Luxury real estate for sale Upper Matecumbe Key, United States

Nothing compares to life at the one and only historic Cheeca Lodge Resort and Spa. Located in the heart of beautiful Islamorada, the sportfishing capital of the world, is your opportunity to procure an exceptional income-producing property that allows nightly rentals, with onsite management. This beautiful turnkey double queen bed suite provides you with resort style living and completely hands-off income generation. Enjoy the outstanding 5-star dining at multiple onsite venues or in-room dining if you prefer; two open-air tiki bars; the spa and fitness studio; three heated swimming pools; a stunning palm lined 1,200' sandy beach with complimentary cabanas; boat dockage and the longest fishing pier in the Florida Keys; an executive golf course; six lighted sport courts, including tennis, pickleball and basketball; over 15,000 square feet of event space; Camp Cheeca for the little ones; a complete line of watersports including, snorkeling, family fishing trips, eco tours, sunset cruises, kayaks, sailboats, paddleboards and parasailing; yoga and water aerobics; and lush tropical gardens for walking/jogging and enjoying nature throughout. Live the resort life at Cheeca Lodge, and yet, if you feel the spirit of adventure, Cheeca Lodge is centrally located within a short distance to outstanding restaurants, clubs, spas, salons, galleries, shoppes, breweries, and Islamorada's famous arts district.

Nothing compares to life at the one and only historic Cheeca Lodge Resort and Spa. Located in the heart of beautiful Islamorada, the sportfishing capital of the world, is your opportunity to procure an exceptional income-producing property that allows nightly rentals, with onsite management. This beautiful turnkey double queen bed suite provides you with resort style living and completely hands-off income generation. Enjoy the outstanding 5-star dining at multiple onsite venues or in-room dining if you prefer; two open-air tiki bars; the spa and fitness studio; three heated swimming pools; a stunning palm-lined 1,100' sandy beach with complimentary cabanas; boat dockage and the longest fishing pier in the Florida Keys; an executive golf course; six lighted sport courts, including tennis, pickleball and basketball; over 15,000 square feet of event space; Camp Cheeca for the little ones; a complete line of watersports including, snorkeling, family fishing trips, eco tours, sunset cruises, kayaks, sailboats, paddleboards and parasailing; yoga and water aerobics; and lush tropical gardens for walking/jogging and enjoying nature throughout. Live the resort life at Cheeca Lodge, and yet, if you feel the spirit of adventure, Cheeca Lodge is centrally located within a short distance to outstanding restaurants, clubs, spas, salons, galleries, shoppes, breweries, and Islamorada's famous arts district.

Nothing compares to life at the one and only historic Cheeca Lodge Resort and Spa. Located in the heart of beautiful Islamorada, the sportfishing capital of the world. This is your opportunity to procure an exceptional income-producing property that allows nightly rentals, with onsite management. This beautiful turnkey king bed suite with a kitchenette provides you with resort style living and completely hands-off income generation. Enjoy the outstanding 5-star dining at multiple onsite venues or in-room dining if you prefer; two open-air tiki bars; the spa and fitness studio; three heated swimming pools; a stunning palm lined 1,200' sandy beach with complimentary cabanas; boat dockage and the longest fishing pier in the Florida Keys; an executive golf course; six lighted sport courts, including tennis, pickleball and basketball; over 15,000 square feet of event space; Camp Cheeca for the little ones; a complete line of watersports including, snorkeling, family fishing trips, eco tours, sunset cruises, kayaks, sailboats, paddleboards and parasailing; yoga and water aerobics; and lush tropical gardens for walking/jogging and enjoying nature throughout. Live the resort life at Cheeca Lodge, and yet, if you feel the spirit of adventure, Cheeca Lodge is centrally located within a short distance to outstanding restaurants, clubs, spas, salons, galleries, shoppes, breweries, and Islamorada's famous arts district.

Opulent and stylish island castle; the epitome of class and luxury make this home one to remember. Located on a quiet and private island with only three residences, your secret great escape tucked away in the heart of downtown Islamorada awaits. Adorned with Swarovski crystal chandeliers, beautiful finishings sweeping staircase, elevator, 9 hole golfing green, 5 car garage, extreme storage options and parking, double living rooms, open and spacious relaxing and entertaining verandas throughout, third floor primary suite, and multiple ample docking areas example just a few rarities this property has to offer.

Prime location! Rare bayfront property in a private gated community located in the heart of downtown Islamorada with gorgeous sunset views, private pool and dockage! This original 4 bed/4 bath concrete home has a concrete roof and is ready for you to come in and make it your own, or take advantage of the existing building right to create your dream home in Islamorada's most exclusive community. Tucked into its own private corner of prestigious Pen Key Club, this ground level concrete home is one of only seven in the 31-home community directly on the open bay and is on one of the largest lots. It also has its own private dock (in need of repair) and a large private pool, in addition to enjoying use of the community boat basin and the community pool if desired. The current home is 2/2 in the main house and has 2 separate 1/1 guest suites, each with its own private entrance. Outside is a large shady grass yard with beautiful mature trees, including a stunning Haden mango. Another unique feature of Pen Key is that the club employs a full-time property manager living on site to maintain the grounds and common areas. After a day out fishing or boating, come home and watch the sunset from your own back yard and then stroll through the meticulously landscaped neighborhood and out the secure front gates to enjoy fine dining just steps away at Ziggie & Mad Dog's. This community is also perfectly situated in downtown near fine dining, bars, boutiques, salons, shops, art galleries, museums and of course, the monthly Art Walk and famous monthly Full Moon Party. The Village of Islamorada also offers Freebee Electric Vehicle Ridesharing for added convenience. If you are ready to live the good life in the heart of downtown Islamorada, then it's time to discover the peace, security and lush tranquility of Pen Key.

Private, exclusive, and gorgeous describes this spacious three bedroom, three bath recently updated townhome. The unit is located on the ocean and overlooks the white sandy beach and 155-foot pier. Features include impact glass windows and doors, an open kitchen concept, granite countertops, modern baths, and wood floors. This enclave of 21 units has open verandas, ample covered parking spaces, a large free-form swimming pool, a beachside chickee hut with outdoor grills, and an elevator. Located in the heart of Islamorada and minutes from nearby island galleries, restaurants, shops & marinas.

Oceanfront acreage in the heart of Islamorada! Discover a unique opportunity to own oceanfront acreage right in the heart of Islamorada, the jewel of the Florida Keys. This remarkable property encompasses over 7 acres of pristine upland, complemented by bay bottom, and comes with a coveted building right, allowing you to create your dream estate. With an astonishing 700 feet of direct Atlantic beachfront, your oasis in paradise awaits. Nestled in the vibrant community of Upper Matecumbe Key, you have the canvas to craft your vision, with space for your main residence, a caretaker cottage, a detached guest house, a tennis court, and even a charming boardwalk leading to your very own private sandy beach. Not only does this piece of paradise offer unparalleled beauty and space, but it also boasts zoning that allows for weekly rental potential, making it a valuable investment. Seize the opportunity to make your waterfront dreams a reality in the Florida Keys. This is your chance to create a legacy estate that combines coastal luxury with the convenience of town living. Don't miss out on this once-in-a-lifetime opportunity!

Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with a TDR and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

Located on Upper Matecumbe Key in Islamorada this property boasts a 1/1 frame house as well as a 2/1 CBS house on an 8,100 sq ft lot on a quiet dead-end street. The Cbs house was remodeled a few years ago and has been consistently rented on a long-term basis.Live in one house and rent the other and generate income while enjoying your piece of paradise. This property is located within one block of Publix in Islamorada. Easy to show

Experience true elegance in 'Southern Paradise' - casual coastal design on the Atlantic Ocean. An unsurpassed location at Mile Marker 83 with direct 'Old Road' access for walking, biking and carting! More than 200 ft of beachfront and 1.5 acres, the main residence features sunny verandas, 5 bedrooms, 6.5 baths and more than 5,600 sqft of living space under air. Separate Guest cottage adds 2 bedrooms, 2 baths. A paved 'old brick' driveway leads up to both entrances as well as a two-car garage. From the moment you step into the inviting French door entrance your eyes are fixated on blue sky, beach and water. First floor living leads to cool grassy lanai, beach, lap-pool and hot tub. Spacious patios allow for a house full of guests to enjoy the Caribbean breezes! The pier, skiff lift & kayak launch provide easy access just steps to the ocean. The main residence features expansive ceilings and spaces for entertaining. The floor plan provides for an East wing & newly added West wing. All generously appointed bedrooms each feature their own ensuite bath, providing ultimate privacy and comfort for all family and guests. 1st Floor: All East facing first floor French doors lead out to more than 1,900 sqft of covered terrace. Just inside the lofty open-concept great room is the kitchen featuring Wolf gas range and double SubZero refrigeration and attached wine cellar all built around an expansive island counter. Family & friends will enjoy the shared times and good vibes in this kitchen! Also, adjoining the kitchen is a wet bar and powder room for convenience. In the West wing-enter through to an exercise room with full ensuite spa bath, then to the Master bedroom where the bath boasts a windowed ocean view soaking bathtub, double vanities & separate shower, bidet and water closet. Convenient access to a laundry equipped with dual machines, storage cabinetry, an office alcove and door entering garage. 2nd Floor: 2 Guest rooms share a sitting room, wet bar & terrace.

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, where there is room for a pool or an orchid house. 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.

Absolutely stunning waterfront property! Nestled on a rare point lot along Snake Creek in the premier area of Venetian Shores, this gated estate offers unparalleled boating opportunities with water on two sides & easy access to the Atlantic Ocean via Snake Creek Bridge or venture to Florida Bay to experience the Keys National Marine Sanctuary. Boasting an expansive 155 ft along the canal with 125 ft directly on Snake Creek, this cul-de-sac location is a paradise for boating & sunset enthusiasts. Immerse yourself in breathtaking sunsets over Snake Creek's vast waterway, whether relaxing on your private elevated balcony or lounging in the waterside pool. This gated two-story all-concrete home features four bedrooms and three baths with a spacious open floor plan to take advantage of the water views in every direction. Living room, dining area & gourmet kitchen w/island seating all have front row seats to Creek views along with the Primary Suite. Additionally, there are two guest bedrooms on the main level, plus a breakfast nook & bar. Entertainment abounds with an elevator leading to the ground-level theater room, complete with a wet bar & ample seating for game days. A guest bedroom, laundry/craft room, plus a two-car garage enhance the convenience of the ground-level enclosure. Outside, the in-ground pool, artificial grass, keystone patios, fire pit, seating/dining areas & covered BBQ grill create an inviting oasis among native palms. Additionally, a rare private cut-in boat slip with a 15,000 lb lift on a 100 ft wide canal provides protected dockage while easily accommodating multiple boats/yachts. It is truly a boater's dream come true. Located in Venetian Shores on Plantation Key within the Village of Islamorada, this Keys Estate offers the best of both worlds- deep water-protected dockage with unobstructed open-water views. Experience the passing parade of manatees, dolphins, yachts, deep sea fishing boats, kayaks & jet skis while relishing the unique beauty of this one-of-kind estate.

Venetian Shores 3/3 all concrete home with 95 ft. of deep-water dockage and a new seawall in Islamorada's premier boating community. Enjoy near instant access to both the Atlantic Ocean and Florida Bay via Snake Creek with a drawbridge on the ocean side to accommodate tall and large boats. Solid concrete home with a concrete roof. Upstairs is a 2/2 with a spacious great room plus a large, enclosed porch/Florida Room with expansive water views. Downstairs is a separate 1/1 guest apartment with a private entrance plus a garage and carport. The home is nicely maintained and also offers a view of Snake Creek from the Florida Room. Plenty of space in the large yard for a pool on either side of the home and the front yard also offers plenty of parking for boats, trailers etc. Call today!

This fantastic oceanfront property is located in the heart of the best fishing in Islamorada! A large 24,394 sq. ft. vacant lot awaits complete with an ACTIVE PERMIT. This prime property is located directly on the most beautiful clear water. Enjoy direct ocean access and seamless bay access through Channel 5. Permit also in hand for an observation pier with a tiki hut. This property, already cleared, stands ready for a fresh residence. The approved plans encompass a 2,560 sq. ft., four-bedroom, four-bathroom layout with a three-car garage. Property to the south is preserved, which allows for plenty of privacy! With the permits secured and paid for, this is the perfect opportunity to create your dream home in the Florida Keys.

''Southern Shore'' This modern coastal residence boasts an unobstructed 180-degree panorama of the Atlantic Ocean. This all concrete superior built residence spans 3,790 square feet of indoor living space and 815 square ft of outdoor terraces. It offers four en-suite bedrooms, custom floor-to-ceiling kitchen cabinetry, sleek quartz countertops, state-of-the-art smart home infrastructure, custom-made closets, and the convenience of an elevator. This property delivers awe-inspiring ocean vistas from the bedrooms, living spaces, and kitchen, embodying the essence of a tropical paradise. Outdoor gatherings are elevated to new heights with a rooftop deck, multiple terraces, and a pool area with an outdoor kitchen (under construction). The interior elements are curated by John Rudolph Designs. This estate provides the complete package, featuring a prime oversized oceanfront location, gated entry, secure dockage facilities, a boat lift, and a misting system, all situated on an expansive lot within the tranquil Plantation Key community. Owner financing is available, and the owner is a Florida-licensed real estate agent.

Bask in the original elements of the Florida Keys way of life at Kids Cay. Now being offered for the very first time, this one of a kind legacy property boasts three charming homes; a timeless four bedroom main house, an expansive four bedroom guest house and a lovely two bedroom caretaker's cottage. Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. This tropical and tranquil estate has nearly 8.5 acres of upland plus 7.98 acres of ocean bottom plus ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals.

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating open water views and is situated on 1.3 acres of land. Complete with three bedrooms and two bathrooms, this ground-level, and updated residence is the perfect place to entertain while basking in all of the beauty the Keys offers. Zoned residential estate, this income-producing home qualifies for weekly rentals, which provides ample opportunities for a discerning buyer.

Discover a rare opportunity to own this hidden gem in the prestigious Port of Call community. Nestled in an oceanfront complex, this meticulously updated townhome offers an unparalleled coastal lifestyle. The townhome offers two bedrooms and two full bathrooms, one half bathroom and is spaciously and elegantly designed, providing comfort and privacy. With three balconies, enjoy breathtaking sunrises and salty sea breezes from multiple vantage points. The heated community pool lets you dive into luxury just steps from your front door. Complete with an assigned boat slip ideal for boating enthusiasts, with direct access to the ocean. A large private yard provides a lush oasis with ample green space for relaxation and outdoor activities. Prime Plantation Key location makes you close to shopping, restaurants, and Founder's Park. This unit is more than a home; it's a lifestyle. Don't miss out--schedule your private tour today!

This two bedroom, one bathroom home is perfectly situated with close proximity to the Florida Bay and breathtaking sunset views! Property is on a 3,600 SF parcel. A large screened porch is attached for lovely outdoor living. Separate laundry facility and storage building on site. Also included is a Keys style concrete guest cottage behind the home. This property has an immediate building right should you choose to demo and rebuild. A quote is available to demo and re-build a 1,169 SF, three bedroom, three bathroom new modular residence. The home is conveniently located near Founders Park, restaurants, schools and shopping. This is a fantastic opportunity to find your place in the Florida Keys!

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires' Row... Islamorada's premier address. New dock with two new boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for great income potential. The sandy backyard is shaded by palms and the large pool is fenced for privacy. The winding drive from the gate to the home is dotted with seating spots for enjoying the wildlife and tropical foliage. There is also a separate storage room and workshop downstairs, a gardening shed, landscape lighting along the driveway. Call today!