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

Total Listings 95
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$1,150,000
Marathon
Tranquility Bay   - MM: 48.50
3 Bed, 3 Baths, 1,320 SqFt Days Listed: 7
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Rare Prime Beachfront Rental Property at Tranquility Bay. Directly on the sand, 3-bedroom, 2.5-bath beachfront townhome in sought-after destination in the Florida Keys directly on the sand. One of the most requested rental units in the heart of Marathon. Boasting uninterrupted Gulf views from your private porch, this two-story home offers the ultimate in coastal living with strong, consistent rental income and professional onsite management. A proven income producer with multiple TripAdvisor accolades, this property is the perfect hands-free investment or luxurious personal getaway. The incredible amenities include a marina, multiple pools, putting green, gym, waters sports, award winning beach front restaurant and tiki bar. This is truly the Keys living at its best!

$1,150,000
Marathon
Indigo Reef Marina Homes   - MM: 52.50
3 Bed, 3 Baths, 1,690 SqFt Days Listed: 192
-4.56% ($55,000) 1 Price Change : Last Change 125 Days Ago
Townhouse - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip35ft.

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!

$1,200,000
Marathon
Indigo Reef Marina Homes   - MM: 52.50
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 106
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat S

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!

$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 432
-3.92% ($50,000) 1 Price Change : Last Change 286 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip30ft.

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.

$1,225,000
Marathon
Seawatch   - MM: 53.50
2 Bed, 2 Baths, 2,000 SqFt Days Listed: 111
-5.70% ($74,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip35ft.

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

$1,295,000
Marathon
Seawatch   - MM: 53.50
3 Bed, 3 Baths, 1,602 SqFt Days Listed: 97
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

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.

$1,300,000
Key West
Harbour Lodge   - MM: 2.00
2 Bed, 2 Baths, 1,351 SqFt Days Listed: 897
Condo - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock26ft.

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!

$1,300,000
Key Largo
Buttonwood Bay   - MM: 96.00
2 Bed, 2 Baths, 1,278 SqFt Days Listed: 27
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat S

Premier Location in Buttonwood Bay Club.Experience breathtaking open water views the moment you step into this top-floor end unit, perfectly situated in the most desirable location within Buttonwood Bay. This is a true boaters dream, complete with a 29 boat slip in a deep-water, protected marina featuring an on-site fuel dock and ships store stocked with bait, ice, snacks, and essentials. Enjoy sweeping views of the crystal-clear blue waters by day and unforgettable sunsets each evening from your private balcony. The fifth-floor elevation offers unmatched privacy and uninterrupted ocean breezes. This fully-furnished and beautifully updated two-bedroom, two-bath condo features sleek frosted glass doors, custom built-ins, newer appliances, and impact-resistant windows and doors throughout. Buttonwood Bays amenities are second to none with 3 heated and chilled pools, private beach, 8 pickleball courts, 3 tennis courts, waterfront fitness center, 8 martini docks, boat ramp and trailer parking, marina and ships store, saunas, party room, rooftop sundeck, library, game room, basketball court, gated entrance with guard, on-site management, rental and sales office all on 42 acres of lush tropical landscaping with walking and biking paths. The community also boasts a lively year-round calendar of activities, clubs, and events that make it easy to feel right at home.

$1,350,000
Marathon
Bougainvillea Villas Condomin   - MM: 53.50
3 Bed, 3 Baths, 1,493 SqFt Days Listed: 104
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

**For Sale: Stunning Marathon Florida Gulffront Waterfront Home** Welcome to your dream coastal escape! This exceptional 3-bedroom, 3-bath townhome offers breathtaking rooftop views of the sparkling Gulf of Mexico, providing the perfect backdrop for a relaxed lifestyle by the sea. Experience luxurious living with two hot tubs -- one thoughtfully located on the ground floor for easy access, and the other perched atop the rooftop, ideal for soaking under the stars or admiring spectacular sunsets. This three-story townhome is not only fully furnished with stylish decor, but it also comes equipped with an elevator, ensuring convenience and ease for all. Located just a stones throw away from the beautiful Key Colony Beach, you can enjoy sun-soaked days on the shoreline and enjoy dining on the Ocean or shopping in the eclectic nearby stores. Dont miss the opportunity to own this slice of paradise, where coastal charm meets modern comfort. Whether youre looking for a primary residence, a vacation getaway, or an investment property, this home is sure to exceed your expectations! See it in person and start imagining your life in this Turnkey waterfront oasis.

$1,425,000
Marathon
Tranquility Bay   - MM: 48.50
3 Bed, 3 Baths, 1,345 SqFt Days Listed: 9
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

This 3 bedroom Beach Home is found in a PRIME location at Tranquility Bay Resort. Additionally this property offers the largest floor plan with an extended dining space with natural light flowing in from all around the surrounding sandy beaches. Beautifully designed and located directly on the WHITE SANDY BEACH- an excellent choice for families or groups. With spacious layouts and modern amenities, this home provides a comfortable and relaxing environment for your entire family to enjoy. INVESTMENT POTENTIAL IN THIS LOCATION is exceptional and with Tranquility Bays reputation and high occupancy rates, the property has strong rental potential, especially for vacationers seeking a luxurious getaway. The ability to reserve personal time while still generating income makes it an attractive option for investors. Make this your income producing family place to make memories for a lifetime.The lagoon-style pool offers a tropical feel, perfect for unwinding under the sun. The onsite Butterfly Cafe Restaurant is a long standing favorite of locals, which in itself speaks volumes. The restaurant overlooking the pool and grounds is a convenient option for guests to enjoy dining without leaving the resort. The fitness center, adult pool, and putting green add to the recreational options available.Being located on the white sandy beach is exclusive to ONLY a handful of beach homes. The location also allows for easy access to water activities like swimming, snorkeling, and kayaking. After a day in the sand or on the water take in our Breathtaking Florida Keys sunsets from your expansive porch. The surrounding area is rich with opportunities for exploring nature, local wildlife, and the vibrant marine ecosystem in our FABULOUS Florida Keys! Call for further details.

$1,499,000
Marathon
Indigo Reef Marina Homes   - MM: 52.50
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 382
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip3

LUXURIOUS townhome in desirable INDIGO REEF located in Marathon! One of the most beautiful units in this upper end development with immaculate interior finishes and spectacular OPEN WATER views right out your back door. Take a short walk to your deeded 31 boat slip offering the only BOAT LIFT in the development. Easy bay and Atlantic Ocean access to enjoy amazing fishing, snorkeling and diving or take a boat ride to nearby waterfront restaurants. Fully furnished and spacious 3bd/2.5ba, open living area floor plan. Enjoy breathtaking sunsets from the large patio off of the living room or master bedroom. Indigo Reef offers beautifully manicured grounds with lush tropical landscaping. Assigned covered parking and enclosed a/c spacious storage area. Outstanding amenities include a resort style pool and fitness center. Weekly rentals allowed making this an amazing investment. You will truly love living the FL Keys Lifestyle in Indigo Reef! Following is a list of outstanding features.....12,000 LB custom boat lift with remote and auto stop. PVC dipped piles. 2022 Trane A/C with new composite A/C condenser platform. Foam insulated walk around attic storage, climate controlled with ceiling drop down attic ladder. Second attic storage in carport with ceiling drop down attic ladder. 2022 ADT monitored touch screen alarm system with CCTV camera system and app controlled viewing. App controlled keypad door lock and Wifi hub. App controlled A/C thermostat. Whole home Surge Protector. Sony wall mounted LED smart TVs. Built in Samsung Surround sound System in living room. Sony Surround sound in Master Bedroom. Custom kitchen wall tile, above and below LED cabinet lighting with custom cabinet crown. Matching GE Profile kitchen appliances with glass top oven. Reverse Osmosis drinking water and ice. Ultra high end silver imbedded window treatments. Exotic ceiling fans in all bedrooms and living room. Samsung washer and dryer.

$1,699,000
Key West
Roosevelt Annex   - MM: 2.00
3 Bed, 3 Baths, 1,320 SqFt Days Listed: 86
-5.35% ($96,000) 1 Price Change : Last Change 57 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Key West Waterfront Paradise - Private Dock & Pool!Welcome to one of the most exclusive waterfront homes in Key West, located in the prestigious gated community of Gulfview Pointe. This rare gem is one of the few properties in Key West offering both a private dock and private pool, making it the ultimate island retreat!Step inside to an open concept living and dining space, where ocean views of the Gulf from your living room create a breathtaking backdrop. The gourmet kitchen is a chefs dream, featuring granite countertops, stainless steel appliances, and coastal wood cabinetry.Through French doors off the living room, step out onto your expansive back patio--a private oasis with a covered seating area, grill, sparkling pool, and direct access to your private dock. Whether youre hosting sunset dinners, enjoying a swim, or casting a line off your dock and reeling in a fish, kayaking, or paddleboarding, this outdoor space is designed for effortless island living.With 3 bedrooms and 3 full baths, this home offers ultimate comfort. Both upstairs bedrooms feature en suite baths and private balconies, perfect for enjoying morning coffee with Gulf breezes.Located just a 15-minute bike ride to Duval Street, youll enjoy the best of Key West: secluded waterfront serenity with quick access to the islands top dining, nightlife, and attractions.Investment Highlights:*Prime vacation rental potential in a sought-after waterfront community*High demand for luxury Key West rentals* Move-in ready with high-end finishes and modern amenities*Low-maintenance tropical landscapingAdditional Perks:*Covered parking + guest parking*Gated community for privacy & security*Launch pad for kayaks & paddleboards*Fish off your private dock and soak in the island lifestyleThis is a rare opportunity to own a true Key West waterfront treasure! Contact us today to schedule your private showing today!

$1,949,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 71
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage,None

Condo living with hotel caliber amenities, this 3rd floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors/windows are designed to exceed building codes & rated for 175 mph winds. On-site resort amenities include private beach, heated waterfront pool, spa, poolside bar/grill, valet parking, concierge, on-site management company, gourmet restaurant & the islands largest conference center.

$1,949,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 71
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Condo living with hotel caliber amenities, this first floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/ gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors & windows are designed to exceed building codes & rated for 175 mph winds. On-site resort amenities include private beach, heated waterfront pool, spa, poolside bar/grill, valet parking, concierge, on-site management company, gourmet restaurant & the islands largest conference center.

$2,950,000
Upper Matecumbe Key Islamorada
Bay Colony Villas   - MM: 81.50
4 Bed, 4 Baths, 2,072 SqFt Days Listed: 139
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock150ft

Only sophistication and class represented in Islamoradas most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off its manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maids quarters with more amazing views from the private balcony. If amenities are what youre after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-16-2025.
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