location just steps from the Gulf and pristine white sandy beaches, this stunning property boasts direct open-water views of the bay. The ground floor features a spacious living area, a convenient half bathroom, and a private porch perfect for relaxing or entertaining. Upstairs, the primary bedroom includes an en-suite bath and a large private porch with mesmerizing water views, while two additional guest bedrooms, a full bathroom, and a laundry area complete the second floor.Tranquility Bay Resort offers an array of amenities, including two resort-style pools, a sandy beach, a tiki bar for sipping cocktails while enjoying stunning sunsets, a fitness center, a Jack Nicklaus putting green, and the award-winning Butterfly Cafe. With beautifully landscaped grounds and endless opportunities for watersports, this is the ultimate destination for relaxation and recreation.As one of the top income-producing properties in the Middle Keys, Tranquility Bay Beach Homes have earned multiple TripAdvisor awards and are a favorite among guests. Owners can enjoy up to 35 days annually for personal use while generating rental income. On-site management handles all operations, providing effortless ownership and peace of mind.This turnkey property is more than a home--its your opportunity to balance personal enjoyment with smart investment potential. Experience the Florida Keys lifestyle, where relaxation and returns meet. Dont wait--your slice of paradise awaits at Tranquility Bay Resort!

Welcome to waterfront luxury living at Buttonwood Bay south Key Largo. This gated community 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.

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.

Welcome to your dream waterfront retreat in the highly sought-after Buttonwood Bay community in Key Largo! This beautifully updated 2-bedroom, 2-bathroom condo offers breathtaking open bay views, allowing you to enjoy spectacular sunsets right from your living room. Step inside to find a thoughtfully designed space featuring tasteful updates and an open-concept layout that maximizes both comfort and style. The bright and airy living area seamlessly extends to a private balcony, where you can relax and take in the beauty of the Florida Bay. Both bedrooms provide a tranquil escape, with the primary suite offering bayfront vistas and an en-suite bath. The second bedroom is equally inviting, perfect for guests or a home office. Additional features include ample storage and a washer/dryer in-unit. Located in Buttonwood Bay, a 42 acre gated community, residents enjoy a marina, a private beach, three heated pools, a fitness center, tennis, pickleball and basketball courts, rooftop sundeck, library, game room AND a clubhouse. This unit comes with an assigned 34ft boat slip right by the fuel dock . A full-service marina offering fuel, ice, and a boat ramp, this is a boaters paradise! Whether youre looking for a weekend getaway or a full-time residence, this turnkey condo is an exceptional opportunity to experience the best of the Florida Keys lifestyle. Dont miss your chance to wake up to panoramic bay views every day! Schedule your private showing today!

VERY RARE CORNER UNIT, Freshly painted inside and out & READY TO ENJOY the Ultimate Keys Lifestyle ! Located in INDIGO REEF, a luxurious town-house style community located directly on the Gulf of Mexico just minutes from the heart of Marathon, yet quiet & tucked away from it all. Situated on over 10 Acres of private land and gated, Villa 25 boasts tons of natural light as an end/corner unit, Incredible OPEN WATER views, vaulted ceilings, quick and easy ocean access through the Vaca cut and an OPEN concept floor plan along with a BONUS room with added square footage on the main level. This OVERSIZED 3 bed/2.5 bath, 1690 Sqft. townhome comes with a deeded 35 ft boat slip located just steps away from the unit. Indigo Reef community offers a spacious HEATED resort style pool with plenty of cushioned lounge chairs, Ice machine, Kayak storage, professional GYM room and ample owners storage located in the temperature controlled HOA building with room for bikes and fishing gear. This home also comes with its own covered parking spot just steps from the front HOA building where more parking can be found along with additional storage on top. This unit comes fully furnished and is a successful weekly vacation rental. Enjoy nightly sunsets while sipping a Key lime margarita from your GULF VIEW unit! You will LOVE sitting under your covered porch while you gaze over the gorgeous BLUE tones of the Gulf & relax after a successful day out on the water. This villa was recently modernized and freshly painted inside and out. Other features include, tile flooring throughout, Large bonus room that could be converted into a 4th bedroom if desired, GRANITE counter tops & STAINLESS steel appliances. SOLD FURNISHED & TURN KEY, ready for you to rent, relax & enjoy the Keys life style all year long. Call today to make this oversized & rare corner/end unit your island dream home!

Beautiful Townhome with Deeded Boat Slip in The Landings of Largo!Welcome to the waterfront lifestyle youve been dreaming of--complete with Deeded Boat Slip #3 and an 8,000 lb boat lift just steps from the community boat ramp. This spacious 3-bedroom, 2-bath upstairs townhome also features an enclosed lower-level recreation area approximately 1000 sf., with a full bath, ideal for guests, hobbies, or flexible living.Inside, youll find vaulted ceilings, beautiful wood-look tile flooring throughout, custom wood cabinetry, and impact windows and doors (excluding the rear balcony). The front balconies have been enclosed, creating additional air-conditioned living space, while the L-shaped screened balcony offers a relaxing view of the main pool.Other highlights include covered parking directly beneath your unit. A concrete structure with metal roof and no assessments with a healthy budget. Located on the bayside at Mile Marker 98, Landings of Largo is a well-maintained, gated community offering resort-style amenities: two heated pools, a new marina, boat ramp, clubhouse, fitness room, Sunset Pier, trailer parking, and a fish cleaning station. Its also pet-friendly and perfect for those seeking peace and quiet, with a 28-day minimum rental policy.Whether youre looking for a full-time residence or a relaxing retreat, this home offers it all--convenience, comfort, and a true boaters paradise.

TURNKEY Indigo Reef villa is now available! This 3-bedroom, 2.5-bathroom townhome is a boaters dream and income-earning gem. Villa 47 offers breathtaking open-water views, vaulted ceilings, and an open-concept downstairs living space that is ideal for entertaining. Throw open the French doors to expand the space further and unwind in the shade of the covered porch while overlooking the manicured grounds and water. Upstairs, youll find a well-thought design encompassing the 3 bedrooms, 2 bathrooms, and laundry. Each bedroom features balcony access with the 2nd and 3rd bedrooms opening to the front-covered balcony; perfect for watching the sunrise. The primary ensuite opens to the private, upper back deck where you can soak up the sun, relish stunning sunset views, or stargaze while overlooking the sparkling Gulf.Amenities abound in Indigo Reef. The private community is conveniently located minutes from the heart of Marathon and all that the island has to offer, while peacefully tucked away from the noise, situated on 10+ acres along the waters edge. The gated, resort-like community features a spacious, heated pool with comfortable lounge chairs, an ice machine, kayak storage, a professional-grade gym, and ample owner storage in the temperature-controlled HOA building -- perfect for bikes and fishing gear. This home comes with an assigned covered parking space steps from the front entrance. Off the back porch, youll find some of the best boating and fishing in the world. The 31 deeded boat slip is protected by mangroves while the deep-water channel is easy to maneuver and allows quick access to the Gulf and ocean via Vaca Cut.Fully furnished and currently a successful weekly vacation rental, the new owner can start earning income immediately with bookings in place through June. This home is a must-see! Call today to make it yours!

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.