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94 Sunrise Dr, Marathon
$2,899,000
619491 MLS
Build your dream oceanfront home in the prestigious gated community of Sunrise Isle, a coastal island of just 20 properties located next to beautiful Sombrero Beach in the heart of Marathon. Build anytime you like as the property comes with a deeded City of Marathon Transferrable Building Right subject to the conditions of the City of Marathon. Generous 40,249 sq. ft. ocean and canal front lot (a rare find in the Keys) boasts approximately 104 ft. beach frontage and approximately 467 ft. deep water canal frontage with the option for boat dockage on two separate sides of the canal. A brand new concrete seawall offers superb boating access to both the Ocean and Gulf for world-class fishing and diving. Fly into Marathon's Jet Center just minutes away and once home walk to beautiful Sombrero Beach or enjoy golf, dining and shopping just seconds away. Don't miss this opportunity to build your custom waterfront home in the Fabulous Florida Keys.

94 Sunrise Dr, Marathon

1320 South Street, Key West
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 619665 MLS
Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you're just moments from beautiful beaches, top-tier dining, vibrant bars, museums, and all the attractions the area has to offer.Upstairs features three generously sized bedrooms, each with its own en suite bathroom and walk-in closet, providing privacy and convenience for family and guests alike. The main level is designed for living and entertaining, large open floor plan. An additional bedroom and bath on main floor with a door to the pool/deck area. The chef's kitchen is a standout, equipped with high-end stainless steel appliances including a 48-inch Viking gas range, refrigerator, ice maker, dishwasher, built-in steamer, wine cooler, and rich cherry cabinetry. Additional highlights include: Efficient 2-zone HVAC system, Impact windows and sliding glass doors, Beautiful Tigerwood flooring throughout. The exterior is equally impressive, featuring durable Hardi plank siding for low maintenance, Ipe wood decking, and a private pool surrounded by lush tropical landscaping. The fully fenced yard creates a serene and secluded outdoor retreat. The house also offers two off-street parking spaces, plus ample street parking for guests. A rare opportunity to own a spacious, well-appointed home in a prime location--this one truly has it all.

1320 South Street, Key West

34 Atlantic Dr, Key Largo
$2,890,000
5 Beds ⋅ 4 Baths ⋅ 619621 MLS
Huge Direct Oceanfront Compound -- One-of-a-Kind with 276-Foot Concrete Dock Adjacent to World-Famous John Pennekamp, Coral Reef State Park & Molasses Reef. Discover a truly exceptional and private oceanfront compound designed for boating enthusiasts, investors, or multi-generational living. Spread across three expansive lots, this rare property includes two distinct homes and direct water access -- a combination that's nearly impossible to find in today's market. The primary residence features a Modern Style 3 bedrooms and 2 full baths, offering bright, comfortable living spaces and sweeping ocean views. The second home, complete Modern Style 2 bedrooms and 2 baths on a separate meter, is ideal for guests, or extended family. Step outside to unparalleled oceanfront living with a 276-foot concrete dock, perfect for accommodating large vessels, fishing, and launching watercraft. The grounds offer generous room for entertaining, expansion, or simply enjoying the peaceful surroundings of this secluded coastal haven. Highlights: 3 lots with two homes and a 276-ft dock, Turn-Key Direct ocean access -- idea for boating on the Ocean or Bay. Steps from John Pennekamp Coral Reef State Park Perfect for entertaining, investing, or creating a family retreat Unmatched privacy and coastal lifestyle potential. Seller will consider all reasonable offers.

34 Atlantic Dr, Key Largo

1501 White St, Key West
$2,880,000
4 Beds ⋅ 3 Baths ⋅ 619469 MLS
Key West Oasis - A Tropical Compound Steps from the Sea. House, Pool & Guest Retreat located near by Casa Marina and steps from Old Town. Welcome to your own private tropical compound just blocks from the beach, tennis and pickleball courts, and the iconic White Street Pier where you're perfectly positioned for sunrise strolls, sunset views, and everything in between. Nestled on a lush corner lot surrounded by swaying palms and vibrant tropical foliage, this property offers both privacy and proximity to the best of island living. The main house blends timeless Key West charm with modern comfort, featuring sunlit living spaces and breezy indoor-outdoor flow. Step outside to your resort-style backyard, where a sparkling pool is the centerpiece for relaxation and entertaining. The separate pool house offers flexible space for guests, a studio, or home office. Whether you're hosting sunset gatherings, enjoying a dip after a morning beach walk, or strolling to local shops and cafes, this is island living at its finest. Experience the perfect blend of tranquility, convenience, and tropical beauty—right in the heart of Key West. Here, mornings begin with the sound of the ocean in the distance, afternoons are spent floating in the pool, and evenings bring gatherings under starlit skies. This is more than a home—it's a slice of paradise in the heart of Key West. All you need is to move in and start living your Key West dream. Built with storm readiness in mind, the residence features hurricane-impact windows and doors, offering enhanced safety, sound reduction, and energy efficiency. Complementing these upgrades is a whole-house generator, delivering seamless power during outages and elevating everyday comfort with true peace of mind.

1501 White St, Key West

92295 Old State Rd Unit 4A, Tavernier
$2,850,000
6 Baths ⋅ 619473 MLS
SELLER FINANCING $500,000 down payment, 6% interest rate, 5-year balloon... Prime US-1 Mixed-Use Opportunity in Tavernier! Exceptional investment opportunity in the heart of Tavernier with 313 feet of prime US-1 highway frontage offering outstanding visibility and high traffic exposure. This solid concrete mixed-use commercial building features approximately 6,214 sq. ft. of space situated on a 37,477 sq. ft. fenced lot. The property is thoughtfully configured with six separate units/suites, all connected by exterior walkways, providing flexibility for multiple tenants or diverse business operations. Each unit includes a half bathroom, with two additional restrooms accessible via exterior walkways. Positioned on the northbound side of US-1 with convenient access via a cross street to the southbound lane, this location ensures excellent accessibility for customers and clients. Ideal for a wide range of uses including retail, office, medical, educational, fitness, or storage. Whether you're an investor seeking income-producing property or an owner-user looking for a highly visible location, this property offers endless potential. Survey on file. Rare opportunity to own a highly visible commercial property in the Florida Keys!

92295 Old State Rd Unit 4A, Tavernier

124 Orchid St, Tavernier
$2,849,000
4 Beds ⋅ 4 Baths ⋅ 621261 MLS
Exceptional Brand New Waterfront Home in a prime Plantation Key location. This striking three-level contemporary residence offers 60 feet of protected deep-water dockage and seawall with direct canal access to Tavernier Creek, providing immediate Atlantic Ocean and Florida Bay access, truly a boater's dream. The ground level features an open-air two-car garage and generous covered space. On the first living level, an expansive recreation room/possibly 4th bedroom, opens seamlessly to the poolside patio, complete with a full cabana bathroom, creating an ideal setting for entertaining and relaxed island living. The second level showcases a bright, open-concept design with an expansive living area, dining space, and a gourmet chef's kitchen outfitted with European Italian cabinetry and premium finishes, in addition to a well-appointed laundry room with sink and built-ins. Living areas extend to a covered waterfront terrace, perfect for indoor-outdoor living. The third level features a luxurious primary suite featuring a walk-in closet, spa-inspired bath with a two-person shower, and a private open-air balcony overlooking the water. Two additional guest bedrooms and a beautifully finished guest bathroom complete the level. Outdoor amenities include a pool, covered terrace, and a professional outdoor kitchen, ideal for entertaining year-round. Ideally located in the Upper Florida Keys with walking distance to multiple desirable restaurants, a quick boat ride to Tavernier Creek Marina for fuel, ice and snacks, and minutes to boutiques, breweries and 5-star dining in Islamorada. A rare blend of modern luxury and the ultimate Florida Keys waterfront lifestyle. SELLER WILL ENTERTAIN DESIRED REVISIONS OR OFFER CREDIT FOR UPGRADES.

124 Orchid St, Tavernier

17041 Marlin Dr, Sugarloaf
$2,849,000
3 Beds ⋅ 2 Baths ⋅ 618874 MLS
Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid house for the gardening enthusiast. The main living level showcases a stunning Great Room with soaring tongue-and-groove ceilings and panoramic water views. The open kitchen overlooks Sugarloaf Sound and offers bar seating, stainless appliances, and gas range. A dining area with Dade County Pine accent wall adds warmth and character. The entire second floor is devoted to the private Primary Suite retreat, complete with walk-in closet, sitting room, and spectacular water views for morning coffee with the sunrise and evenings watching the Keys' famous sunsets. Outdoor living is exceptional with a waterfront heated and chilled pool, covered lanai for entertaining, outdoor shower, tiki hut, and private dock with 12,000 lb boat lift offering easy open water access. Every evening, the sky ignites in gold and crimson as the sun melts into Sugarloaf Sound. This is not just a home, it is a front-row seat to one of the Florida Keys' most extraordinary natural performances.

17041 Marlin Dr, Sugarloaf

580 & 590 10th St, Key Colony
$2,845,000
7 Beds ⋅ 7 Baths ⋅ 617788 MLS
Exceptional canal-front opportunity with proven income potential. This expansive 7-bedroom, 7-bath residence offers outstanding flexibility as a legal duplex with an interior lockout, allowing it to function seamlessly as a large single-family home or as two separate living spaces. The configuration includes a generous 5BR/4BA main residence paired with a private 2BR/2BA guest wing, topped off by a convenient pool bath located in the game room, making it ideal for multigenerational living, guests, or vacation rental use. The main living space welcomes you with a dramatic two-story entry, an open-concept great room, multiple dining areas, wet bar, and a well-appointed kitchen that flows to a waterside balcony. The lower-level unit features its own open living and kitchen area, providing privacy and versatility. Four bedrooms are ensuite, complemented by 2 primary suites overlooking the water. Recent upgrades include complete concrete spalling repairs and a fresh exterior repaint, adding peace of mind and refreshed curb appeal. Mediterranean-inspired design elements are carried throughout, along with impact windows and doors, multiple balconies, and inviting indoor-outdoor living spaces. Outside, enjoy a heated pool, spa, covered poolside lanai, and 75 feet of concrete dockage with quick boating access to both the Atlantic Ocean and the Gulf of America. Additional features include a two-car garage and ample off-street parking. This property has a strong, established vacation rental history and is currently an active rental.

580 & 590 10th St, Key Colony

77481 Overseas Hwy, Islamorada
$2,800,000
620931 MLS
Rare oceanfront Pristine parcel offering approximately 0.56 acres (100 x 244') with 100 feet of Pristine Atlantic Shoreline and active building permit for your dream home/estate. Features a new 80-plus foot dock with a tiki hut and direct access to world-class fishing, diving, snorkeling, and boating. Enjoy sweeping sunrise views over the beautiful Atlantic Ocean and sightlines to the iconic Alligator Reef Lighthouse. Situated on prestigious Millionaire's Row and adjacent to protected preserve land for privacy. Directly across to famous Robbie's Marina and market place ,dining, shopping, and local attractions. An exceptional setting to build a custom waterfront estate in one of Islamorada's most desirable location.'

77481 Overseas Hwy, Islamorada

121 Calle Ensueno, Marathon
$2,800,000
4 Beds ⋅ 4 Baths ⋅ 620899 MLS
Welcome to prestigious Sombrero Isle, one of the Middle Keys' most exclusive waterfront communities. This exceptional 4-bedroom, 4-bath residence blends timeless elegance with the relaxed luxury of the Florida Keys lifestyle. Step inside to a grand living room highlighted by soaring volume ceilings, gleaming marble floors, a gracefully curved staircase, and a wraparound mezzanine that leads to the spacious bedrooms and private guest quarters. Designed for both everyday living and entertaining, the home offers an open, inviting atmosphere with impressive Mediterranean architectural details throughout. The well-appointed kitchen features granite countertops, stainless steel appliances, and abundant cabinetry, providing both style and functionality. Outdoors, enjoy your own tropical retreat with a heated freeform swimming pool and over 40 feet of dockage with approximately 5 feet of controlling depth, offering convenient access for a variety of boats. Nestled within the private island community of Sombrero Isle, this intimate enclave consists of only 32 waterfront homes, each situated on approximately one-half acre. Boaters will appreciate the quick access via Sister's Creek to the Atlantic Ocean and some of the finest fishing and diving waters in the United States. Residents also enjoy close proximity to the renowned Sombrero Beach, scenic parks, shopping, fine dining, and vibrant local restaurants and waterfront bars. Marathon International Airport is just 10 minutes away, making travel to and from paradise effortless. Experience the perfect combination of luxury, privacy, and premier boating access in one of Marathon's most coveted waterfront neighborhoods.

121 Calle Ensueno, Marathon

1009 Whitehead St, Key West
$2,800,000
2 Beds ⋅ 2 Baths ⋅ 620355 MLS
High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

1009 Whitehead St, Key West

21640 Overseas Hwy, Cudjoe
$2,800,000
4 Beds ⋅ 3 Baths ⋅ 619615 MLS
SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

21640 Overseas Hwy, Cudjoe

23950 Overseas Hwy, Summerland
$2,799,000
5 Beds ⋅ 4 Baths ⋅ 620578 MLS
Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Keys. Recognizable by its signature pink façade and blue metal roof, this exceptional Summerland Key residence captures the spirit of island living while offering the quality, comfort, and peace of mind of modern CBS construction. Set along a protected canal with 125 feet of concrete dockage, two boat lifts, and direct deep-water access to both the Atlantic Ocean and Gulf of Mexico, this waterfront home is perfectly positioned for effortless days on the water, from world-class fishing and diving to sunset cruises and sandbar adventures. Impact windows and doors and thoughtfully designed indoor-outdoor living spaces create a home that is as durable as it is inviting. Sweeping open ocean views from the main living level and third-story observation deck provide the perfect backdrop for sunrise mornings and starlit evenings. A charming detached guest cottage connected by a covered breezeway creates a private compound ideal for hosting family and friends. The oversized homesite offers exceptional flexibility with ample room to add a custom pool, expand outdoor entertaining areas, or further enhance the property to suit your vision. Just 35 minutes from Key West, Pink Sands feels as though it belongs on Harbour Island while remaining firmly rooted in the authentic charm of Summerland Key. Blending Bahamian-inspired architecture with the confidence of newer CBS construction, exceptional boat dockage, direct ocean and Gulf access, and endless opportunities for future customization, this is a rare opportunity to own a distinctive Florida Keys waterfront home. Minutes from Looe Key Reef, Content Keys, and the backcountry flats, this exceptional location offers unparalleled access to some of the Florida Keys' most sought-after boating, fishing, diving, and paddleboarding destinations right from your private dock

23950 Overseas Hwy, Summerland

837 Copa D Oro, Marathon
$2,799,000
4 Beds ⋅ 4 Baths ⋅ 620205 MLS
Discover elevated waterfront living in this newly constructed custom two-story concrete residence, offering 4 spacious bedrooms, each with its own private en-suite bath. Thoughtfully designed for both comfort and entertaining, the home features a seamless open-concept layout that effortlessly connects indoor and outdoor spaces. At the heart of the home is a designer chef's kitchen appointed with premium stainless steel appliances, including double convection ovens, a smart refrigerator, dishwasher, vented range hood, and wine cooler. A large center island with prep sink, quartz countertops, custom cabinetry, and elegant LED pendant lighting complete the space. Throughout the home, porcelain tile flooring, designer finishes, and expansive windows create a bright and sophisticated atmosphere. A first-floor guest suite offers balcony access with views overlooking the pool, dock, and canal. The striking floating staircase, accented by a custom LED chandelier, leads to the upper level where three additional en-suite bedrooms await. The luxurious primary suite serves as a private retreat, featuring a freestanding soaking tub, dual vanities, an oversized porcelain tile shower, and a MOEN smart multi-head shower system with app-controlled temperature and spray settings. Additional features include impact windows and doors, a web-connected security camera system, energy-efficient LED lighting, 8-foot interior doors, 4K Smart TVs throughout, dual 3-ton 16 SEER air conditioning systems, a standing seam metal roof, aluminum railings, and spacious balconies on both levels. The property offers dual staircases leading to the outdoor living area, a 12' x 26' custom pool and a 50 foot dock. Ideally located in Marathon's desirable Flamingo Island neighborhood, this exceptional property is just minutes from Sombrero Beach, restaurants, and local attractions. Built with quality, durability, and style in mind, this remarkable waterfront home captures the essence of luxury living.

837 Copa D Oro, Marathon

835 Copa D Oro, Marathon
$2,799,000
4 Beds ⋅ 4 Baths ⋅ 620204 MLS
Experience luxury waterfront living in this custom-built, new construction two-story concrete home featuring 4 bedrooms and 4 private en-suite baths. Designed for entertaining, the open-concept layout seamlessly blends indoor and outdoor living. The chef's kitchen boasts top-of-the-line stainless steel appliances including double convection ovens, Smart refrigerator, dishwasher, vented range hood, prep sink, wine chiller, quartz countertops, custom cabinetry, and a large island. Porcelain tile flooring, custom fixtures, LED lighting, and abundant natural light enhance every space. A first-floor en-suite bedroom offers balcony access overlooking the pool, dock, and water. The dramatic floating staircase with custom LED chandelier leads to three additional en-suite bedrooms upstairs. The primary suite features a floating soaking tub, double vanity, custom porcelain tile shower, and MOEN programmable multi-head shower system with smartphone controls. Additional features include impact windows and doors, web-enabled security camera system, 4K Smart TVs in every room, 8-foot interior doors, two 3-ton 16 SEER A/C units, standing seam metal roof, aluminum railings, and expansive balconies on both levels. Situated on an oversized 11,319 sq. ft. corner lot, the property includes a 12' x 26' pool with custom pavers, two stairways to the outdoor living area, and a 36 foot dock completed in January 2024. Located in the desirable Flamingo Island neighborhood of Marathon, just minutes from Sombrero Beach, dining, shopping, and entertainment. Enjoy quick access to open water, world-class fishing, boating, diving, and the crystal-clear turquoise waters of the Florida Keys. Built to impress and built to last, this exceptional waterfront retreat offers the ultimate Florida Keys lifestyle. Adjacent property at 837 Copa D'Oro is also available, featuring an 8,200 sq. ft. lot and 50-foot dock.

835 Copa D Oro, Marathon

333 Indies Rd, Ramrod
$2,795,000
4 Beds ⋅ 6 Baths ⋅ 621324 MLS
Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 5½ bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis. This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a panoramic 360° view from the rooftop widow's walk. The expansive open-concept living, dining, and kitchen area features cathedral ceilings, creating a bright and inviting space. The updated kitchen boasts quartz countertops with a counter-to-ceiling quartz backsplash, stainless steel appliances including a gas range, and a whole-house maintenance-free Allini water purification system. Enjoy the custom indoor/outdoor sound system, 85' flat-screen TV, and private bathrooms in every bedroom. The office can easily be converted into a fifth bedroom, as it already includes its own full bath. Additional features include front and rear access stairs, covered porches overlooking the new custom pool with heater and chiller, PebbleTec pool finish, and a custom paver pool deck. The property is well-equipped for both comfort and boating with an elevated whole-house Kohler propane generator, garage, large storage area, custom rod racks, ice machine, outdoor shower, 9' x 60' concrete dock, 15,000 lb boat lift, shaded fish cleaning station, and an in-ground 1,000-gallon propane tank for all your propane needs. Other highlights include impact windows and doors, a fenced yard with multiple gates, covered parking, a covered outdoor bar and entertainment area, and a gas hookup for the BBQ grill. Enjoy direct deep-draft Atlantic Ocean access for the perfect day on the water. This stunning home is completely turnkey--just bring your T-shirts, shorts, and toothbrush and start enjoying the Keys lifestyle. Come see this exceptional property before it's gone. Easy and a pleasure

333 Indies Rd, Ramrod

20 Center Ln, Key Largo
$2,795,000
4 Beds ⋅ 4 Baths ⋅ 620703 MLS
Modern elegance defines this exceptional custom-built waterfront estate offering 4 bedrooms, 3 full baths, and 1 half bath, complete with every amenity for luxury coastal living. Designed for effortless entertaining, the open-concept floor plan showcases a stunning gourmet kitchen featuring premium stainless steel appliances, quartzite and marble countertops, designer lighting, a beverage cooler, ice maker, and an elevator for added convenience. Expansive floor-to-ceiling sliding glass doors flood the home with natural light while seamlessly blending indoor and outdoor living. The entire third floor is dedicated to a luxurious primary suite, featuring a spa-inspired bath, an oversized walk-in closet, and a private retreat designed for comfort and relaxation. Perfectly situated in one of Key Largo's premier boating locations, the property offers a deep-water dock and an 18,000-pound boat lift and two jet ski docks with quick access to Florida Bay and the Atlantic Ocean.

20 Center Ln, Key Largo

20920 5th Ave, Cudjoe
$2,795,000
4 Beds ⋅ 3 Baths ⋅ 618526 MLS
Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully arranged for relaxed living and effortless entertaining. Recent renovations elevate the home even further, with the kitchen and primary bath completely and tastefully reimagined by D'Asign Source. The stunning chef's kitchen now features Omega cabinetry, elegant quartzite stone surfaces, premium KitchenAid appliances, and a striking black walnut round dining table that anchors the space with warmth and natural beauty—perfect for gathering with family and friends. Pocket sliding doors open the living areas to a spacious screened Florida Room (approx. 494 sq. ft.), seamlessly blending indoor and outdoor living. Outside, enjoy mature tropical landscaping, extensive paved driveways and walkways, and resort-style spaces designed for relaxing and entertaining. For boating enthusiasts, this property truly shines: approx. 4' control depth, quick access to the reef and backcountry, protected canals, and proximity to a full-service marina. The seawall is fully equipped with a cut-in boat slip, 15,000 lb. boat lift, davits, swim ladder, and outdoor shower—everything you need for life on the water. Additional highlights include a barrel tile roof, an attached 2 car garage, a versatile 676 sq. ft. garage space ideal for storage, hobbies, or island toys. Whether you're hosting sunset gatherings by the pool, heading out for a day on the water, or simply unwinding in your own tropical retreat, this remarkable property offers the perfect blend of comfort, style, and true Florida Keys lifestyle. Come see this exceptional canal-front retreat, where every day feels like a getaway.

20920 5th Ave, Cudjoe

75055 Overseas Hwy, Islamorada
$2,790,000
3 Beds ⋅ 2 Baths ⋅ 621394 MLS
Wake up to endless ocean views and the effortless simplicity of life on the beach. This pristine three-bedroom, two-bath oceanfront retreat offers a private, gated setting with a pool, spacious covered patio, and beautiful beach and ocean views from the upper porch, lower-level patio, living area, and two of the three bedrooms. Fully remodeled in 2021, this charming getaway was thoughtfully refreshed throughout, including impact windows and doors, a metal roof, new flooring, appliances, central air conditioning, pool equipment, and an electric entry gate. Coastal cottage-inspired furnishings and finishes create a casual, welcoming atmosphere designed for effortless island living. From mornings overlooking the ocean to afternoons by the pool, this beautifully maintained home captures the relaxed simplicity of the Florida Keys lifestyle.

75055 Overseas Hwy, Islamorada

1405-1409 United St, Key West
$2,790,000
3 Beds ⋅ 3 Baths ⋅ 616089 MLS
Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently featuring a two-story home with 2 bedrooms and 2 bathrooms, and an in-ground pool. In addition, there is a detached studio/cottage, with each separately fenced from one another. On the third lot is a garage. Come and explore these three (3) contiguous, separate lots that all have the City of Key West's, Building Permit Allocation System (BPAS). Total lot SQ FT is 11,968. If you're seeking an opportunity to either build/renovate your future home, or a lucrative development opportunity, or simply to own one of Key West's most unique properties, look no further! It's time to make the move! Come to 1405/1409 United and see that it has the best of all the locations that Key West has to offer. Walking to all the amenities that Key West has, but far enough away from all the noise of the downtown. Plenty of room to make your own mark here. Location, Location, Location is this property. Call today for your private showing!

1405-1409 United St, Key West

443 Sombrero Beach Rd, Marathon
$2,789,000
5 Beds ⋅ 5 Baths ⋅ 619236 MLS
Weekly rental income-producing property with open water access and dockage on desirable Sombrero Beach Road. This 5-bedroom, 5-bath coastal villa is a proven vacation rental offering immediate income potential in the heart of Marathon, just moments from Sombrero Beach. Thoughtfully designed across three levels, the home features light-filled interiors with a coastal palette of soft blues and crisp whites, creating a relaxed luxury feel. Modern finishes, spacious living areas, and seamless indoor-outdoor flow enhance the overall appeal. An elevator provides convenient access to all levels, and multiple balconies capture tropical breezes and water views. Private dockage with direct open water access makes this an ideal property for boating and fishing enthusiasts. The outdoor area includes a private pool and ample space for entertaining, adding to its strong rental performance. Located just a short walk or bike ride to Sombrero Beach, known for its sandy shoreline, calm waters, and beautiful sunsets. Ideal as an investment property, second home, or full-time residence with income potential.

443 Sombrero Beach Rd, Marathon

19 W Playa Largo Blvd, Key Largo
$2,780,000
3 Beds ⋅ 3 Baths ⋅ 619005 MLS
Welcome to Tranquility, an exceptional three-bedroom oceanfront residence at Playa Largo Ocean Residences, an intimate and private luxury waterfront enclave in the heart of Key Largo, Florida. Thoughtfully designed as a secluded coastal retreat, this gated community offers a rare sense of privacy and exclusivity while remaining moments from the island's finest dining, boating, and resort amenities. Positioned within a low-density, purpose-built oceanfront development, the residence was constructed to the highest coastal engineering standards, ensuring durability, performance, and long-term value. Offered fully furnished with a designer-curated interior package, the home delivers a seamless turnkey experience with refined finishes, clean architectural lines, and thoughtfully designed living spaces. Expansive terraces extend the living environment outdoors, offering a tranquil setting for both relaxation and entertaining. The open-concept kitchen, dining, and living areas are filled with natural light and oriented toward the water, while each private bedroom suite provides a serene retreat for owners and guests alike. Every detail has been considered to balance comfort, elegance, and effortless livability. Owners enjoy access to a private clubhouse, resort-style swimming pool, and beautifully landscaped grounds. When you participate in the Playa rental management program, you can enjoy the renowned Playa Largo Resort & Spa world-class waterfront dining, spa services, beach amenities, and ramp access, elevating both daily living and rental appeal. A defining attribute of this offering is its rare flexibility of ownership and income potential, providing uncommon control over both personal use and revenue strategy. This residence presents an exceptional opportunity as a private vacation retreat, a luxury short-term rental, or a long-term investment in one of the Florida Keys' most established and highly sought-after communities.

19 W Playa Largo Blvd, Key Largo

14 Ave F, Marathon
$2,780,000
4 Beds ⋅ 4 Baths ⋅ 618953 MLS
SERIOUS BOATERS--THIS IS THE ONE TO SEE. Exceptional waterfront opportunity in Marathon offering 110 feet of concrete dockage with dual 40-foot finger piers on an approximately 200-foot-wide canal with direct Atlantic access. Bring the boats, jet skis and kayaks--this property was designed for enjoying life on the water. This private waterfront retreat offers over 3,200 square feet with four bedrooms and three-and-a-half baths, a dramatic two-story great room, expansive windows and generous spaces for gathering and entertaining. Outside is where this property truly separates itself: extensive dockage for multiple vessels, floating jet ski and kayak docks, davits, fish-cleaning station and ice machine, plus a heated pool and spa surrounded by tropical landscaping. Weekly rentals are allowed, offering an attractive opportunity for buyers seeking a Florida Keys second home with the potential to generate additional rental income when not in personal use. Morning boat rides. Afternoons by the pool. Evenings overlooking the water. This is the Florida Keys lifestyle buyers come here to find.

14 Ave F, Marathon

139 Marina Ave, Key Largo
$2,750,000
4 Beds ⋅ 6 Baths ⋅ 620421 MLS
Resort-style living just got better! Turnkey waterfront living in prestigious Port Largo. This rare turnkey property offers a legally permitted duplex with ocean views, exceptional flexibility, and strong income potential in one of Key Largo's most desirable waterfront communities. The residence features two side-by-side townhomes, each with 2 bedrooms and 2.5 bathrooms, for a total of 4 bedrooms, 4 full baths, and 2 half baths. Every bedroom includes a private en-suite bath, providing comfort and privacy for owners and guests. Situated on 75 feet of waterfront, the property boasts a brand-new heated saltwater pool, concrete dock, and 20,000-pound Neptune boat lift. The wide, 80-foot deep-water canal offers quick ocean access, placing you on the first channel to the Atlantic with ocean views and easy access to world-class fishing, diving, and boating. Built entirely of concrete and fully renovated, this home combines durability with modern coastal style. Tastefully updated kitchen, flooring, baths, and more, this home was thoughtfully designed. Located on sought-after Marina Avenue, just steps from the private Port Largo homeowners' park, you'll enjoy beautiful sunrise views from the balconies and the privacy of a nature preserve directly across the street. The ground level includes a spacious storage room, covered parking, and a spacious tiki hut perfect for outdoor living and entertaining. Additional features include all impact windows and doors, an electric gated entrance on both sides, separate electric and water meters for each unit, and furnishings and décor included. Ideal as an investment property, family compound, or waterfront retreat, this unique Port Largo opportunity delivers the best of the Florida Keys lifestyle. Call today. Owner/Agent.

139 Marina Ave, Key Largo

139 Marina Ave, Key Largo
$2,750,000
4 Beds ⋅ 6 Baths ⋅ 620392 MLS
Resort-style living just got better! Turnkey waterfront living in prestigious Port Largo. This rare turnkey property offers a legally permitted duplex with ocean views, exceptional flexibility, and strong income potential in one of Key Largo's most desirable waterfront communities. The residence features two side-by-side townhomes, each with 2 bedrooms and 2.5 bathrooms, for a total of 4 bedrooms, 4 full baths, and 2 half baths. Every bedroom includes a private en-suite bath, providing comfort and privacy for owners and guests. Situated on 75 feet of waterfront, the property boasts a brand-new heated saltwater pool, concrete dock, and 20,000-pound Neptune boat lift. The wide, 80-foot deep-water canal offers quick ocean access, placing you on the first channel to the Atlantic with ocean views and easy access to world-class fishing, diving, and boating. Built entirely of concrete and fully renovated, this home combines durability with modern coastal style. Tastefully updated kitchen, flooring, baths, and more, this home was thoughtfully designed. Located on sought-after Marina Avenue, just steps from the private Port Largo homeowners' park, you'll enjoy beautiful sunrise views from the balconies and the privacy of a nature preserve directly across the street. The ground level includes a spacious storage room, covered parking, and a spacious tiki hut perfect for outdoor living and entertaining. Additional features include all impact windows and doors, an electric gated entrance on both sides, separate electric and water meters for each unit, and furnishings and décor included. Ideal as an investment property, family compound, or waterfront retreat, this unique Port Largo opportunity delivers the best of the Florida Keys lifestyle. Call today. Owner/Agent.

139 Marina Ave, Key Largo

900 101st Street Ocean St, Marathon
$2,750,000
6 Beds ⋅ 6 Baths ⋅ 620132 MLS
Welcome to your dream waterfront retreat in the heart of the Florida Keys! This stunning 6-bedroom, 6-bathroom pool home in Marathon offers the perfect blend of luxury, comfort, and investment potential. Situated on an expansive 150 feet of deep-water dockage, this property is a boater's paradise, with easy access to the Atlantic Ocean and the Gulf of Mexico. Whether you're setting sail for a day of world-class fishing or cruising to nearby islands, this home's premier location ensures smooth sailing. Designed for both relaxation and entertainment, the home boasts an open-concept living space with breathtaking water views, a gourmet kitchen, and spacious en-suite bedrooms. Step outside to a tropical oasis featuring a resort-style pool, ample patio space, and a covered outdoor entertaining area—perfect for enjoying the Florida Keys lifestyle This property also delivers excellent vacation rental income, making it a fantastic investment opportunity. With strong rental demand in Marathon, this home is an ideal choice for investors looking for a high-performing rental property or a luxurious personal retreat with income potential. Don't miss out on this rare deep-water waterfront gem in the Keys—your slice of paradise awaits!

900 101st Street Ocean St, Marathon

101 Ocean Shores Dr, Key Largo
$2,750,000
4 Beds ⋅ 4 Baths ⋅ 619905 MLS
Welcome to 101 Ocean Shores Drive -- a rare opportunity to own a spacious, concrete-constructed coastal retreat in the heart of the Upper Keys. Situated on an oversized corner lot, this expansive residence offers over 4,000 square feet under air, but true Keys living happens outdoors -- and this home was designed for exactly that. Large terraces on every level create the perfect setting for entertaining, relaxing, and enjoying the island breeze year-round. Thoughtfully designed for large families or multi-generational living, the home features two bedrooms and two bathrooms on each living level, including an oversized primary suite. Laundry rooms on both levels add everyday convenience, while the elevator servicing all three floors makes access effortless throughout the home. The ground level offers even more versatility with a dedicated garage, tackle room, bonus room, and cabana bath -- ideal for boating, guests, hobbies, or additional storage. Built with solid concrete construction and complete impact windows and doors, the home offers both durability and peace of mind. Step outside to your private backyard oasis featuring a heated concrete pool and spa with the perfect blend of sun and shade. Located in a highly desirable neighborhood, you're just a short golf cart ride from local favorites including Pilot House Restaurant & Marina, Sharkey's Pub and Skipper's Dockside, along with nearby parks, pickleball courts, playgrounds, and community amenities. This is the kind of home that truly must be seen in person to appreciate everything it has to offer.

101 Ocean Shores Dr, Key Largo

149 Lake Rd, Tavernier
$2,750,000
3 Beds ⋅ 2 Baths ⋅ 619095 MLS
Don't let the address fool you, this home has easy bay access! Welcome to relaxed waterfront living in the Village of Islamorada, where open water views and nightly sunsets set the tone for an effortless Keys lifestyle. This inviting three-story home is designed to capture light, breezes, and the beauty of its surroundings. Inside, vaulted tongue-and-groove ceilings and an airy open floor plan create a warm coastal ambiance, while expansive impact windows and doors frame sweeping water views. The main living spaces flow seamlessly together, making it easy to entertain or simply unwind after a day on the water. Three comfortable bedrooms and two baths provide plenty of room for family and guests. Step outside to enjoy open terraces on both levels--perfect for morning coffee, sunset cocktails, or watching boats glide by on their way to Florida Bay just minutes away. Boaters will appreciate the concrete dock and quick access to some of the Keys' most spectacular waters. Thoughtfully equipped with impact windows and doors and a whole-house generator for peace of mind, this waterfront retreat blends comfort, practicality, and the timeless charm of Islamorada living--where every evening ends with a sunset over the bay.

149 Lake Rd, Tavernier

202 Atlantic Blvd, Key Largo
$2,700,000
3 Beds ⋅ 4 Baths ⋅ 621331 MLS
PORT LARGO GEM | BRING THE BIG BOAT! A charming, beautifully maintained Keys retreat with the complete boater's package! This turnkey & furnished pool home with bonus guest quarters and entertainment area is warm and inviting from the moment you arrive, surrounded by beautiful tropical landscaping that gives the property its own private island-retreat feel. For the serious boater, it gets even better: 75 feet of deep-water dockage leading to quick ocean access. The heavy-duty boat lift. ice machine and storage / tackle room make it easy to keep your boat right at home and be ready for your next day on the water. After fishing, diving or cruising, come home to your refreshing pool, easygoing outdoor lifestyle made for entertaining and relaxing. ✓ 75 FT Deep-Water Dockage with Heavy-Duty 27,000 lb Boat Lift ✓Bonus Guest Quarter ✓ Turnkey & Ready to Enjoy ✓ Desirable Port Largo Location Concrete home with concrete roof, Impact windows and doors. Nothing to do here just move-in and enjoy. Big-boat capability with the charm of a true Keys retreat. Owner financing is available. Call to learn more. Escape to the Tropics!

202 Atlantic Blvd, Key Largo