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$2,890,000
3 Beds 3 Baths 620743 MLS
Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenities. Residents enjoy a private homeowner's beach and boat ramp, enhancing the ease of life on the water. This solid CBS construction home offers approximately 75 feet of dockage, a 12,000 lb boat lift, and a convenient fish cleaning station--perfect for avid boaters and anglers alike. After a day on the water, unwind by the beautifully designed pool where a spa cascades into the water, complete with a swim jet, heater, and chiller for year-round enjoyment. Upstairs, the open floor plan is bright and inviting, anchored by a well-appointed kitchen featuring stainless steel appliances, quartz countertops, and a generous island ideal for gathering. Two spacious bedrooms and baths provide comfort and privacy, while a versatile Florida room serves perfectly as a home office and gym. Built for durability and peace of mind, the home includes a concrete roof, impact windows and doors, and an Arlo security system. A rooftop deck offers additional space to relax and take in the coastal surroundings. Downstairs, an expansive covered entertaining area flows seamlessly to the pool and tiki hut--thoughtfully equipped with lighting, ceiling fan, grill, side burner, sink, and refrigerator--creating the ultimate setting for outdoor living. Elevated above flood, the guest quarters feature a private living area, bedroom, and bath with access from both the pool and interior, making it ideal for visitors. A perfect blend of comfort, function, and island charm--this is Port Antigua living at its finest.

101 Madeira Ct, Islamorada

$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

$2,888,000
4 Beds 5 Baths 613026 MLS
A Secluded Waterfront Paradise in the Heart of the Florida Keys. Step into a world of minimalistic elegance and tranquility at this one-of-a-kind coastal oasis. Tucked away on over an acre of lushly landscaped, private property stretching from highway to water, this architecturally unique home offers serene luxury and endless possibilities. Arrive via a tree-lined driveway to discover a striking three-story coastal retreat. Featuring four private en suite bedrooms, each with its separate entrance, the home is designed to provide privacy and relaxation for family and guests alike, great rental property for corporate retreat. This property has just received a vacation rental license which brings enhanced opportunities for income producing short term vacation rentals. The sleek, contemporary design integrates seamlessly with the natural surroundings, offering captivating water views from every vantage point. Designed with entertaining in mind, this property boasts multiple spacious outdoor entertainment areas, including verandas overlooking the sparkling pool, sand-laden grounds, and tranquil waterfront oasis. Gather around the expansive fire-pit with seating for up to 14, perfectly situated at the water's edge for unforgettable evenings under the Keys' starry skies. Adding to its versatility, a secondary garage structure—measuring over 700 sq. ft. with soaring 11-foot ceilings—has been artfully re-imagined as a flexible guest space or personal retreat. With SR zoning permitting vacation rentals, this unique property offers endless opportunities, whether as a family compound, corporate retreat, or lucrative investment. Its layout, designed to maximize privacy and individuality, makes it especially appealing for those seeking a distinctive and adaptable space. Additional features include: Ample parking and storage, ideal for all your waterfront toys. •A kayaker's or paddleboarder's dream, with access to nearby mangrove trails. A secluded yet accessible location, offering privacy while remaining close to the best of the Keys. Don't miss the opportunity to own this unparalleled Keys sanctuary, where modern sophistication meets natural beauty. Schedule your private tour today and experience the allure of this remarkable retreat.

98701 Overseas Hwy, Key Largo

$2,859,000
3 Beds 4 Baths 616807 MLS
Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a wall of stackable impact glass doors that seamlessly connect the indoors with the private outdoor oasis. Just beyond the doors, you'll find a custom heated pool with tranquil water fountains, surrounded by lush tropical landscaping that offers both beauty and privacy, all complemented by a brand-new travertine pool deck that enhances the space with both elegance and durability. Each bedroom features its own en suite bath and walk-in closet, offering comfort and convenience for you and your guests. Storage is abundant throughout the home--a rare find in Key West. For added peace of mind, the property is outfitted with full impact-rated windows and doors. The modern kitchen is equipped with sleek stainless steel appliances, perfect for entertaining or everyday living. The home features two-zone central AC (one unit per floor), and the third-floor primary suite offers a loft-like retreat with both central air and a mini-split system for personalized comfort. Currently operating as a successful vacation rental, this property offers excellent income potential. The home can be sold turnkey with furnishings included, giving buyers the option to move right in or start generating rental income immediately.

814 Ashe St, Key West

$2,850,000
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

$2,850,000
4 Beds 4 Baths 614443 MLS
One of the most sought-after canal properties in Jupiter. Welcome to 934 Penn Trail, a captivating waterfront residence in the heart of Jupiter, Florida. This single-story home, built in 1986, offers 2357 sq ft of living space, featuring 4 bedrooms and 2 full bathrooms and 2 half bathrooms. Interior highlights include an open floor plan, fireplace and a fully equipped kitchen as well as four comfortable bedrooms. The expansive outdoor space features a deck and patio as well as a screened porch for outdoor entertaining Florida style. Direct canal frontage and ample dock space with no fixed bridges to open water makes for unparalleled boating access. This home is located close to top rated schools, shopping, dining and recreational facilities.

934 Penn Trl, Other

$2,850,000
5 Beds 6 Baths 615149 MLS
Welcome to Villa Dolce, a 3,074 sq ft luxury retreat in Seagrove Beach, FL steps from Pelayo Public Beach Access on the exclusive 30A highway. This custom-built 5-bed, 5.5-bath seamlessly blends modern elegance with coastal living. The 1st flr features an open-concept layout, including a chef's kitchen w/ top-of-the-line appl, quartz & granite c-tops, & gas range, spacious primary suite w/ walk-in closet, garden tub. The outdoor oasis offers a covered back porch & entertaining area, heated pool, spa, outdoor TV, firepit, grill, dining area, & outdoor shower, surrounded by lush landscaping & sprinkler irrigation system. Upstairs, 4 guest beds w/ensuite baths & 2nd living area provides space for family & guests. A large laundry room w/sink, 4x8 storage unit, hurricane-impact doors & windows. Close to restaurants & shopping

75 Pelayo Ave, Other

$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

$2,849,000
4 Beds 4 Baths 618527 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

$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

$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

$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 exclusive 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

$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

$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

$2,799,999
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

$2,799,000
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

$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

$2,795,000
4 Beds 6 Baths 619101 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

$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

$2,790,000
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

$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

$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

$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

$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

$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

$2,750,000
3 Beds 3 Baths 616500 MLS
'Turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of Islamorada' Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully renovated 3-bedroom, 3.5-bath concrete residence delivers the ultimate Florida Keys lifestyle--where luxury, durability, and world-class boating converge. Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. Designed for serious boaters, the property boasts 90 feet of deepwater dockage with immediate access to both the bay and the Atlantic Ocean--no bridges, no delays, just open water within minutes. Inside, the home is completely turnkey, with updated finishes and a seamless indoor-outdoor flow ideal for entertaining or extended stays. Expansive balconies and a large outdoor patio overlook the wide canal, creating a private waterfront setting perfect for sunset dining or relaxing after a day on the water. The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles -- an uncommon convenience in this area. What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle that is seldom available in a single property. Whether you're seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals.

122 Court Contessa, Islamorada

$2,749,000
3 Beds 4 Baths 620237 MLS
A waterfront home that is truly the kind of place that makes people stop scrolling, not because it is flashy or overdone, but because it feels rare and real. Set in the highly desired Sombrero Golf Course neighborhood, this property offers a combination that is hard to find in the Florida Keys, a beautiful home, a prime waterfront setting, strong elevation, and a layout that makes everyday life easy while still feeling special. Inside, you will find three bedrooms, each with a private en suite bathroom, plus an additional half bath off the living room for guest convenience. The spacious open floor plan is built for easy living and entertaining, with the kitchen as the true centerpiece. Custom designed with hickory cabinetry, granite countertops, Wolf cooking appliances, a full size Sub Zero fridge and freezer, a 105 bottle wine cooler, and a Miele espresso machine, it is both beautiful and functional. The oversized island seats four and includes smart built in storage to keep everything organized and clutter free. Outside, enjoy a fully screened in pool deck with a built in outdoor kitchen, plus 125 feet of recently repoured dockage with a 15,000 pound boat lift, davits, and two 50 amp shore power stations, along with immediate Ocean and Gulf access for the ultimate Florida Keys boating lifestyle. One of the biggest advantages of this home is its rare ground level, above flood construction. That alone makes it stand out, but the high and dry elevation makes it even more desirable. With new impact windows and doors, a metal roof, and a whole house generator, the major upgrades are already done, offering comfort, confidence, and true peace of mind for Keys living.

2919 Sombrero Blvd, Marathon