luxury houses for sale Monroe County, United States

3200 Harriet Avenue , Key West, FL Tucked away on a desirable corner lot, this spacious 2-bedroom, 1.5-bath townhouse offers 1,332 square feet of comfortable living and one of the largest floor plans in the community. Combining privacy, generous living space, and exceptional outdoor amenities, this home is a rare find in Key West. One of the property's most appealing features is the absence of HOA fees, allowing you to enjoy all the benefits of homeownership without monthly association dues or restrictive community fees. It's a rare opportunity to own a spacious townhouse with the freedom and flexibility typically associated with a single-family home. Step outside to your own private pool, creating the perfect setting for entertaining, relaxing, or enjoying the tropical island lifestyle year-round. The corner-lot location provides added privacy and outdoor space, making this home feel even more secluded. Inside, the well-designed floor plan offers bright, inviting living spaces with plenty of room to gather, work from home, or simply unwind after a day on the water. Conveniently located in New Town, 3200 Harriet Avenue is just minutes from shopping, dining, schools, beaches, and all that Old Town Key West has to offer. Whether you're looking for a primary residence, vacation home, or investment property, this home delivers an outstanding combination of space, privacy, and the quintessential Key West lifestyle.

Welcome to Casa Sirena, a refined waterfront retreat in Marathon offering comfort, privacy, and strong investment appeal. This five bedroom, three bath home includes a convenient outdoor pool bath and is ideally positioned with water frontage on two sides. Boaters will appreciate 100 feet of durable composite dockage, a jet ski lift, and a private boat ramp shared with just one neighbor. The home enjoys close proximity to Boot Key Harbor, with easy access to waterfront dining by boat, as well as a straightforward route to the bayside via Knight Key Channel and immediate Ocean access. The surrounding Vaca Key and Boot Key provide a natural buffer, offering added protection from the elements. Outdoor living is central to the property, with lush tropical landscaping, a saltwater pool, tiki hut, and expansive wraparound patios accessible from all rooms. Inside, the open floor plan connects the living, dining, and kitchen areas, creating a comfortable and functional space. The kitchen is equipped with high end appliances suited for everyday use or hosting. Additional features include a spacious two car garage with ample storage, an extra washer and dryer, refrigerator, freezer, and workbench. The home is offered fully furnished and turnkey, ready for personal use or as a vacation rental. Privacy fencing, a security system, and gated dock and ramp access complete the offering.

A unique opportunity to enjoy the Florida Keys boating lifestyle without the cost of waterfront ownership. This well-maintained dry lot home in desirable Tollgate Shores includes a deeded boat slip directly across the street, complete with a new dock, boat lift, water, power, and a fish cleaning station. Enjoy the convenience of direct sight lines to your boat from the living room and front porch, with peekaboo views of Florida Bay and the iconic Channel 5 Bridge beyond. Upstairs, the home features two generously sized bedroom suites, each with its own ensuite bathroom. A pantry and laundry room are conveniently set off of the well-appointed, modern kitchen. The open-concept living area is highlighted by vaulted ceilings with exposed wood trusses and bamboo flooring. A clean interior offers a comfortable, move-in-ready space, with furnishings negotiable. The lower level includes covered parking, an air conditioned garage, a spacious bonus room, and a dedicated tackle storage closet, providing ample space for boating gear, hobbies, and everyday storage. A metal roof, high quality insulation and impact windows and doors add to the integrity and efficiency of this home. Located adjacent to the neighborhood park, the property benefits from additional open green space. The voluntary HOA is $250 annually. With quick boating access to both Florida Bay and the Atlantic Ocean via Channel 5, this property is well suited as a full-time residence, weekend retreat, or investment opportunity. Whether your priority is boating, fishing, or embracing the relaxed Florida Keys lifestyle, 321 Tollgate Shores offers a distinctive combination of convenience, functionality, and value with a niche setup.

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

Welcome to Port of Call--an intimate oceanfront enclave on Plantation Key where refined coastal living meets the effortless rhythm of the Florida Keys. Tucked within this exclusive 10-residence boutique community, 136 Aregood Lane offers a rare blend of luxury, privacy, and true serenity. This beautifully appointed 2-bedroom, 2.5-bath townhome is designed for both relaxation and adventure, featuring weekly rental eligibility, assigned dockage, a community pool, and a private rooftop deck with sweeping ocean views. Flooded with natural light, the main living level flows seamlessly to a private balcony where gentle breezes and glimpses of turquoise water set the tone for quiet island living. The thoughtful floor plan provides generous space for entertaining, while the additional half bath on this level ensures comfort for guests. Upstairs, two spacious en-suite bedrooms--each with its own balcony--offer peaceful retreats after a day on the water. With all impact windows and doors, the home delivers both beauty and peace of mind, allowing you to enjoy the Keys lifestyle with ease. For boating enthusiasts, the assigned boat slip with direct ocean access opens the door to world-class fishing, diving, and cruising. Spend your days exploring the Atlantic, then return to unwind by the community pool or stroll the private beach area as the sun dips below the horizon. Perfectly positioned in the heart of Islamorada, you're just minutes from Islamorada's renowned dining, shopping, and cultural experiences--yet worlds away from the everyday. Whether you envision a full-time residence, a weekend escape, or a high-demand investment property, this exceptional townhome delivers unmatched flexibility with its weekly rental capability and coveted oceanfront amenities. Port of Call is a place where luxury feels effortless, the ocean is your backyard, and every day begins with possibility.

Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key with expansive water views, white sand beach, and a true resort-style experience in the Florida Keys. An exceptional investment opportunity, Casa Feliz is a strong producing vacation rental with rental history and future bookings already in place. Set on over 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, this exceptional estate is designed for both relaxation and entertaining. A 148-foot observation dock invites kayaking, paddleboarding, fishing, and endless enjoyment of marine life, while the unique orientation captures both breathtaking sunrise and sunset views over the water, a rare and coveted feature in the Keys. Outdoor living is elevated with a resort-style saltwater pool featuring cascading waterfalls, spillover spa, and fully equipped poolside cabana complete with wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit create the ultimate setting for entertaining or unwinding beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was thoughtfully redesigned to maximize sweeping ocean views from nearly every room. Offering four custom bedroom suites, each with private en-suite bath, the home comfortably accommodates guests in luxury. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Expansive accordion impact glass doors seamlessly blend indoor and outdoor living throughout. The gourmet kitchen showcases Café appliances, induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas ideal for hosting. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, local artist mural, and more. Discover why Grassy Key is the place to be.

of Marathon’s most vibrant & amenity rich, waterfront communities, this beautifully appointed 2 bedroom, 2 bath residence offers the ideal blend of island living, convenience, and value; without the traditional Florida Keys price tag. From the moment you arrive, the setting feels elevated, vibrant and unmistakably island inspired. Ideally situated within the community offering beautiful open water views, this residence enjoys a premier location with sweeping vistas from the top-level balcony, perfect for morning coffee or sunset cocktails. Inside, the light-filled interior features a stylish granite and stainless-steel kitchen, central air, interior laundry, and thoughtfully designed living spaces. Enjoy covered parking, under-home space, and easy access to the dock and waterfront gathering areas. Resort-style amenities include a beautiful pool, kayak launch, fire pits, outdoor kitchen, sun deck, and community lounge spaces. Walk, bike, or golf cart to waterfront restaurants, bars, live music, kayak and jet ski rentals, the iconic Seven Mile Bridge, and the scenic pedestrian bridge. $22,500 in secured rental income already in place for 2027. One of the most affordable newer construction opportunities in the Keys offering this level of lifestyle, amenities, and location. Please note: ownership is subject to monthly lot rent.

This exceptional waterfront residence in Key Colony Beach offers the perfect blend of refined comfort, thoughtful design, and effortless island living. Lovingly owned, gently used, and never rented, the home reflects true pride of ownership throughout. An elevator, updated kitchen, and custom baths set the stage, while soaring wood ceilings and an open-concept kitchen, dining, and living area create a light-filled space that flows seamlessly through stackable sliders to a spacious screened porch ideal for entertaining or unwinding in the coastal breeze. The generous primary suite is a private retreat with porch access and a skylit spa-style bath featuring a jetted tub, walk-in tiled shower, and dual vanities. The lower level is designed for true indoor-outdoor living, featuring an custom, inground swimming pool surrounded by elegant marble decking, along with expansive covered and uncovered paved patios. Mature tropical landscaping enhances privacy, while ample covered and uncovered parking adds everyday convenience. Boaters will love the 37.5 foot dock with 15k boat lift, located on a wide, deep canal with quick, easy access, just minutes to both the open ocean and the Gulf via Vaca Cut. A permitted third full bathroom on the lower level sits next to a large air-conditioned storage area with sliders directly to the patio and dock, making it ideal as an angler's room for fishing gear and water toys. Key Colony Beach is one of the Florida Keys most desirable island communities, known for its wide, walkable streets, city-maintained infrastructure, and relaxed coastal charm. Residents enjoy access to marinas, a nine-hole golf course, tennis and pickleball courts, playgrounds, dining, and waterfront Sunset Park all just steps or a short bike ride away. Perfectly positioned in the Middle Keys, Key Colony Beach offers a rare combination of small-town island living, world class boating, and easy access to Marathon's shopping, dining, and local airport.

MOTIVATED SELLER! Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for coastal living. Built for both comfort and peace of mind, the home features a metal roof installed in 2018 along with impact-rated windows and doors throughout. Enjoy added privacy and nightly sunset views over the protected salt marsh directly across the street—an unspoiled natural backdrop that will never be developed. Boaters will appreciate the free-flowing, clear-water canal with excellent access to both the ocean and the bay. The private dock with a 7,000-lb side-lift boat elevator makes heading out for fishing, diving, or sunset cruises effortless. The spacious lot offers a large driveway, double covered parking, and ample room for boat trailers and additional vehicles. Downstairs, a full concrete pad and enclosed angler's room provide the perfect space for storing fishing gear, dive equipment, and all your island toys. Located near mile marker 28.5, Jolly Roger Estates is a peaceful, palm-lined waterfront community on the Atlantic side of Little Torch Key, offering direct access to Pine Channel and world-class boating, fishing, and diving at nearby Looe Key Reef. Just 24 miles from Key West, this exceptional property delivers the perfect blend of island tranquility and convenient access to dining, entertainment, and amenities—an ideal full-time residence, second home, or investment in the Florida Keys lifestyle.

Discover exceptional waterfront living in the heart of Key Colony Beach. This concrete constructed half duplex offers over 2,100 square feet with three bedrooms, three bathrooms inside and 37.5 feet of dockage. A highly desirable interior staircase welcomes you from the above flood first floor, seamlessly connecting both levels of the home. Downstairs is completely built above flood and features a one-bedroom, one-bathroom suite with an additional living area, ideal for guests or extended family. Step through sliding glass doors to a spacious wood deck and 37.5 feet of dockage. Enjoy the ocean breeze and shade under the lush buttonwood tree. Upstairs, enjoy open-concept living with a bright, airy kitchen, dining, and living area designed for effortless entertaining. The primary suite boasts a recently renovated bathroom with step-in tiled shower, quartz topped double vanity and tiled flooring. Nearby, a second guest bedroom offers its own ensuite for added comfort and privacy. Recent updates include a newer AC, a 2018 standing seam metal roof, and termite tenting with a transferable warranty, providing peace of mind for years to come. With its downstairs living, expansive square footage, and thoughtfully designed layout, this property presents a unique opportunity to own a well-cared-for waterfront residence in one of the most desirable areas of the Florida Keys. Key Colony Beach welcomes primary and seasonal guests with the 9-hole par 3 golf course, tennis and pickle ball courts, Sunset Park, City Hall, police department, multiple restaurants, boat ramp and marina. Enjoy the island lifestyle with amenities galore!

Welcome to your slice of paradise in the heart of the Florida Keys. This Conch-style home is tucked away on a wide, clear, deep-water canal just 5 minutes from the crystal blue Atlantic Ocean. Boaters and anglers alike, will love the 60 ft concrete dock with boat lift—ideal for easy ocean access and unforgettable adventures on the water. World-class fishing, diving, snorkeling, and marine wildlife encounters all begin at your dock. Entertain in island style on the decked pool area, huge tiki hut, and screened patio, perfect for relaxing or hosting. The interior boasts a huge, updated kitchen with tons of cabinetry, seamlessly flowing into an open living, dining, and kitchen area with views of the screened patio, Tiki Hut, and pool. Enjoy resort-like living on Key Colony Beach with access to incredible amenities: golf, marina, pickleball, tennis, horseshoes, bocce ball, basketball, playgrounds, and Sunset Oceanfront Park. Everything you need is within reach—restaurants, shopping, post office, police & building departments, and 15 streets to walk, jog or bike. No problem getting here, only 3 miles to Marathon's Airport, 53 miles to Key West International Airport, 108 miles to Miami International Airport, and 139 miles to Ft Lauderdale Airport. Whether you're seeking a full-time residence, vacation retreat, or investment property, this home captures the best of island living in one perfect package.

Welcome to this solid concrete home in the Florida Keys, located in Tavernier and built for durability, comfort, and island living. Featuring all-concrete construction with a concrete roof, this property offers strength, low maintenance, and peace of mind—ideal for Keys conditions. The upstairs level includes a fully remodeled 2-bedroom, 2-bathroom living space with peek-a-boo ocean views from the porch and views overlooking the community park, creating a relaxing setting with open green space and ocean breezes. The downstairs level offers a remodeled 1-bedroom, 1-bathroom area, providing flexible options for guests or extended family. Situated on a rare double lot, this property offers additional space for outdoor living, parking, or future possibilities. A large covered carport provides convenient parking and storage for vehicles, boats, or recreational gear. Enjoy an unbeatable location overlooking the community park and just steps from the boat ramp, making this home ideal for boating, fishing, and outdoor enthusiasts. Whether you're searching for a primary residence, vacation home, or investment opportunity, this Tavernier property delivers location, versatility, and Florida Keys lifestyle appeal.

Located in the heart of Old Town Key West, 914 Windsor Lane is the quintessential Key West conch cottage that captures the island's timeless charm. Behind the classic white picket fence and vibrant turquoise front door awaits a thoughtfully updated 1-bedroom, 1-bath retreat blending historic character with modern comforts. Inside, vaulted cathedral ceilings, Dade County pine accents, quartz countertops, stainless steel appliances, and abundant natural light create an inviting island atmosphere. French doors open to a generous rear covered porch, perfect for outdoor dining and entertaining. The private tropical yard offers room for a pool and plenty of space to relax and enjoy the laid back Key West lifestyle. Additional highlights include a whole house generator, central A/C, metal roof, tankless water heater, private deeded parking area, and an unbeatable Old Town location just moments from dining, galleries, nightlife, and the best of island living.

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.

Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8,988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

This luxury bayfront home in the Florida Keys offers discriminant buyers a complete coastal lifestyle package with year-round sunset views, hurricane-rated construction, and premium boating amenities. The residence features 3,200 square feet of living space with four bedrooms, four and a half bathrooms, natural stone floors, and custom cabinetry throughout. Built with reinforced concrete, galvanized rebar, and a solid concrete roof, the home carries a 175-mph hurricane rating that provides exceptional durability and peace of mind for coastal living. Automatic hurricane curtains on the main porch add convenient storm protection. For boating enthusiasts, the property includes deepwater access with two heavy-duty boat lifts rated at 25,000 pounds and 12,000 pounds. A 200-square-foot enclosed tackle room and workshop with a refrigerator provides organized storage for fishing gear and marine equipment. These features enable owners to launch boats easily and pursue fishing or water activities on their schedule. The rooftop sun deck offers panoramic bay views and includes a fire pit for evening entertaining. This elevated outdoor space creates a private setting for watching daily sunsets over the water. The property's sunset-facing orientation means consistent western exposure throughout the year. Low-maintenance exterior features include artificial turf, coral hardscaping, and irrigated tropical landscaping designed for the Florida Keys climate. A 1,300-square-foot covered carport with 9.5-foot ceilings provides generous vehicle parking and additional storage space. The home is sold furnished and turnkey-ready, allowing new owners to begin their coastal lifestyle immediately without renovation or decoration needs. This combination of hurricane-resistant construction, superior boating infrastructure, low-maintenance design, and sunset views represents a rare opportunity in the Florida Keys luxury market for buyers seeking hassle-free waterfront living.

Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the island's highest natural elevation, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed during the Henry Flagler railroad era, the home has been thoughtfully updated while preserving the warmth and authenticity that make Key West architecture so iconic. Inside, rich Dade County pine walls, hardwood flooring, and tall ceilings create an inviting atmosphere filled with natural texture and timeless charm. Impact windows and curated high-end finishes blend seamlessly with the home's historic roots. The kitchen was designed with both style and function in mind, featuring Dade County pine countertops and a collection of premium appliances, including a Sub-Zero refrigerator and Big Chill gas range. Flexible living areas allow the home to function as either a spacious two-bedroom retreat or a three-bedroom layout depending on your needs. Outdoor living is equally special. A lush backyard filled with mature tropical landscaping and fruit trees creates a private island setting that feels worlds away from the bustle of town, with space to potentially add a pool in the future. The welcoming front porch serves as a timeless gathering space, perfectly suited for morning coffee, evening cocktails, and enjoying the laid-back rhythm of Old Town living. Just a short stroll from Truman Waterfront Park, Fort Zachary Taylor Beach, galleries, restaurants, and marinas, this property captures the essence of classic Old Town living -- historic, relaxed, and unmistakably Key West.

Step into a fresh take on coastal living in this newly built Key Largo home, where contemporary design meets the relaxed charm of the Florida Keys. Elevated in traditional stilt fashion, the residence is constructed for both beauty and strength, featuring a solid concrete roof and impact-rated windows and doors that provide durability and peace of mind. The interior offers a spacious and welcoming atmosphere with five bedrooms, eight-foot ceilings, and large-format tile flooring that enhances the home's clean, modern aesthetic. The open-concept layout creates an effortless flow throughout the main living spaces, ideal for both everyday living and hosting guests. A separate lower-level living area adds valuable versatility, complete with two bedrooms and a full bathroom, providing a comfortable space for guests, extended family, or additional private accommodations. Upstairs, the main living area opens onto a generous outdoor patio, where you can enjoy gentle island breezes and the beauty of the surrounding tropical environment. The well-appointed kitchen is both stylish and functional, featuring ample counter space, sleek modern finishes, and a large statement sink that stands out as a unique design feature. Designed with entertaining in mind, the outdoor space includes a ground-level BBQ kitchen set on pavers, creating the perfect setting for gatherings after a day of boating, fishing, or exploring the Keys. Ideally located, the property is within walking distance to local restaurants, grocery markets, marinas, and boat ramps. Close proximity to Key Largo Park, which offers pickleball and tennis courts, swimming pools, and scenic walking trails, adding to the vibrant lifestyle this area provides. Combining brand-new construction, contemporary finishes, and an unbeatable Key Largo setting, this home offers an outstanding opportunity as a primary residence, vacation retreat, or income-producing investment in the Florida Keys.

Tucked away at the end of a quiet cul-de-sac, 24 Dispatch Creek Court offers a rare combination of privacy, scale, and waterfront living in one of Ocean Reef's most desirable settings. Situated on an expansive 30,542-square-foot homesite with 280 feet of water frontage along picturesque Dispatch Creek, this exceptional residence is just a short boat ride from the Main Marina and the Ocean Reef entrance channel. Designed to accommodate large families and multigenerational living, the home encompasses approximately 8,600 square feet of thoughtfully designed living space. The floor plan features two primary suites, three additional guest bedrooms with ensuite baths, and an elegant study with private bath that can easily serve as a sixth bedroom. A chef's kitchen with butler's pantry serves as the heart of the home and opens seamlessly to a spacious family room, creating an inviting gathering space for everyday living. Formal living and dining rooms, soaring first-floor ceilings, abundant natural light, an elevator, and two separate laundry rooms further enhance the home's comfort and functionality. Walls of glass open to an impressive outdoor living environment where covered seating areas, a summer kitchen, and a stunning infinity-edge pool create the perfect backdrop for entertaining family and friends. Lush tropical landscaping surrounds the property, enhancing both beauty and privacy while framing long water views. The lower level offers a two-car garage with generous additional space for golf carts, vehicles, and scooters, along with substantial storage areas for boating gear, recreational equipment, and seasonal belongings. With extensive dockage, exceptional privacy, and a flexible floor plan designed for comfortable everyday living, 24 Dispatch Creek Court presents a rare opportunity to enjoy the very best of the Ocean Reef lifestyle.

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1+ acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views. An arcaded hallway with a hand-tiled barrel-vaulted ceiling connects interiors featuring Italian finishes, exquisite marble details, five fireplaces, hand-painted ceiling frescoes, and a one-of-a-kind imported tile roof. Florentine-inspired quatrefoil windows, Juliette balconies, wrought-iron railings, copper rain gutters, and hand-carved marble corbels enhance the home's architectural character. The floor plan includes four bedrooms with three guest suites on the main level and a private third-floor primary retreat featuring two fireplaces, an office, tea room, sitting room, custom walk-in closet, private laundry room, spa-inspired bath, and balconies overlooking the living spaces below. The chef's kitchen is appointed with Viking, Miele, U-Line, and Sub-Zero appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen with a Viking grill, refrigeration, ice maker, bar seating, and covered dining overlooking the pool, beach, and bay. Additional spaces include a formal dining room with a hand-painted ceiling fresco, wellness room, sauna, private theater with wet bar, and a billiards lounge with mahogany coffered ceilings and coconut wood flooring. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep-water dockage, a white-sand beach, and crystal-clear waters provide immediate access to world-renowned fishing, diving, snorkeling, and boating. Additional features include an air-conditioned boat room with skiff ramp, over 4,000 SF of collector's garage space, Control4 smart home integration, an elevator, Sonos, and secure walled & gated grounds.

Embrace the RARE opportunity to own 1.75 acres of open water paradise in the prestigious, gated community of Stirrup Key. Over 600' feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Five protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary.

This is set to become one of the most striking homes on Shark Key and it's already underway. A rare opportunity to own a completely brand new waterfront home in one of the Florida Keys' most exclusive gated communities. Positioned on Sea Lore Lane, this 18,750 sq ft waterfront lot offers more than 90 feet of pristine shoreline and uninterrupted open water views. Designed by Artibus Design, the residence is currently under construction and envisioned as a nearly 6,000 sq ft modern coastal showpiece with 6 bedrooms and 6.5 bathrooms. Every inch of this home is being thoughtfully built for modern waterfront living, combining bold architecture, expansive walls of glass, elevated finishes, and seamless indoor outdoor flow throughout. This is the appeal of brand new construction in the Keys. Fresh design. Modern materials. Current building standards. A home created for the way buyers want to live today. Inside, expansive open living spaces, gallery style proportions, striking focal points, an indoor gym, and a large entertainment room create a setting that feels both sophisticated and inviting. Outside, a resort style waterfront environment takes center stage with a pool, expansive covered outdoor living spaces, and a large three car garage beneath the home, all designed to maximize the incredible setting and open water views. For a limited time, a buyer has the rare opportunity to step in and customize finishes and details, helping shape the final vision while avoiding the years of planning, approvals, and uncertainty that can come with building in the Florida Keys. With construction already in progress, this is an opportunity to secure one of the most exciting new builds coming to Shark Key before completion. This is more than new construction. It's the opportunity to own one of the island's most exciting new waterfront homes and create something truly exceptional in the Florida Keys.

Lowest-Priced In-Ground Pool Home in Marathon with Weekly Rental Potential! Embrace the laid-back Florida Keys lifestyle in this charming tropical cottage, ideally located in the desirable Little Venice subdivision of Marathon. Offering 2 bedrooms, 2 bathrooms, and beautiful peek-a-boo ocean views, this bright and airy stilt home is perfectly designed for both relaxation and entertaining. The spacious deck provides the perfect setting for enjoying ocean breezes, morning coffee, or evening gatherings with family and friends. Inside, the open-concept living area features vaulted ceilings and abundant natural light, while the updated kitchen boasts stainless steel appliances, granite countertops, and ample cabinetry for effortless entertaining. Recent improvements include updated bathrooms, a new A/C system (2024), hot water heater (2026), and a durable metal roof (2013). Tastefully furnished with coastal-inspired décor, this home is being offered fully furnished, making it move-in or rental ready. Situated on a rare double corner lot, the property features a sparkling in-ground heated pool surrounded by tropical landscaping, along with covered parking, generous workshop/storage space below, and ample room for boat and trailer parking. An assumable low-cost flood insurance policy adds additional value and peace of mind.

Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

Perfectly positioned on an expansive corner lot within the exclusive island enclave of Duck Key, this exceptional 3-bedroom, 3-bath residence captures breathtaking ocean views and a sense of openness rarely found in the Keys. Set directly across from the ocean and adjacent to a privately owned great lawn, the property enjoys an enhanced feeling of space, privacy, and tranquility. The upper level offers 2 bedrooms and 2 full baths, thoughtfully designed to maximize natural light and showcase stunning water views. The open-concept living, dining, and kitchen spaces flow effortlessly together, creating an airy, sun-filled interior where the outdoors become part of everyday living. Sliding glass doors from both the primary suite and main living area open to a beautiful balcony, where sweeping ocean views create a captivating backdrop from sunrise to sunset. From the moment you enter, the views command your attention. The lower level offers a 1-bedroom, 1-bath layout with laundry and is designated as legal non-conforming--ideal for guests, extended family, or flexible lifestyle needs. Outside, a spectacular private resort-style pool creates a true tropical retreat, complete with a cascading waterfall, spray fountains, and a zero-entry beach-style entrance. Life in Duck Key is about far more than the home itself. This sought-after island community offers walkability, golf-cart convenience, and relaxed coastal elegance. Enjoy two marinas with fuel, boat storage, and watersport access, along with optional Club Duck Key amenities including pickleball, tennis, swimming, and a vibrant social atmosphere. Two island restaurants further enhance the ease of daily living. Perfectly positioned midway between Miami and Key West, Duck Key offers exceptional convenience with easy access to Marathon and its private airport, all while preserving the privacy, charm, and exclusivity of island living. This is your chance to embrace the island life.