luxury seaside houses for sale Duck Key, United States

Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key with expansive water views, white sand beach, and a true resort-style experience in the Florida Keys. An exceptional investment opportunity, Casa Feliz is a strong producing vacation rental with rental history and future bookings already in place. Set on over 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, this exceptional estate is designed for both relaxation and entertaining. A 148-foot observation dock invites kayaking, paddleboarding, fishing, and endless enjoyment of marine life, while the unique orientation captures both breathtaking sunrise and sunset views over the water, a rare and coveted feature in the Keys. Outdoor living is elevated with a resort-style saltwater pool featuring cascading waterfalls, spillover spa, and fully equipped poolside cabana complete with wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit create the ultimate setting for entertaining or unwinding beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was thoughtfully redesigned to maximize sweeping ocean views from nearly every room. Offering four custom bedroom suites, each with private en-suite bath, the home comfortably accommodates guests in luxury. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Expansive accordion impact glass doors seamlessly blend indoor and outdoor living throughout. The gourmet kitchen showcases Café appliances, induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas ideal for hosting. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, local artist mural, and more. Discover why Grassy Key is the place to be.

Welcome to your dream waterfront escape in the Florida Keys! This beautifully updated 3 bedroom, 2 bath home is nestled in an exclusive neighborhood and offers the perfect blend of luxury, comfort, and island charm. Boasting 142 feet of protected dockage on an open bay, it's a boater's paradise with direct access to world-class fishing and diving. Enjoy stunning sunrises from this east-facing property. Soaring vaulted ceilings add to the airy, open feel of the home, while the convenience of an elevator makes access effortless. Step outside to your private coastal oasis featuring a large pool and a spacious downstairs entertaining areaideal for gatherings, grilling, or relaxing after a day on the water. This is more than just a homeit's a true Florida Keys lifestyle!

This waterfront residence in Key Colony Beach offers the perfect blend of refined comfort, thoughtful design, and effortless island living. Lovingly owned, gently used, and never rented, the home reflects true pride of ownership throughout. An elevator, updated kitchen, and custom baths set the stage, while soaring wood ceilings and an open-concept kitchen, dining, and living area create a light-filled space that flows seamlessly through stackable sliders to a spacious screened porchâ€''ideal for entertaining or unwinding in the coastal breeze. The generous primary suite is a private retreat with porch access and a skylit spa-style bath featuring a jetted tub, walk-in tiled shower, and dual vanities. The lower level is designed for true indoor-outdoor living, featuring a custom, inground swimming pool surrounded by elegant marble decking, along with expansive covered and uncovered paved patios. Mature tropical landscaping enhances privacy, while ample covered and uncovered parking adds everyday convenience. Boaters will love the 37.5-foot dock with boat lift, located on a wide, deep canal with quick, easy access, just minutes to both the open ocean and the Gulf via Vaca Cut. A permitted third full bathroom on the lower level sits next to a large, air-conditioned storage area with sliders that open directly to the patio and dock, making it ideal as an angler's room for fishing gear and water toys. Key Colony Beach is one of the Florida Keys' most desirable island communities, known for its wide, walkable streets, city-maintained infrastructure, and relaxed coastal charm. Residents enjoy access to marinas, a nine-hole golf course, tennis and pickleball courts, playgrounds, dining, and waterfront sunset parksâ€''all just steps or a short bike ride away. Perfectly positioned in the Middle Keys, Key Colony Beach offers a rare combination of small-town island living, world-class boating, and easy access to Marathon's shopping, dining, and local airport.

Experience ultimate waterfront luxury living with this stunning 5-bedroom, 3-bath residence (versatile bonus den can be used as 5th bedroom), perfectly positioned on a tranquil, sheltered waterway in a tucked away neighborhood. Thoughtfully designed and impeccably furnished, this home showcases high-end finishes and designer dcor throughout, creating a sophisticated yet comfortable coastal retreat. A rare highlight of this property is the indoor swimming pool, allowing for year-round enjoyment in complete comfort and privacy. Outside, you'll find a tropical oasis backyard for relaxing or entertaining. Feel free to cast a fishing line off your private dockage with 30 ft of waterfront. With direct access to the Atlantic Ocean or Gulf of Mexico, this is a dream for boating and fishing enthusiasts. Enjoy paddle boards or kayaks in your own private lagoon. The spacious open concept living areas are ideal for entertaining. Each bedroom opens up to the indoor pool providing a relaxing sanctuary for family and guests alike. Whether you're seeking a full-time residence or a luxury vacation escape, this exceptional waterfront home combines resort-style amenities, impeccable design, and an unbeatable location for the perfect Keys lifestyle.

Experience sweeping ocean views and breathtaking sunsets, from both floors of living in this beautifully updated oceanfront residence in Key Colony Beach—the gem of the Florida Keys. The spacious primary suite features an extended living area on the enclosed balcony with amazing blue water & sunset views, a custom bath, and a generous walk-in closet. Two large guest bedrooms offer comfort and privacy for family or visitors. The gourmet kitchen boasts abundant cabinetry, stunning granite countertops, and opens to a light-filled living and dining area complete with a wet bar and panoramic ocean vistas—perfect for entertaining. This home suits any lifestyle: a high-performing vacation rental, a seasonal retreat for snowbirds, or a full-time residence in a meticulously maintained community of just 31 condos and townhomes. Enjoy resort-style amenities including a large oceanfront pool surrounded by expansive sun decks, a fishing pier with breathtaking sunset views, grilling and private lounging areas, covered parking garage, bike and kayak storage, plus guest parking, shuffleboard, and tennis/pickleball courts. Ideally located near marinas, restaurants, shopping, and local attractions, your island dream awaits in paradise.

Experience Key Colony Point with sweeping ocean views and unforgettable sunsets from both levels of this beautifully updated end-unit oceanfront residence in Key Colony Beach— a true gem of the Florida Keys. With a coveted corner location, this residence is wrapped in extra windows and natural light, creating a bright, airy coastal atmosphere you'll feel the moment you walk in. The spacious primary suite is a private retreat, featuring an extended sitting area on the enclosed balcony with mesmerizing blue-water and sunset views, a custom-designed bath, and a generous walk-in closet. Two large guest bedrooms provide comfort and privacy for family and friends, making hosting effortless. At the heart of the home, the gourmet kitchen offers abundant cabinetry and stunning granite countertops, flowing seamlessly into the sun-filled living and dining areas. A wet bar and panoramic ocean backdrop set the stage for easy entertaining, sunset cocktails, or quiet mornings with the sound of the waves. Whether you're seeking a full-time island residence, a seasonal escape, or a strong vacation rental investment, this delivers. The impeccably maintained community of just 31 condos and townhomes offers resort-style amenities, including a large oceanfront pool with expansive sun decks, a fishing pier with postcard-worthy sunsets, grilling and private lounging areas, covered garage parking, bike and kayak storage, guest parking, shuffleboard, and tennis/pickleball courts. Perfectly located near marinas, dining, shopping, and local attractions, this light-filled end unit offers the best of oceanfront living—privacy, views, and the effortless Florida Keys lifestyle you've been waiting for. It is a licensed 7-day rental with rental history.

Join us for Brokers Open House today 4-6 pm! This stunning, fully renovated waterfront home in Key Colony Beach offers the ultimate Florida Keys lifestyle, combining high-end finishes with practical, top-tier enhancements for durability and comfort. Step into a bright, open-flow sanctuary anchored by wood-look tile flooring and crisp custom shiplap walls. The heart of the home is a culinary showpiece, featuring an expanded island with hand-selected quartzite countertops, a farmhouse sink, and an instant hot water system. The sunroom offers an elevated retreat with its tongue-and-groove ceiling, while the bathrooms have been transformed with sleek barn-door glass showers and designer finishes. Designed for the elite boater, the outdoor oasis features a 15,000 lb boat lift and a newly replaced dock (2026). The backyard is a private tropical resort, finished with limestone pavers, a composite raised deck, and a brand-new tiki hut. For the dedicated angler, the garage is thoughtfully equipped with a commercial-grade ice maker and a dedicated bait freezer, ensuring you are always ready for a day on the reef. Every inch of the property has been modernized, from the hurricane impact glass that frames every view to the all-new PVC sewer infrastructure installed in 2023. The saltwater pool is optimized for year-round perfection with a dedicated heater and chiller, while new landscaping and privacy palms create a secluded sanctuary. A circular paver driveway and an expanded outdoor storage closet provide the final touches of convenience to this masterpiece. Call today for your private tour! No sign on the property.

Embrace the RARE opportunity to own 1.75 acres of open water paradise in the prestigious, gated community of Stirrup Key. Over 750' feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Five protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary.

Ultimate Waterfront Compound - A Rare Package Deal! A unique opportunity to own two exceptional oceanfront homes in Marathon, FL, offering breathtaking open water views, direct ocean access, and premium boating amenities. This combined offering provides a total of six bedrooms and four bathrooms, making it an ideal family compound, luxury retreat, or investment property with excellent rental potential. Property Highlights: Total of 141 feet of direct ocean frontage Two private seawalls (85 feet and 56 feet) with a boat lift and ramp Expansive open water views of the Atlantic Built for durability with impact windows, metal roofs, and elevated structures Exterior elevator for added accessibility (1043 property) Room for a pool with plans and quote available Covered parking and additional storage space Short-term rental potential with weekly rentals allowed The properties are situated in a prime location for boating, fishing, diving, and waterfront relaxation. With direct access to the ocean, the homes offer an unparalleled coastal lifestyle. Whether you are looking for a private retreat, a multi-generational family estate, or an investment opportunity, this offering provides the space, privacy, and flexibility to meet your needs. Do not miss this rare chance to own a piece of paradise in Marathon. Contact us today for more details on this exceptional waterfront package.

Florida Keys luxury redefined! Experience this newly constructed 2025 oceanfront masterpiece perfectly balancing coastal elegance, craftsmanship, and timeless design. With 6 bedrooms, 6.5 baths, and 3,102 sq ft under air plus 2,000+ sq ft of balconies, it offers seamless indoor-outdoor living framed by endless turquoise views. An elevated infinity-edge pool merges visually with the Atlantic beyond. Inside, a bright open floor plan captures light, air, and ocean vistas. The great room flows into a designer kitchen and dining area, creating spaces that feel both connected and serene. Each ensuite bedroom is a private retreat, beautifully scaled and positioned for comfort and privacy. See Documents Tab for a full list of luxury features. Furnished and appointed throughout showcasing ''Design by Lily,'' the interior blends beach-cottage warmth with sophisticated Keys luxury. Custom furnishings, curated color palettes, and natural textures create a refined yet welcoming aesthetic. Every detail--from driftwood-toned floors to sculptural fixtures--exudes coastal elegance. Built by a long-time Florida Keys contractor with decades of local expertise, construction was overseen daily by the owners to ensure perfection in every finish and structure. Nothing escaped their eye, and it shows in the integrity and grace of the final result. Outdoor living shines with multiple covered terraces for dining and lounging, the infinity pool reflecting the sea, and gentle breezes completing the ambiance. The 157' dock ending in a 32' L-shaped terminus is complete. Newly built, fully furnished, and ready for immediate enjoyment, this residence is a rare opportunity--an oceanfront sanctuary minutes from the Marathon airport's two FBOs. Whether a private retreat or luxury vacation investment, this property embodies comfort, craftsmanship, and coastal allure.

Tons of upgrades, gorgeous open water views, and the very best of Florida Keys waterfront living -- you have to come see Lot 2 at Shipman Point. This brand-new waterfront home is positioned just two in from open water, offering beautiful views, excellent boating access, and a protected canal setting for your vessel. Boaters will appreciate approximately 63 feet of dockage, canal protection, a hardened shoreline secured by both a concrete retaining wall and concrete seawall, plus room for a boat lift. Whether heading out for a day on the water or enjoying the peaceful views from home, this location is designed for true Keys living. Inside, the home is fully furnished and professionally designed, with bright coastal finishes, tile flooring throughout the entire downstairs level, a spacious kitchen with a gas stove, double sink, and a well-appointed layout for entertaining. One of the ensuite bedrooms also features an additional private porch, creating another relaxing space to take in the island lifestyle. The exterior is complete with landscaping, a large concrete pad driveway with turf accents, and a clean, modern coastal look with ample parking. With weekly rentals permitted, this property offers outstanding versatility as a primary residence, second home, or income-producing investment. Updated photos coming soon.

&127969; Welcome to Emerald Flats a Waterfront Community in the heart of Marathon! Your brand-new dream home is here: Gated community entryway Gulf front water views and private boat docking. Built for efficiency and comfort there are 5 Bedrooms 4 Bathrooms - space for everyone High ceilings & open floor plan for a modern feel KitchenAid stainless appliances + quartz countertops Separate bar/entertainment space Fully furnished with luxury coastal style - just bring your suitcases! Boat Slip 30 included (45' long x 14.75' wide) &128205; Location: Emerald Flats. 818 39th Street Gulf

&127969; Welcome to Emerald Flats a Waterfront Community in the heart of Marathon! Your brand-new dream home is here: Gated community entryway Gulf front water views and private boat docking. Built for efficiency and comfort there are 4 Bedrooms 4 Bathrooms - space for everyone High ceilings & open floor plan for a modern feel KitchenAid stainless appliances + quartz countertops Separate bar/entertainment space Fully furnished with luxury coastal style - just bring your suitcases! Boat Slip 29 included (45' long x 14.75' wide) &128205; Location: Emerald Flats. 815 39th Street Gulf

Casa De Artista is a rare luxury estate in the exclusive community of Sombrero Isle. Set on more than an acre with 415 feet of waterfront, this property combines privacy, elegance, and the ultimate Florida Keys lifestyle. With only 27 homes on the island and Sombrero Beach just one block away, the location is both secluded and highly desirable. Extensively renovated by D'Asign Source in 2016, the 4,649 sq. ft. main residence offers 4 bedrooms and 3.5 baths. The open-concept living and dining areas feature stunning tongue-and-groove ceilings, while the chef's kitchen showcases premium appliances, dual wine refrigerators, and double islands designed for entertaining. Expansive sliding glass doors connect to a waterfront patio with outdoor kitchen, beverage coolers, and resort-style ambiance. The grounds are landscaped with exotic palms and feature a pool with spa, and deep-water dockage. For boaters, two lifts (24K and 5K) and an 86-foot dock provide direct access to world-class fishing and diving. A 299 sq. ft. detached artist studio with half bath offers flexible use as a creative retreat or guest space. Additional highlights include a 5,176 sq. ft. garage and storage level, ideal for vehicles, boats, and equipment. Just 10 minutes from Marathon Airport and offering strong weekly rental potential, Casa De Artista is a true trophy property and one of Sombrero Isle's most exceptional estates.

Coastal Elegance Meets Timeless Craftsmanship in Safety Harbor- Welcome to 'Piece of Quiet', a winner of the Miami Herald 'Fame' award for custom homes with unique architecture. Nestled in the coveted Safety Harbor neighborhood, this CBS construction home is a masterful blend of strength, style, and coastal luxury. Wrapped in island-style siding, the home exudes character and seaside charm, while grandeur arched French doors in the main living area flood the space with natural light and frame stunning waterfront views. Delight your senses with the custom terrace floors that were modeled after those at the Historic Cheeca Lodge & Spa. Step inside to the rich beauty of white oak flooring, offering both durability and sophistication throughout. The open-concept design seamlessly connects indoor and outdoor living, perfect for entertaining or enjoying peaceful moments by the water. Boating enthusiasts will revel in the 70 feet of dockage on a serene, protected deepwater basin, providing direct access to the bay and quick ocean access via the two bridges at Channels 2 and 5. Whether you're setting sail at sunset or savoring the gentle breezes from your private dock, or waterfront decks, this home is a rare gem not to be missed. Don't miss the opportunity to own this waterfront retreat—schedule your private showing today!

Seller Financing Available Pre-Construction Waterfront Retreat Deep Water Sunrise Views Located right across from the island of Boot Key, this exceptional pre-construction offering combines protected deep-water living, open-water views, and one of the most desirable boating locations in Marathon. Explore scenic kayak trails for beginners and advanced paddlers, surrounded by rich nature and wildlife where dolphins and manatees are frequently seen. The property faces east for breathtaking sunrises, while Boot Key provides natural protection during stormscreating an ideal, secure harbor environment. With approx 60 feet of deep-water dockage, enjoy ample space for large or multiple vessels, excellent maneuverability, and direct access to world-class boating. Inside the harbor, convenience is unmatched with 5 restaurants and 3 gas docks just minutes away. Commencing soon on this with construction, the custom home is designed with modern coastal style and true Keys practicality. The residence will feature 3 bedrooms and 2.5 bathrooms, offering elevated living spaces perfectly oriented toward panoramic Boot Key Harbor views. Whether you're a dedicated boater, nature lover, investor, or seeking a peaceful Keys escape, this rare property delivers the ultimate blend of location, protection, and lifestyle. Seller will finance with half down!

Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represents one of the rarest opportunities in the Upper Keys: a private, gated, resort-style compound offering expansive open-water views, unmatched privacy, and the timeless charm of classic Florida Keys architecture. Set on a generous parcel with a sandy beach, and direct ocean access, Casa Matecumbe delivers the ultimate coastal lifestyle--one defined by serenity, natural beauty, and the freedom to enjoy the water at a moment's notice. The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Lower-Level Finished area of 1,065 is included in square footage. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.

Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a spacious garage for ultimate flexibility. The gourmet kitchen flows seamlessly to a fully equipped outdoor kitchen and shaded lounge area—ideal for al fresco dining by the pool amid lush tropical landscaping. A rare combination of classic design, modern amenities, and timeless island charm. Effortless boating and space for all of your waterfront toys with 75' of deepwater dockage and quick access to both ocean and bay. Nearby homeowner’s park provides the added bonuses of a private, sandy beach and boat ramp. With the serene, wide canal views and cooling bay breezes, and this is where luxury, comfort, and natural beauty, convenience converge.

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 amenities continue with a lagoon-style pool, putting green, and ample deep-water dockage with a boat lift, providing Bay to Ocean access in minutes via Channels 2 or 5. This offers effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

Seize the rare opportunity to build your dream home in one of Islamorada's most coveted locations! This Ocean Front estate located directly across from the iconic Alligator Reef Lighthouse. Across the street from a protected preserve that will never be developed, and featuring a deep water channel capable of accommodating boats up to 40 feet, this property offers unmatched privacy and access.Imagine living just a short stroll from the legendary Square Grouper, Midway Cafe, Robbie's. Down the road from some of the best restaurants in Islamorada like Ziggie's, Mad Dog's, and Chef Michael's. This oversized lot, just shy of an acre, provides the perfect canvas for a builder, developer, or savvy end user to craft a stunning, custom-designed home in an unparalleled location.