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

FULL Duplex in the Gem of Key Colony Beach! Whether you are looking for a private family home or an investment property in the FL Keys this Boaters Paradise could be yours! This duplex with an open balcony overlooks a 100 wide deep water canal with 75 ft. of dockage with quick access to the Gulf or Atlantic Ocean that could be yours! New windows throughout, 4 bedrooms and 4 baths with ample parking and storage. Currently a vacation rental. Key Colony Beach features recreational facilities include 4 parks, 2 playgrounds, Brand new pickleball courts, tennis courts, shuffleboard, and a 9-hole par-3 golf course. Call today for your private tour. Property is also listed individually in the MLS #615272 & 615273.

Amazing, well built home, located in Sombrero Isle. Home is a weekly vacation rental with many bookings and repeat guests. All kitchen white cabinets and new granite countertops are being fabricated to complete this coastal inspired renovation. There is an unexpected element of privacay from this oversized corner lot not often found in the Florida Keys. This home is being sold rental ready right down to the silverware and advanced bookings for a true turnkey experience. Please be patient as showings will need to be scheduled around the vacation guests. Cash sales only please

Coastal Luxury Meets Keys Living - Dock, Pool & Guest Suite!Welcome to your slice of paradise in the Florida Keys! This beautifully appointed 3-bedroom, 3-bath home blends laid-back island vibes with refined comfort. Whether youre looking for a full-time retreat, a vacation haven, or a high-performing rental investment--this one checks all the boxes.Enjoy the privacy of a separate guest suite and relax in the resort-style lagoon pool, perfect for lazy afternoons or starlit evenings. Boaters will love the 75-ft private dock with a 15,000 lb electric lift and quick access to open water--your next adventure is always just minutes away.The home also features two garages (one-car + two-car) with plenty of space for gear, water toys, or even your workshop setup. And when youre ready to hit the sand, Sombrero Beach is just around the corner.With a strong rental history and location that truly captures the Keys lifestyle, this is more than a home--its your launchpad for sun, sea, and serious relaxation.📞 Call today for more info or to schedule your private tour--paradise is calling!

Endless Possibilities. This well-built waterfront home, offering 110 feet of deep-water canal frontage, a private boat ramp, and dock space for multiple LARGE vessels, is ready for its next chapter. With easy ocean access and a 200-foot wide canal, its the perfect setting to embrace the island lifestyle. Conveniently located within walking distance of Coco Plum Beach adds to the homes appeal both on and off the water. The main living area features an expansive open-concept design, with vaulted ceilings that amplify the already ample space across the living, dining, and kitchen areas. Multiple sliding glass doors lead to a sprawling screened-in lanai spanning over 700 square feet-- offering additional outdoor living space perfect for relaxing, dining, or hosting while enjoying peaceful water views and refreshing ocean breezes. The generously sized primary suite includes a spacious en-suite bath, walk-in closet, and direct lanai access. A second bedroom also connects to the lanai, enhancing the homes seamless indoor-outdoor flow. A third bedroom, two additional full baths, and laundry room complete the main living level. The lower level features a legal one-bedroom, one-bath suite with a private entrance, its own screened-in patio, a kitchenette, laundry room, and 9-foot ceilings--ideal for accommodating in-laws, guests or crew with privacy and comfort. While the home is structurally sound and move-in ready, cosmetic updates would elevate its appeal and transform it into a truly show-stopping island retreat. The expansive lot also offers ample room to add a pool, further enhancing its outdoor living possibilities. Not a Drive-By! The true scale, layout, and impressive outdoor spaces must be experienced in person to appreciate this remarkable homes potential. This property presents an exceptional opportunity for motivated buyers or contractors to transform it into a show-stopping Keys retreat. Bring Your Vision. Live the Dream.

First time on the market in 49 years, this exceptional waterfront estate is a rare gem located on the Sombrero Golf Course. Boasting over 110 feet of pristine waterfront, 50-foot wood dock, 12,000 lb boat lift, and 120+ foot wide deep-draft canal, this residence is a true haven for both avid boaters and golf enthusiasts. Designed with timeless vision and concrete construction, the home spans over 3,000 interior square feet with four bedrooms and two bathrooms, nestled on a beautifully landscaped 11,950 square foot lot. From the moment you arrive, the lush tropical grounds, elegant landscape lighting, and brick-paved circular driveway set the tone. The detached 30 x 30 foot double car garage offers immense storage, a workshop, and even a full second level for additional space. Inside, a gracious foyer and wood staircase lead you to the expansive open living space, where walls of glass invite sweeping water views and golden sunsets. The full-width screened porch is perfect for indoor-outdoor living. The gourmet kitchen is a chefs dream, featuring a Wolf six-burner gas cooktop, oven, Subzero refrigerator and freezer, generous prep space, built-in cabinetry, and charming retro tile backsplash illuminated by a skylight. The primary suite offers a tranquil retreat with a walk-in closet, updated ensuite bath, and nearby private office. Downstairs, discover three more bedrooms, full bathroom, laundry area, and versatile bonus space--ideal for an art studio or second living area. Outdoors, host unforgettable gatherings beneath two tiki huts on the expansive waterfront deck with room for a future pool. With an assumable flood policy at just $773 per year (and no history of flooding, ever), recent updates including concrete restoration, mangrove trimming, and a 24kW whole-house generator with 500-gallon propane tank--this legacy property is ready to elevate your waterfront lifestyle.

One-of-a-Kind Canal Front Home in Duck Key. Rare opportunity to own this large, custom-built split-level home overlooking the iconic Yacht Club Bridge and sparkling flowing waters of Duck Key with easy ocean access and ocean views. This unique property offers unparalleled water views from the spacious primary suite, where you can relax and watch the hawks and pelicans from your private balcony. Inside, the expansive gourmet kitchen is perfect for culinary enthusiasts, featuring a dining area, ample cabinetry, a built-in desk area, and a seamless flow into a cozy patio ideal for enjoying your morning coffee. The grand entrance, framed by wrought iron gates welcome you. Brick paver walkway leads to a beautifully landscaped garden offering a peaceful retreat. This home is ideally located on a large waterway where three canals converge, making it perfect for those with a large boat and offering a 75 seawall. With expansive balconies, hurricane shutter roll-downs on the second-floor front bedrooms, an oversized garage with storage, brick paver walkways and driveway, this home provides both luxury and convenience. Additional lower level bonus space being used as non-conforming guest quarters. Experience the relaxed island lifestyle that Duck Key has to offer. With easy access to world-class amenities at the Hawks Cay Resort, nearby boat ramps, dining options, and a variety of activities. Membership to the exclusive Club Duck Key is available to further enhancing the island experience. This one-of-a kind home is an exceptional find in a sought-after location. Dont miss your chance to own a piece of paradise--schedule your showing today! Offers encouraged. B&BATVAI.

Expansive and elegant waterfront residence situated on the canal, offering an eastern exposure overlooking the in-ground pool and 100-foot wide canal. The property features a covered patio on the lower level and a spacious wooden deck on the upper level, complete with spiral stairs leading from the living room to a tropical keys-inspired kitchen. Ideal for hosting gatherings and unwinding in comfort. This 5-bedroom, 3-bathroom home includes two bedrooms and two baths upstairs, as well as three bedrooms and one bath downstairs. The circular paver driveway provides ample parking space. A large family home or corporate retreat boasting a Corian kitchen, fireplace, and separate living and dining areas on both floors. Equipped with a boatlift and convenient access to the Atlantic, whether you are looking for a vacation rental or a permanent residence, this property has it all.

Discover the ultimate Florida Keys retreat at this stunning waterfront estate in Key Colony Beach. This 5 bedroom, 3 bathroom home blends tropical elegance with modern luxury, offering an unparalleled coastal lifestyle.A lushly landscaped entrance welcomes you to an open-concept living space with soaring ceilings, large windows, and seamless indoor-outdoor flow. The gourmet kitchen boasts stainless steel appliances, custom cabinetry, and a spacious island, perfect for entertaining.Step outside to your private paradise featuring a resort-style pool, spa, and expansive patio surrounded by lush greenery. A private dock with deepwater access makes this a boaters dream, providing quick access to the Atlantic and Gulf.The primary suite offers a spa-like en-suite bath, while spacious guest rooms ensure comfort for family and friends. Additional amenities include a two-car garage, high-end finishes, and a prime location near pristine, dining, and world-class fishing.Whether as a primary residence, vacation home, or investment, this waterfront oasis delivers the best of the Florida Keys lifestyle.

Casa de la Playa -- Your Private Keys Retreat on Grassy KeyIf youve been dreaming about owning a private beach house in the Florida Keys, Casa de la Playa is calling your name. Set on over half an acre of lush, tropical grounds, this waterfront home on Grassy Key delivers everything you love about island living -- wide-open ocean views, your own sandy beach, and plenty of space to relax and entertain.From the moment you pull into the long, palm-lined driveway, youll feel the world slow down. Inside, this bright and breezy home features 4 large bedrooms and 4 bathrooms, perfect for family getaways or hosting friends. The open living area and kitchen (complete with stainless steel appliances and a huge island) make gathering easy -- and those panoramic water views from almost every room will never get old.Step out onto the spacious second-level veranda, and youve got the ideal spot for morning coffee, lazy afternoons, or sunset happy hours. Down below, your backyard paradise is ready: a sparkling private pool, a full sandy beach you can actually use, and tropical landscaping that feels like a resort -- complete with irrigation and lighting.Other major perks? Brand-new impact windows and doors, durable Hardi Board siding, and tons of parking for your boat, cars, and toys.Whether youre looking for a forever home, a vacation getaway, or an investment that guests will fight to book, Casa de la Playa checks all the boxes. B&BATVAI

Waterfront Pool Home with Deep-Water Dockage & Direct Gulf Access!Welcome to 10980 3rd Avenue Gulf -- a true boaters paradise tucked away on an oversized private lot along a wide and deep canal. With multiple dockage options for large boats, a boat lift, and instant Gulf access (plus ocean access just minutes away via Vaca Cut), this property is ideal for serious anglers and water enthusiasts alike.This well-maintained home offers spacious living areas, a nicely updated kitchen with granite countertops, and a tranquil screened-in porch perfect for relaxing after a day on the water. The layout is open and inviting, providing plenty of room to entertain and unwind.Step outside to enjoy the screened-in pool, covered patio, summer kitchen, and generous yard space. With ample parking, a detached garage, and all the must-have outdoor features -- including a boat dock, lift, and fish cleaning station -- this home offers everything you need for effortless Keys living.

Discover an extraordinary waterfront oasis in the heart of the Florida Keys. Located just moments from the pristine sands of Sombrero Beach, this elegant estate blends modern sophistication with the relaxed charm of coastal living. Designed for the discerning buyer, every detail of this property reflects luxury, comfort, and an unparalleled boating lifestyle. Elevated foundation - permitted for finished interior living space, unlike many other properties in the area.Expansive Two-Story Detached Garage - At 50 feet in length, this impressive structure is ideal for storing all your Florida Keys toys--boats, jet skis, and luxury vehicles or even your class A motorcoach. Composite Dock & Boat Lift with 69 feet of premium dockage, enjoy easy deep-water access to the Atlantic Ocean. The high-capacity boat lift is perfect for safeguarding your vessel while offering effortless on-the-water adventures. Two-Car Garage An additional attached two-car garage provides even more space for vehicles and storage. Whether youre an avid boater, a beach lover, or simply seeking a private retreat, this estate delivers a lifestyle where every day feels like a vacation. Schedule your private tour today and experience the best of Marathons waterfront luxury. Live where others vacation - 415 Sombrero Beach Rd is your gateway to paradise.

Mesmerizing sunsets, the iconic Sombrero Lighthouse, and the famed Seven Mile Bridge define the backdrop of this exceptional oceanfront offering. Set on an oversized 13,875 sq ft lot--an impressive size by Keys standards, with 80 feet of direct ocean frontage--this property presents a truly special opportunity to embrace island living at its finest. In the same family since 1981, this cherished property was thoughtfully designed and built in the mid-1990s to complement its outstanding setting. This two-bedroom, two-bath home is neat, inviting, and move-in ready. Living, dining, and kitchen areas are positioned to capture panoramic open water views--even down to the kitchen sink. A spacious garage and full lower-level footprint provide versatility. Direct ocean access from the dock makes it easy to enjoy boating, fishing, and nearby sandbars. For those with a larger vision, the oversized lot offers room to expand while preserving the tranquility of this remarkable location. An exceptional offering in one of the Keys most iconic settings,

Welcome to your Keys dream home! This beautifully crafted residence, built in 2019, offers 2,464 square feet of luxurious living space, perfectly blending comfort and elegance. With 4 generously sized bedrooms, 3 full bathrooms, open floor plan kitchen and living area, and with deep waterfront balconies on both levels theres ample space for family and guests. Take advantage of outdoor living with expansive covered entertainment area, lounge by the sparkling swimming pool or enjoy direct access to open water from your own 100-foot composite dock. Situated on a serene canal, this home is a haven for water enthusiasts and for those seeking a tranquil retreat. Located just a short walk to beautiful sandy Sombrero Beach, this home offers a unique blend of modern luxury and waterfront living. Whether youre looking for a permanent residence, a vacation getaway, or an investment property, this house is sure to exceed your expectations. This is a currently active vacation rental with excellent income potential. Call today for information and to schedule a private walk-thru of your Keys dream home.

Live the dream in the stunning Florida Keys! Welcome to your ideal coastal retreat at The Reserve at Sombrero Beach, one of the most coveted neighborhoods in the area. This exceptional waterfront residence offers the perfect blend of luxury and comfort, featuring five bedrooms and five and a half bathrooms. Each bedroom is equipped with its own private bathroom, ensuring convenience and privacy for both you and your guests.The spacious owners suite is a true sanctuary, complete with a walk-in closet and a spa-like bathroom with a walk-in shower. Ideal for entertaining, the first-floor living area boasts a large open-concept kitchen with granite countertops, top-of-the-line stainless-steel appliances, and a central island bar. Elegant crown molding and high-end vinyl plank flooring run throughout, enhancing the homes sophisticated atmosphere.Step outside to your private, fenced backyard, where a lushly landscaped paradise awaits. The heated pool and attached Jacuzzi, surrounded by a paved pool deck and lounge chairs, offer the perfect spot to bask in the Florida Keys sunshine. With three balconies to choose from, enjoy panoramic views of the Atlantic Ocean, canals, and waterways as you take in the stunning sunrises and sunsets.For water lovers, the private boat dock is equipped with water, electricity, and a fish cleaning station, making it easy to launch your boat and explore the open waters. Located in a secure, gated community of only eight residences, this home is just a short walk from Sombrero Beach and conveniently close to shopping, dining, and Marathons private airport.Professionally decorated and fully furnished, this home is ready for you to move in and experience unparalleled luxury. Dont miss the opportunity to make this dream home yours and live the Florida Keys lifestyle at its finest!

Discover the refined elegance of this beautifully appointed home located on a canal front in Stirrup Key. Every aspect of this residence reflects high-end finishes, executed with tasteful sophistication. The kitchen boasts granite countertops and stainless-steel appliances, while the floors are premium vinyl for a touch of luxury underfoot. Enhanced for your peace of mind, all windows and doors are impact resistant. Beyond the aesthetic appeal, this home is equipped with a whole-house generator and features a spacious workshop on the ground level, adding both practicality and convenience. The property offers direct to the Gulf of America via a deep-water canal, concrete dock and boat lift, perfect for nautical enthusiasts.Nestled within the gated community of Stirrup Key, this home is among predominantly owner-occupied residences, ensuring a peaceful living environment. The community maintains a strict no short-term rental policy, preserving the areas exclusivity and tranquil ambiance.Adding to its allure, this property includes bonus features not accounted for in the total square footage, offering additional private balcony and terrace spaces. This home is truly a gem that needs to be seen to fully appreciate the unique value it offers. Dont miss the chance to make this exquisite property your own.

Island Living at Its Finest - Escape to the ultimate coastal oasis with this exquisite 2021 built home, offering breathtaking open water views of the Atlantic Ocean. Perfectly blending luxury and tranquility, this stunning residence features 3 bedrooms, 3.5 baths, and all the amenities youve been dreaming of, making it the ultimate island retreat and an incredible investment opportunity. Light-Filled, Open Concept Living - Step inside and be greeted by a sun-drenched living space where panoramic windows showcase unobstructed vistas of the turquoise waters. The open floor plan effortlessly connects the living, dining, and kitchen areas, making it perfect for both relaxation and entertaining. Chefs Dream Kitchen - Whip up gourmet meals in a state-of-the-art kitchen featuring stainless steel appliances, sleek countertops, and generous storage space. Prepare dinner while soaking in the soothing ocean views - it doesnt get better than this! Dine with a View - Take your meals al fresco on the expansive outdoor porch, where the gentle sea breezes and spectacular sunsets create the perfect atmosphere for dining or unwinding after a long day. Retreat to your luxurious master suite, where you can relax in spacious surroundings with tranquil ocean views. The spa-like ensuite bath features a soaking tub, a separate shower, and plenty of room to unwind. Waterfront Living - Step outside to a sparkling pool, perfect for cooling off, or soak up the sun on your expansive patio. With 45 feet of seawall and a boating canal, youll have endless opportunities for aquatic adventures, whether its boating, fishing, or simply enjoying the peaceful surroundings. Boaters Paradise - Convenient boating access means youre just moments away from exploring the open water. With generous parking, arrivals and departures are a breeze. A Smart Investment - This home doesnt just offer unparalleled luxury, it also boasts an impressive rental revenue track record.

Experience tranquility at its finest with this exquisite property by DAsign Source, ideally situated in the Heart of the Florida Keys and just a short stroll away from the renowned Sombrero Beach Park. Located in an area that allows for seven-day vacation rentals A brief boat jaunt to the ocean, this property boasts a heated concrete pool surrounded by tastefully landscaped grounds for ultimate privacy. The brick paver driveway, adorned with low-maintenance pea rock, leads to a home that is immaculately designer furnished, encompassing everything from wall art to lines. Constructed with superior quality materials, including hurricane impact windows and doors, a durable metal roof, and a sturdy concrete block with stucco structure, this residence ensures longevity and safety. Nestled in a tranquil neighborhood complete with a bike path and an array of native and tropical foliage, this idyllic setting is conveniently close to amenities such as a shopping center, restaurants, a hospital, and school. Additionally, the Marathon International Airport is a mere 10-minute drive away for added convenience. A 37-foot dock is in place, enhancing the appeal of this exceptional property. For those seeking even more space, the adjacent twin home is also available for purchase.

Tropical Oasis with Spectacular Open Water Views!!!! World Famous Sombrero Beach- This Newly remodeled 2/2 up & 2/2 down. Completely New Beautifully Landscaped Tropical Yard with Artificial grass - Custom Pool covered with 2 inviting Tiki Huts, and Dual Boat Lifts -10,000 & New 24,000. This oversized Lot provides ample space for all your toys, and the in-law suite adds flexibility for guests or extended family. Impact windows and doors, a metal roof, and an elevated position above flood level. This home features abundant storage space with a Carport and pool storage, room to meet all your needs. Close to World Famous Sombrero Beach, this property is the perfect blend of Luxury, Convenience, and Tropical charm. Centrally located near Shopping, School & Restaurants. Quick access to the Ocean and Bay.

Welcome to The Tides at Vaca Cut #7, a stunning 4-bedroom, 3-bathroom waterfront retreat offering 2,607 square feet of luxury living, expertly built and designed by DAsign Source in 2020. The oversized master suite is a true sanctuary, featuring a spa-like ensuite with serene water views, a freestanding soaking tub, spacious walk-in shower, double vanities, and a massive closet. The bright, open-concept living area flows seamlessly to a private pool and outdoor space, where breathtaking Vaca Cut views and unbeatable boat-watching create the perfect backdrop for relaxation. For boating enthusiasts, 36 feet of dockage with a 12,000-lb boat lift provides direct access to the Atlantic Ocean and Gulf of America. A dedicated laundry room, spacious downstairs enclosure, and storage closet offer extra convenience--ideal for stowing all your Florida Keys lifestyle essentials. Built for durability and efficiency, the home features concrete block construction, impact windows and doors, and a metal roof. With strong rental history and exceptional income potential, this turnkey waterfront home is a rare opportunity in one of the most sought-after locations in the Florida Keys.

Brand New Coming in 2025: A Luxurious Waterfront Haven with Unparalleled Water Vistas, and Deep-Water Dockage! Experience the pinnacle of Florida Keys living in this 3,200 Sq Ft waterfront masterpiece, offering 5 Bedrooms 5 Bathrooms, and a seamless blend of elegance and comfort. Designed for the discerning buyer, this home features a private pool, an elevator, and a stunning rooftop deck, your front row seat to breathtaking sunsets over Boot Key Harbor. Work with Keys Dream Properties to personalize every detail, from interior and exterior colors to high-end tile, quartz countertops, lighting, and fixtures. Create a dream home that reflects your vision. Nestled in the heart of Marathon, this premier location offers easy access to world-class dining, boutique shopping, and the vibrant boating lifestyle. Your protected 50 foot Deep-Water dock places you just minutes from the Atlantic and Gulf, making fishing, snorkeling, and open-water adventures effortlessly accessible. On windy days when the open water of the Atlantic Ocean is not pleasant, Boot Key Harbor provides calm waters for social boating, on the water dining, and cocktails. Best of all, this exclusive property comes with no HOA fees, and allows 7-day rentals, offering both lifestyle flexibility and a lucrative investment opportunity in Marathons thriving vacation rental market. With permits secured and construction set to begin, now is your chance to claim this rare opportunity. Contact us today to start designing your custom Florida Keys retreat!