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119 Simonton St, Key West
$3,600,000
4 Beds ⋅ 4 Baths ⋅ 620913 MLS
Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West. The interior features new white oak flooring that leads you through an open-concept living space. The kitchen is a true standout, boasting elegant granite countertops and a custom kitchen island--a unique feature in the community. For the ultimate convenience, a private elevator services all four floors of the home, transporting you from the air-conditioned two-car garage to the spectacular rooftop terrace where you can view daily sunrises over the Historic Key West Marina and sunsets over Mallory Square, both a very short walk away. The top floor features a rare full bathroom and a flexible bonus room ideal for a home office or guest suite. Whether you're mixing drinks at the custom wet bar or lounging on the terrace, this level serves as the ultimate private retreat for taking in breathtaking panoramic views. Peace of mind is built into the architecture with full impact-rated windows and doors and a durable metal roof, ensuring the home is as secure as it is beautiful. The third floor has two primary bedrooms featuring large walk-in closets and balconies. The lifestyle offered here is unparalleled, situated just one block off the vibrant energy of Duval Street. You are steps away from the island's best dining and boutiques, yet you can retreat instantly to the quiet security of a gated community. Spend your afternoons lounging by the large tropical community pool and cabana area, enjoying a level of comfort and convenience unsurpassed in the heart of Old Town. With a rare two-car garage and an unbeatable location, this residence captures the very best of the Florida Keys lifestyle.

119 Simonton St, Key West

101 Stromboli Dr, Islamorada
$3,600,000
620556 MLS
RARE WATERFRONT OPPORTUNITY! With BPAS allocations becoming increasingly limited, this is your chance to build the waterfront home of your dreams in the prestigious Venetian Shores, one of islamorada's most desirable boating communities. This oversized 8,700+ sq ft. waterfront lot offers significant advantages with house permits APPROVED and ready for pickup and the dock permit close to approval, allowing you to build almost immediately. Boaters will appreciate the exceptional access to both the Atlantic Ocean and Florida Bay, making it easy to spend your days offshore fishing, diving, snorkeling, or exploring the renowned backcountry waters of the Florida Keys. Whether you're envisioning a luxury full-time residence of the ultimate island getaway, this is a rare opportunity to build in one of the Keys' premiere waterfront neighborhoods.

101 Stromboli Dr, Islamorada

186 Atlantic Blvd, Key Largo
$3,599,000
4 Beds ⋅ 3 Baths ⋅ 620735 MLS
Welcome to your Florida Keys waterfront paradise in the highly sought-after Port Largo community of Key Largo. This exceptional 4-bedroom, 3-bathroom home is designed for those who appreciate quality construction, effortless boating, and the ultimate island lifestyle. A true boater's dream, the property offers an impressive 110 feet of deep-water dockage, a 50,000-pound boat lift, and direct ocean access in less than five minutes making every day on the water as easy as it gets. Whether you're heading offshore for world-class fishing, diving the nearby reefs, or enjoying a sunset cruise, this location is second to none. The outdoor living spaces are designed for unforgettable entertaining, featuring a sparkling pool, a fully equipped outdoor kitchen, and plenty of room to relax with family and friends. Just inside, the lower level showcases a custom wine room, a stylish bar area, and a pass-through bar window that opens directly to the pool deck, seamlessly blending indoor and outdoor living. An oversized detached garage provides ample space for vehicles, boats, and all your toys, along with a separate storage room offering the potential to build additional living space above creating endless possibilities for a guest suite, office, or private retreat. Combining solid concrete construction, exceptional dockage, luxury amenities, and one of Key Largo's most desirable waterfront neighborhoods, this remarkable home truly has it all. Experience the best of the Florida Keys lifestyle where every day feels like a vacation.

186 Atlantic Blvd, Key Largo

13759 Overseas Hwy, Marathon
$3,599,000
4 Beds ⋅ 5 Baths ⋅ 620305 MLS
Rare Florida Keys mixed-use development opportunity with approx. 124,300 sq. ft. of uplands plus additional bay bottom ownership. Property includes 4 verified building rights with Letter of Site Condition on file. Existing improvements include a duplex and single-family home. Mixed Use (MU) zoning allows for a wide range of future possibilities, including commercial, residential, storage facility, marina-related use, workforce housing, market-rate housing, or potential subdivision into multiple parcels. Current zoning allows up to 6 market-rate units per acre or up to 15 affordable units per acre, buyer to verify per City of Marathon. The property offers approximately 216 feet of highway frontage, plus additional east-side access through an access easement, creating multiple entry points and flexibility for future site planning. A neighboring gas station adds convenience and commercial synergy for future development concepts. A unique feature is the sleeper asset of this property which is ownership/control of bay bottom extending behind approximately 12 lots along Cocoplum Drive, creating potential value tied to dockage, marina concepts, water access, assemblage opportunities, or long-term redevelopment. Deep-water access, good depth, multiple boating configurations, and proximity to the marked channel entrance add to the site's appeal. Large mixed-use tracts with water access and verified building rights are increasingly rare in the Florida Keys, making this a strong opportunity for an investor, developer, marina operator, or long-term land holder. Seller states property will be delivered vacant and free of personal belongings before closing. Buyer to verify zoning, density, building rights, permitted uses, dockage, water depth, access easements, permitting, and development potential.

13759 Overseas Hwy, Marathon

1501 Georgia St, Key West
$3,599,000
4 Beds ⋅ 5 Baths ⋅ 618829 MLS
1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and out. This is true Mid Century Modern, authentically executed. A single story design with 4 bedrooms and 4.5 baths, wrapped in glass and stone, where skylights, pocket doors, and oversized windows flood the interiors with natural light. Every room frames the landscape, transforming the gardens into living artwork. Designed for both refined entertaining & comfortable family living, the home features stone floors throughout and a modern floor plan with garden views in every direction. Natural light fills the interiors, blurring the boundary between architecture and nature and creating a seamless indoor outdoor lifestyle that defines island living. At the heart of the home, a newly renovated showpiece kitchen elevates everyday life and gatherings alike, featuring dramatic Cambria quartz countertops with a waterfall island, warm wood cabinetry, pendant lighting, and stainless steel appliances. A full wall opens directly to the 55 foot heated and chilled saltwater pool and stone terrace, creating effortless flow for events large or intimate. The primary suite offers privacy and tranquil garden views, while all four bedrooms provide generous proportions and high ceilings. Oversized glass highlights the extraordinary tropical landscaping surrounding the home. The grounds showcase native and exotic flora from around the world, tropical atriums, a water garden with koi, multiple water features, an outdoor shower, and exceptional privacy inside & out. Properties of this caliber and architectural significance rarely become available, so don't wait, schedule your private showing today!

1501 Georgia St, Key West

110 Gulfview Dr, Islamorada
$3,524,000
7 Beds ⋅ 4 Baths ⋅ 618670 MLS
A Keys compound built to enjoy now-grow into the future, or internally convert to a 3,524 sq ft primary home without structural changes, while retaining a Waterfront Transferable Development Right (TDR/TBR) in Islamorada (approx. $650K value). Exceptional opportunity in the coveted White Marlin Beach community at MM74, this canal-front luxury family compound offers rare multi-family autonomy, strong income performance, & resort-style amenities; ideal for an owner-user, investor, or legacy Keys retreat. With two autonomous 2BR/1BA residences upstairs & a separate 3BR/2BA finished, a/c area downstairs, providing privacy, flexibility, & seamless multi-generational or guest use. In total, the compound offers 7 bedrooms & 4 bathrooms, comfortably accommodating up to 24 guests. Designed for both lifestyle & performance, when fully rented, can generate $16,000+ per month in rental income. Zoning & multiple building rights support future expansion or redevelopment. Outdoors, enjoy a resort-style waterfront setting with a private pool, expansive concrete sun deck, outdoor shower, & 70-foot concrete dock with fish-cleaning station, all situated on a 6' control-depth canal with easy access to both bay & ocean waters; ideal for boating, fishing, diving, and paddle sports. Interior finishes reflect modern coastal luxury, including updated kitchens with quartz countertops & stainless appliances, spa-inspired baths with glass-enclosed showers, large-format tile flooring, recessed lighting, & turnkey furnishings. Multiple balconies & patios capture steady breezes & tranquil water views, with manatees frequently passing by. Enjoy private gated access to White Marlin Beach, just a short walk away, offering bay-side sunset views, with the Atlantic Ocean beach also nearby. Grocery stores, marinas, restaurants & bike paths are all within minutes. Rarely does a property offering this level of unity with autonomy, along with amenities, income potential in Islamorada

110 Gulfview Dr, Islamorada

1642 Churchill Downs, Key Largo
$3,511,000
4 Beds ⋅ 5 Baths ⋅ 621244 MLS
New construction waterfront home with all the bells and whistles. Situated on a large corner lot of nearly 14,000 sq. ft., the property features two electric gated entrances with plenty of space for RV and trailer parking. The backyard was designed for exactly why you live in the Keys: an amazing pool with hot tub, low-maintenance turf, 57' concrete dock with two boat lifts (15,000 lbs & 10,000 lbs), outdoor kitchen and bar, cabana bath, and outdoor shower. Through the front entry, you'll find an elevator servicing all three floors, along with an ultra-wide interior staircase. Head to the third floor, where the open-concept kitchen, living and dining areas take advantage of the impressive bay views. Step onto the third-floor porch for sunset views, or take it to the next level on the rooftop deck with panoramic views of the bay and nightly sunsets as the home faces due west. The primary bedroom and bath, along with a powder room, complete the third floor. The second floor offers three additional bedrooms and two bathrooms. The entire home was professionally designed by an interior designer, and the attention to detail shows throughout. Located just around the corner from Adams Cut for quick access to the ocean, while the bay offers endless opportunities to enjoy the water right from your backyard. New construction, incredible outdoor living, great dockage, sunset views and quick ocean access, this one checks all the boxes.

1642 Churchill Downs, Key Largo

58030 Overseas Hwy, Marathon
$3,500,000
3 Beds ⋅ 2 Baths ⋅ 621475 MLS
Great opportunity in the Middle Florida Keys! Owner financing available. This beautifully remodeled luxury oceanfront home is ideal as a full-time residence, vacation retreat, or income-producing investment. The property has a weekly vacation rental license and is currently used by the owner as a second home and part-time vacation rental. The home features three bedrooms, plus an additional room currently used as a fourth bedroom. Enjoy a beautiful, heated oceanfront pool, a smokeless fire-pit area, and breathtaking, unobstructed Atlantic Ocean views from all three levels. The property also includes boulders seawall. Recent improvements include a new roof and new air-conditioning unit, both installed in 2025. Completely remodeled with high-quality finishes, this exceptional property offers comfort, luxury, spectacular views, and excellent vacation-rental potential. Please note: The listing agent has a personal interest in this property.

58030 Overseas Hwy, Marathon

Overseas Highway, Islamorada
$3,500,000
621407 MLS
A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada.

Overseas Highway, Islamorada

25361 1st St, Summerland
$3,500,000
3 Beds ⋅ 3 Baths ⋅ 620742 MLS
Experience the pinnacle of Florida Keys waterfront living in this exceptional 3-bedroom, 3-bathroom oceanfront estate offering breathtaking open water views, deep-water dockage, and sophisticated modern design throughout. Thoughtfully designed for luxury, comfort, and entertaining, this stunning residence seamlessly blends elegant architecture with the beauty of its coastal surroundings. The open-concept living area is filled with natural light from expansive arched windows and walls of glass, creating a seamless connection between the interior and the sparkling Atlantic. The chef's kitchen features a dramatic waterfall quartz island, premium stainless steel appliances, custom high-gloss cabinetry, designer lighting, and generous space for gathering with family and friends. The spectacular primary suite spans over 1,000 square feet, creating a true private retreat. The spa-inspired primary bath is a showpiece featuring striking blue agate-inspired porcelain walls, an oversized walk-in rainfall shower, freestanding soaking tub, dual vanities with custom wood countertops, and an expansive custom walk-in closet with illuminated cabinetry. Two spacious guest bedrooms and beautifully appointed bathrooms provide exceptional accommodations for family and visitors. Throughout the home, luxury finishes include oversized porcelain tile flooring, custom ceiling details, recessed LED lighting, contemporary glass accents, and designer fixtures that elevate every space. Step outside to your private waterfront oasis where tropical landscaping, a sandy beach area, and a deep-water dock provide direct access to world-class boating, fishing, paddleboarding, kayaking, and the crystal-clear waters of the Atlantic Ocean. Enjoy spectacular sunrises and endless ocean breezes from multiple outdoor living areas designed to embrace the Florida Keys lifestyle.

25361 1st St, Summerland

416 Fleming St, Key West
$3,500,000
5 Beds ⋅ 5 Baths ⋅ 620434 MLS
First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

416 Fleming St, Key West

59720 Overseas Highway Unit 8, Marathon
$3,500,000
4 Beds ⋅ 5 Baths ⋅ 609718 MLS
CONSTRUCTION COMPLETE! MOVE-IN AND RENTAL READY! SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys adjacent to Duck Key. A rare find of just 14 new construction residences offering four and five-bedroom floor plans all with direct Atlantic Ocean views, a resort style pool, pickleball court, sandy beach, and the flexibility of a weekly rental. The first floor offers a private two car garage and covered cabana with spacious outdoor living space that leads out to the private beach and pool deck. The second floor features an open floor plan with spacious kitchen, dining and great rooms all overlooking the Atlantic Ocean. One en-suite bedroom on this floor provides seclusion for guests. On the top floor you'll find the primary suite with luxurious spa bath and three additional guest bedrooms. The homes are finished with high end KitchenAid appliances, waterfall quartz countertops, full height backsplashes, custom closets and much more. Additionally this residence offers upgrades including: elevator, outdoor summer kitchen, exterior spiral staircase to first floor, custom millwork, brass fixtures and fire pit. SeaGlass Cove is barefoot luxury at its best.

59720 Overseas Highway Unit 8, Marathon

323 Overseas Hwy, Big Coppitt
$3,500,000
1 Baths ⋅ 598957 MLS
Investment Opportunity - Self-storage facility with excellent exposure to passing traffic, located directly on US Highway 1 near Mile Marker 10, just outside the City of Key West. Built in 2020, the property features approximately 90 climate-controlled interior storage units of various sizes, including both lockers and traditional units with roll-up doors. The site is also approved for 11 external stackable containers or can be utilized as open parking for trailers, RVs, or additional storage. The elevated three-story building consists of approximately 6,912 SF and is constructed with a poured concrete foundation and concrete/steel frame, along with impact-resistant windows and doors. The property includes a fully gated lot of approximately 22,500 SF, as well as security systems, a fire sprinkler system, elevator lift, two staircases, office space, and a restroom. Ideal for both investors and owner-users, offering strong income potential with the ability to generate passive income from the upper levels, while utilizing the ground floor as a large office or operational space. The expansive lot provides ample room for additional storage, equipment, vehicles, or business use. Please do not disturb business.

323 Overseas Hwy, Big Coppitt

0000 13th, Key Colony
$3,499,999
621346 MLS
Amazing Opportunity to build on this Open Water lot facing Vaca Cut on 13th Street in Key Colony! Imagine creating your own private retreat in one of the Florida Keys' most desirable island communities. Key Colony Beach is surrounded by the waters of the Atlantic Ocean and Gulf of Mexico. For the boating enthusiast, Key Colony Beach is exceptionally well positioned for fishing, diving, snorkeling, paddleboarding, kayaking and exploring the incredible waters of the Florida Keys. Life here is about getting outside and enjoying every day. Residents have access to parks, walking and jogging paths, tennis, PICKLEBALL, bocce, shuffleboard, playgrounds and a public 9-hole par-3 golf course. Sunset Park provides a beautiful waterfront setting to unwind and watch the sun go down! Call today!

0000 13th, Key Colony

2483 Yellowtail Dr, Marathon
$3,499,977
6 Beds ⋅ 7 Baths ⋅ 618743 MLS
Marathon is one of the Florida's Keys most desired cities as its home to the famous Seven Mile Bridge, has its own International Airport, offers some of the best fishing in the Keys & allows weekly vacation rentals. Currently there are very few New Construction Waterfront Pool Home opportunities available, especially for larger estate homes over 3,800 sqft. This under construction Modern Waterfront home, which has Western Rear Exposure for those stunning Florida Keys Sunsets. Over 2500 sqft of porches and 6 Beds, including 2 Primary Suites with attached Offices, 6.5 Baths, 3976 sqft of living space with an additional 1200 sqft of Exterior Porches overlooking the Canal and 1397 sqft of ground floor outdoor decking with a Custom Heated Saltwater Pool including a Sunshelf & Spa with Color Changing LED Pool Lights and Paver Pool Deck. Exterior Highlights will include a Modern Paver Driveway that leads to the home's Enclosed 2-Car Garage, which will have an EV charging station, Concrete Block Construction, Poured Solid Columns, Metal Roof, Energy Efficient Spray Foam Insulation in the ceilings and Hurricane Impact Windows & Doors throughout. The home will be pre-wired for a Home Generator. Inside you'll find Vinyl Plank Flooring throughout, 10 FT Ceiling Heights, 8FT Solid Core Doors, Custom Built Modern Railings, a Modern Kitchen with 42'' Upper Cabinets, Led under Cabinet Lighting, S/S Appliances, Quartz Counters including a Large Island & a Modern Backsplash. Each of the Baths will have Custom Designer Tiled Showers with Frameless Shower Glass & Modern Lighting, Smart Mirrors, Faucets, Toilets. For you boaters, there is 58 feet of boat dockage offering immediate open water direct Bay Access and just 15 minutes to the Atlantic Ocean and a neighborhood boat ramp. Why settle for someone else's design choices as right now you still have time to make your own selections for colors, finishings, fixtures, etc. Offered By Design Centers Luxury Estates Collection.

2483 Yellowtail Dr, Marathon

141 Canal St, Islamorada
$3,499,000
5 Beds ⋅ 6 Baths ⋅ 619367 MLS
Stunning Plantation Key canal front pool home! This exceptional all-concrete residence boasts a rare layout with five bedrooms, five full baths, and one-half bathroom, perfect for family living and entertaining. The chef's kitchen is a true standout, featuring a sprawling granite island, top of the line appliances, and abundant cabinet space, making it a culinary dream. A gorgeous exotic wood staircase leads you through the home's three magnificent levels, starting from the welcoming entryway and ascending to the stunning primary suite on the third floor. The suite is an oasis of tranquility, with ample space and stunning views of the surrounding beauty.Enjoy the marble floors as you make your way to the private concrete rooftop deck, where you can soak in breathtaking panoramic ocean views. On the first level, enjoy the cozy theater room for movie nights, a legal one bedroom, one bathroom guest suite offering privacy and comfort, and a tackle room ideal for storing fishing gear and outdoor equipment. The home is designed for peace of mind, elevated above potential flooding, and offers ample storage space throughout. Adventure awaits just minutes away in Tavernier Creek, providing quick access to both the Atlantic Ocean and Florida Bay for fishing enthusiasts or anyone who loves water. The exterior features a heated and chilled swimming pool, outdoor entertainment area, and a 24,000-pound boat lift, making this home the ultimate in luxury coastal living.

141 Canal St, Islamorada

710 Caroline St, Key West
$3,495,000
4 Beds ⋅ 5 Baths ⋅ 620222 MLS
Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable. What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings. Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town. Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day. Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs. The kitchen was built for how people actually entertain here: a six-seat island, full JennAir appliance package, open flow to the living and dining rooms. And it earns from day one. Six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible. Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.

710 Caroline St, Key West

414 E Caribbean Dr, Summerland
$3,495,000
4 Beds ⋅ 4 Baths ⋅ 620024 MLS
OCEANFRONT, CBS, POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful newly painted exterior, this elevated 4 bed 3.5 bath home offers 2,766 sq. ft. of beautifully designed living space where soaring ceilings and walls of glass frame endless turquoise water views. Rare 3 bedroom suites with ensuite bathrooms, and a 4th bedroom or office with ensuite half bath. The expansive open-concept living and entertaining areas create a seamless indoor-outdoor flow perfect for relaxing or hosting guests after a day on the water. Separate laundry room is a bonus. A rare concrete dock with a protected cut-in boat slip provides quick deep-water access to the Atlantic with no long canal commute--placing you minutes from world-class offshore fishing, reef diving, sandbars, and endless boating adventures. Step outside to your private oceanfront oasis featuring a sparkling pool and spa, expansive lounging decks, and a poolside kitchen designed for sunset entertaining and waterfront gatherings. Panoramic open-water views and ocean breezes create the perfect Keys atmosphere. Upstairs, the spacious primary suite offers stunning ocean views, a private balcony, and a peaceful retreat overlooking the Atlantic. Additional features include impact windows and doors, a metal roof, a chef's kitchen with granite countertops and stainless steel appliances, plus convenient access to the nearby Summerland Key Cove Airport for easy fly-in/fly-out travel in light aircraft. This rare offering combines luxury living, protected deep-water dockage, immediate ocean access, and unforgettable open-water views in one of the Florida Keys' most sought-after waterfront communities

414 E Caribbean Dr, Summerland

58652 Overseas Hwy, Marathon
$3,495,000
4 Beds ⋅ 4 Baths ⋅ 619913 MLS
Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key offering expansive water views, a white sand beach, and resort-style living. A strong-producing vacation rental with established history and future bookings in place, this exceptional estate presents an attractive investment opportunity. Set on more than 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, Casa Feliz is designed for relaxation and entertaining. An observation pier provides access for kayaking, paddleboarding, fishing, and enjoying abundant marine life. Dockage is available nearby at Duck Key Marina or Grassy Key Marina, if desired. The property's unique orientation captures both sunrise and sunset views, a rare feature in the Keys. Outdoor amenities include a saltwater pool with cascading waterfalls, spillover spa, and a fully equipped poolside cabana featuring a wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit offer inviting spaces to gather beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was redesigned to maximize ocean views throughout. Four custom bedroom suites, each with a private en-suite bath, comfortably accommodate guests. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Accordion impact-glass doors create a seamless connection between indoor and outdoor living. The gourmet kitchen features Café appliances, an induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, and a mural by a local artist. Come discover why Grassy Key is the place to be.

58652 Overseas Hwy, Marathon

80639 Old Hwy Unit 201, Islamorada
$3,495,000
4 Beds ⋅ 5 Baths ⋅ 616523 MLS
Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open plan connects casual dining, island seating, and a gourmet kitchen outfitted with Sub-Zero and Wolf appliances, Caesar-stone counters, and abundant storage. Oversized covered terrace expand your living space outdoors, where multiple seating areas, TV, a fireplace, and an infrared/gas grill create the ultimate setting for entertaining against the ocean backdrop. The master suite features king-sized accommodations, terrace access, and a spa-inspired ensuite with a luxurious tub and glass shower. Three additional guest suites, 2 with king beds and private balconies, 1 with two twin beds and all with en-suite baths that provide comfort and privacy. This exclusive enclave sits between the Atlantic Ocean and Florida Bay on Islamorada's most vibrant island, Upper Matecumbe Key. Maison's private grounds include over 350 feet of natural sand beach, a 155-foot day pier, lavish 86-foot lagoon-style pool, heated jacuzzi, and space for every water activity. Details such as porcelain tile, U-Line beverage center, Lynx grill, Kohler fixtures, built-in closets, and energy-efficient construction reflect luxury and comfort at every turn. Owning at Maison Residences gives you the rare flexibility to enjoy your home while also generating income. With 7-day minimum rentals approved, you can use your residence as a private retreat and still take advantage of strong demand for luxury short-term stays in Islamorada. This makes Unit 201 not only a lifestyle purchase with world-class boating, fishing, diving, and snorkeling, but also a smart investment opportunity!

80639 Old Hwy Unit 201, Islamorada

1215 Duval St, Key West
$3,475,000
2 Baths ⋅ 620701 MLS
Rare chance to own a piece of the most iconic street in the Florida Keys. This turn-key commercial building at 1215 Duval Street is offered at a 7.04% cap rate with a solid, established long-time successful restaurant as the tenant and a lease already in place. (Note: the business is not for sale; the real estate and the income-producing lease are.) Positioned in the heart of Old Town's high-traffic corridor, the property benefits from year-round foot traffic, world-famous Duval Street exposure, and the enduring demand that makes Key West commercial real estate so limited and so coveted. With a dependable tenant and stabilized income from day one, this is a true passive, hands-off investment in one of the strongest small-market commercial locations in the country. Opportunities to acquire well-located Duval Street commercial real estate with an in-place lease and a proven tenant are exceedingly rare. Whether you're a 1031 exchange buyer seeking reliable cash flow or an investor looking to plant roots in paradise, 1215 Duval Street delivers location, income, and long-term upside. Schedule your private showing today.

1215 Duval St, Key West

69 Tingler Ln, Marathon
$3,450,000
5 Beds ⋅ 4 Baths ⋅ 621171 MLS
This tropical Sombrero Beach 2-Home Compound is set on a spacious 17,600 sq ft fenced lot with Pool, 2 Tikis and located just 2 properties in from the ocean. Fantastic deep water boating access from the 97' dock with 2 Boat Lifts, 15,000 lbs and 3,000 lbs. . The main house features 2,540 sq. ft. with 3 Bedrooms, 3 Full Baths and a spacious living room with direct Pool views, cathedral tongue-and-groove ceilings, a dedicated laundry room, and a thoughtful layout with a separate guest wing. The Primary Suite connects to a versatile sunroom with direct walk-out access to the Pool deck, while a full wall of sliding glass doors seamlessly connects the indoor and outdoor spaces. A covered walkway conveniently connects all front entrances. Guest will love the stand-a-lone 2 Bedroom 1 Bath 704 sq. ft. Guest House offers guests lots of privacy and conveniences with Living Room and morning Kitchen. Step outside to your own personal oasis, featuring a heated/chilled pool complete with a waterfall and a custom mural painted by a local artist. The outdoor entertaining area highlights two Tiki huts, one equipped with a built-in outdoor grill perfect for enjoying the Keys lifestyle. Built for peace of mind and ultimate convenience, the property includes a brand-new metal roof, impact windows for both homes, a whole-house generator powered by an in-ground propane tank, an outdoor shower, a storage shed, and a carport accommodating 4+ vehicles. Enjoy easy access to the nearby Marathon Jet Center, plus a short walk or bike ride to Sombrero Beach for breathtaking sunrises and sunsets and holiday festivities making this move-in ready or investment-ready Keys retreat truly complete.

69 Tingler Ln, Marathon

250 W Seaview Cir, Duck Key
$3,450,000
3 Beds ⋅ 3 Baths ⋅ 619042 MLS
Motivated Seller...Welcome to your dream coastal retreat on Duck Key, where BREATHTAKING COASTLINE VIEWS and refined island living exist in perfect harmony. This beautifully curated DESIGNER RESIDENCE is a three-bedroom, three-bath oceanfront concrete home by D'Asign Source, blending timeless elegance with modern comfort through soft earth tones, quality finishes, and sweeping panoramic views of the turquoise waters beyond. Inside, a spacious chef's kitchen anchors the home--ideal for entertaining--while a thoughtfully designed split floor plan offers privacy and flow. Two guest bedrooms enjoy direct ocean views, and the expansive primary suite is a serene sanctuary featuring a luxurious en-suite bath with designer tile, dual vanities, custom cabinetry, and a built-in makeup station. Step outside into your private waterfront oasis. A custom oceanfront pool deck and generous covered patio create the perfect setting for relaxation after a day on the water. A 25,000 POUND BOAT LIFT and seawall provide effortless access to the open ocean with no fixed bridges, making this an exceptional location for boating, paddleboarding, and kayaking directly from your dock. Additional features include a screened-in balcony with electric shutters, two large storage rooms, an L-shaped two-car garage, ample outdoor parking, and a wide driveway. Located on a golf cart-friendly island, Duck Key offers convenient access to restaurants, bars, shops, and social clubs. Whether you enjoy fishing, boating, or simply soaking in spectacular sunsets, Duck Key delivers an unparalleled waterfront lifestyle. Surrounded by crystal-clear waters and shallow sandbars teeming with marine life, this home is not just a residence--it's a destination. Schedule your private showing today and experience the very best of Duck Key living.

250 W Seaview Cir, Duck Key

168 Indian Mound Trl, Tavernier
$3,425,000
4 Beds ⋅ 3 Baths ⋅ 620762 MLS
This exceptional waterfront estate situated on two lots and on a deep water canal with a 50ft dock is situated in the heart of Plantation Key. The property features a grand three story residence framed by established palm trees and a striking, patterned paver driveway. The expansive grounds are clean but unplanted, offering a clear blank canvas for you to design your ultimate custom tropical landscaping and privacy screening. The backyard focuses entirely on the water, featuring a lagoon style pool with cascading waterfalls, rock formations, and elevated sun decks. A private waterfront dock provides instant access to boating, fishing, or cruising to the open waters of Florida Bay. Inside, this well maintained home is incredibly clean and move in ready. The living spaces are generous and bright, with large windows that seamlessly connect to outdoor terraces overlooking the canal. Enjoy breathtaking, panoramic sunset views from the spacious rooftop observation deck, which provides vistas over the mangrove preserve and surrounding waterways. This property is perfect for someone looking for an immaculate, turnkey home with significant upside potential to add value and personality through their own landscaping vision. It offers the true keys lifestyle just minutes from world class fishing and attractions. This is more than a home; it is a true island destination.

168 Indian Mound Trl, Tavernier

1401 Atlantic Blvd, Key West
$3,400,000
5 Beds ⋅ 4 Baths ⋅ 621477 MLS
Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West

1401 Atlantic Blvd, Key West
$3,400,000
5 Beds ⋅ 4 Baths ⋅ 621476 MLS
Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West

141 Simonton St, Key West
$3,400,000
3 Beds ⋅ 3 Baths ⋅ 619959 MLS
Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

141 Simonton St, Key West