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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 6
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$699,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 21
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

LOVE AT FIRST SIGHT! This is an Unbelievable opportunity to own a TURN KEY unit at The Palms of Islamorada. Endless views of the Atlantic Ocean including Alligator Reef Lighthouse from the balcony or the over 200 feet of seawall. Unit comes completely furnished - ready to move in or rent. Conveniently located within walking distance to fine dining with sunset views, marinas and dive opportunities. All you need to settle into this exceptional unit are your personal items. Everything is done and ready for you. All furnishings, linens, kitchen essentials and artwork are included. There are two large bedrooms both with king size beds. The master suite features a full wall of built-in closets and drawers hidden behind attractive sliding cabinet style and mirrored doors. The ensuite bath is completely updated featuring a Jacuzzi jetted bathtub, large tiled stall shower, and a double vanity - your own PRIVATE spa! The 2nd bedroom area has a king bed, full closet, private updated bathroom and pocket door for a private experience for your guests. The kitchen has everything...updated cabinets in todays colors, new Cambria quartz countertop and all newer stainless-steel appliances. You will love having your own new Bosch stack front loading washer and dryer in the unit. The kitchen offers casual dining with 4 bar stools for casual dining at the counter and youll love the hand carved teak dining table for more formal dining. The living room seating provides a cozy place to relax after a hard day of fishing and diving. The balcony overlooking the ocean presents endless views of the ocean and comfortable outdoor furnishings. Hurricane impact certified. Passed the Milestone inspection. Covered parking space. EVERYTHING is included!!The Palms is one of the most sought-after condo complexes in the Islamorada area due to the unparalleled ocean views. There have been very few units for sale in the past several years. Now is your opportunity to own one!

$725,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 186
-6.45% ($50,000) 1 Price Change : Last Change 2 Days Ago
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.

$725,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 341
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

***Seller Financing now an option! ***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.

$935,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 840 SqFt Days Listed: 434
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.

$2,950,000
Upper Matecumbe Key Islamorada
Bay Colony Villas   - MM: 81.50
4 Bed, 4 Baths, 2,072 SqFt Days Listed: 71
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: 118
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 04-09-2025.
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