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Middle Keys Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Total Listings 175
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$3,700,000
Duck Key
Plantation Island   - MM: 61.00
4 Bed, 4 Baths, 3,166 SqFt Days Listed: 125
-1.33% ($50,000) 1 Price Change : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift82ft.Concre

Exclusive Duck Key Waterfront Retreat with Breathtaking Ocean ViewsExperience the pinnacle of coastal living in this exceptional open-water home on Duck Key. Designed to capture stunning ocean vistas and mesmerizing sunsets, this 4-bedroom, 3 bathroom gem offers the perfect balance of luxury, comfort, and outdoor paradise.Expansive Living Areas: Open-concept design featuring a gourmet kitchen with granite countertops, spacious dining, and living areas perfect for entertaining or relaxing by the water.Panoramic Views: Two large enclosed porches provide year-round enjoyment of ocean breezes and views. Ascend the spiral staircase to a rooftop deck with 360-degree vistas - a perfect spot for sunset cocktails.Unmatched Convenience: The home includes a dumbwaiter shaft for effortless transport of groceries or luggage, plus a solid oak staircase leading from the grand foyer.Outdoor Haven: A private tiki hut offers shade and tranquility, while the 15K boat lift caters to boating enthusiasts. Theres also ample space to add a pool for the ultimate outdoor escape.Exceptional Storage & Garages: Two oversized garages provide plenty of room for vehicles, watercraft, and more, with additional storage throughout the home for all your needs.Meticulously Maintained: This home has been lovingly cared for inside and out, offering a move-in-ready opportunity to enjoy life on Duck Key.Situated in one of the Florida Keys most sought-after locations, this property is a dream come true for those seeking serene surroundings, endless water views, and the best of island living.Schedule your private showing today and make this coastal retreat your forever home!

$3,750,000
Marathon
Pearces Subdivision   - MM: 47.50
4 Bed, 4 Baths, 2,469 SqFt Days Listed: 140
-2.60% ($100,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift35ft.

Welcome to 830 50th Court, a stunning Gulf-front property in Marathon, Florida, offering breathtaking open water views and spectacular sunsets. This tropical oasis is situated on two expansive lots totaling over 27,500 square feet, providing ample space and privacy. This home features 4 bedrooms and 3 bathrooms within approximately 2,469 square feet of living space. Pre-Firm home will allow the downstairs living area, which is a huge bonus on additional square footage, and insurance cost. The second floor is the crown jewel of this home. Absolutely stunning views of the gulf and sunsets. The second floor has a large living room that seamlessly connects to the new updated kitchen for a full entertainers dream. Split floor plan with each bedroom on either side of the second floor.Downstairs two bedrooms and one bathroom that is perfect for guest or family, an amazing lanai connects the two bedrooms. This is just a great home to sit and relax and cook the catch of the day with friends and family!Outdoor amenities include a 35-foot dock, with a 15,000 pound boat lift, providing direct access to the Gulf of Mexico, ideal for boating enthusiasts. The property also features a volleyball pool which is 3.5 feet deep on each side and 5.5 deep in the middle, perfect for relaxation and enjoying the Florida Keys sunshine. Additional highlights of this property include a gated entrance, fully fenced grounds, and lush tropical landscaping with fruit-producing trees. The concrete block construction, hurricane impact windows, shutters and metal roof offer durability and peace of mind. Located in the heart of Marathon, this property provides convenient access to local amenities, shopping, dining, and the Marathon Airport. This is an active vacation rental, so amazing for any investor, boater, lover of nature and fantastic sunsets, maybe youre a lover of them all. Call today for your private showing!

$3,795,000
Key Colony
Coury Subdivision   - MM: 53.50
5 Bed, 5 Baths, 2,741 SqFt Days Listed: 198
-1.43% ($55,000) 1 Price Change : Last Change 107 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits30ft.

Welcome to your dream home in the heart of Key Colony Beach. This stunning 5-bedroom, 4.5-bath canal-front home, built in 2022, offers modern coastal elegance and top-tier features, making it a true waterfront paradise. Boasting 80ft of water frontage, a 30ft composite dock, and 5ft control depth on a 100ft wide canal, this home provides easy access to both the Ocean and Gulf, perfect for boating enthusiasts. Step inside through the show-stopping Echo pivot door into a sunlit foyer with soaring 10ft ceilings. The spacious, open-concept living area greets you with 12ft ceilings and expansive accordion glass doors that blur the lines between indoor and outdoor living. Enjoy seamless flow from the living and dining areas to the covered porch, outdoor kitchen, and a heated/chilled pool--all perfect for entertaining or relaxing. Take the stairs to the rooftop sundeck and savor breathtaking water views. The gourmet chefs kitchen is a masterpiece, featuring Dolomite countertops, an expansive center island, and premium appliances, including a Miele induction stove top and Liebherr refrigerator. The abundant cabinetry provides ample storage, while the design and finishes elevate the heart of this home. The split-bedroom layout offers privacy, with the luxurious primary suite featuring two walk-in closets and porch access. Two ensuite bedrooms are perfect for guests, while a poolside bedroom provides access to a full bath. The home also includes a 5th bedroom, currently used as a private office, laundry room, powder room, and easy 2 stall garage access. With 7-day vacation rentals allowed, this property is ideal for generating lucrative rental income. Located near beaches, parks, golf courses, tennis courts, and top-tier dining, this home invites you to experience the true Florida Keys lifestyle. This property could be sold turnkey--dont miss your chance to own this incredible waterfront retreat. Contact me to schedule your private tour.

$3,870,000
Key Colony
Key Colony Beach   - MM: 53.50
4 Bed, 4 Baths, 3,616 SqFt Days Listed: 85
-2.52% ($100,000) 1 Price Change : Last Change 13 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Exquisite Craftsmanship Meets Coastal Elegance. This custom-built four-bedroom, three-and-a-half-bath residence reflects superior craftsmanship from a builder known for exacting standards, blending refined living and open water views from multiple vantage points. The heart of the home is an expansive main living area, where living, dining, and kitchen spaces flow beneath 9-foot ceilings. French doors open to a wraparound 40x28 veranda, offering multiple spaces for entertaining, dining, and relaxing while taking in the sweeping ocean views. A thoughtfully designed kitchen features premium appliances, generous walk-in pantry, and high-end finishes. Also on this level is a bedroom with en-suite bath and a half bath for guests. An elevator provides effortless access to every floor. Elegant interior details, including 8-foot solid-core doors, crown molding, and travertine flooring, enhance the homes bright, airy ambiance. The top floor offers a private sanctuary, with the primary suite spanning the entire rear of the home. A dedicated balcony, echoing the wraparound veranda below, provides a serene retreat with breathtaking open water views. The suite includes two spacious walk-in closets and a spa-inspired bathroom. Also on this level are a guest bedroom, guest bath, laundry room, and a fourth bedroom currently used as a walk-in closet with an adjoining sitting area or office. The ground level offers practical amenities, including a two-car garage and a large storage and workshop area. Crafted for outdoor living, the backyard features a spacious covered patio, a sparkling pool, and a 60-foot seawall with T-dock. Boating amenities include a 16,000-pound lift and an additional 3,000-pound lift, perfect for a skiff or jet skis. Immediate open water access and a short 6-8 minute boat ride to the Gulf. This residence artfully combines luxurious interiors with thoughtfully designed outdoor spaces, showcasing open water views and capturing the true essence of island living.

$3,900,000
Marathon
Stirrup Key Subdivision   - MM: 52.50
4 Bed, 4 Baths, 3,414 SqFt Days Listed: 26
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock

Nestled in Marathons most renowned gated community, this gulf front Stirrup Key CBS-built home offers four bedrooms and three bathrooms. Featuring a gourmet chefs kitchen with stainless appliances, boasting with beautiful water views throughout the house. Perfect for entertaining, with its expansive indoor-outdoor living space, you can enjoy year-round. A community boat ramp where fishing and boating is not just a hobby but a lifestyle. Catch the magnificent sunrise as you sip your morning coffee or the alluring sunset as you enjoy your evening limitation. This home is offered with an adjacent lot and building right. Build your dream guest house and give your guests their secluded privacy. A lift to make groceries and handicapped access a breeze. Stirrup Key is a 60-acre golf cart community where getting around is very convenient. This home captures the true essence of the true Florida Keys lifestyle and seclusion that is nonpareil.

$3,950,000
Marathon
Grassy Key   - MM: 58.90
5 Bed, 5 Baths, 3,011 SqFt Days Listed: 506
+3.95% ($150,000) 1 Price Change : Last Change 214 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Weekly rentals permitted! SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys adjacent to Duck Key. A rare find of just 14 new construction residences offering four and five-bedroom floor plans all with direct Atlantic Ocean views, a resort style pool, pickleball court, sandy beach, and the flexibility of a weekly rental. The first floor offers a private two car garage and covered cabana with spacious outdoor living space that leads out to the private beach and pool deck. The second floor features an open floor plan with spacious kitchen, dining and great rooms all overlooking the Atlantic Ocean. One en-suite bedroom on this floor provides seclusion for guests. On the top floor youll find the primary suite with luxurious spa bath and the option of two or three additional guest bedrooms. The homes are finished with high end KitchenAid appliances, waterfall quartz countertops, full height backsplashes, custom closets and much more. Additionally, SeaGlass Cove offers select upgrade options including, elevator/lift, exterior spiral staircase, summer kitchen, custom millwork and Wolf/Sub-Zero appliances. SeaGlass Cove is barefoot luxury at its best.

$3,950,000
Duck Key
Yacht Club Island   - MM: 61.00
4 Bed, 4 Baths, 3,295 SqFt Days Listed: 134
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift75ft.Concre

Welcome to your ultimate waterfront sanctuary in the heart of the Florida Keys. This stunning home in Duck Key offers a perfect blend of luxury and durability, with no detail spared in the design. Built in 2022, this home surpasses the latest building codes and is crafted to withstand the test of time. Inside, youll find a spacious living area with custom-made contemporary furniture. The Poggenpohl kitchen boasts top-of-the-line Miele appliances, including a combi speed oven, combi steam oven, induction cooktop, and a wine climate cabinet. The four bedrooms and three and one half bathrooms are fully equipped, with spa-like features such as rain showers, glass doors, and sleek Dornbracht faucets. The primary suite has its own bathtub, body shower, and private sundeck. The 35-foot high concrete rooftop offers 360-degree views of the island, canal, and ocean, perfect for sunbathing, stargazing, or hosting a party. The downstairs outdoor space is finished with AZEK(r) composite decking, making adding an outdoor kitchen to the covered area easy. Boaters will be impressed by the substantial concrete dock and pilings featuring two High-Tide boat lifts: a remarkable 40,000 lb lift alongside a 6,000 lb lift currently utilized for jet skis. The dock is also equipped with electricity and water connections, and a fish prep table. Using the roller system, you can easily access your kayaks and store all your water sports equipment in the air-conditioned garage. This modern home is designed for a lifestyle of comfort, luxury, and adventure. So why wait? Make this exclusive waterfront property your own and experience the ultimate Florida Keys lifestyle. Dont miss out on this once-in-a-lifetime opportunity. Live the dream, feel the breeze, and own a piece of paradise.

$3,999,000
Marathon
Tinglers Island   - MM: 49.50
4 Bed, 4 Baths, 3,222 SqFt Days Listed: 113
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Sprawling Sombrero Beach newly renovated retreat on an oversized lot with pool, private sandy beach and Open Water Views! Currently utilized as a successful vacation rental this home boasts loads of space and elevated amenities for a family or income-producing investment opportunity! An expansive dock allows for frequent, deep-draft boating adventures with ease, just minutes to excellent fishing and diving. Fillet your fresh catch at the convenient fillet station. Cool off after a day on the water in the in-ground pool, and enjoy a cocktail paired with stunning Sunset Views in the shade of a tiki hut from your private sandy beach! Inside, this home boasts two spacious floors with loads of room to relax and unwind. Downstairs, a generous guest bedroom and bonus room used as fourth bedroom are located just off of a sizable recreational room with access to a large covered porch and the sparkling pool beyond. Upstairs features gorgeous Open Water Views as the focal point of the open concept main living space. The newly designed kitchen features quartz counters, new cabinetry & appliances surrounded on all sides by walls of impact glass and Open Water Views, an ideal backdrop for cooking and entertaining. The well-appointed primary suite comes complete with walk-in closet, porch access, and new ensuite bathroom. An additional guest bedroom offers comfortable accommodation also with newly renovated en suite bathroom. The sprawling upstairs covered porch provides ample space for grilling and al fresco dining. Take in breathtaking views of the Open Ocean, beach, pool, and manicured yard from this breezy vantage point. Nestled on nearly half an acre, with lush tropical landscaping, this spectacular property feels tranquil and private while still just minutes to Sombrero Beach, fantastic restaurants, and grocery stores in town.

$3,999,000
Marathon
Crains Subdivision   - MM: 58.00
6 Bed, 6 Baths, 5,757 SqFt Days Listed: 170
-11.11% ($500,000) 2 Price Changes : Last Change 52 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

Tropical Bayfront Estate nestled into almost 2 lushly landscaped private acres with 3 building rights included! Everything you could possibly need is right here! Main House, Guest House, Pool, Pool Apartment, Storage Building, Dock, Boat Basin, Boat Ramp, Boat lift, and UNBELIEVABLE never-ending turquoise sea views! Well-appointed details found throughout the main home include soaring wood planked ceilings. Spacious kitchen featuring granite counters, upgraded stainless steel appliances, island, and built-in cabinetry and bar plus a separate dining room. The Master Retreat encompasses the entire second floor with a grand Master Bathroom featuring double vanity sink, and soaking tub overlooking the bay, and a comfortable loft; the perfect vantage point for taking in the stunning Open Water Views. Plenty of room for all with two en suite guest bedrooms, and a home office which could easily be converted to a third guest bedroom. Outside the main house, youll find an attached pool house with its own entrance, and additional living space and guest bedroom, as well as a private guest cottage, separate from the main residence. The main house is CBS construction, with impact doors and windows, with a new metal roof in 2021. Peace and privacy abound at this exemplary Marathon paradise! Dont miss this must see property!

$4,175,000
Marathon
Sombrero Subdivision   - MM: 49.50
4 Bed, 4 Baths, 3,458 SqFt Days Listed: 147
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 50ft.

Welcome to 2010 Sombrero Beach Rd. This contemporary oceanfront luxury home awaits you. Custom construction in 2016 this concrete home offers spacious elegance with unparalleled oceanfront views and a premier location just steps from Sombrero Beach and direct Atlantic Ocean access. The property is fenced with lush tropical landscaping, heated pool and spa, covered parking and 50 of dockage. The interior is finished with exotic Brazilian quartzite, plank tiled flooring, custom cabinets, stone showers, elevator, and stainless steel appliance in a an open concept kitchen that would make any chef proud. Balconies are on each floor with open water views, as well as a rooftop deck that offers truly exceptional views. Enjoy the waterside entertaining area down by the pool when youre not out on the water. Call today for more information and to schedule your private viewing of this incredible Keys oasis.

$4,195,000
Key Colony
Coury Subdivision   - MM: 53.50
5 Bed, 5 Baths, 3,600 SqFt Days Listed: 275
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 30ft.

A rare opportunity, not to be missed! Located on prestigious Coury Drive, a hidden enclave in Key Colony Beach, you will find this beautiful home and neighboring lot. Nestled at the end of the canal, the home was specifically designed to take advantage of the breathtaking views straight up the long canal. A second or connected home can be built on the neighboring lot, which also has canal views.From the moment you arrive, you will appreciate the casual elegance of the home. Natural stone floors in a soft, neutral tone flow seamlessly throughout the house. High-end and thoughtful finishes are exquisitely appointed. The open floor plan with large glass doors provides an abundance of natural light, serene views, and easy indoor/outdoor living. The beautiful end-of-canal views grab your attention from the main living areas, primary bedroom and guest room, and the spacious wrap-around balconies. Perfect for your peaceful enjoyment or entertaining guests.The private backyard oasis offers another favorite spot for relaxation and fun with a large lap pool, hot tub, lanai and dock for your boat!Enjoy 3600 SF of well-appointed living space in addition to a generous 5000 SF of outdoor living space between the 2 open balconies and lanai. This does not include first-floor fully tiled enclosed area or garages.In 2007, the owner spared no expense building the home. Intentionally selecting the finest materials and workmanship and engineered the home for safety and beauty. For safety, the house comes with a concrete roof and walls, epoxy-coated rebar, impact glass, and an on-demand propane generator. For beauty, details include matched natural stone floors throughout, solid core doors, rounded walls, and more. See attachment for Property Highlights. The home has a good rental income history. Both Parcel IDs 00079872-006200 and ID 00079872-006100 to be sold together. Lot square footage is both parcels combined. Come take a look...you will be happy you did

$4,300,000
Key Colony
Key Colony Beach 2nd Addn   - MM: 53.50
5 Bed, 5 Baths, 5,567 SqFt Days Listed: 132
-10.40% ($499,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift122ft.Concr

Experience luxury living in this spectacular Mediterranean home, situated on 1.5 lots with a 122 ft wide concrete dock. This furnished property is a masterpiece of design and craftsmanship.Floor-to-ceiling windows offer breathtaking views of the canal, while the expansive 20-foot high ceilings create a sense of grandeur in the living room, which seamlessly flows into the open kitchen. The kitchen is a chefs dream, featuring a Wolfe propane stove, Sub Zero refrigerator and top-of-the-line appliances. Enjoy casual meals in the eat-in kitchen or host formal dinners in the dining area with a balcony.The outdoor kitchen overlooks the pool area, complete with a propane built-in grill and dining table for al fresco dining. For movie enthusiasts, the media room offers a cozy retreat with five leather recliners and a popcorn machine.The first floor features one of two primary suites, spanning from the front to the back of the house with balconies on each end. Two walk-in closets and a luxurious primary bathroom with a glass-enclosed shower, large soaking tub, and separate commode and bidet. A half bath and laundry room are also conveniently located on the first floor.The second floor boasts the second primary suite.. Two additional large bedrooms with private balconies share a bathroom with a double vanity and glass-tiled shower.An elevator provides easy access to all floors, including the rooftop deck with 360-degree views, speakers, and lighting. The property also features a 1000 sq ft man cave.Outdoor amenities include a saltwater infinity-edge pool, hot tub, shallow end for kids,and an outdoor half bath. Boating enthusiasts will appreciate the two boat lifts (15k & 20k), fish cleaning station, and in-water lights. Additional features include two large deep freezers, an ice machine, a 50KW propane house generator, six wireless access points, wifi lights, an irrigation system, and much more.Indulge in the ultimate luxury lifestyle.

$4,445,000
Duck Key
Plantation Island   - MM: 61.00
4 Bed, 4 Baths, 2,519 SqFt Days Listed: 134
-3.35% ($154,000) 1 Price Change : Last Change 72 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 71ft.Concrete

Fully Renovated Oceanfront Home in Duck KeyThis stunning, completely remodeled oceanfront 4 bedroom 4 bath home offers luxury living in the heart of Duck Key. Recent upgrades include a brand-new sparkling swimming pool, privacy wall, and electric roll-down shutters for added convenience. Designed with a Coastal Chic aesthetic, the home features light, airy tones of whites, soft blues, and sandy neutrals that blend beautifully with the seascape. The main living room balcony offers panoramic views of the coast, perfect for relaxing and enjoying the scenery.Inside, the open-concept floor plan includes two en-suite bedrooms and the main living area on the upper level. The chefs kitchen is equipped with top-of-the-line appliances, and the formal dining room is ideal for both intimate meals and family gatherings. The cozy living room boasts a wall of glass showcasing breathtaking ocean views, with a decorative fireplace as the centerpiece. Each bathroom is a work of art, featuring modern finishes throughout.The master suite, located on the lower floor, offers a tranquil retreat with direct pool access and a luxurious en-suite bath. The lower level also includes a guest bedroom, laundry room, and a one-car garage.The property is fully enclosed by a privacy wall for ultimate seclusion. The covered patio, complete with a low-maintenance pool deck, grill area, and artificial lawn, is perfect for entertaining.A newly installed seawall provides robust protection from storms, ensuring peace of mind. Just a short kayak ride from your private dock, explore the pristine shallows of Toms Harbor Island or relax on the white sandy beach at Duck Keys Breakwater (best at low tide). SELLER FINANCING offered below market rates with respectable down payment.Duck Key is a golf-cart-friendly island with access to the exclusive Club Duck Key, an optional private club offering social and wellness amenities. B&BATVAI

$4,500,000
Key Colony
Key Colony Point   - MM: 53.50
5 Bed, 5 Baths, 3,580 SqFt Days Listed: 200
Single Family - Active - Waterfront Yes
Side of Island: Median - Dockage: 70ft.

Experience tranquility just steps from the water in this luxurious 5-bedroom, 4-bathroom waterfront residence. Combining high-end finishes with comfort, this home boasts designer marble accents, hurricane impact windows, a metal roof for added durability, and 100% concrete block construction.Enjoy high ceilings, Italian-crafted cabinets, and natural wood floors throughout. The property also features a private gym, a 70-foot wooden T-dock, and a modern pool (10x28 ft, 5 ft deep) with a wraparound bench--perfect for family gatherings.Key Colony Beachs unique weekly rental policy makes this home an excellent short-term rental investment. With owner financing available, owning this home is more accessible than ever. The community offers tennis and pickleball courts, a golf course, and a private beach. A nearby boat ramp and private airport make it ideal for vacationers seeking easy access by land, sea, or air. Additional conveniences include a nearby supermarket, local dining, a church, and the communitys own police station.Spend your days boating, exploring nearby sandbars like Grassy Key, or enjoying some of the best fishing and reef access in the area. With stunning waterfront and sunset views, this home captures the essence of relaxed island living.Key Features:Travertine flooring throughoutCustom solid wood doors from SpainItalian-crafted kitchen cabinetryThermador appliancesAll impact windows10x6 pivot doorMetal roof for durabilityThis one-of-a-kind residence offers luxury, comfort, and a strong investment opportunity in prestigious Key Colony Beach. Act now to add your personal touches and make this dream home your own.

$4,650,000
Duck Key
Plantation Island   - MM: 61.00
3 Bed, 3 Baths, 1,923 SqFt Days Listed: 12
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift72ft.

Welcome to your dream coastal retreat on Duck Key, where stunning ocean views and island living come together in perfect harmony. This beautifully designed 3-bedroom, 3-bath oceanfront concrete home by DAsign Source blends timeless elegance with modern comfort, featuring soft earth tones, quality finishes, and panoramic views of the turquoise coastline.Inside, youll find a spacious chefs kitchen, ideal for entertaining, along with a smart split floor plan--with two bedrooms enjoying direct ocean views. The expansive primary suite includes a luxurious en-suite bathroom with designer tile, dual vanities, custom cabinetry, and a built-in makeup station.Step outside to your private paradise: a custom oceanfront pool deck with a generous covered patio--perfect for relaxing after a day on the water. The 25,000 lb. boat lift and seawall provide effortless access to the open ocean, with no fixed bridges in sight. You wont find a more beautiful place to paddle board and kayak off your dock. Additional highlights include:A screened-in balcony with electric shutters,Two large storage rooms and an L-shaped two-car garage,Ample outdoor parking and a wide driveway,Located on a golf cart-friendly island with access to restaurants, bars, shops, and social clubs.Whether you love fishing, boating, or simply soaking in breathtaking sunsets, Duck Key offers an unbeatable waterfront lifestyle. Surrounded by crystal-clear waters and shallow sandbars teeming with marine life, this home is not just a place to live--its a place to thrive.Just bring your toothbrush and bathing suit, this home is being offered furnished and turn key.Schedule your private showing today and experience the best of Duck Key living.

$4,999,000
Marathon
Crains Subdivision   - MM: 58.00
3 Bed, 3 Baths, 5,220 SqFt Days Listed: 138
-15.98% ($951,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin

Nestled on a secluded 2-acre lot in Grassy Key, Marathon, this gated waterfront estate boasts 5,220 sq. ft. and is highlighted with a ton of amenities including two docks, 4 post boat lift, private sandy beach and an infinity-edge elevated pool blending seamlessly with the gulf and featuring a built-in table and chairs for relaxing or entertaining. Expansive covered areas by the pool offer shaded spots for lounging and has direct access to the living areas. Double entry doors with intricate carved wood details welcome you into a light-filled home. The open-concept living area is graced by large windows and sliding glass doors that frame panoramic views and create a seamless connection between indoors and outdoors. A striking marble fireplace serves as the focal point. Every element of this home reflects thoughtful design, from the impact-rated doors and windows, in-house elevator plus marble floors, exquisite cabinetry, and refined finishes enhancing the homes timeless appeal. The main kitchen is a chefs delight, featuring granite countertops, two wine coolers, and abundant cabinetry. A cozy dining nook encased in windows offers stunning gulf views, creating the perfect setting for every meal. The primary suite is a sanctuary of luxury, featuring panoramic gulf views, a two-sided fireplace, and direct access to the pool. The en-suite bathroom offers a private sauna, jetted tub, walk-in shower, and makeup counter, creating a spa-like retreat. The guest quarters are designed for comfort and independence, offering a morning kitchen and two guest suites. Each suite includes its own en-suite bathroom and generous closet space, ensuring privacy and convenience for visitors. The large office can also serve as a 4th Bedroom. Additional amenities include a home theater room complete with reclining seats and bar plus an oversized 3-car garage with lift.

$4,999,000
Marathon
Woodburns Subdivision   - MM: 49.50
3 Bed, 3 Baths, 2,428 SqFt Days Listed: 74
-10.17% ($566,000) 2 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage90ft.

Private Waterfront Estate in the Florida KeysThis gated, one-acre estate offers the ultimate blend of privacy, nature, and waterfront living in the heart of the Florida Keys. Nestled among lush, mature tropical landscaping, the property feels like a secluded island retreat. As you pass through the gates, you are welcomed by a beautifully manicured paradise with a coral-cut shoreline, a firepit at the waters edge, and panoramic sunset views over the open water. Just offshore, two small uninhabited islands provide a unique opportunity for exploration.The 3-bedroom, 3-bathroom home is designed for comfort and indoor-outdoor living, with an open concept living room, kitchen, and dining area that seamlessly flows into multiple outdoor living spaces. The upper level includes two spacious bedrooms and two bathrooms, while the conforming lower level offers an additional bedroom, bath, sitting area, and a separate entrance--perfect for guests or an in-law suite. A tool/storage room on the ground floor adds to the convenience of this beautiful estate. The wraparound balcony that surrounds the entire home includes several screened-in areas, enhancing the flow of indoor-outdoor living.Updated with a new metal roof in 2024, the home features stainless steel appliances and breathtaking water views. The property boasts approximately 520 feet of shoreline and a custom dock, including an 84-foot by 4-foot dock with a 21-foot by 8-foot extension and a double floating dock for two jet skis--perfect for boating enthusiasts. Covered parking for four cars is available under the elevated home, with additional parking along the entrance way leading to a circular driveway.Set on three originally platted lots (12, 13, and 14), the property offers the flexibility to separate, redevelop, or keep as a private compound. Located just a short walk from fine dining, shopping, and more, this rare waterfront offering combines serenity, convenience, and endless possibilities.

$5,245,000
Long Key
Long Key Ocean Bay Colony   - MM: 66.00
7 Bed, 7 Baths, 7,941 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Costal Elegance - Live the Dream in this Resort Style, Luxurious Beachfront, Pool Home. Wake up to stunning sunrises with Spectacular Oceanfront Views! 100 ft. of Private Sandy Beach. The sprawling indoor and outdoor spaces provide the perfect setting for large gatherings and entertaining. Gourmet Kitchen with double ovens. 15 mins. from the best dinning and shopping options. Seabird Marina is only 3.5 miles away. More than just a home, its a lifestyle. Let this piece of paradise be yours and experience the ultimate private retreat. Owner is Agent.

$5,500,000
Marathon
Fat Deer Key   - MM: 53.00
10 Bed, 10 Baths, 6,128 SqFt Days Listed: 32
Multi-Units - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Live and/or work in this RARE 100 of waterfront re-development opportunity with DEEP WATER DOCKAGE APPROVED! 200 HIGHWAY FRONTAGE! Huge 74,890 SQ FT site with an ACTIVE Conditional Use PERMIT for 10 unit and 4 affordable staff group home units, price INCLUDES 6 MARKET RATE TBRs, which could be sold off separately if desired. This MIXED USE ZONING has many commercial-residential possibilities...for example: could go to 10 market rate units on site, or higher density with affordable housing, or boutique HOTEL if you bring transient rights, etc. Includes a two-story raised CBS 6,128 SQ FT building that could be used in so many different ways, includes 2,340 SQ FT of extra outdoor porches. This would make an amazing live-work setup, or re-hab the huge building into whatever your imagination could create. BEST LOCATION near Vaca Cut for easy Ocean-Bay access, easy airport access, SHORT-TERM RENTAL FRIENDLY! Contact Peter and Ewa Schwarz for more info and a private viewing of this amazing opportunity to get into THE KEYS LIFESTYLE...live, work, business, family compound...you can do it all right here on the water!

$5,750,000
Duck Key
Plantation Island   - MM: 61.00
4 Bed, 4 Baths, 3,304 SqFt Days Listed: 347
-4.17% ($249,999) 1 Price Change : Last Change 138 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 78ft.

Step into paradise with this stunning retreat in Duck Key, Florida! This 4-bedroom, 4-bathroom haven offers an escape from the ordinary, with 72 feet of deep-water dockage, a 10,000 lb and 20,000 lb boat lift. The house is wrapped in shell stone, calacatta stone, le cornu stove, and features furniture from Restoration Hardware, marble floors, and baseboards.Florida is renowned for its incredible quality of life, with no state income tax and a consistently warm climate perfect for year-round enjoyment. Enjoy more than 230 days of sunshine each year and average temperatures ranging from the mid-70s in winter to the low 90s in summer. The state boasts a range of pristine beaches and turquoise waters that beckon for relaxation and adventure.Duck Key is not only a haven for water enthusiasts, but it also provides access to exceptional educational opportunities, with a mix of highly-rated public, private, and charter schools. Additionally, the area is known for its strong sense of community and character, contributing to a desirable and secure island lifestyle.Spend your days exploring vibrant marine life, diving into crystal-clear waters, or unwinding on pristine beaches. Nearby, discover a wealth of waterfront dining options where you can indulge in fresh seafood while soaking in breathtaking sunset views.Dont miss this opportunity to live in the second house from the entrance to Duck Key. This secure and luxurious island living opportunity is waiting for you!

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 05-09-2025.
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