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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 10
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$399,500
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
1 Bed, 1 Baths, 409 SqFt Days Listed: 266
-0.13% ($500) 1 Price Change : Last Change 114 Days Ago
Condo - Active - 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.

$720,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 257
-7.10% ($55,000) 1 Price Change : Last Change 85 Days Ago
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

**Nightly Rental Condotel at Historic Cheeca Lodge Resort and Spa**1. **Condo Features**: - Private King bedroom with full-size soaking bathtub and private dressing area - Spacious separate living room with queen sofa-bed - Fully equipped kitchen - Turnkey - Hands-off income generation through nightly rentals - Balcony with a view2. **Luxurious Amenities**: - 5-star dining at multiple onsite venues - Two open-air tiki bars - Three heated swimming pools - 1,100 sandy beach - Boat dockage and fishing pier - Executive golf course - Six lighted sport courts (tennis, pickleball, basketball) - Over 15,000 square feet of event space - Camp Cheeca for children - On-site full service watersports facility3. **Resort Lifestyle**: - Resort-style living with impeccable service - Instant passive income stream with condotel ownership - Impressive occupancy rate - Walking distance to outstanding restaurants, spas, galleries, boutiques, breweries, and Islamoradas famous arts district - Freebee rideshare service in the Village of IslamoradaExperience the epitome of luxury and investment potential at the historic Cheeca Lodge Resort and Spa. Own a piece of paradise in the sportfishing capital of the world with this exceptional income-producing property. Live the resort life, enjoy unparalleled amenities, and indulge in the vibrant island lifestyle of Islamorada.

$725,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 207
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: 52
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.

$795,000
Upper Matecumbe Key Islamorada
Sand Pebbles   - MM: 80.50
5 Bed, 5 Baths, 3,264 SqFt Days Listed: 307
-36.40% ($455,000) 5 Price Changes : Last Change 4 Days Ago
Condo - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Significant price adjustment ... Owner looking for an offer on this on of a kind property in central Islamorada! Rare opportunity to own this detached Condominium/Home which sits apart and on its own providing a single family home and includes a 2 car garage/storage. Large and spacious two story concrete home offering 5 bedrooms & 3 baths, two living areas, over 3,200 square feet, partially remodeled in 2018, new kitchens, quartz counters, stainless steel appliances, tile floors, central AC, private walkway, porches, and privacy. Separate 2 car garage assigned to this condo. Located on the grounds of the Sand Pebbles Condominium, you will also enjoy the exceptional amenities including a Heated POOL, grand lawn, outdoor grilling area, walkway to watch the daily Sunsets, Bayfront observation deck, trailer storage, and pristine kept grounds. There is simply nothing else like this in Islamorada. Walk to Midway Cafe, Square Grouper, Safe Harbor Angler House Marina, Restaurants & Shops.

$795,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 278
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Cheeca Lodge Resort and Spa--the very name conjures up images of swaying palms, salt-kissed air, a rich history, and the promise of an idyllic escape. Where the Sun Kisses the Sea and Dreams Come to Life.Historic Charm, Modern Luxury: Cheeca Lodge--a time capsule where history whispers. Turnkey suites, nightly rentals, and savvy investment. Feast Fit for Poseidon: Five-star dining, tiki bars, and ocean-view room service. Bon appetit! Beachfront Bliss: 1,200-foot sandy beach, palm-lined. Cabanas for sun-kissed souls. Sport & Serenity: Fishing pier, pools, sport courts. Yoga by sunrise, gardens for strolls. Beyond the Horizon: Explore Islamoradas heartbeat--restaurants, clubs, galleries. Your Key Awaits: Unlock your private condotel at the one and only Cheeca Lodge. Dip your toes, sip your cocktail, and let the waves serenade you. Ready to write your island tale? Call it home, call it heaven--just call it yours.

$899,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 840 SqFt Days Listed: 27
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 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: 300
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.

$1,275,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 121
-1.92% ($25,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

LOCATION, DOCKAGE. Dockage on the oceanside of Upper Matecumbe Key! ALSO Parking for car and a boat!! .... Beautiful Beacon Reef, a well-known and loved condo complex located on Upper Matecumbe Key is expertly and exquisitely maintained top to bottom. First class amenities include resort style tropical landscaping with shady palm trees, lush green grass & sandy beach w/ lounge chairs. Zero entry, large walk-in pool. Chickee hut and multiple BBQs for entertaining. Newly renovated pier with plenty of dockage, can fit up to 35 boat, shore power available. Private sauna & gym overlooking the ocean. Club house with kitchen available to homeowners for private functions. This particular unit is immaculate and cared for, same owner since 94, amazing open water ocean views from covered balcony and primary bedroom. Comes with coveted covered parking, one space from elevator, room for two cars or one car w/ boat & trailer. Kitchen has been updated with stainless steel appliances and custom cabinetry. Primary bathroom has been updated as well with added closet space. All windows are impact.

$3,195,000
Upper Matecumbe Key Islamorada
Misc Condo Upper Mat   - MM: 81.00
4 Bed, 4 Baths, 2,539 SqFt Days Listed: 111
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Maison Residences #204, 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 11-26-2024.
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