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54 Sunset Rd, Key Largo
$4,695,000
621254 MLS
Waterfront opportunity in Key Largo! This rare offering includes two lots with approximately 200 feet of crystal-clear bay frontage, breathtaking sunset views, and calm, clean bay waters. A ROGO letter allows for two residences to be built on the property, The U.S. Army Corps of Engineers previously approved a 250-foot dock. Buyer is responsible for conducting due diligence to verify current requirements and obtain any necessary permits and approvals Architectural plans are included for building your dream waterfront home. Investors and builders may have the opportunity to divide the two lots and construct two separate bayfront residences, subject to applicable approvals. Water, sewer, and electric are already in place. Nearby public park with a convenient boat launch. A unique opportunity to create a private waterfront retreat or develop an investment in the Florida Keys.

54 Sunset Rd, Key Largo

709 Eaton St, Key West
$4,695,000
4 Beds ⋅ 5 Baths ⋅ 618470 MLS
Old Town Seaport Grand Home Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a wonderful, covered porch. Discover the timeless elegance of its living room, dining room, and a fantastic den with an open kitchen floorplan complete with Viking appliances. Step outside to enjoy your covered patio, private pool, and inviting outdoor living areas surrounded by lush tropical foliage on the oversized 6,150 SF lot. Driveway for two cars with one covered parking space. Perfectly situated for exploring Key West's vibrant attractions, this home offers a rare opportunity to own a piece of island history while indulging in the ultimate Key West luxury lifestyle.

709 Eaton St, Key West

851 104th St, Marathon
$4,675,000
3 Beds ⋅ 3 Baths ⋅ 621314 MLS
Welcome to Your Private Oasis in the Heart of the Florida Keys! Discover this hidden gem, a secluded gated estate nestled amidst the stunning landscape of the Florida Keys. Located directly on the sparkling waters of the Atlantic Ocean with 120' of protected deep-water dockage on canal, this property is perfect for boating enthusiasts. This half-acre estate exudes charm and casual elegance, with wide, sweeping porches at both the front and back, providing the perfect setting for outdoor relaxation and entertaining. Inside, you'll find three spacious bedrooms, three luxurious baths, and a cozy den that offers versatile living space. Beautifully landscaped with mature tropical plants, this home features a stunning pool set amidst lush gardens, creating your own slice of paradise. Plus, you're just a short walk from the Millionaire FBO Jet Center, making travel to and from this exquisite location a breeze. Don't miss the opportunity to own this exceptional estate in the Florida Keys! Schedule your private showing today!

851 104th St, Marathon

1028 Flagler Ave, Key West
$4,650,000
4 Beds ⋅ 5 Baths ⋅ 621710 MLS
A CASA MARINA ORIGINAL. Some houses capture a moment in time. Others seem to have understood, from the beginning, what makes Key West such an extraordinary place to live. Built in 1958, 1028 Flagler Avenue is a striking example of tropical mid-century modern architecture, set within a private three-building compound on 11,586 square feet in Casa Marina, one of the island's most distinguished neighborhoods. Behind substantial privacy walls lies a world of its own. Winding pathways lead through lush native and tropical gardens that seem borrowed from a movie, connecting the main residence, separate two-bedroom guest quarters, and detached garage/workshop. Mature palms, flowering gardens, shaded terraces, and a custom swimming pool create an extraordinary sense of seclusion. Inside, clean architectural lines, high ceilings, and generous proportions celebrate indoor-outdoor living. Expansive living and dining areas, a library, and a separate study offer room to gather or retreat. Impact-rated windows and doors provide modern peace of mind without sacrificing the home's character. The guest quarters include their own living area and kitchen, ideal for family and visitors. Together, the three buildings offer 3,589 square feet of combined enclosed space: 3,173 square feet of living area plus a 416-square-foot garage/workshop. Covered outdoor dining, an outdoor kitchen, and abundant off-street parking make this compound as practical as it is beautiful. Just two blocks from Higgs Beach and the Atlantic Ocean, with White Street Pier, waterfront parks, tennis, pickleball, and some of Key West's best-loved restaurants close at hand. Old Town is minutes away, yet the privacy and tranquility of Casa Marina remain entirely your own.

1028 Flagler Ave, Key West

109 Valencia Dr, Islamorada
$4,650,000
5 Beds ⋅ 6 Baths ⋅ 620757 MLS
Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offering 70 feet of protected dockage, this property is a premier boating opportunity with quick access to the bay and ocean via Snake Creek Bridge. Designed to accommodate family and guests with ease, the oversized home features five spacious bedrooms, four-and-a-half baths, a garage, and an upstairs flex space with a private balcony overlooking the pool and wide canal. Timeless finishes include a charming foyer, rich hardwood flooring throughout, a dedicated office, game room complete with a custom built-in bar, and abundant natural light that enhances every level of the home. Built for both comfort and peace of mind, the residence is equipped with impact-rated doors and windows, a whole-home generator, and a propane tank, providing year-round reliability and resilience. Whether you're entertaining poolside, hosting extended family, or setting out for a day on the water, this exceptional waterfront residence embodies the relaxed luxury and boating lifestyle that define Islamorada.

109 Valencia Dr, Islamorada

36 Sunset Rd, Key Largo
$4,650,000
4 Beds ⋅ 2 Baths ⋅ 616004 MLS
A LEGACY KEYS BAYFRONT PROPERTY OFFERING ENJOYMENT TODAY AND ENDLESS POSSIBILITIES FOR TOMORROW! Preserve and enhance the charm of a Florida Keys homestead, or reimagine the property to fit your future vision, with immediate use short-term and strong long-term investment potential. The rare double lot spans nearly one acre on a prime point of land along Florida Bay. With over 200 feet of improved shoreline, this property nearly doubles the width of typical waterfront parcels. Tucked away among native hardwoods at the Southern edge of Key Largo and the Village of Islamorada, this parcel offers exceptional privacy with both sunrise and sunset views. Features include a sandy beach, a cut-in boat basin with deep-water channel access, 2 ramps for launching pleasure watercraft, a resort-style pool, a concrete pier, aquarium-like waters with crystal-clear blue tones, and a sandy bay bottom teeming with marine life. The existing 4BD/2BA concrete residence provides instant enjoyment and valuable building rights, allowing you to create a custom waterfront retreat without waiting for a Monroe County ROGO allocation. A rare opportunity for a family compound or legacy estate in one of the Upper Keys' most unique bayfront settings.

36 Sunset Rd, Key Largo

36 Sunset Rd, Key Largo
$4,650,000
613012 MLS
WHERE SUNRISE MEETS SUNSET- CREATE YOUR WATERFRONT MASTERPIECE IN THE FLORIDA KEYS! Remarkable and rare bayfront building opportunity in South Key Largo awaits on this unique property that spans nearly an acre of upland across two contiguous lots offering 200 feet of prime waterfront with a highly coveted building right already in place. Design and build your dream estate to your exact specifications, with the unparalleled bonus of both sunrise and sunset views from its exclusive point of land. Boating enthusiasts will appreciate a quarter acre of sandy baybottom below two docking areas, a concrete seawall, a protected boat basin, and ample space for your waterfront escapades. Enjoy the natural beauty of a sandy beach framed by sea oats, swaying palm trees, and mature native foliage, all tucked away behind a quiet, family-oriented neighborhood far from the highway's hustle and bustle. Whether you're seeking serenity, privacy, or a blank canvas to create your ultimate island retreat, this property is truly one of a kind. Don't miss this extraordinary opportunity to create your literal peace of paradise in the Florida Keys! Bonus: There is an existing single family home/bungalow & pool on-site that can be utilized as your primary building right or kept as a guest house for your larger estate...the choice is yours! Duplicate Listing, see MLS #616004

36 Sunset Rd, Key Largo

105 Palm Ave, Islamorada
$4,600,000
1 Beds ⋅ 4 Baths ⋅ 618814 MLS
This is an exceptionally rare chance to secure a versatile mixed use commercial property in Islamorada's most established business corridors. Sale does not include real estate business. These three building and the land are ideally positioned for a wide range of commercial uses. Its central location within the Village of Islamorada provides strong access to both local residents and year-round visitor activity, making it an appealing option for investors and owner-operators. The building features a practical, adaptable layout suitable for professional offices, medical or wellness services, boutique retail, administrative operations, or specialty businesses. Large front-facing windows bring in natural light and enhance street presence, creating an inviting entry point for customers and clients. The interior opens into a flexible main area that can function as a reception space, retail floor, open office environment, or showroom. The footprint also supports the creation of private offices, treatment rooms, or storage areas, allowing businesses to tailor the space to their operational needs. On-site parking adds significant value, providing convenient access for customers and employees--an important advantage in Islamorada's commercial zones. Excellent signage opportunities ensure strong brand exposure. Easy ingress and egress make the location suitable for both destination-based and walk-in business models. Surrounded by established businesses, restaurants, marinas, and residential neighborhoods, the property benefits from a diverse and active customer base. Islamorada's strong local economy and tourism-driven demand enhance the long-term appeal of this location. With limited standalone commercial inventory available in the Upper Keys, 81579 Old Highway offers a unique setting for multiple uses within walking distance to Cheeca Lodge, The Moorings, and Worl Wide Sportsman. Totally renovated in 2019. Virtual tour www.166bayviewdrive,com

105 Palm Ave, Islamorada

117 Leoni Dr, Islamorada
$4,600,000
5 Beds ⋅ 6 Baths ⋅ 617341 MLS
Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout. Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation. On the main floor, the gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock. This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

117 Leoni Dr, Islamorada

88 Tingler Ln, Marathon
$4,599,000
619871 MLS
Seize Your Dream with Fast-Tracked Building Permits!** Unlock the potential to construct your ideal oceanfront retreat on this exceptional estate-sized lot. This stunning 1.5-acre parcel is completely cleared and filled to grade, allowing for an expedited permitting process. With the preexisting home already removed, you can start building in just two to three months after submitting your architectural plans. (ROGO exempt) This property has been divided into two parcels, offering the flexibility to create one or two homes, depending on your vision. It's perfectly situated in the heart of Marathon, just a short stroll away from the renowned Sombrero Beach and Park. Enjoy access to a scenic bike and walking path that meanders through the nearby golf course and connects to the Publix Shopping Center, the best beach in the Keys, and charming neighborhoods. You'll find Marathon International Airport, Fisherman's Hospital, and Home Depot within a quick five-minute drive. Marathon is known for its friendly fishing and diving community, boasting an array of restaurants and shops. The boating access from this lot can accommodate vessels with a draft of up to 4 feet, and a dock permit is already applied for and readily obtainable. Don't miss this rare opportunity to make your seaside dream a reality!

88 Tingler Ln, Marathon

2394 Coco Plum Dr Unit 2, Marathon
$4,500,000
6 Beds ⋅ 7 Baths ⋅ 621946 MLS
Welcome to one of the most exclusive waterfront parcels in the Florida Keys. Located just steps from Coco Plum Beach and the Atlantic Ocean, this rare investment opportunity is the ultimate blend of luxury, lifestyle, and income potential. Professional Designed and built by D'Asign Source in 2019, this home is testament to timeless architecture, sophisticated interiors, and exceptional craftsmanship. Spanning 4,066 square feet and featuring 6 spacious bedrooms and 6.5 bathrooms with custom millwork and designer fixtures. The interiors are professionally furnished with a curated blend of comfort and elegance, complemented by expansive ceiling heights, open-concept living areas and balconies throughout. Designed with privacy in mind, this home includes its own private pool, tiki hut, and a dock offering deepwater and direct ocean access. Impact windows and doors provide storm security and peace of mind, while the three (3) air conditioning units to ensures optimal climate control on each level. Boating an abundance of storage on each level, an oversized laundry room, walk in pantry and en- suite accompanying each room. Whether you envision a serene primary residence or a luxury short-term rental business this property offers incredible versatility and value. Zoned for weekly rentals, the income potential is substantial, making this one of the most attractive investment opportunities in the Florida Keys. With seller financing available up to 50% of the purchase price, acquiring this rare trophy property is as strategic as it is luxurious. ALSO AVAILABLE TO PURCHASE AS A PORTFOLIO WITH THE TWO ADJACENT HOMES.

2394 Coco Plum Dr Unit 2, Marathon

90184 Overseas Hwy, Tavernier
$4,500,000
7 Beds ⋅ 9 Baths ⋅ 621308 MLS
90184 Overseas Highway presents an opportunity to acquire a commercial asset positioned along the Florida Keys' primary transportation corridor. The two-story building is located on U.S. Highway 1 in Tavernier, providing visibility and accessibility within the Upper Keys. The property sits within the established Tavernier business district, an area that includes government offices, healthcare facilities, educational institutions, retail services, and daily-needs destinations that support year-round commercial activity. The building was originally developed for financial-services use and offers a layout suitable for a variety of office, professional, service-oriented, and retail users, subject to local regulations. Its corner positioning and frontage along Overseas Highway enhance exposure to residents, visitors, and businesses traveling throughout the Keys. The surrounding area benefits from limited commercial land availability and serves as a key service hub between Key Largo and Islamorada. Tavernier's location within Monroe County provides access to a stable mix of tourism, marine industries, local services, healthcare, and government employment. The property's placement near Mariners Hospital, Coral Shores High School, and major retail destinations contributes to consistent activity throughout the surrounding area. Combined with direct access to U.S. Highway 1, the asset offers connectivity to the broader Florida Keys market while maintaining proximity to local demand generators. The property's existing improvements, established commercial setting, and prominent highway presence create potential for investors and owner-users seeking a recognizable commercial location in the Upper Keys.

90184 Overseas Hwy, Tavernier

155 Palo De Oro Dr, Islamorada
$4,500,000
3 Beds ⋅ 5 Baths ⋅ 620441 MLS
An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and quick access to both the Florida Bay and the Atlantic Ocean via Snake Creek. This extraordinary opportunity allows you to complete what was envisioned as one of the Florida Keys' most premier luxury estates. Elevated above flood on **100 feet of canal frontage**, this solid concrete home features a striking concrete roofline and nearly all impact-rated windows and doors already installed, providing an exceptional foundation for your dream home. Designed with **5,559 square feet of air-conditioned living space**, the residence offers an ideal blend of luxury and boating lifestyle. The first level includes **1,467 square feet** of living space, an oversized **897-square-foot garage**, and plans for an expansive entertainment area, fishing gear room, and direct waterfront access. The second level features **2,361 square feet** of living space plus over **1,100 square feet of covered porches**, with plans for three spacious guest suites, each with a private bath, a half bath, laundry room, chef's kitchen, and open-concept living area. The entire third floor is dedicated to the **1,731-square-foot primary retreat**, designed with ocean views, a spa-inspired bath, oversized custom closet, executive office, and private covered porch. An elevator shaft is already in place for easy access to every level. Plans also include a canal-front pool and cabana overlooking Snake Creek Bridge. With a concrete dock, 100 feet of waterfront, deep-water boating, and one of the Keys' finest locations, this property offers the rare opportunity to complete a truly remarkable custom estate while selecting every finish to reflect your own vision. Property is being sold as is. Some images are AI computer generated to show future potential.

155 Palo De Oro Dr, Islamorada

8070 Gulfstream Blvd, Marathon
$4,500,000
3 Beds ⋅ 2 Baths ⋅ 620143 MLS
Welcome to your slice of paradise in Marathon's highly sought-after ''Behind the Airport'' neighborhood. Live the ultimate Florida Keys lifestyle with unobstructed open water Gulf views, unforgettable sunsets, and exceptional outdoor living. Situated on an oversized 11,250 sq. ft. fenced lot, this 3-story CBS home offers 3 bedrooms, 2 bathrooms, and endless possibilities. Wake up each morning to panoramic water views from every level and spend your evenings watching the sun melt into the Gulf from multiple vantage points throughout the property. Boaters will appreciate the 80 foot dock direct access to world-class fishing, diving, and watersports. Nature lovers will enjoy the abundant marine life right in their backyard. Outdoor amenities abound with an in-ground swimming pool, two chickee huts, expansive entertaining area, and extensive storage space rarely found in the Keys. This is more than a home, it is a front-row seat to paradise.

8070 Gulfstream Blvd, Marathon

31449 Ave I, Big Pine
$4,500,000
5 Beds ⋅ 4 Baths ⋅ 617356 MLS
Waterfront views of mesmerizing sunrises and moonrises. Imagine having your own private dock on the canal, with vessel access to the Gulf and Atlantic Ocean. Fishermen, bridge clearance is 11 ft. Dolphinus del Sol is a luxury waterfront estate! A full video walkthrough is available on video platform. Use property address to view. Sit back and enjoy a voice-activated, smart home. This new construction, solid precast concrete home, features vaulted ceilings, sleek contemporary lines, and expansive windows showcasing panoramic water views. View distant islands, bridges, boats cruising by, sea life. Entertain in style with the upper level, grand open living room and kitchen area featuring soaring ceilings and walls of glass, with 8 ft opening to the deck. The sleek contemporary kitchen has black stainless steel smart appliances and black, dazzling mirror-fleck countertops. A mirror door reveals a sliding appliance tray from the pantry. In the master bedroom relax on the settee sipping coffee topped with crème de la crème views and a tropical breeze. The en-suite master bath is an expansive oasis. Chill out in the jetted, heated tub, soaking in the views. Elevated ceilings, a 5'x5' shower and floating double vanity offer room to breathe. Adjacent is the walk-in closet. The lower living level great room features a large theater/entertainment area with sweeping waterfront views. Stained floors throughout mimic flowing marbled stone. This 3500 sq ft, 5 bedroom, 4 bath home has outdoor space on two upper decks and a 500 sq ft ground-level patio featuring sea life art. Park up to 6 vehicles under the house or utilize the locking garage. The 2300 sq ft waterfront area has ample space to add amenities. The construction exceeds 180 mph hurricane code. This is a solid, precast concrete panel construction: walls, floors, roof and stairs. The poured concrete pilings go 9 ft below grade, 5 ft into caprock, connected with a 20 in deep grade beam. Tour this amazing fortress!

31449 Ave I, Big Pine

1500 Atlantic Blvd Unit 308, Key West
$4,499,999
3 Beds ⋅ 3 Baths ⋅ 620745 MLS
Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially secure condo communities. This 3 bed, 3 bath residence encompasses 2,309 sq ft of thoughtfully designed living space with views of the Atlantic Ocean. Offered fully furnished, every detail has been curated to blend contemporary elegance with the relaxed refinement of island living. A robust high-speed WiFi system with multiple access points & 800 Mbps of service enhances the home's modern convenience. Walls of pocket glass doors frame endless ocean vistas while filling the living spaces with natural light. Designer lighting, Hunter Douglas Luminette sheer window treatments, and exceptional craftsmanship are showcased throughout. The kitchen features Miele appliances, integrated cabinet lighting, custom-organized drawers, and an innovative smart-glass circular window connecting the kitchen and dining area. With the touch of a button, the glass transitions from opaque to transparent. Designed for both entertaining and everyday living, the open-concept living and dining areas flow seamlessly. The dining space is highlighted by striking brass architectural lighting, while a custom-built bar with a wine cooler and ice maker creates an inviting entertaining alcove. The terrace extends the living space outdoors, offering a comfortable setting to enjoy the surrounding views. The primary suite features a distinctive white oak accent wall, built-in workspace and vanity with concealed power outlets, a spa-inspired bath, generous closet space, dual shoe closets, and a private waterfront terrace. One guest bedroom doubles as a media room with designer floral wall covering and club chairs that convert into twin beds. The third guest bedroom is a spacious ensuite retreat offering comfort and privacy. Residents enjoy gated access, exceptional amenities, covered deeded parking space, & private storage.

1500 Atlantic Blvd Unit 308, Key West

150 List St, Islamorada
$4,499,500
618920 MLS
Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal for a comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A PERMIT HAS BEEN ISSUED to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada

150 List St, Islamorada
$4,499,500
1 Beds ⋅ 1 Baths ⋅ 618918 MLS
Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A PERMIT HAS BEEN ISSUED to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada

1903 Sombrero Blvd, Marathon
$4,499,000
5 Beds ⋅ 5 Baths ⋅ 621660 MLS
Located right on coveted Sister Creek discover exceptional waterfront living in this expansive Marathon estate overlooking the golf course and a deep-water canal with deep water access to both the Atlantic Ocean and Gulf. Offering 4,836 sq. ft. of combined living space, the property features a 4-bedroom, 3.5-bath Main Residence and detached 1-bedroom, 1-bath Guest Suite. A grand entry welcomes you with soaring ceilings and a sweeping curved wood staircase, while elegant travertine flooring flows throughout the main living areas. The spacious Living Area showcases private water views, a fireplace, wet bar and multiple glass doors opening to the pool deck. The well-appointed Kitchen features granite countertops, custom cabinetry, GE Monogram range and breakfast bar overlooking the Dining Area. The main-level Primary Suite offers long water views, a generous walk-in closet and luxurious Bath with soaking tub, dual vanities and steam shower. Upstairs, two ensuite Guest Bedrooms enjoy water views, while a versatile fourth Bedroom opens to a private balcony overlooking the golf course. Designed for effortless indoor-outdoor entertaining, the expansive waterfront patio features a covered outdoor Kitchen, heated pool and raised spillover spa surrounded by tropical landscaping. Boating enthusiasts will appreciate an 89' dock, additional 10' x 14' floating platform, 20,000 lb. boat lift and angler's prep station. The detached Guest Suite offers private accommodations with a sitting area, wet bar and full Bath. Additional highlights include impact windows and doors, 2-car garage, dual laundry areas and irrigation system. A rare opportunity to enjoy spacious waterfront living, exceptional boating access and golf course views in the heart of the Florida Keys.

1903 Sombrero Blvd, Marathon

129 Marina Ave, Key Largo
$4,495,000
5 Beds ⋅ 4 Baths ⋅ 621058 MLS
Welcome to La Mar-A-Villa on Marina, an exceptional newly built contemporary waterfront residence offering 4,001 sq. ft. of luxury living in the heart of the Florida Keys. This stunning 5-bedroom, 4-bath home combines sophisticated modern design with the ultimate boating and outdoor lifestyle. Designed for entertaining and everyday living, the home features expansive interiors, an elevator providing convenient access between levels, impact-resistant windows and doors, sleek impact-glass railings, a metal roof, and a beautifully appointed kitchen featuring premium Wolf and Sub-Zero appliances. For the boating enthusiast, 70 feet of concrete dockage is complemented by two boat lifts with impressive 30,000-lb. and 10,000-lb. capacities, creating an outstanding setup for enjoying the surrounding waters. Step outside into your own private resort featuring a heated pool with waterfall, private putting green, and an inviting outdoor seating and entertainment area with TV, surrounded by low-maintenance artificial turf. Above it all, the rooftop deck and outdoor kitchen featuring a DCS grill and Perlick under-counter refrigeration create an incredible setting for entertaining, dining under the open sky, enjoying tropical breezes, or relaxing at the end of the day. Additional features include a one-car garage and thoughtfully designed indoor and outdoor spaces throughout. La Mar-A-Villa on Marina is more than a home--it is a modern waterfront retreat where luxury, boating and the Florida Keys lifestyle come together.

129 Marina Ave, Key Largo

865 50th St, Marathon
$4,490,000
5 Beds ⋅ 5 Baths ⋅ 619048 MLS
Stunning Gulfside Waterfront Residence with Panoramic Water Views. Experience exceptional waterfront living in this 2022 built home featuring 5 bedrooms and 4.5 bathrooms, perfectly positioned on the Gulf side with breathtaking water views from nearly every room. The main level offers a bright and open layout designed for both comfort and entertainment. A spacious modern kitchen showcases elegant cabinetry, quartz countertops with a striking waterfall edge, and premium stainless-steel appliances. The kitchen flows seamlessly into the large dining and living areas, complete with a stylish wet bar, creating the perfect space for hosting and relaxing. This level also includes a convenient half bath and a utility room with laundry. Upstairs, the second-floor features five generously sized bedrooms and four full bathrooms. The expansive primary suite offers ample space, a beautifully designed modern bathroom, and a private porch where you can enjoy breathtaking sunset views over the water. Two additional bedrooms share a Jack-and-Jill bathroom and provide access to a balcony overlooking the pool and waterfront. A fourth bedroom, currently used as a home office, is located near another full hallway bathroom. The fifth bedroom is a private suite with its own ensuite bathroom. Outdoor living is just as impressive, featuring a large patio area ideal for entertaining, a spacious saltwater pool, and a 55-foot dock with a 20,000 four post Cradle Boat Lift, making this property perfect for boating enthusiasts and waterfront relaxation. Over 1,000 Square Feet of balconies covered porches and patios for added outdoor living space. Additional highlights include a 1,550 ft square foot paver driveway and a 2 ½ Car plus garage with ample storage space. This exceptional property combines modern design, generous living space, and stunning Gulfside views, creating a truly remarkable coastal home offering excellent convenience for boat owners.

865 50th St, Marathon

51 Mutiny Pl, Key Largo
$4,475,000
5 Beds ⋅ 4 Baths ⋅ 619382 MLS
Nestled along the Florida Bay in exclusive Buccaneer Point, this exquisite bay front estate offers an unparalleled fusion of opulence, tranquility, and sweeping water views, redefining luxury living in the Florida Keys. Perfectly positioned at the tip of the peninsula, this exceptional property offers breathtaking panoramic views of the bay from every major living area. Experience unrivaled privacy and serenity with conservation land bordering the property to the West, ensuring unobstructed vistas and a tranquil setting. This meticulously updated 5-bedroom, 4-bathroom estate combines modern elegance with resort-style amenities. The open-concept gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and seamless flow into the expansive living and dining spaces--all with stunning water views. A sleek glass elevator provides effortless access to all levels, making every part of this home easily accessible. Step outside to your personal paradise: a lush backyard with low-maintenance turf, a custom putting green, and an inground pool equipped with heaters for year-round comfort. Boating enthusiasts will appreciate the 15,000-pound boat lift, offering direct access to the bay for endless adventures on the water. Additional highlights include a spacious two-car garage, ample storage, and a quiet cul-de-sac location that ensures privacy. Whether you're relaxing poolside, savoring sunsets from the expansive balcony, or entertaining guests in style, this home truly embodies the ultimate in luxury coastal living. Don't miss the rare opportunity to own this spectacular bayfront retreat in coveted Buccaneer Point Estates--schedule your private showing today!

51 Mutiny Pl, Key Largo

3742 Seagrape St, Big Pine
$4,450,000
3 Beds ⋅ 3 Baths ⋅ 619696 MLS
Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, plus a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip, set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architect's masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chef's kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, this is ultimate Keys living without compromise!

3742 Seagrape St, Big Pine

88 W Plaza Del Lago, Islamorada
$4,450,000
5 Beds ⋅ 5 Baths ⋅ 615676 MLS
Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a spacious garage for ultimate flexibility. The gourmet kitchen flows seamlessly to a fully equipped outdoor kitchen and shaded lounge area--ideal for al fresco dining by the pool amid lush tropical landscaping. A rare combination of classic design, modern amenities, and timeless island charm. Effortless boating and space for all of your waterfront toys with 75' of deepwater dockage and quick access to both ocean and bay. Nearby homeowner's park provides the added bonuses of a private, sandy beach and boat ramp. With the serene, wide canal views and cooling bay breezes, and this is where luxury, comfort, and natural beauty, convenience converge. Photos reflect when there were furnishings, now unfurnished.

88 W Plaza Del Lago, Islamorada

1618 South Street, Key West
$4,400,000
4 Beds ⋅ 3 Baths ⋅ 621671 MLS
BRAND NEW CONSTRUCTION MIDTOWN WEST Meticulously crafted by a local luxury builder, this exceptional new 4 bedroom 3 bath residence combines superior construction, thoughtful architectural design and exquisite attention to detail to create effortless tropical elegance. Step inside to soaring 20-foot ceilings, a light-filled open floor complimented by 12'x40' tile flooring. A striking floating staircase with open wood treads adds architectural flair. The gourmet kitchen showcases custom Hanson and Bringle cabinetry, granite countertops and premium stainless steel Thermadore appliances, with a central island and built in wet bar. The second level features two bedrooms with a Jack-and-Jill bath, while the third level offers an expansive mezzanine, with wet bar and luxurious second primary suite with soaking tub and separate shower. Custom white oak flooring, motorized Hunter Douglas Pirouette window treatments and designer lighting reflect the exceptional quality throughout. Designed for seamless indoor-outdoor living, the lush tropical setting features a heated 10' x 20' saltwater pool with six-foot swim-out, outdoor shower and exquisite outdoor kitchen with built-ins, refrigeration and grilling area. Five private porches invite morning coffee, afternoon breezes and relaxed evenings under the stars, buffeted by lushly landscaped grounds. Quality is evident in every detail, from premium Andersen impact-resistant windows and a standing-seam metal roof to Hardie board siding, AZEK trim, extensive closed-cell insulation and dual high-efficiency Mitsubishi A/C systems. A two-car tandem garage completes this thoughtfully designed island retreat, where enduring craftsmanship meets sophisticated tropical luxury in a family friendly neighborhood. Completion date Jan '27. More images to follow. Front image has been digitally created.

1618 South Street, Key West

318 E Seaview Cir, Duck
$4,400,000
618564 MLS
Rarely available, this 8,190 SF vacant homesite sits along a deep water canal on Duck Key, with open ocean views that are simply priceless. The lot already includes a concrete dock, boat lift, and seawall, giving boaters immediate deep water access without the wait or expense of new construction. That same seawall will provide lasting storm and wave protection for whatever home is built here. Because a home previously stood on this site, the lot is ROGO exempt, meaning you can build without competing in Monroe County's growth ordinance lottery, a rare and valuable advantage in the Florida Keys. Located next to Hawks Cay Resort, residents enjoy easy access to dolphin swims, dining by a Michelin rated chef, and a full service marina. Duck Key sits centrally in the Middle Keys, close to luxury restaurants, the Grassy Key sandbar, deep drops for offshore fishing, clear Bahamian like waters, nearby reefs for lobstering and reef fishing, and the Islamorada Humps for tuna. Weekly rentals are not permitted on the island, preserving a quiet, residential feel with more full time locals than tourists. Bring your builder and bring your vision, this is a rare opportunity to create your dream home on one of the best kept secrets in the Keys. Schedule a viewing today.

318 E Seaview Cir, Duck

115 Windy Point Cir, Marathon
$4,400,000
3 Beds ⋅ 3 Baths ⋅ 617542 MLS
Experience the charm and character of this Gulf-front Old Florida Keys fishing lodge located in Stirrup Key, one of Marathon's most exclusive gated communities. Known for its large estate lots, deep-water access, and serene open-Gulf vistas, Stirrup Key offers privacy, prestige, and a true island lifestyle, just minutes from the conveniences of Marathon. The property consists of two lots in total for a combined size of 39,500 sf. The home sits on one of the few deep-water sites in Stirrup Key with upgraded 165 foot pier dock with 6 new pilings, where the water is so clear you can watch tarpon, angelfish, snapper, nurse sharks, lobsters and rays gliding beneath the dock. Beautifully maintained and elevated above flood, the residence features 3 bedrooms, 3 baths, and a loft that can serve as a fourth bedroom or home office. Brand new roof and impact windows and sliders were recently installed for peace of mind. The open-concept great room boasts massive ceilings and walls of windows showcasing 180-degree Gulf views. A spacious kitchen with center island and new range, Gulf front bar, wide overhanging eaves, exposed wood beams, and natural stone accents showcase classic tropical lodge architecture, perfect for entertaining. The primary suite with a large ensuite bath provide comfort and style, while a screened porch opens to the heated pool, positioned behind lush landscaping for afternoon shade. Outdoors, you'll find a sandy beach area, irrigated native landscaping, and expansive decks perfect for sunset gatherings. Additional amenities include two garage bays, one carport bay, a workshop, garden shed, and abundant storage. Stirrup Key residents enjoy the peace of a gated, low-density community with a 365 day rental minimum, ensuring tranquility and exclusivity year-round. With its unmatched combination of deep water, open-Gulf views, and spacious multi-lot layout, this property is a true rarity in the Florida Keys with potential for expansion.

115 Windy Point Cir, Marathon

520 Sombrero Beach Rd, Marathon
$4,399,000
4 Beds ⋅ 5 Baths ⋅ 621797 MLS
Breathtaking water views and immediate ocean access set the stage for an exceptional waterfront lifestyle at this stunning and impeccably kept modern 2-story home in Sombrero Beach, an exclusive neighborhood of high-end homes just steps to the beach and minutes to Marathon Jet Center. Offering 4 bedrooms, 5 bathrooms, and 3,704 sq. ft. of beautifully appointed living space, this waterfront retreat places the Atlantic Ocean just moments from your dock. Soaring ceilings and an expansive open floor plan create a bright, inviting atmosphere with stunning water views from the main living areas. The chef's kitchen features marble countertops, premium stainless steel appliances, a wine cooler, and a spacious island with seating for four, flowing seamlessly into the dining and living areas. A separate sitting area offers additional space to unwind. Upstairs, two generously sized primary suites each feature private balconies with glass railings showcasing panoramic ocean views, along with luxurious en suite baths featuring soaking tubs and separate rain showers. A wet bar with an ice maker, mini refrigerator, and wine cooler sits between the suites. Two additional guest bedrooms are located on the main level with a bath for each. Outside, an expansive lanai surrounds the heated saltwater pool and spa which is fully automated to work from your cell phone and is complemented by a poolside tiki hut with a fully equipped outdoor kitchen, grill, refrigerator, microwave, and TV. A convenient cabana bath provides easy access from the pool area. Boating enthusiasts will appreciate the 50' dock, 14,000 lb. boat lift, fish-cleaning station, and immediate Atlantic Ocean access. Solid CBS construction with concrete roof and impact doors and windows. Offered Turn-Key. Seller financing offered to qualified buyers! Zoned for weekly vacation rentals, this property offers solid rental history and presents an excellent investment opportunity.

520 Sombrero Beach Rd, Marathon

108 Sunset Dr, Marathon
$4,399,000
3 Beds ⋅ 4 Baths ⋅ 620861 MLS
Set along the Gulf on 2 lots within the sought-after gated Stirrup Key community, this beautifully appointed CBS residence captures panoramic open-water views, unforgettable sunsets, and a rare sense of privacy. Electronic gated entry and tropical surroundings create an immediate sense of arrival while extensive upgrades reflect elevated living and effortless enjoyment. Contemporary design and relaxed coastal living come together through an open, light-filled floor plan. Expansive impact windows and sliding glass doors frame the water from every angle, bringing the ever-changing Gulf backdrop into the interior. The chef's kitchen features quartz countertops, Bosch stainless appliances, custom cabinetry, and a seamless connection to the dining and living areas. Solar panels further enhance the home's thoughtful, energy-conscious design. The thoughtfully designed layout includes two spacious primary suites, each offering private balcony access and sweeping water views. A third guest bedroom, guest bath, private gym, and an additional full bath add comfort and versatility. Outdoors, the property unfolds as a private tropical escape. A waterfront pool, covered entertaining area, outdoor shower, and multiple gathering spaces create the perfect setting for relaxed afternoons and memorable evenings. Mature fruit trees surround winding garden pathways leading to peaceful seating areas and a waterfront fire pit. A deeded boat slip with lift in the private marina is located just steps from the front door, offering exceptional convenience on the water. Along the open-water shoreline, a private kayak dock with lift provides direct access to exceptional kayaking and paddleboarding from your own backyard. Just minutes from shopping, dining, and The Marathon International Airport, this exceptional residence offers a rare combination of open-water beauty, boating access, privacy, and effortless island living

108 Sunset Dr, Marathon

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