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Upper Matecumbe Key Islamorada Condos for Sale - Condominiums, Florida Keys Real Estate

Upper Matecumbe is a great place to purchase condos for sale in the Florida Keys.  Condos in Upper Matecumbe Key often come equipped with top amenities, including designer fixtures, resort style swimming pools, and boat dockage for residents.  Popular condo communities in Upper Matecumbe Key include Beacon Reef and Palms of Isla.  The key is located within Islamorada, one of the most highly sought after areas in the Florida Keys.  If you are looking Upper Matecumbe apartments for sale, browse the Florida Keys MLS below.

Total Listings 8
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$399,500
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
1 Bed, 1 Baths, 409 SqFt Days Listed: 369
-0.13% ($500) 1 Price Change : Last Change 268 Days Ago
Condo - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp

Who says oceanfront living in the heart of the Florida Keys is not affordable? This cute 1-bedroom studio condo, with amazing view of Alligator Reef Lighthouse is nestled within the prestigious Palms of Islamorada. It offers 409 square feet of all the space you need. Begin your days in serene bliss as you greet the sun rising over the Atlantic, painting the sky with hues of pink and gold right from your own doorstep. Take advantage of the Mens Gym or Womens Gym before enjoying the views from the Oceanfront pool, providing the perfect oasis of relaxation. For the adventurers at heart, the legendary Bud & Marys Marina is merely a stones throw away, offering endless fishing expeditions into the bountiful waters of the Keys. Culinary delights await next door at Lazy Days, where you can savor your catch with a backdrop of the oceans expanse or explore the flavors of the Keys across the highway at the newly revived Papa Joes Restaurant /Tiki Bar, an ideal spot to unwind and enjoy the sunset.Located at mile marker 79.9, the Palms of Islamorada places you at the center of it all, surrounded by the natural beauty and vibrant culture of the Keys.

$725,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 310
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the Sportfishing Capital of the World. Condo Features -This spacious King Bed Suite offers a large living room area with a pull-out queen bed, a grand bathroom with walk-in shower and soaking tub, a fully equipped kitchenette, and a private screened in porch with views of the lush landscape and large coconut palms. This exceptional income-producing property allows nightly rentals. Owners use their units up to 28 days a year and receive a monthly check for the remainder of the time. Its a hands-off income generator!The Resort -Enjoy 27 acres of Islamorada oceanfront that include 3 world class restaurants, 2 open-air tiki bars, 1,200 of private beach, 525 fishing pier, 2 family pools, 1 adults only pool, beach and pool side cabanas, 9 hole golf course designed by Jack Nicklaus, 6 sports courts, 15,000 sqft of event space, valet parking, 24 hour shuttle service, concierge service, on site boat trailer parking, watersports activities, fitness center and Camp Cheeca.

$775,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 155
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Fabulous top floor location with spectacular ocean views! This spacious condo has tile floors throughout and a lovely open terrace to enjoy the ocean view and breezes. Both bedrooms are spacious and the primary bedroom opens to the oceanfront terrace. The Palms of Islamorada is conveniently located close to the downtown Islamorada area. You are only minutes from enjoying shopping in the boutiques and galleries and eating in numerous restaurants that are very close by. The Palms has an oceanfront pool, hot tub, assigned parking with plenty of guest parking, 2 gyms as well as kayak and paddleboard storage. A fantastic view of Alligator Lighthouse is included at no extra cost.

$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.

$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.

$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.

$2,950,000
Upper Matecumbe Key Islamorada
Bay Colony Villas   - MM: 81.50
4 Bed, 4 Baths, 2,072 SqFt Days Listed: 40
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.

$3,495,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
4 Bed, 4 Baths, 2,539 SqFt Days Listed: 87
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

LAST New developer unit for sale in Maison Residences!Maison Residences #201, a 4 bedroom residence with 4.5 bathrooms features an open floor plan with a grand room and oversized covered terraces for oceanside living. So open and airy! The grand living room leads into casual dining, island seating and kitchen for gatherings during inside time. This private enclave is nestled between the turquoise waters of the Atlantic Ocean and the Bay of Florida in the quaint seaside village of Islamorada. Maison is located on the Island of Upper Matecumbe Key- the most fun, artsy, beautiful island! Its situated within very private commons featuring more than 350 of natural sand beach, 155-foot day pier, with room for all water play activity. The most popular amenities are the lavish 86-foot lagoon-style pool, heated jacuzzi and the beach! After spending outdoor time head to your private elevator which takes you to your private entryway. Youll walk into the grand living room leading to the terrace that overlooks the ocean, beach and pool. Gourmet kitchen provides storage a-plenty and counter space that includes the casual island separating the kitchen from the dining area. Upscale Sub-Zero and Wolf Gas appliances are featured. The grand room features 9-foot stacked sliders for entertainment flow out to the oversized terraces where entertaining is a must with multiple seating areas, large flatscreen TV, fireplace, and infrared/gas grill. The master suite features King-sized bedding, 9-foot sliders, luxurious tub bath and glass shower ensuite, with private terrace access. Three more Guest rooms feature King sized beds and bath en-suites, with two of the rooms featuring private balcony access. Detail: PRIVATE opening elevators into residence, 10-foot ceilings, Caesar-stone counters, porcelain tile, Sub-Zero and Wolf appliances, U-Line bev center, Lynx gas grill, Kohler plumbing fixtures, exceptionally furnished in luxurious comfort by design!

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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