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$3,999,999
2 Beds 2 Baths B26001957 MLS
Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living.

77340 Overseas Highway, Islamorada

$479,000
2 Beds 2 Baths R11078483 MLS
Nestled right between Key Largo and Key West, you'll discover a lovely condo association with a gorgeous beach and inviting turquoise waters--perfect for your getaway! This charming ground-level condo features two cozy bedrooms and two bathrooms, offering a wonderful spot that's close enough to the fun of Key West and Key Largo while still being a peaceful retreat where you can relax and unwind. You'll love how easy it is to explore everything the area has to offer! Whether you're in the mood for dining at local favorites, indulging in some shopping, or setting off on exciting fishing and diving adventures, all your favorites are just a short bike ride or a leisurely stroll away. And don't forget to check out Sunset Park while you're at it! Unit 203A is in the rental pool and can be rented for a minimum of 14 days, making it a great investment opportunity. Plus, it's fully furnished and turnkey just pack your suitcase and enjoy your stay! Reservations for the season are already starting, so don't miss your chance to experience this fantastic getaway!

601 W Ocean Dr Drive Unit 203a, Key Colony Beach

$1,150,000
2 Beds 3 Baths R11156123 MLS
Exquisite high-end corner residence offering breathtaking, unobstructed views of the Atlantic Ocean and the pristine beaches of Key Colony Beach. This 2 bedroom, 2 ½ bath luxury condo is bathed in natural light, featuring expansive windows that showcase endless ocean vistas and spectacular sunrises. Thoughtfully designed with an open, airy layout, the residence blends refined elegance with coastal sophistication. Enjoy seamless indoor-outdoor living from your private corner vantage point, where the sights and sounds of the ocean create a truly serene retreat. Located in the heart of Key Colony Beach, this exceptional property offers the perfect balance of privacy, comfort, and premier island living. ACTIVE VACATION RENTAL

1133 W Ocean Drive Unit 17, Key Colony Beach

$3,300,000
3 Baths R11164709 MLS
74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. Commercial fishing zoning allows for uses such as a restaurant, seafood market, marine outfitter, charter or fishing headquarters, or other enterprises aligned with the working waterfront.

74560 Overseas Highway, Islamorada

$2,249,000
4 Beds 3 Baths R11162784 MLS
Over 3400 sqft of Luxury Living is featured with this 2007 custom built CBS in the gated community of Stirrup Key Sub in Marathon. Elevated water views, a deeded boat slip, protected community marina, multiple outdoor living areas and a private pool. Designed for both everyday comfort and entertaining, this multi-level home offers generous interior space, flexible living areas, and a thoughtful indoor-outdoor layout. The ground level features a three-car garage, ample storage, and direct access to the pool area, creating an easy flow for relaxing, hosting, and enjoying the Keys lifestyle. The second floor serves as the main living level with two bedrooms, two full baths, a full kitchen, and open living and dining areas that extend onto a large screened lanai. This level is ideal for casual gatherings, quiet mornings, and evening breezes. The third floor offers a private primary suite, sitting area or fourth bedroom, bar/kitchenette, fireplace, spa-style bath, and an expansive lanai with peaceful elevated views. A spiral staircase leads to the fourth-floor widow's walk, finished with travertine flooring and a water hookup. From this vantage point, panoramic views stretch across Marathon and toward the Gulf, creating a quiet setting for sunrise, sunset, and open-air relaxation. A private nature path winds through preserved surroundings and leads to a Gulf-front observation dock, ideal for wildlife viewing and enjoying the surrounding natural setting. Additional features include a lift to the second floor for added convenience. Centrally located in Marathon, the home offers convenient access to shopping, dining, & daily necessities. With a deeded marina slip, elevated water views, pool, garage space, storage, multiple lanais, and a flexible custom layout, this property offers a rare combination of privacy, space, and boating access in Marathon. Schedule a private showing to experience this custom home and deeded marina slip in person.

205 Stirrup Key Boulevard, Marathon

$3,495,000
5 Beds 5 Baths W7882829 MLS
LOCATION LOCATION LOCATION DIRECTLY ON THE GULF W/ GULF OF AMERICA AND MARINA VIEWS! Welcome to an extraordinary opportunity to own a newly constructed, luxury waterfront residence in the heart of the Florida Keys. Located in the exclusive Emerald Landings community in Marathon, this exceptional home offers breathtaking open-water views, a private 50' boat slip included, and a rare private beach, kayak launch, blending high-end coastal living with unmatched boating convenience. Thoughtfully designed for both luxury and functionality, this stunning property features 5 bedrooms and 5 bathrooms, including two spacious primary suites with private balconies overlooking the water. An open-concept floor plan showcases a chef's kitchen with quartz countertops and waterfall island, seamlessly flowing into the living and dining areas--ideal for entertaining or relaxing with panoramic sunset views. Outdoor living is elevated with a heated resort-style pool, expansive patios, and multiple spaces designed for al fresco dining and sunset gatherings. Premium finishes, coastal-inspired design, and modern technology are found throughout the home, offering a turn-key experience for owners and guests alike.This property is the perfect investment opportunity, boasting a proven short-term rental history and strong income potential, while also serving as an ideal future personal residence for those dreaming of a private retreat in the Keys. Whether used as a high-performing vacation rental, a seasonal escape, or a full-time waterfront home, this property offers unmatched versatility. Centrally located near world-class boating, dining, shopping, and beaches, this rare offering combines luxury, location, and lifestyle--a true Keys dream home with income-producing potential. Being offered furnished.

805 39th Street Gulf, Marathon

$16,900,000
6 Beds 7 Baths F10548717 MLS
Escape to your own tropical paradise with this dreamy, ultra-luxurious 6-acre estate on Key Largo Bay, just one hour south of Miami. This extraordinary private retreat features a main residence w/in-law suite, plus three accessory dwelling units, offering a total of 6 bedrooms, 6 full bathrooms, and 1 half baths, perfect for hosting family and friends or creating a secluded personal sanctuary. The estate delivers true resort-style living with a stunning brand-new heated /chilled pool and a natural pool with a tranquil fountain, all set within a lush tropical landscape. With 300 feet of private waterfront, including 100 feet of sandy beach overlooking the Gulf, the property enjoys unobstructed panoramic views and some of the most breathtaking sunsets in the Florida Keys. Designed around a wellness-focused lifestyle, the property includes a sauna, cold plunge, outdoor shower, and dedicated workout and yoga areas, ideal for meditation, fitness, and holistic living surrounded by nature.Boating enthusiasts will appreciate the exceptional waterfront infrastructure, featuring multiple dock spaces, a covered boat house, a private basin, and an approved 99’6” private dock & tiki hut with an approximately 6-foot draft. The new dock adds flexibility to accommodate larger vessels and comfortably welcome multiple boating guests. This estate is positioned near Snake Creek and Tavernier Creek and provides quick access to both the Atlantic Ocean and the Florida Bay, making it a premier launch point for backcountry flats fishing, offshore adventures, sandbar days, and sunset cruises.The location also places you by iconic Florida Keys destinations, including the Islamorada Sandbar, Alligator Reef Lighthouse, and several popular waterfront restaurants easily accessible by boat, offering the ultimate Keys lifestyle of dining, cruising, and coastal exploration.The estate is home to hundreds of tropical plants and trees, ensuring unmatched privacy and natural beauty. An urban garden with organic herbs and vegetables supports a true farm-to-table lifestyle. Outdoor living is elevated with tiki huts, outdoor kitchens, expansive entertaining areas, and ample parking, making the property ideal for intimate retreats, wellness gatherings, or peaceful island living.This one-of-a-kind Key Largo estate is more than a home, it’s a lifestyle. Truly unforgettable and irreplaceable, it must be experienced in person to fully appreciate its scale, serenity, and extraordinary details.*Information is believed to be accurate but not guaranteed. Buyer & Buyer agent/broker to verify all details.

95410 Overseas Highway, Key Largo

$3,690,000
3 Beds 3 Baths W7882338 MLS
Stunning Furnished Coastal Modern 3-bedroom, 3-bath modern waterfront estate built by the Florida Keys' premier builder, D'Asign Source. This three-story solid concrete home offers exceptional design, craftsmanship, and strength, perfectly positioned on over a quarter acre with 110 feet of deep-water frontage along a 300-foot-wide canal. Boaters will love the 10,000 lb boat lift, 85 feet of dockage, and direct deep-water access to the Gulf and Atlantic. A fish cleaning station with water, bait freezer, and commercial ice machine make this property a dream for anglers and water enthusiasts. Inside, expansive glass doors and windows flood the living space with natural light and showcase panoramic canal views. The chef's kitchen features Viking appliances, quartz countertops, wine cooler, and premium finishes, while the open-concept design connects seamlessly to multiple balconies and outdoor living areas. The master suite includes an oversized rainfall shower and a private balcony overlooking the water, while two guest bedrooms provide bright, inviting retreats. Outdoor living is the heart of this home, featuring a custom 440 sq. ft. pool with hot tub and sunshelf, surrounded by soft sand, hammocks, and lush tropical landscaping. Entertain in style at the covered outdoor bar and grilling area, or unwind with sunsets from the private rooftop lounge overlooking the Gulf of Mexico. Additional features include four+ parking spaces, trailer parking, high-speed WiFi, multiple smart TVs, and a fully fenced yard that's pet-friendly. Tis property combines luxury, durability, and a true Keys lifestyle — offering modern design, deep-water access, and spectacular views in one of Marathon's most sought-after waterfront neighborhoods.

118 Avenue E, Marathon

$399,000
2 Beds 2 Baths R11147301 MLS 19 BLDG.
Ocean Breeze makes island living easy in this Florida Keys waterfront enclave. This fully furnished, newly constructed manufactured home is outfitted with tasteful coastal decor across the sunny 2 bed, 2 bath space. The upstairs private balcony overlooks the ocean for morning coffee. All modern appliances including washer and dryer and dishwasher complete the package. Enjoy full amenities in this well-maintained community including swimming pool, marina access, kayak launch, BBQ area, and proximity to all Marathon has to offer including watersports, dining, the local airport and quick access to the Gulf and Ocean. This residence is organized on a leasehold principle making home ownership stress-free.

101 11th Street Unit 19, Marathon

$1,800,000
2 Beds 2 Baths R11107393 MLS
Welcome to Paradise! this home sits on almost 3/4 of an acre along a direct access canal with 100 ft of waterfront! Want to park your RV and Boat under your home, done! Want to build your own luxury oasis, here you go. Want to just enjoy easy access to open water and majestic Sunsets from your private observation deck, got that covered! Fully screened wrap around porches allow you to open up and let the East - West trade winds breeze right through the entire home. Professionally landscaped perfection from your private dock with davits, boathouse and garden paths to the exterior elevator and massive shop/storage area downstairs. Close to Adams Cut for easy oceanside access. 1 hour from Miami international airport.

1514 Shaw Drive, Key Largo

$649,000
2 Beds 2 Baths R11077294 MLS
Discover a breathtaking oceanfront villa at Hawks Cay Resort! This exquisite Two-bedroom end unit is flooded with natural light, creating an inviting atmosphere. As one of the resorts premier properties, it is conveniently located steps from the marina and the main resort area. Villa has been recently upgraded with most of the New Era resort furniture. Enjoy stunning views of the vibrant turquoise waters of the ocean and the bay while staying close to all of the excitement that Hawks Cay Resort has to offer. And to top it off, rental dock options are available just a short distance away from your back door. Imagine yourself sitting back and relaxing on your porch, watching the charter boats come and go from the marina or take a leisurely stroll along the dock to Angler and Ale for dinner. New owners have the opportunity to enroll into the Hawks Cay Resort's rental management program which allow you to enjoy access to 61 acres of exceptional amenities, including a freshwater sandy beach lagoon, Marina, Dock store, 5 food and beverage outlets (Restaurants, Bars, Tiki), tennis, pickleball courts, a luxurious spa, children's club and an endless array of watersports right at your doorstep. Whether you're looking for a fantastic investment property or a dream second home in a tropical paradise, this charming villa offers the best of both worlds. Don't miss your chance to own a piece of paradise at The Village at Hawks Cay!

2002 Marina Villa Drive, Duck Key

$599,000
2 Beds 2 Baths R11086990 MLS Hawks Cay Resort BLDG.
Big Price Drop!!! The Perfect fully furnished weekend escape, or high yield, fully managed resort style rental property! Experience the charm of the Florida Keys in this beautifully updated 2-bedroom, 1.5-bath villa at The Village at Hawks Cay. Set along a beautiful and wide canal, this waterfront property offers spectacular views and a peaceful setting ideal for relaxation and entertaining (and the color of the water truly is that amazing)! The interior was renovated a few years ago, featuring clean white cabinetry, stone countertops, a uniquely large remodeled bathroom upstairs and powder room downstairs. Rentable or ownable dock space is directly out back! Enjoy the gentle sea breeze and scenic waterway views from both upper and lower balconies — perfect for quiet mornings or watching passing boats. In addition to being the perfect weekend hideaway, this property also offers the potential of a high-yield investment with rare daily rental potential! This property currently qualifies for, and is enrolled in, the Hawks Cay Resort's rental management program. Owners have the option to join the onsite rental program, which offers a turnkey solution by managing everything from bookings to cleanings and maintenance. For those who choose to participate, the perks are exceptional including access to more than 60 acres of resort-style amenities. Highlights include five pools, a saltwater lagoon, a full-service marina, spa, tennis courts, five dining venues, a kids' club, retail shops, and endless water adventures like fishing, snorkeling, sailing, paddleboarding, and parasailing. A part of the prestigious Preferred Hotels and Resorts collection, Don't miss your chance to own a piece of paradise call today to explore this exceptional opportunity!

7051 Harbor Village Drive, Duck Key

$939,500
2 Beds 2 Baths R11139241 MLS
2-bed, 2-bath waterfront home, perfectly positioned on a corner lot in neighborhood of Marathon. CBS construction, this home seamlessly blends modern comfort, coastal elegance, and exceptional boating access. Situated on a wide, flow-through canal that leads directly to open water, this property provides effortless navigation to both the Gulf and the Atlantic Ocean, making this property a true boater's paradise. The 55-foot dock invites you to step aboard and set out for a day on the water or simply unwind with panoramic canal views framed by swaying palms and unbelievable sunsets. Step inside to find bright, open living spaces, in this beautifully updated home with new roof (2022), new A/C system, and new impact-resistant windows and doors. Back on market due to buyer financing

11725 3rd Avenue Ocean, Marathon

$9,499,000
R10963178 MLS
Nestled along the serene waterfront, these two picturesque parcels offer an unparalleled opportunity to indulge in the quintessential Florida Keys lifestyle. Boasting breathtaking panoramic views of the glistening waters, these two expansive plots of land / bay bottom present the perfect canvas for your dream waterfront retreat and /or commercial ventures. The Northern parcel consists of about 1,400 ft. of pristine shoreline, providing ample space for waterfront activities such as swimming, fishing, kayaking, and paddleboarding with deep water on one side and shallow bay bottom on the other side. Spanning 2.03 acres of Mixed Use upland and a total of 45 acres, including bay bottom. Potential uses on the Northern parcel could be Commercial retail, restaurant uses, or any combination there thereof, imagine a floating restaurant, small marina, Commercial recreation uses including amusement or sea life park, opening doors to community-centric projects that serve the needs of locals and visitors alike. The off shore island along the channel offers great camp sites. With Mixed Use zoning in place, commercial fishing docks are permitted, providing an excellent opportunity for entrepreneurs in the fishing industry to establish a thriving business. The Southern parcel consists of 50 acres of mangrove forest, beach berms, hammocks, and trails with approx. 6 acres of upland. So many possibilities. Build your own Equestrian Estate, ''The Southernmost stables''. This property would be an excellent place to host large events like concerts, weddings, farm to table / wine tastings, or possibly therapeutic programs or retreats. Beautiful beach areas. Easy to get to, as the island has access to the mainland via a ½ mile land bridge. The property is also located next to one of the largest mega yacht marinas and close to two upscale hotels. The Southern parcel of Cow Key can be purchased by itself. See MLS RX-10804772.

7000 5th Street, Key West

$635,000
2 Beds 2 Baths R11053135 MLS The Village At Hawks Cay BLDG.
This elegant villa is perfectly situated just steps from the Sunset Pool, offering breathtaking water views. As an end unit, it enjoys an abundance of natural light, brightening up the cozy two-bedroom space located in the renowned Hawks Cay Resort in the stunning Florida Keys. Beautifully remodeled in 2021, the villa is decorated in an elegant coastal style, complete with custom made built-in furniture that complements the serene surroundings. Luxury vinyl tile flooring runs throughout, adding a touch of sophistication and durability. Relax on the porch while taking in spectacular sunsets, or launch a kayak from your back door for an easy adventure. A small, serene pocket beach is also just right around the corner. Whether you're looking for a second home or an investment, this villa offers great income potential through the resort's rental program, with daily rentals allowed making it a valuable waterfront property. Why just dream of paradise when you can own it? At The Village at Hawks Cay in the stunning Florida Keys, you'll enjoy the best of both worlds, a luxurious vacation home and a profitable income producing property. When you're not relaxing at your villa, let the resort's optional rental management program handle everything from the reservations to property management, making earning income completely effortless. As a Hawks Cay Villa owner in the rental program, you'll have exclusive access to over 60 acres of premium amenities and activities. Imagine 5 sparkling swimming pools, a lagoon style beach area, marina, a full-service spa, 5 restaurants, tennis courts, a children's center, a gift shop and endless water sports. Whether you're fishing, sailing, diving, snorkeling, paddleboarding, or parasailing, adventure is always right outside your door. Plus, with Hawks Cay Resort being part of the Preferred Hotels and Resorts collection and undergoing a multi-million-dollar renovation, the value just keeps getting better. Don't miss out, call today to secure your own slice of paradise and explore this incredible investment opportunity!

5092 Sunset Village Drive, Duck Key