43 houses for sale in Matecumbe

Directly overlooking the crystal-clear waters of the Atlantic Ocean, Château On The Ocean stands as one of the most extraordinary and private estates in the Florida Keys. Located in exclusive Islamorada—often referred to as “The Hamptons of Miami”—this remarkable oceanfront compound redefines luxury coastal living through an unparalleled combination of architecture, scale, privacy, and lifestyle. Completely reimagined and rebuilt in 2023, the estate is the result of a visionary, no-compromise approach that seamlessly blends contemporary design, advanced engineering, and world-class construction quality. Set across nearly two acres of private oceanfront land, the property offers almost 20,000 square feet of thoughtfully designed space dedicated to living, entertaining, and wellness, including more than 10,000 square feet of climate-controlled interiors. From the moment of arrival, the estate conveys an unmistakable sense of exclusivity, with its commanding architectural presence set aga

Only sophistication and class represented in Islamorada's 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 it's 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 bedroomsu002F2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maid's quarters with more amazing views from the private balcony. If amenities are what you're after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare

Experience unparalleled oceanfront living at Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship. Set on just under 2 acres of pristine coastline, the property offers 19,784 SF of total living and entertaining space, including 10,182SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors wu002F natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, putting green, a Baccarat-inspired grand ballroom

Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada—just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear—ideal for entertaining or unwinding in complete privacy—while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can hold boats up to 5,000Lbs. Adding to its appeal,

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities al

Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five gener

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities al

Simply the best location, exclusive & extremely private. It's tucked away in the prestigious'Plantation Lake Estates, a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach, tennis courts, a full-service marina, a dog park, sports fields, and Olympic-size lap pools. This home boasts a stunning great room with a gorgeous coral fireplace and soaring wood beam ceilings. They all overlook the glistening Atlantic Ocean, providing priceless views and sunrises. The home has a modern kitchen and updated baths, as well as impact windows and doors. The exterior has been reinforced with rebar and stucco. There are three inviting bedrooms, including a third-floor primary en-suite with a private porch

Oceanfront luxury living in Islamorada. Experience the ultimate in coastal elegance with this breathtaking 4-bedroom, 4-bath oceanfront estate in the heart of Islamorada, offering 3,052 square feet of beautifully crafted living space. Nestled on over half an acre, this three-story residence boasts unobstructed 180-degree views of the Atlantic, deep water dockage, a rare, private boat ramp and room for a pool. The perfect blend of privacy, luxury, and island lifestyle. Enjoy peace of mind with high-impact, missile-rated windows and doors on all three floors, built to withstand up to 240 mph winds. Inside, the home features a mix of wood and tile flooring, including custom pine and tile floors in the luxurious third-floor master suite, complete with panoramic ocean vistas and private balcony access. Additional upgrades include a newer roof replaced in 2019, fresh landscaping, and two new AC units replaced in 2025 on the second and third floors ensuring year-round comfort and efficiency.

A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound. The grand porte-cochere entry sets the tone, leading to a single-level main residence with soaring ceilings, white oak floors, and 12' retractable glass walls that frame sweeping ocean views. The chef's kitchen is anchored by a Calacatta marble island, Thermador appliances, and a walk-in pantry, opening to a spacious great room and dining area ideal for entertaining. The main home features four bedrooms, six full bathrooms, and a soundproof theater room. The primary suite is a private retreat with a fireplace, dual walk-in closets, a safe room, and a spa-inspired bath with a steam shower. Each additional bedroom includes an en suite bath, private balcony, and ocea

Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage-all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand th

Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling approximately 1,500 square feet, and 2 bedrooms and 1 bathroom downstairs totaling approximately 1,140 square feet. The private resort-style backyard features a heated pool with sun shelf, hot tub, expansive patio, hammock lounge, and mature palms creating a true tropical setting. Enjoy deep-water canal frontage with 70 feet of dockage and two boat lifts rated at approximately 15,000 pounds and 20,000 pounds, providing exceptional boating capacity. Located on one of Venetian Shores' desirable 100-foot-wide canals, the property offers generous maneuvering space and convenient access to both the Atlantic Oce

Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise views. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys. An extraordinary pairing of true beachfront living and convenient boating access. Inside, the home's 3,860 square feet is designed for easy Keys living with generous main-level living areas and bedrooms, plus a spacious upstairs suite with private bath and roof-top deck capturing panoramic ocean vist

Welcome to Islamorada living at its finest in one of the most sought-after bayfront communities. This beautifully appointed townhome features 2 bedrooms plus a large loft, 2.5 baths and offers an effortless blend of comfort, style, and coastal charm. Thoughtfully designed to comfortably sleep seven or more, the versatile layout is ideal for hosting family and friends or maximizing rental potential. Inside, the remodeled kitchen shines with quartz countertops, stainless appliances and generous workspaces. Updated tile flooring flows throughout the living areas, while a custom wood-and-steel staircase adds architectural interest and easy access to the second floor bedrooms. Upstairs, you'll find a serene primary suite with private bath, along with a comfortable guest bedroom and full guest bath. The loft, accessed from the hallway, has been thoughtfully finished to provide added privacy from the primary bedroom, making it an ideal bonus sleeping area, home office, or peaceful retreat. Na

Commanding 170 feet of private Florida Bay frontage and situated on over an acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors, providing vast screened porches both upstairs and down. The kitchen anchors the home with gorgeous views and a function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired ame

If you're looking for a property with potential in a highly desirable area of Islamorada and are prepared to put in the work, this is an opportunity worth considering. Sellers are motivated and will entertain offers. This 3-bedroom home offers a chance to purchase in one of Islamorada's most desirable areas and update the property to fit your needs, investment goals, or long-term plans. The home sits on an oversized lot and features a functional floor plan with generously sized rooms and a kitchen that opens to the living and dining areas. The concrete construction and larger homesite provide a solid starting point for renovation and improvement. Located directly across from Founder's Park, the property offers convenient access to a bayfront beach, community pool, public boat ramp, baseball fields, playgrounds, dog park, and community events throughout the year. The oversized lot also provides additional outdoor space compared to many nearby properties

Oceanfront luxury living in Islamorada. Experience the ultimate in coastal elegance with this breathtaking 4-bedroom, 4-bath oceanfront estate in the heart of Islamorada, offering 3,052 square feet of beautifully crafted living space. Nestled on over half an acre, this three-story residence boasts unobstructed 180-degree views of the Atlantic, deep water dockage, a rare, private boat ramp and room for a pool — the perfect blend of privacy, luxury, and island lifestyle. Enjoy peace of mind with high-impact, missile-rated windows and doors on all three floors, built to withstand up to 240 mph winds. Inside, the home features a mix of wood and tile flooring, including custom pine and tile floors in the luxurious third-floor master suite, complete with panoramic ocean vistas and private balcony access. Additional upgrades include a newer roof, fresh landscaping, and two new AC units on the second and third floors ensuring year-round comfort and efficiency. The expansive entertainment areas

A once-in-a-lifetime opportunity to own one of South Florida's most iconic properties. Welcome to Tea Table Key, a breathtaking 15-acre private island estate, accessible by car or by boat, located just minutes from downtown Islamorada and directly across from the famous Alligator Reef Lighthouse. Surrounded by vivid turquoise waters, this extraordinary sanctuary offers complete privacy and a front-row seat to nature's daily spectacle. Herons and egrets gliding overhead, pelicans diving at sunrise, and eagles soaring above your shoreline. Enjoy the rare luxury of total seclusion without sacrificing convenience. Within minutes, you're immersed in Islamorada's finest restaurants, art galleries, and shopping, yet at home you're embraced by the stillness of your own island world. Conveniently located approximately 1 hour and 30 minutes from Miami International Airport, or a 25-minute helicopter or seaplane ride, Tea Table Key offers an unmatched combination of accessibility and exclusivity.

Commanding 170 feet of private Florida Bay frontage, and situated on over and acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors providing vast screened porched both upstairs and down. The kitchen anchors the home with gorgeous views and function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amen

A once-in-a-lifetime opportunity to own one of South Florida's most iconic properties. Welcome to Tea Table Key, a breathtaking 15-acre private island estate, accessible by car or by boat, located just minutes from downtown Islamorada and directly across from the iconic Alligator Reef Lighthouse. Surrounded by vivid turquoise waters, this extraordinary sanctuary offers complete privacy and a front-row seat to nature's daily spectacle — herons and egrets gliding overhead, pelicans diving at sunrise, and eagles soaring above your shoreline. Enjoy the rare luxury of total seclusion without sacrificing convenience. Within minutes, you're immersed in Islamorada's finest restaurants, art galleries, and shopping, yet at home you're embraced by the stillness of your own island world. Conveniently located approximately 1 hour and 30 minutes from Miami International Airport, or a 25-minute helicopter or seaplane ride, Tea Table Key offers an unmatched combination of accessibility and exclusivity

Newly Remodeled 3-Bed, 3-Bath Home in the Heart of IslamoradaThis newly remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect blend of modern comfort and island living. The unique layout features 1 bedroom and 1 bathroom downstairs, and 2 bedrooms and 2 bathrooms upstairs-ideal for guests or extended family. Built with solid concrete construction and impact windows, this home is elevated above flood and designed for peace of mind. Inside, enjoy an open-concept living area perfect for entertaining, a spacious kitchen with stainless steel appliances and granite countertops, and bright, generously sized bedrooms. Modern finishes and high-quality craftsmanship shine throughout. Step outside to a large deck perfect for soaking up the Florida Keys sunshine. Located on a quiet street with beach access at the end of the road, this property offers convenience and tranquility. Close to world-class restaurants, shops, and some of the best

Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom. Ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to

Estate Opportunity. Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage-all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living

Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom. Ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to

Beautiful 100' of oceanfront property on Lower Matecumbe Key. This offering consists of a 100' lot with a triplex apartment building (3 TDRs). This gives you lots of possibilities for redevelopment of the property. Fantastic near 180 ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Note: One of the owners is a State of Florida Real Estate Licensee