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

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.

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...

Indigo Reef is one of Marathons hidden gem. Nestled in the heart of coastal charm, 23 Indigo Reef is a captivating residence that seamlessly blends luxury with the tranquility of a seaside escape. This immaculate property invites you to experience the epitome of refined coastal living, offering a perfect balance of elegance and comfort.Key Features:Prime Waterfront Location: Situated along the pristine shoreline, 23 Indigo Reef boasts unparalleled views of the azure waters that stretch as far as the eye can see. The gentle lapping of waves and breathtaking sunsets become a daily spectacle from the comfort of your own home.Architectural Splendor: This residence is a testament to architectural excellence. From the moment you enter, you are greeted by an open-concept design that maximizes natural light, seamlessly connecting indoor and outdoor living spaces. The thoughtful layout ensures every room enjoys panoramic views of the surrounding beauty.Coastal Interiors: Step into a world of tranquility. The kitchen is a chefs dream, equipped with top-of-the-line appliances, while the bedrooms offer a tranquil retreat with spacious layouts and breathtaking vistas.Private Outdoor Oasis: The allure of 23 Indigo Reef extends beyond its interiors. The meticulously landscaped grounds provide a private oasis for relaxation and entertainment. Lounge on the expansive terrace, take a dip in the sparkling pool, or unwind in the shade of swaying palm trees - this property is a haven for those seeking the perfect blend of privacy and outdoor enjoyment.Waterfront Lifestyle: Boating enthusiasts will appreciate the private dock, offering direct access to the open waters. Explore the nearby coves, embark on fishing adventures, or simply cruise along the coastline - the possibilities are as boundless as the ocean. BOAT DOCK SPACE SW 31 is slip 26.

Waterfront corner GEM meticulously maintained in beautiful Buttonwood Bay Condo. Offers privacy and convenience with a 36 boat slip right behind your unit, a true boaters paradise. Turn-Key and ready to move in. Looking for the resort life? Experience unparalleled waterfront living in this beautifully updated 2-bedroom, 2.5-bath corner unit located in an exclusive gated community with resort amenities. Modern upgrades, including impact windows and doors, granite countertops, tiled floors throughout, two walk-in showers. Built-in dressers. Balconies have been enclosed allowing more space, natural light and beautiful waterfront sceneries. Nestled in the heart of Key Largo, Buttonwood Bay spans 42 acres of tropical beauty, featuring a deep-water coral rock harbor with direct access to the Florida Bay and Intracoastal Waterway. Residents enjoy resort-style amenities, including three heated swimming pools, five tennis courts, a state-of-the-art fitness center, saunas, a clubhouse with a full kitchen, a game room, basketball courts, and eight sunset martini docks. This community also boasts a rare sandy beach, a marina with fuel pumps, ice, beverages, and snacks, as well as a boat launching ramp and on-site storage for trailers. With a 24-hour manned gatehouse and a welcoming community atmosphere, Buttonwood Bay offers the perfect blend of luxury, security, and island-style living. Dont miss this rare opportunity to own a corner unit with more side yard. The perfect place to enjoy your days in Paradise.

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!

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!

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!

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

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.

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!

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 premier gated community, residents enjoy a marina, a private beach, three heated pools, a fitness center, tennis & pickleball courts, and a clubhouse. This unit comes with a 34ft boat slip assigned. With 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!

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.

Are you ready to experience luxury living at its finest? Lets explore a unique opportunity in Marathon, where comfort meets style in a fully renovated apartment that sets the standard for high-end living. Situated on the 4th floor and boasting stunning views overlooking a crystal-clear pool, this residence is a perfect getaway. Featuring three beautifully designed bedrooms and two modern bathrooms, it ensures ample space and privacy for all residents, with each room radiating a sense of calm and luxury. The heart of this home is its custom kitchen, equipped with all-new appliances-ideal for both seasoned chefs and casual cooks, the modern layout and design will inspire your culinary creativity. Additionally, entertain your guests effortlessly with the sleek wet bar and built-in wine cooler, perfect for storing your favorite vintages. Enjoy peaceful afternoons on your open porch overlooking the pool, with impact windows and doors featuring shutters for safety during hurricane season. The community offers resort-style amenities including an expansive pool, exclusive access to tennis courts, an on-site spa, and unparalleled peace of mind within a secure, gated complex. Located in Marathon, youll have proximate access to the Florida Keys stunning beaches, dining, and local culture, with nature trails and leisure activities just a short drive away. This apartment has undergone a complete transformation, boasting new state-of-the-art kitchen appliances and modern finishes throughout, providing you with a contemporary, move-in-ready home. If this sounds like your dream home, dont miss out on this amazing opportunity. With a combination of luxury amenities and an unbeatable location, this Marathon apartment offers a lifestyle like no other. Arrange your viewing today and step into your new life of comfort and style.

Welcome to this beautifully designed third-floor condo in the exclusive Seawatch community. This spacious 2,000 sqft, 2-bed, 2-bath residence offers a dual master layout and breathtaking water views from every room. The fully glassed rear of the unit provides an uninterrupted view of the marina, including your deeded 35-foot boat slip. With direct access to both the Atlantic Ocean and the Gulf of Mexico, this home is perfect for boaters. The large living room is filled with natural light, with expansive windows creating a seamless connection to the picturesque surroundings, as the floor to ceiling glass enclosed unit overlooks the Gulf of Mexico and the whole marina with an uninterrupted view directly over your very own deeded boat slip. The dual master suites each offer a private retreat with floor-to-ceiling glass windows, walk-in closets, and open-water views. A completely renovated primary bathroom features a soaking tub & walk-in glass shower. The renovated kitchen, features white cabinetry, rare blue granite countertops, a stainless steel/white appliance package, a new stainless steel refrigerator (2024), dual dishwasher drawers, and ample storage. Has a generous walk-in pantry, dedicated wet bar near the entrance, and a dining area. The guest bath includes a walk-in shower, while an enclosed washer/dryer and deep utility sink in the second master add convenience. The main living area features tile flooring, while updated carpet in the bedrooms adds warmth. Wood plank flooring transitions from the living area to the sunroom, where you can enjoy breathtaking waterfront views. Seawatch is a private, gated 17 acre community designed for relaxation and recreation. Amenities include a resort-style pool with cabana, a fully equipped fitness center, tennis and pickleball courts, and a large storage barn for boats, RVs, golf carts, and kayaks. Known for its exclusivity, privacy, and immediate water access. No rentals are permitted for the first 2 years of ownership

Closest living to OLD TOWN with a boat slip!! Peace and quiet and a boaters delight! This small condo complex located in the beautiful Meadows neighborhood has an ordinance against vacation rentals which ensures consistent tranquility with a virtually private pool. One of the only properties close to Old Town where you can keep your boat in the water with an assigned boat slip. With the rising cost of boat slips and marina rates, the slip can save you upwards of a $1000 per month. This third floor 2BR/2BA unit allows for panoramic views of the marina and Key West. The property has had many upgrades during this ownership including new decorative floors with a coastal feel, an upgraded bathroom, new AC, washer and dryer, and some appliances. Enjoy entering a cool car with the covered parking, a rare find in The Meadows. Large private exterior storage space is included. The views are a must see!