Upper Matecumbe Key Islamorada Homes for Sale, Single Family Houses, MLS Home Listings

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.

This lovely home is classic Keys on the outside, with modern elegance on the inside. Secluded on high ground in the heart of downtown Islamorada, this accommodating three-bedroom, two-bath residence offers abundant space for relaxation and entertainment, including an inviting back porch, surrounded by lush landscaping that enhances the serene atmosphere. The expansive front and back yards provide ample room for outdoor activities and gatherings. Ideally situated, you are within easy walking distance to the beaches, great restaurants, and grocery shopping. Experience the perfect blend of comfort and convenience in this idyllic retreat.

Welcome to 100 Parker Drive, a delightful 2-bedroom, 2-bath all-concrete home nestled in one of Islamoradas most sought-after neighborhoods. Tucked away between the Overseas Highway and the Old Highway, this quaint, quiet, and family-friendly street is a hidden gem, offering the perfect blend of island charm and small-town community living.This partially updated retreat boasts a private, fenced-in paver patio, ideal for outdoor entertaining, morning coffee, or a peaceful evening under the palms. Surrounded by lush tropical landscaping, it offers a serene escape just minutes from the heart of downtown Islamorada.Whether youre looking for a full-time residence, a seasonal getaway, or an investment property, this home is turn-key and a prime opportunity for both long- and short-term (28 day or more) rentals. The Parker Drive community is vibrant and welcoming, with plenty of families and children, making it an excellent choice for those seeking a neighborhood feel with the perks of island life.Location is everything! From here, you can bike to Islamoradas best restaurants, boutiques, art galleries, breweries, and marinas--all just a short ride away. Take a quick drive to the local schools, parks, and waterfront attractions that make Islamorada one of the most desirable places to call home.Dont miss your chance to own a piece of paradise! This unbeatable location and potential for return on investment make it a rare find in Islamorada. Schedule a showing today!

Historic and charming 1936 Red Cross Home - Fully Remodeled - on 1/2 acre - in the heart of town! Step into history with this beautifully remodeled 1936 Red Cross home, originally built by the Red Cross to shelter hurricane survivors. Constructed entirely of concrete, including a solid concrete roof topped with durable metal, this home is built to last. Modern upgrades include impact windows and doors for added security and energy efficiency. Situated on over half an acre with tropical landscape in the heart of town, this 2-bedroom, 1-bathroom home offers both historic charm and modern convenience. The fully updated interior blends timeless character with contemporary comforts, making it move-in ready. Located on a road popular with walkers, joggers, and bicycle riders, this home is just moments from many shops, restaurants, and the vibrant Morada Way Arts District. Close to world famous Cheeca Lodge and the newly renovated Islander Resort which welcomes locals to its beach/pool bar and restaurants. With plenty of room for a pool or future expansion, the possibilities are endless. RV hookup. Dont miss this rare opportunity to own a true Florida treasure!

This beautiful 4-year-old ground-level home features 3 bedrooms and 2 bathrooms. The kitchen boasts stunning all-wood cabinets, granite countertops, and stainless steel appliances. Marble tile floors extend throughout the house, creating a luxurious and cohesive feel.The home includes a large screened porch off the back two bedrooms, perfect for enjoying the surrounding tropical tree canopy. The house is well-lit with all LED lights and features ceiling fans inside and on the porches, providing comfort and energy efficiency.The bathrooms have been thoughtfully designed with backing that will allow for the installation of handicap bars, ensuring accessibility for all. The two-car garage with doors at the front and back provides easy access to the backyard. The low-maintenance landscaping is complemented by a sprinkler system, making upkeep a breeze.For those with a penchant for boating, the home is conveniently close to marinas. Additionally, it is near shopping facilities and some of the best restaurants in the Florida Keys, offering a blend of convenience and leisure.

Paradise Found: Renovated Jungle Treehouse!Welcome to your dream retreat in the heart of the Florida Keys. Nestled in the highly sought-after village of Islamorada, this exquisitely remodeled 3-bedroom, 3-bath estate redefines luxury living- 2/2 up and legal nonconforming 1/1 down. Perfectly situated on a sprawling 15k+ square-foot lot (14k sf residential dry and 1k sf easement) , this property offers an unparalleled combination of elegance, privacy, and tropical charm. Concrete roof fully resurfaced in 2024, and electrical, and state-of-the-art impact windows, providing peace of mind and protection while letting in abundant natural light. The interiors have been meticulously updated whilst keeping the Old Florida Charm alive. The kitchen is a true chefs dream.

Your Slice of Paradise Awaits in Downtown IslamoradaDiscover the perfect blend of modern coastal living and convenience with this beautifully remodeled ground-level duplex in the heart of Islamorada. Located just a moment from the famous Cheeca Lodge and the vibrant Arts District, youll be surrounded by charming shops, restaurants, and galleries.Property Highlights: Two Separate Units PLUS a Guest Space: Each of the two dwellings is thoughtfully designed with a bright, airy ambiance to complement the island lifestyle. Use one unit for yourself and rent out the other, and/or welcome family and friends to visit! Durable Construction: Built with concrete and topped with a sturdy metal roof, this home is designed to withstand the elements. Impact windows and doors provide added protection and energy efficiency. Private Outdoor Oasis: The fully fenced yard features an electric gate, artificial turf for low maintenance, and lush landscaping with vibrant tropical foliage, perfect for relaxing or entertaining.Why Youll Love It:Whether youre looking for a permanent home or a vacation retreat, this property delivers the ideal Florida Keys lifestyle. The Village of Islamorada recognizes two dwelling units, adding significant value to the property.Dont miss your chance to own this coastal gem in an unbeatable location! Buyers should be able to convert this building in to one single-family home and transfer one of the building rights to another Village non-waterfront lot that is deemed appropriate by the Village. Two units are recognized by the Village. Buyers must confirm all with Village of Islamorada.

Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an oversized lot with a pool, outdoor entertaining area, plenty of storage, parking, and handicap access. The home features 3 bedrooms & 3 bathrooms with two of the bedrooms ensuite. The home offers a great floor plan and has been tastefully decorated with a beautiful kitchen including stainless steel appliances. This is a great investment with rental history. Dont miss the opportunity to own where you can walk and ride your bike to all the places downtown Islamorada has to offer including shopping, restaurants, bars, and all the amenities The Sports Fishing Capital of the World has to offer!

Welcome to one of downtown Islamoradas most exclusive properties- a spacious estate thats hitting the market for the first time in generations. This ranch-style home sits proudly on four contiguous lots in the peaceful Grove Park Subdivision, offering something thats increasingly scarce in the Keys: space to breathe. With two bedrooms, a 3rd Bedroom option, and an oversized garage (50 x 26) thats perfect for an artists studio with office Loft, boat and car storage plus a Workshop, and Utility buildings. Space to park your RV or Camper. This property gives you room to live and create.Step outside and youll find yourself in a tropical paradise. Fruit trees dot the landscape, and carefully planned gardens create a private sanctuary. Lounge in your Gazebo and an in-ground pool (25 x 40) beckons on those warm Florida afternoons, while the lush landscaping ensures your privacy from the world beyond.Location? It doesnt get better than this. Take a short stroll and youre in the vibrant heart of Islamorada. Wander through Artists Alley, browse local shops, or treat yourself to dinner at some of the Keys finest restaurants - all just minutes from your front door.This property isnt just a home - its a blank canvas of possibilities in paradise. And with properties like this becoming increasingly rare in the Keys!

Little Basin Key Lime Villa #3 is a beautifully appointed, 3 bedroom, 3.5 bath townhome with proven rental income. Nestled amongst a quaint row of rocking chair adorned porches, this residences design takes inspiration from Old Town Key West and features postcard views of sunset from deck and docks. The immaculate, tropically landscaped grounds lead to the shared dockage, pool, tiki hut, and cabana. Parrot fish and mangrove snapper swirl around the waterfront with room for boats up to 30 ft, and a floating dock for guest use. Located on Upper Matecumbe Key, Bayside, in the Heart of Islamorada, the compound is right next door to Library Beach and is situated within walking distance to the best local sunset venues in the American Caribbean. Watch Sunset Celebrations each day and Full Moon Parties each month from your private porch! Across, on the Oceanside of the island, The Morada Way Art Walk is every Third Thursday and many local boutiques, breweries and fine dining restaurants are within walking distance. The first floor is designed in an open concept with soaring ceilings featuring dining area, kitchen, half bath and guest bedroom with ensuite bathroom. Upstairs leads to two more bedrooms with ensuite bathroom, and the master bedroom features french doors leading to lovely covered porches. Fully furnished in immaculate white decor - come stay for a week .... or, forever! Boats up to 30 allowed at dock on a first come, first serve basis. Note: Easy to show! Agent must accompany.

Discover Your Private Tropical Oasis in Islamorada.Welcome to your dream retreat in the heart of the Florida Keys in the sport fishing capital of the worldaa stunning Key West-style home nestled amidst lush greenery in an exclusive gated bayfront private club community. This residence is more than just a home; its a lifestyle defined by serenity, elegance, and the natural beauty of Islamorada.From the moment you pass through the palm-lined gated front entrance, you will notice the manicured tropical beauty of this community as you make your way to the classic architectural gem that will captivate you. Vibrant hues, large sitting porches, and timeless craftsmanship create a warm, inviting ambiance. Inside, open living spaces are bathed in natural light, blending seamlessly with the lush surroundings visible through every window.Step outside and find yourself in your very own tropical sanctuary. Towering palms, old growth trees, vibrant bougainvillea, and lush greenery surround the property, offering privacy and tranquility. Relax by the pool, host unforgettable gatherings on the expansive patio, or simply unwind as the breeze carries the scent of salt air.Nestled within a private club community, this home offers access to a range of world-class amenities, including a marina, sunset point, beach, and community pool. Plus, the vibrant culture and stunning waters of Islamorada are yours to explore from the protected marina.Whether youre seeking a permanent residence or a vacation escape, this property provides the perfect balance of seclusion and connection. From sunrise strolls on pristine beaches to evenings under the stars, every moment here feels like a slice of paradise.Dont just dream of the Keys, live it. Schedule your private tour today and experience firsthand what makes this home and private community so extraordinary.

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.

Welcome to this beautiful concrete home in the highly sought-after Venetian Shores subdivision in Islamorada! This beautifully remodeled 5-bedroom, 3-bathroom home offers a spacious, open living floor plan perfect for modern living and entertaining. Venetian Shores is renowned for its deep control depth and exceptional deep-water dockage. With 70 of dockage featuring TWO boat lifts--one 15K and one 20K--this home is a boaters dream.Step into the backyard oasis where youll find a sparkling pool with both heater and chiller, as well as an inviting tiki hut, ideal for relaxing or hosting friends and family. Enjoy quick and easy access to both the Atlantic Ocean and Florida Bay through the nearby Snake Creek Channel.This property is completely fenced for privacy, with two electric gates and meticulously landscaped grounds that offer outstanding curb appeal. Dont miss your chance to own a slice of paradise in the Florida Keys!

Discover Coconut Cottage, Your Tropical Paradise in Islamorada! Coconut Cottage beckons you to the quintessence tropical living in Islamorada. This oceanfront haven boasts a 90ft. Sandy Beach, a boat basin, and an inviting waterfront pool, creating an idyllic backdrop for both relaxation and adventure. The main residence, featuring 4 bedrooms and three bathrooms, exudes vintage Florida coastal comfort. The charm of the property is further enhanced by a screened-in porch, where one can savor panoramic ocean vistas and gentle sea breezes.A separate one-bedroom, one-bath guest cottage offers additional privacy and comfort, making it ideal for hosting friends and family. Constructed with durability in mind, both homes feature concrete walls and metal roofing, ensuring a sanctuary that stands the test of time.The propertys lush tropical landscaping and gated entry promise a secluded retreat, fully fenced to ensure your exclusive slice of paradise remains undisturbed. Ample parking accommodates a fleet of cars, boats and trailers, while a dedicated storage shed keeps your water toys, lawn essentials and fishing gear organized.Coconut Cottage isnt just a residence; its a lifestyle choice for those who dream of natural tropical setting. Envision your special day at this perfect wedding venue, where a 7-day rental policy aligns seamlessly with celebrations and gatherings. With a charming Boutique Hotel nearby, your guests will enjoy the convenience and luxury that this unique property affords.Discover the rare gem that is Coconut Cottage, a treasure nestled in one of Islamoradas most sought-after locations, where every day feels like a blissful escape from the ordinary! Truly a rare find!

This remarkable 34,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay.One of the key highlights of the lot is its exceptional dockage, (65 ft), which has previously accommodated a 36-foot boat, making it perfect for boating enthusiasts. The property also offers plenty of room for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds creating a tranquil atmosphere for evening relaxation.The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aquatic species like fish, birds, manatees and a multitude of different birds. Its a perfect canvas for your dream residence or vacation retreat.With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this property is one of the best properties on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation.May also purchase the vacant lot up front that has a Market Rate TDR on it. Total asking for both is $4,975,000,Owner / Agent

The Islands of Islamorada Beach Club is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a bunk room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.MODEL VILLA OPEN DAILY FOR VISITS AND TOURS OF THE PROPERTY. COME AND VISIT US FOR REFRESHMENTS AND MILLION DOLLAR VIEWS.

The Villas at the Islands of Islamorada is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a twin room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.MODEL VILLA OPEN DAILY FOR VISITS AND TOURS OF THE PROPERTY. COME AND VISIT US FOR REFRESHMENTS AND MILLION DOLLAR VIEWS.

The Villas at the Islands of Islamorada is a meticulously designed private gated enclave offering waterfront single-family residences. With every comfort considered, this residence exudes coastal living with four bedrooms, four and one-half bathrooms, and stunning ocean views. The three-floor villa offers 3,137 sq ft of interior and 930 sq ft of exterior contemporary island architecture with an open, airy, and light-filled design. Three bedrooms are king-sized with en-suite bathrooms; the fourth is a twin room. Additionally, the residence is being offered fully furnished with artwork from local Florida artists. Residence amenities include a top-of-the-line kitchen, open-concept kitchen, dining, and living spaces, a powder room, ample closets, two oceanfront balconies, a ground floor waterfront loggia, a laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. This turn-key home is maintenance-free, providing the possibility of passive income. The safe and secure environment within the club allows for effortless multigenerational vacations with a gated entry and attentive staff. The Beach Club delivers a luxurious experience with its 615 ft of pristine crescent-shaped swimming beach and a private boat basin with ample dockage. Enjoy two oceanfront pools, an oceanfront bar, and pickleball courts for some friendly competition. Golf enthusiasts can practice their swing at the unique driving range that extends into the ocean. The well-equipped fitness center caters to health enthusiasts, while children can have fun in the dedicated play area. Surrounded by lush, mature landscaping, the Beach Club also provides a plethora of water activities, allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this area set it apart as a secluded destination.MODEL VILLA OPEN DAILY FOR VISITS AND TOURS OF THE PROPERTY. COME AND VISIT US FOR REFRESHMENTS AND MILLION DOLLAR VIEWS.

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost comfort. Located in a serene cove with a pristine natural beach, the home features floor-to-ceiling windows that offer stunning 180-degree panoramic views of the ocean. Every corner is meticulously designed with tasteful decor, exuding elegance while providing a personal, comfortable atmosphere. The property is in downtown Islamorada, Florida Keys, and includes a private beachfront terrace, a third-story private balcony, and a tranquil pool with a tiki hut, making it ideal for relaxation and entertaining. The outdoor spaces feature a cozy firepit, offering the perfect setting for intimate gatherings with the sound of the waves as a backdrop. As a vacation rental, this residence is a lucrative investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.

Built in 2014, Bahia Bonita is an ultra-private bayfront estate in the heart of downtown Islamorada designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and open water views from every room. If you have been wishing for an exceptional piece of Florida Keys paradise where natural beauty and luxury living meet modern, solid concrete construction, this thoughtfully designed home may exceed your expectations. Begin your day by stepping out of your primary suite to your bayfront terrace and into a second floor Infinity Edge pool. In the evening, slide open the wall of glass on the top floor to experience the brilliance of Islamoradas sunsets from your great room, gourmet kitchen or outdoor decks. Feel like grilling? Just one step away is an outdoor kitchen with adjacent bay view dining. For stargazing, venture up the spiral stairs to the rooftop deck for a breathtaking front row seat. Built to withstand sustained 200 mph winds, this home also includes accordion shutters over impact glass for the ultimate defense. Outside, enjoy 250+ linear feet of open water frontage and a 100 dock with commercial-grade piles, composite decking and two boat lifts fitted with hurricane and storm surge protection. This unparalleled storm resiliency is combined with modern sustainability features including a large cistern with state-of-the-art water purification system, a grid-tied solar array and integrated Tesla Power Walls eliminating the need for a generator. Other functional luxuries include an elevator, professional camera/security system, central wet-dry vacuum system, mature landscaping and an enormous three-car garage, complete with workshop and storage. This home also boasts marble floors throughout and a spectacular floating staircase. Plus, a fourth bedroom and bathroom can be easily added without modifying the structure or footprint at minimal expense. All within walking distance of Islamoradas favorite dining spots... call today!