Middle Keys Real Estate for Sale, Homes and Condos in the Florida Keys

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 double car garage offers rare storage, a workshop, and even a full second level for additional storage. 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, 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.

Stirrup Key is one of Marathons most established Gated Communities, which offers it owns private boat ramp to all residents & this is a very RARE opportunity to own a Brand New Construction Custom Built home behind the gates of Stirrup Key by the local and well respected builders Design Center who have chosen to take a high-end modern design with this 3 Story, 4 Bed plus Den, 4.5 Bath Pool Home with 3467 sqft living with multiple rear patios overlooking the homes water view. Exterior highlights include a Custom Modern Long Paver Driveway that leads to the homes Enclosed Garage and also Carport for additional parking, EV charging station, Concrete Block Construction, Poured Solid Columns, a Metal Roof, Energy Efficient Spray Foam Insulation, Hurricane Impact Windows & Doors thru out including a pre-wire for a Home Generator providing peace of mind. The home is designed so entry will be on the ground level adjacent to the garage to simplify things. On the rear of both living levels are Large Balconies with Custom Welded Handrails. The Custom Kitchen will feature Solid Wood Soft Close Cabinets including 42 Uppers and LED under cabinet lighting with Modern Black Hardware and Cabinet Crown Molding, GE profile Appliances, Quartz Counters, a Modern Backsplash & Upgraded Plumbing Fixtures. Each of the 4.5 Baths will have Custom Tile Floors, Designer Tiled Showers with Frameless Shower Glass Enclosures & Modern Lighting, Mirrors, Faucets, Toilets, etc.. Additional Interior highlights include 5 1/4 Baseboards throughout, 8FT Solid Core Doors with Modern Hardware, Led Recess Lighting thru out, Zero Maintenance Vinyl Plank Flooring throughout, Sherwin Williams XP Loxon Exterior Paint and Sherwin Williams Duration Interior Paint, 10FT Ceiling Heights, Expansive Closets in each of the Bedrooms, & so much more. The private backyard will feature a Custom Built Heated Concrete Pool with Travertine Paver Deck, Pebble Pool Finish with Sunshelf & Color Changing LEDs.

Experience the Ultimate in Florida Keys LivingWelcome to your dream coastal retreat! This stunning 3-bedroom, 3-bathroom home offers everything you need for a life of luxury and relaxation. Featuring a private guest suite, this home is thoughtfully designed to provide comfort and style.Situated along a wide canal, the property boasts a 75-ft private dock with an electric boat lift (15,000 lbs capacity), offering quick access to the open water and endless boating adventures. The lagoon-style pool is perfect for soaking up the sun or enjoying tranquil evenings.The home includes two garages--a one-car garage and a two-car garage--providing ample storage space for your boating equipment, water toys, and other essentials.Located just moments from the pristine shores of Sombrero Beach, you can embrace the ultimate Florida Keys lifestyle with ease. Modern amenities, ample storage, and an unbeatable location make this property ideal as a full-time residence, vacation getaway, or investment opportunity.With a strong rental history already in place, this home is not just a dream--its a smart investment.📞 Call us today for more details and to schedule your private tour!

Welcome to 273 W Seaview Dr, your sanctuary in tropical paradise! This concrete fortress, built to withstand hurricanes, ensures peace of mind on a 15,247 sq ft lot. The 3/2 home, completed in 2020, features modern amenities and stylish finishes. The new AC garage (2023) offers space for 12 cars, high ceilings, and ample storage, perfect for vacationing.Enjoy Floridas benefits: no state income tax, an average of 230 sunny days per year, and beautiful beaches. Duck Key also boasts excellent schools (public, private, and charter) and a friendly, welcoming community. Embrace island living in secure, luxurious paradise!

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.

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.

At Oceans Edge A RARE GEM! PRICE IMPROVEMENTUnobstructed Ocean Views, from the 4th floor, lots of natural light, completely remodeled 2024 with Exceptional Finest Luxury, Contemporary in Design and Style, Luxurious Quartz throughout, Stainless Appliances (see list), 4Bed/3Bath, spacious for friends/family entertaining, enjoy sunrises and amazing colors of sunsets from your wrap around balconies, poolside, or the Tiki on the point. Gated with in-house security and private Bch, fishing pier/swim platform and gym.Steps from your Private Garage (one of only 3 garages), awaits the Largest Seapointe Marina 41 Deeded Boat Slip with a 16,000 lb Boat Lift, you may be on the Ocean fishing or diving in minutes, 2 covered parking spaces and a separate storage unit for bikes, fishing gear and water toys, NO rentals are allowed, for added privacy/security.Bring your own style of furnishings or we may offer an Elegant Designer furniture package separately. This is a one of a kind unit with all it offers.Located in desirable Key Colony Beach, near restaurants, shops, airport, park, beach, walking/biking paths and many other amenities.

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.

Relish in contemporary, coastal luxury and harbor views at this recently upgraded waterfront three bedroom, three bathroom, waterfront pool haven. Located on Logans Island, locally known as the old Millionaires Row, enjoy stunning sunsets, 50 feet of deep-water dockage, 20,000 lb boat lift, and 210 feet of shoreline on a 10,633 sf corner lot. You wont have to lift a finger as this residence was completely renovated and professionally decorated in 2020. Licensed weekly vacation rental with over $100,000 in bookings for 2025 and more to come, purchase with rentals in place. Find the open concept great room complete with electric fireplace adorned with custom tile, Miami Dade pine and shiplap accents. Coastal kitchen equipped with sleek Cafe appliances, white shaker cabinets, gold hardware, farmhouse sink, butcher block island, ice maker, dishwasher drawers and mosaic tile backsplash. Breathtaking backyard that features a 13 x 26 in-ground concrete heated pool surrounded by tile decking, AstroTurf, river rock, multiple lounge areas, and all the palm trees your heart desires. After a day on the water, rinse off in the custom-built outdoor shower. something for everyone. This Marathon sanctuary on Millionaires Row isnt just a property, its paradise!

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.

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

Rare Oceanfront Duplex Opportunity in Sombrero Beach Area!Located just a short walk to Sombrero Beach, this oceanfront duplex offers 75 feet of shoreline and incredible potential in one of Marathons most sought-after neighborhoods.The property features a 2 bed / 2 bath unit upstairs and a 2 bed / 1 bath unit downstairs, making it an ideal fixer-upper for those ready to create their dream coastal retreat.This property sits in an AE-10 flood zone, offering favorable elevation for insurance and renovation planning. Whether you choose to restore the existing structure, split the lot and build two new homes, or build one home and transfer the building right to another site, the possibilities are wide open.With ocean access, proximity to the beach, and so much potential, this is a rare find you dont want to miss.Endless potential, unbeatable location, and a solid investment in the heart of the Keys.

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.

Walk right in and Sit right down, this home is ready for you and your toothbrush! This home has everything for your vacation home needs. Or make the Keys your full time residence and live the dream! Spacious living areas, private yard. Pool and 75 feet of dockage. This home is on the beautiful azure canals of Duck key. Nice location with large yard, and ready to move in. Owner financing possible with 50% down. B&BATVAI

Breathtaking views of Sombrero Lighthouse, the famed Seven Mile Bridge, and mesmerizing sunsets define this rare oceanfront opportunity. Situated on an oversized lot spanning 13,875 square feet--an extraordinary size by Keys standards, with 80 feet of ocean frontage--this property offers a unique chance to embrace the quintessential Florida Keys lifestyle. The land has been cherished by the same family for over 40 years; in the mid-1990s they thoughtfully built the current home to complement its exceptional setting, creating a legacy of care and appreciation. This two-bedroom, two-bath home features a clean, inviting design. Neat, tidy, and completely move-in ready, the home was sited to maximize the stunning open water views. The living, dining, and kitchen areas--all the way to the kitchen sink--are framed by sweeping vistas, creating an everyday living experience that feels anything but ordinary. A spacious garage and full lower-level footprint add versatility to the homes thoughtful design. With an oceanfront dock, this property offers direct access to open water, ideal for exploring nearby sandbars, world-class fishing, or enjoying a day on the water. Whether youre drawn to the waters edge or life on the water, this home places the best of the Keys lifestyle at your doorstep. This property is an ideal choice for those seeking the simplicity and charm of an oceanfront Keys retreat without the scale of a sprawling mega-mansion. At the same time, the oversized lot offers ample potential for expansion, providing flexibility for buyers with larger visions, all while preserving the tranquility of its stunning location. Dont miss the opportunity to own a home in this iconic location. Schedule your private showing today and experience the beauty and tranquility this exceptional property has to offer.

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!

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.

Welcome to The Tides at Vaca Cut #3, a stunning 5-bedroom, 4-bathroom luxury retreat in one of the Florida Keys most sought-after waterfront communities. Spanning 2,607 square feet, this newer construction (2020) home was expertly built and tastefully designed by DAsign Source, a premier name in Florida Keys luxury living. Furnished with coastal elegance in mind, this home offers a seamless blend of style and comfort. The bright, open-concept living area flows effortlessly to a private pool and outdoor entertainment space, where breathtaking views of the Vaca Cut create the perfect backdrop for relaxation. Built for durability and efficiency, this home features concrete block construction, impact windows and doors, a metal roof, and double-stacked washers and dryers--ideal for quick turnovers in a high-demand rental market. For boating enthusiasts, 36 feet of dockage provides direct access to both the Atlantic Ocean and the Gulf of America. And if you love to take in the scenery, the boat-watching here is second to none! With a strong rental history of revenues exceeding $200,000 per year and exceptional income potential, this turnkey property is an ideal investment or the ultimate vacation escape. Luxury, waterfront living, and unbeatable design--all in a prime Florida Keys location!