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

Total Listings 117
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$1,150,000
Marathon
Tranquility Bay   - MM: 48.50
3 Bed, 3 Baths, 1,320 SqFt Days Listed: 101
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

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!

$1,200,000
Marathon
Indigo Reef Marina Homes   - MM: 52.50
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 13
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 31ft.Concrete

This end unit at Indigo Reef offers resort-style living, breathtaking Gulf views & prime Marathon location in the middle of the Fabulous Florida Keys!This vacation getaway is offering the perfect blend of investment income and personal enjoyment for you, your friends and family. A spacious, open floorplan, 3 bedrooms with balconies and sweeping Gulf views from the Primary Suite--ideal for enjoying coastal breezes or making memories watching the sunset.Enjoy the best of both worlds with immediate open Gulf access from your deeded dock, perfect for boating, fishing, paddle boarding, kayaking and just about any water sport you can imagine. Dive right into relaxation with a resort-style pool, stay fit in the exercise room, and enjoy the convenience of an ice machine for your refreshments or for a day on the boat. Centrally located near all of the Keys tourist activities, shopping, dining, and some of the very best diving & snorkeling. Dont miss this opportunity to own a piece of paradise in a prime location in the marvelous Middle Keys.

$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 319
-3.92% ($50,000) 1 Price Change : Last Change 176 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
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 89
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip3

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.

$1,300,000
Key West
Harbour Lodge   - MM: 2.00
2 Bed, 2 Baths, 1,351 SqFt Days Listed: 784
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
Plantation Key
Futura Yacht Club   - MM: 88.50
2 Bed, 2 Baths, 1,298 SqFt Days Listed: 140
-13.04% ($195,000) 1 Price Change : Last Change 2 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat Slip3

Florida Keys Dream! Open Bay Views, Sunsets and Great Ocean/Bay Boating Access ... all in Islamorada! This Futura Yacht Club 2/2.5 townhome includes a 39 ft. deeded boat slip with electric and water just steps outside your door. Futura is truly the Swiss Army knife of Keys communities because it offers one of everything you need, including an onsite boat ramp, onsite boat and trailer storage, spacious pool, two tennis and pickle ball courts, basketball court, shady green space for picnics, and lots of open space for walks and bike rides. The townhomes also allow two pets any size AND the HOA allows weekly rentals. The beach area has a fish cleaning station, kayak and stand-up paddle racks, and owners can now put boat lifts in their slips. If great boating in Islamorada is your Keys dream, its time to wake up in Futura Yacht Club!

$1,350,000
Key West
Delancey Hall Condominium   - MM: 1.00
2 Bed, 2 Baths, 1,185 SqFt Days Listed: 66
-8.47% ($125,000) 1 Price Change : Last Change 17 Days Ago
Condo - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Beautiful, comfortable, spacious condominium in historic Delancey Hall. Located on a premier Old Town street a few short blocks from the Key West Seaport and Duval Street (and in the X-flood zone), this condo offers the historic features youd expect from a pedigreed Key West house -- Dade County Pine, crown molding, shutters, wide front porch -- combined with the modern features you need, seamlessly integrated to give you the quintessential Key West experience. Whip up a tasty breakfast in the light-filled kitchen and enjoy it on your large private deck leading to your outdoor shower and the shared pool, or take an easy stroll to Harpoon Harrys or Sarabeths for a little morning pampering. With ample storage and even the option for a one-bedroom lockout, this home serves as the perfect retreat or vacation rental investment property. Its Key West living at its best -- make it yours!

$1,350,000
Key Largo
Buttonwood Bay   - MM: 96.00
2 Bed, 2 Baths, 1,337 SqFt Days Listed: 12
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

Experience breathtaking sunsets and waterfront living in this stunning Buttonwood Bay condo in Key Largo! This beautifully remodeled 2-bedroom, 2.5-bath residence offers direct bayfront views and comes with an assigned 33-foot boat slip just steps away. Step outside to a charming brick patio surrounded by lush natural landscaping.Enjoy resort-style amenities, including a private sandy beach, three newly heated pools, a state-of-the-art gym, a newly decorated clubhouse, and a library. Sports enthusiasts will love the five tennis courts and six pickleball courts. Boaters will appreciate the 280 boat slips, five yacht docks, a convenient gas dock, and on-site management. This gated community offers 24/7 security for peace of mind. Dont miss this rare opportunity to own a slice of paradise in the Florida Keys!

$1,350,000
Key Largo
Buttonwood Bay   - MM: 96.00
2 Bed, 2 Baths, 1,238 SqFt Days Listed: 7
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat S

Introducing a truly exquisite waterfront town home in Buttonwood Bay, complete with a coveted 29 assigned boat slip just steps from your front door. With panoramic open-water bay views from both levels, this home offers an unparalleled setting for peaceful living and unforgettable sunsets. Step out from the back door to your private patio, leading down a lush lawn to the bay, surrounded by tropical palms, foliage, and the iconic Buttonwood trees.This beautifully updated 2-bedroom, 2.5-bath townhome features a sleek kitchen with stainless steel appliances, electric blinds on both floors, impact windows and doors, and a luxurious master bath.The deep-water, protected marina, carved from solid coral rock, is a gem in the Keys. Buttonwood Bay is a boaters paradise, offering an on-site Ships Store with everything from snacks and drinks to bait, ice, and fuel, along with a boat ramp and owners parking for trailers. The communitys high-end amenities are second to none, including five tennis and pickle ball courts, three heated pools, a fully-equipped fitness center with breathtaking marina views, saunas, a basketball court, a meeting and party room with a kitchen, eight sunset martini docks, and a sandy beach. With its vibrant sense of community, 24-hour security, and staffed gatehouse, Buttonwood Bay is a truly special place to call home, offering the ultimate Keys lifestyle.

$1,375,000
Key West
Sunset Marina   - MM: 5.00
2 Bed, 2 Baths, 1,558 SqFt Days Listed: 94
Condo - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

Welcome to luxury waterfront living at Sunset Marina Residence! This unique corner unit offers breathtaking open water and sunset views. Nestled in a premium gated community, enjoy the spaciousness of the largest 2-bed, 2-bath model, spanning 1,558 sq ft of elegantly designed space. The glass-fronted living area floods the home with natural light, complemented by 9 ceilings and an open concept split floor plan. The master suite features private access to a lanai and side balcony, a spa-like bath with a jetted tub, shower, double vanity, and a large walk-in closet. The guest bedroom boasts an ensuite bathroom with plenty of closet space. Additional conveniences include a laundry closet, assigned covered parking with storage closet, and ample guest spaces. Indulge in resort-style amenities: a heated waterfront pool, hot tub, clubhouse, seaside boardwalk that extends the length of the complex, private marina with floating concrete docks offering easy access to the Ocean and the Gulf. Optional 30 (LOA 35) boat slip with deeded sea bottom available for $205,000. Experience unparalleled coastal living, steps from Key West Golf Club.

$1,400,000
Key Largo
Buttonwood Bay   - MM: 96.00
2 Bed, 2 Baths, 1,400 SqFt Days Listed: 27
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock35ft.

This is the one youve been waiting for! Buttonwood Bay EE23 offers a rare and coveted opportunity to own a residence in one of Key Largos most sought-after locations. With unobstructed views of Florida Bay, this home is a true slice of paradise on Earth. Combining breathtaking scenery with luxurious design, this residence embodies the essence of refined living: open, airy, and expansive. Nestled in this exclusive gated community, this condo is perfectly situated close to the protected deep-water cut in the coral rock marina, granting direct access to the pristine waters of the Florida Keys. The residence includes a 35-foot boat slip, ideal for enjoying the boating and fishing lifestyle the Keys are famous for. Every detail of this two-bedroom, two-bath condo has been meticulously remodeled and decorated with high-end finishes. Impact windows and doors flood the interior with natural light and showcase panoramic views of the bay and stunning sunsets. The floor-to-ceiling glass highlights the seamless connection between the indoors and the outdoors. A gourmet kitchen with granite countertops, custom cabinetry, and state-of-the-art appliances creates an inviting space for cooking and entertaining. Buttonwood Bay offers world-class amenities, including five tennis and pickleball courts, three heated pools, a fitness center with saunas, basketball courts, and a clubhouse with a full kitchen for events. Relax on the sandy beach or watch the sunset from the comfort of your own home. Boaters will appreciate the deep-water marina and Ships Store featuring fuel, live bait, ice, and snacks, as well as a convenient boat ramp and on-site trailer storage. With on-site management, 24/7 security, and dedicated on-site maintenance and landscaping teams, Buttonwood Bay promises a lifestyle of effortless luxury and tranquility. Dont miss this exceptional opportunity to experience the ultimate waterfront living. This condo offers an incredible rental opportunity.

$1,499,000
Marathon
Indigo Reef Marina Homes   - MM: 52.50
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 269
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.

$1,795,000
Key West
Sunset Marina   - MM: 5.00
3 Bed, 3 Baths, 1,658 SqFt Days Listed: 54
Condo - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

3 bedroom corner unit with stunning water views!! Live just 20 from the waters edge while relaxing on the HUGE outdoor lanai. Very few 3 bedrooms built and this is the largest and most desirable floor plan here. This single level living condominium has year round sunsets and enjoys a true Key West lifestyle that is ideal for outdoor enthusiasts desiring island living on the waterfront with a marina. Condo has an 1/8 mile seaside boardwalk spanning the entire property for walking your dog, sea life viewing or a sunset stroll. This updated unit is sold furnished and enjoys an open floor plan with tall ceilings, lots of light and a total of 4 balconies to bring the outdoors in. Entire residence features plank porcelain tile flooring for easy upkeep, white corian countertops throughout and all wood white cabinetry with GE profile stainless appliances including double oven. Electric tankless hot water heater with UV lighting and water filtration system designed to remove chemicals. Top line Washer/Dryer. A/C system replaced in 2020. Amazing master suite features water views, spacious spa-like bath with jetted tub, frameless glass shower, double vanities and a large walk-in closet with built-ins. 2nd bedroom is spacious with instant en-suite bath design. 3rd bedroom is currently used as office/bedroom combo design. Traveling? Simply lock it and leave it with easy close impact shutters. Concrete construction, remote gate, elevator, outdoor stairs, trash chute, heated waterfront pool, spa and clubhouse. Assigned garage parking with private storage space. Plentiful bike, moped, kayak, scooter and guest parking. Maintenance fee INCLUDES wind/fire/flood/hazard building insurance, cable & grounds upkeep. Experience quiet coastal living adjacent to Key West Golf Club in this relaxed and comfortable residence. There is nothing like this tropical resort style waterfront paradise in all of Key West. Deeded deep water floating boat slips are available for sale from 30 to 65.

$1,949,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 1056
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.

$1,949,000
Key West
New Town Unlisted   - MM: 2.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 1056
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.

$2,950,000
Upper Matecumbe Key Islamorada
Bay Colony Villas   - MM: 81.50
4 Bed, 4 Baths, 2,072 SqFt Days Listed: 26
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.

$3,950,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
5 Bed, 5 Baths, 3,417 SqFt Days Listed: 127
-6.29% ($265,000) 1 Price Change : Last Change 32 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Fixe

Luxury Waterfront Condo with Transient License - Key West, FL. More pictures and videos coming soon.This stunning 5-bedroom, 4-bathroom waterfront condo in Old Town Key West offers luxury and investment potential with a coveted transient nightly rental license. Enjoy breathtaking marina views from double balconies, a private pool, and a boat dock with deep water access. The home features an island kitchen, a two-car garage, and is built to Cat 5 standards with impact windows. Perfect as a personal retreat or income producing nightly rental. Dont miss this rare opportunity!

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 02-23-2025.
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