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$899,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 840 SqFt Days Listed: 130
Condotel - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

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

$899,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,359 SqFt Days Listed: 167
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Enjoy the vibrant coastal lifestyle of Keys living in this desirable BAYFRONT townhome located in sought-after Executive Bay Club in Islamorada! This furnished townhome offers 2 bedrooms, 2 bathrooms plus a spacious loft, impact windows and doors, along with an open living layout that flows seamlessly through to the outdoor patio offering breathtaking sunsets and unobstructed Florida Bay views. Step out your back door to the sandy beach and dock with 31 boat slips available on a first-come, first-serve basis, for boats up to 28 at the dock or up to 35 tethered to one of the 6 mooring pilings. Perfectly located to enjoy offshore fishing in the Atlantic Ocean or backcountry fishing in the Florida Bay, as well as multiple dining spots nearby. The community offers a wealth of resort-style amenities, including a sparkling pool, clubhouse, two tennis/pickleball courts, a sandy beach, kayak and paddleboard storage and a pet-friendly environment. The dock and the walkway to the beach with new sand are recent upgrades. In addition, the pool, bathrooms and clubhouse are all being redone with assessments paid by seller. Secured with a manned/gated entrance. Located just minutes away from 5-star restaurants, breweries, and boutique shops, this townhome offers both luxury and convenience in this prime location.

$925,000
Plantation Key
Coral Harbour   - MM: 88.00
3 Bed, 3 Baths, 1,553 SqFt Days Listed: 79
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 30ft.

Calling all Anglers. Coral Harbor Club is Located in Islamorada Florida, the fishing capital of the world. They can get gas and ice in the Marina. The Condominium has been extensively remodeled and includes a 30 ft. boat slip # 54 Beach views from your porch. This ground-level condo is situated on the corner of the beach, walk out your screen door and theres the beach. New floors, new kitchen, new stainless steel appliances, New motorized rolling hurricane impact rolling shutters on your 400 sq. Ft. Porch. Newer AC, New washer and dryer, freshly painted. A must-see to appreciate. Comes completely furnished. Coral Harbor Club is completely gated with lunch tropical landscaping and amenities like an oceanfront marina, boat ramp, pool, clubhouse, tennis courts, pickle ball, bocce, baseball courts, beach, paddle board/kayak launch, and picnic tables. You can walk or bike inside your gated community. Closed proximity to the best restaurants, shopping, and entertainment. One hour from Miami. NOTICE TO CHC BUYERS: Coral Harbour reserves are funded to the amount required by law and passed 10 year Milestone inspection with the highest rating available.

$935,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 840 SqFt Days Listed: 403
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

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

$937,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,403 SqFt Days Listed: 74
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock,Othe

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

$985,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
2 Bed, 2 Baths, 1,473 SqFt Days Listed: 48
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip40ft.

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

$994,000
Plantation Key
Port Of Call   - MM: 88.50
2 Bed, 2 Baths, 1,248 SqFt Days Listed: 313
-18.86% ($231,000) 2 Price Changes : Last Change 48 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Boat S

Welcome to Port of Call, an exclusive low-density, private community nestled on the ocean side of Islamorada. With only 5 buildings with 10 units, this hidden gem offers resort-style amenities and the flexibility of short-term vacation rentals.This beautifully updated 2-bedroom, 2.5-bath townhome is designed for comfort and elegance. A standout feature is the sunroom dining area, where you can enjoy meals with direct ocean views.Step onto two expansive screened balconies, soak in the sun on your private rooftop sundeck, or take in breathtaking sunrises from anywhere in the unit. Undercover parking ensures convenience, while the oceanfront pool, beachside tiki hut, and private boat slips make every day feel like a vacation.Located just minutes from shopping, dining, marinas, and Founders Park, this is Islamorada living at its finest. Plus, your only hours from Miami or Key West, making this the perfect getaway or full-time retreat. Call today to experience the charm of Port of Call- where paradise meets opportunity!

$1,000,000
Plantation Key
Coral Harbour   - MM: 88.00
2 Bed, 2 Baths, 1,672 SqFt Days Listed: 77
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 30ft.

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

$1,075,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,888 SqFt Days Listed: 51
PreConstructi - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. Imagine waking up to sunlit mornings, salty breezes, and the soft embrace of warm sand beneath your feet. Welcome to White Marlin Beach, where your vision of paradise comes to life.Vacant lots with active building permits are a rare find, and this one is ready for you to create your dream retreat. Picture a three-bedroom, four-bathroom island escape blending coastal charm with modern luxury. Two spacious, sunlit stories are designed for relaxation, complete with an elevator to ensure comfort and convenience. Expansive porches invite you to unwind, sip your morning coffee with bay views, feel the ocean breeze in your hair, and enjoy evenings under a canopy of stars. New construction offers more than a fresh start--it brings favorable insurance rates, a solid foundation, and the confidence of quality craftsmanship.This is your gateway to maritime bliss. The private homeowners park features one of the few sandy beaches in the Keys, perfect for building sandcastles, watching sunsets, and creating cherished memories.This property offers convenient access to vibrant dining, boutique shopping, and an inspiring arts scene. Its more than just a property; its an invitation to embrace the island lifestyle.Opportunities like this dont wait. Ready to turn your dream into reality? Dive into your future at White Marlin Beach--your tropical oasis is calling!

$1,099,000
Windley Key
Windy Cove   - MM: 84.00
3 Bed, 3 Baths, 1,680 SqFt Days Listed: 21
Townhouse - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a newly developed gated coastal community offering 15 exclusive high-end townhomes in the heart of the Florida Keys. This oceanfront retreat boasts breathtaking views of the renowned Sandbar and Alligator Reef Lighthouse, providing the perfect blend of luxury, relaxation, and investment potential.Each three-bedroom, three-bathroom townhome is thoughtfully designed with expansive balconies on both the second and third floors, a spacious garage, and pet-friendly accommodations. Owners and guests can enjoy stunning sunrises, an oceanfront pool, and dockage available for rent, making it an ideal escape for those who love life on the water.Additionally, Peaceful Palms is designed to accommodate weekly rentals with the proper permitting, offering an incredible opportunity for investors. With the possibility of new building permits becoming unavailable in the Florida Keys, now is the time to secure your place in this sought-after destination. Dont miss the chance to own a piece of paradise!

$1,100,000
Plantation Key
Coral Harbour   - MM: 88.00
3 Bed, 3 Baths, 1,553 SqFt Days Listed: 299
-15.38% ($200,000) 2 Price Changes : Last Change 103 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Boat Slip3

NOTICE TO CHC BUYERS: Coral Harbour reserves are funded to the amount required by law and passed 10 year Milestone inspection with the highest rating available. Step into luxury with this unique top-floor condo at Coral Harbour Club. The kitchen stands out with its custom design, offering modern appliances and plenty of space for culinary adventures. The master bedroom features a bespoke layout with high-end finishes, providing a serene retreat with stunning ocean views.Enjoy the convenience of partial furnishings, allowing you to easily add your personal touch to this beautiful home. The spacious living area is perfect for entertaining guests or relaxing after a day on the water. Speaking of water, the included deeded 35 slip is a rare find and a boaters dream, making this condo an ideal choice for those who love the ocean.Coral Harbour Club offers a range of amenities for residents, including a sparkling pool, a welcoming clubhouse, and private beach access. Located in a prime area, youll enjoy easy access to local shops, dining, and recreational activities, all while being steps away from the beautiful coastline.

$1,179,000
Windley Key
Windy Cove   - MM: 84.00
3 Bed, 3 Baths, 1,680 SqFt Days Listed: 21
Townhouse - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a newly developed gated coastal community offering 15 exclusive high-end townhomes in the heart of the Florida Keys. This oceanfront retreat boasts breathtaking views of the renowned Sandbar and Alligator Reef Lighthouse, providing the perfect blend of luxury, relaxation, and investment potential.Each three-bedroom, three-bathroom townhome is thoughtfully designed with expansive balconies on both the second and third floors, a spacious garage, and pet-friendly accommodations. Owners and guests can enjoy stunning sunrises, an oceanfront pool, and dockage available for rent, making it an ideal escape for those who love life on the water.Additionally, Peaceful Palms is designed to accommodate weekly rentals with the proper permitting, offering an incredible opportunity for investors. With the possibility of new building permits becoming unavailable in the Florida Keys, now is the time to secure your place in this sought-after destination. Dont miss the chance to own a piece of paradise!

$1,200,000
Plantation Key
Ocean Harbor   - MM: 87.50
3 Bed, 3 Baths, 1,536 SqFt Days Listed: 19
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Othe

Oceanfront Paradise in the Florida Keys - 2BR/2BA Condo offering Luxury Resort-Style Living.Escape to your own slice of paradise with this stunning 2-bedroom, 2-bathroom oceanfront cottage like condo, perfectly positioned on the Atlantic Ocean in the heart of the Florida Keys. Wake up to breathtaking sunrises and unwind with the sound of the swaying palm trees as you enjoy ocean views from your private retreat. Surrounded by lush, blooming tropical landscapes, Ocean Harbour offers a true resort-style experience. Indulge in endless amenities, including a resort-style pool, Jacuzzi, and private beach, spa, marina & tennis, pickleball, boat storage and more. Enjoy ultimate relaxation under the tiki huts on the beach, savor an evening barbecue at the outdoor grilling areas, or launch your boat from the boat ramp. (Community dockage available for minimal fees)Every day feels like a vacation at Ocean Harbour with an on-site manager ensuring effortless living, a pristine white sand beach, and the gentle ocean breeze greeting you at every turn. Whether you choose to live here full-time or make it your island getaway, this oceanfront gem offers an unparalleled Florida Keys lifestyle.This is more than just a home--its a dream come true. Step into paradise today! 🌴🌊☀️

$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 103
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.

$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 333
-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
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 224
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

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

$1,279,000
Windley Key
Windy Cove   - MM: 84.00
3 Bed, 3 Baths, 1,680 SqFt Days Listed: 21
Townhouse - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a newly developed gated coastal community offering 15 exclusive high-end townhomes in the heart of the Florida Keys. This oceanfront retreat boasts breathtaking views of the renowned Sandbar and Alligator Reef Lighthouse, providing the perfect blend of luxury, relaxation, and investment potential.Each three-bedroom, three-bathroom townhome is thoughtfully designed with expansive balconies on both the second and third floors, a spacious garage, and pet-friendly accommodations. Owners and guests can enjoy stunning sunrises, an oceanfront pool, and dockage available for rent, making it an ideal escape for those who love life on the water.Additionally, Peaceful Palms is designed to accommodate weekly rentals with the proper permitting, offering an incredible opportunity for investors. With the possibility of new building permits becoming unavailable in the Florida Keys, now is the time to secure your place in this sought-after destination. Dont miss the chance to own a piece of paradise!

$1,395,000
Plantation Key
Ocean Harbor   - MM: 87.50
2 Bed, 2 Baths, 1,736 SqFt Days Listed: 52
-5.42% ($80,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Othe

This updated resort-style condo at Ocean Harbour in Islamorada offers a perfect blend of luxury, convenience, and natural beauty. There are expansive Atlantic Ocean views from the living and primary bedroom. The unit location within a gated community ensures privacy and tranquility, while the lush tropical landscaping adds to the overall peaceful atmosphere. Inside, the condo has been thoughtfully updated, with a spacious 2-bedroom, 2-bath layout that combines comfort with style. The spacious kitchen is ideal for both everyday meals and entertaining guests. Meanwhile, the living room has been expanded by incorporating the screened porch, creating a larger, more inviting space for relaxation and social gatherings.The split floor plan provides privacy and space for all, with the luxurious primary suite offering ocean views, a spa-like en-suite bath, and a generous walk-in closet. The guest bedroom offers a beautiful sized room for family and guest to relax after an incredible day in the Keys.With over 12 acres of meticulously maintained tropical grounds, the community offers top-notch amenities such as a marina, tennis and pickleball courts, a clubhouse, gym, tiki bar with BBQ, car charging stations, and trailer storage.Ocean Harbour is a highly sought-after community in Islamorada, known for its luxury living in one of the most coveted locations in the Florida Keys. Rental boat slips are available in the marina, adding to the allure of this prime oceanfront property.

$1,399,000
Plantation Key
Port Of Call   - MM: 88.50
2 Bed, 2 Baths, 1,248 SqFt Days Listed: 520
-18.90% ($326,000) 4 Price Changes : Last Change 2 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip

Ocean View Completely Remodeled Townhouse in Beautiful Islamorada!This beautifully updated town home offers 2 bedrooms, 2 bathrooms and a powder room including an ocean view Master Suite, with private porch and roof top deck, an amazing kitchen, with sunroom dining, open living space with ocean views and a screened porch. Located in Private Port of Call allowing weekly rentals with only 10 units featuring an ocean front pool, boat slip, sandy beach, carport, storage, laundry room in the unit with a pantry. This is a great investment opportunity with excellent rental income. Call for an appointment today!

$1,400,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 1,344 SqFt Days Listed: 11
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Looking for a home to accommodate you and your guests? This concrete construction property features three bedrooms and two baths on the upper level. Lower level offers two bedrooms and one bath, plus a waterfront screen porch, open floor plan, legally permitted enclosure with a living area that includes a kitchenette, plus living room. Plenty of storage with attached workshop/garage. Located on a plugged canal in Venetian Shores, there is a marina available for lease dockage monthly depending on availability.

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 03-09-2025.
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