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Strattons Homes for Sale, Upper Matecumbe Islamorada, Florida Keys

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Total Listings 9
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$649,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
1 Bed, 1 Baths, 358 SqFt Days Listed: 278
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Discover Your Island Retreat at Cheeca Lodge Resort and Spa Timeless Elegance Meets Contemporary Comfort: Step into Cheeca Lodge, a haven where historic charm mingles seamlessly with modern luxury. With turnkey suites and nightly rental potential, its not only a home, but a savvy investment opportunity. Dining Fit for a King: Indulge on the freshest seafood and five-star cuisine, enjoy two refreshing ocean front tiki bars, and savor the best sushi. Your taste buds are in for a treat! Immerse yourself in 1,200 feet of pristine sandy beach, framed by swaying palms. Relax in cabanas designed for sun-soaked relaxation. Recreation & Relaxation: Whether its fishing off the pier, swimming in the pools, or hitting the sport courts, Cheeca Lodge offers something for everyone. Embrace sunrise yoga and leisurely garden strolls for a balanced lifestyle. Explore Local Treasures: Dive into the vibrant community of Islamorada, with its array of restaurants, lively clubs, and eclectic galleries, and museums. Your Island Escape Awaits: Unlock the doors to Cheeca Lodge--where you can dip your toes in the sand, sip your favorite cocktail, and let the soothing waves serenade you all while you are collecting a stress free income as Cheeca manages everything for you. Ready to Start Your Island Adventure? Make it yours and turn this dream into your everyday reality.

$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.

$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.

$1,350,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
3 Bed, 3 Baths, 1,550 SqFt Days Listed: 105
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This newly remodeled 3 bedroom, 3 bathroom home is located on upper Matecumbe in the heart of Islamorada, Florida. The home features a unique layout with 1 bedroom and 1 bathroom downstairs, and 2 bedrooms and 2 bathrooms upstairs. The home boasts high-quality construction and modern finishes throughout. The open-concept living area is perfect for entertaining, with a spacious kitchen featuring stainless steel appliances and granite countertops. The bedrooms are all generously sized and offer plenty of natural light. Outside, the home features a large deck perfect for enjoying the beautiful Florida weather. The property is within proximity to world-class restaurants and is accessible to some of the best fishing and diving spots in the world. This home is the perfect blend of luxury and convenience, making it an ideal choice for those looking to experience the best that Islamorada has to offer.

$3,150,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
4 Bed, 4 Baths, 2,576 SqFt Days Listed: 621
-1.56% ($50,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 400ft.

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

$10,750,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
6 Bed, 6 Baths, 6,866 SqFt Days Listed: 127
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,BasinConcr

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

More Info
Most Recent Sales - (7) - Strattons as of 2024-11-26
Sale Date Address Sale Price $/SF List Price Sq. Ft. Type Bd/Ba Days Listed
08-05-2024 153 List $585,000 $1,114 $599,000 525 Single Family 1/1 50
07-15-2024 81801 Overseas 631 $505,000 $1,410 $575,000 358 Condotel 1/1 152
03-20-2024 82260 Overseas $850,000 $367 $875,000 2,314 Single Family 3/3 281
01-31-2024 81801 Overseas 722 $710,000 $1,290 $710,000 550 Condo 1/1 93
12-14-2023 207 & 209 Carroll $7,500,000 $1,520 $7,900,000 4,931 Single Family 8/5 122
10-20-2023 81801 Overseas 612 $735,000 $1,336 $735,000 550 Condotel 1/1 1
01-13-2023 81801 Overseas 734 $575,000 $1,045 $485,000 550 Condotel 1/1 33
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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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