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$49,900
2 Beds 2 Baths 1076108 MLS
Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lockout unit deeded timeshare week 46- where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café. Enjoy Key West's renowned annual Boat Float Week featuring an international event with thrilling races, lively race villages, and prime spectator viewing areas right to your island doorstep! Ideally located just two blocks from the iconic Duval Street and steps from the marina and Key West's Historic Seaport Village, you'll be surrounded by endless options for dining, shopping, and entertainment. Stay or rent it out! This unit's potential rental income ranges from $3,885 to $5,775 for the week. Photos and views are of a closely similar unit but not exact.,

617 Front Street, Key West

$550,000
2 Beds 2 Baths B26022409 MLS
Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping. Inside, the home has been completely remodeled from top to bottom, providing a fresh, move-in-ready space. There's ample parking for all your needs, including room for an RV or boat trailer. Plus, a community boat ramp is located less than a mile away, making it easy to get out on the water anytime. Don't miss this unique waterfront property with endless potential!

27910 Porgie Path, Little Torch Key

$32,500
2 Beds 2 Baths 1075831 MLS
Top floor Penthouse end unit! Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate ships pass by just beyond your balcony. In the evenings, open the doors to take in the warm Gulf breeze and the soothing sounds of the water. Walk downstairs or take the elevator to enjoy the Galleon's on-site Tiki bar with live music, the Pirates Cove restaurant, a private beach, a pool, and a hot tub! Week 36 (September 5th-12th) offers an ideal getaway--featuring warm weather, fewer crowds, and a relaxed island atmosphere. Stay or rent it out! This unit's potential rental income ranges from $3,885 to $5,775 for the week. Photos and views of a similar unit, but not exact

617 Front Street, Key West

$847,900
2 Beds 2 Baths B26020292 MLS Key Colony Beach BLDG.
Welcome to your Waterfront Paradise! This beautifully remodeled 2/2 is situated on a deep-water canal, 200' wide, with direct ocean access and no fixed bridges. Step outside to your private dock, complete with a 20,000 lbs. boat lift, making it effortless to get out on the water anytime you please. Inside, the home has been fully updated with modern finishes, and a stylishly renovated interior that's move-in ready. Major upgrades, including new A/C units (2025)and 2019 roof, ensuring comfort and long-term value. Relax under the 2023-built tiki hut, perfect for entertaining or unwinding. Even better, there are no rental restrictions, making this property an excellent opportunity for investors, seasonal rentals, or full-time living. This waterfront gem checks every box!

34 7th Street, Key Colony Beach

$1,375,000
3 Beds 3 Baths B26014069 MLS
Key Largo Waterfront. 14000 LB BOAT LIFT.1 hour from Miami Airport. Ocean side canal front home that blends strength, style, and charm. This 3-bedroom, 3-bath concrete bunker with a concrete roof offers peace of mind and lasting quality, along with impact windows and doors. *Upstairs 2 bedroom / 2 bath & Downstairs Newly updated 1 bedroom / 1 bath with large living space. This home is all about function, durability, and waterfront living. The large kitchen boasts stainless steel appliances, ideal for preparing fresh catch or hosting friends. The living area features beautiful pecky cypress walls, wood beam ceilings and a cozy fireplace that creates warmth and character, while custom blinds throughout the home add a touch of sophistication. The spacious primary suite features cedar-lined a cozy fireplace that creates warmth and character, while custom blinds throughout the home add a touch of sophistication. The spacious primary suite features cedar-lined closets and an updated bath, offering comfort and privacy with a split-bedroom layout that separates it from the guest rooms. Step outside to your waterside screened balcony to enjoy the views, have your morning coffee or evening cocktails. Downstairs, you'll find a spacious storage and workshop area -- ideal for all your gear, tools, and hobbies --New laundry room-- along with plenty of parking for family, guests, and your boat trailer. The large backyard offers endless potential, with room for a pool, a cozy fire pit for stargazing nights, and a covered porch perfect for outdoor gatherings. Your new home is situated on a wide clean ocean side canal with a 7000 LB boat lift to enjoy the Keys waters. Outside showered... Located in a peaceful, sought-after neighborhood, this home is just minutes from shopping, dining, and world-class fishing and diving. Plans for a new Kitchen, seller with work with you on it if you wish. ... $25,000 NEW KITCHEN TO BE INSTALLED -OR- $25,000 OFF THE PURCHSE PRICE. **The seller has a installer ready to do it drawing on site.

180 La Paloma Road, Key Largo

$59,900
2 Beds 2 Baths 1074332 MLS
Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple balconies that maximize the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate ships pass by just beyond your balcony. In the evenings, open the doors to take in the warm Gulf breeze and the soothing sounds of the water. Stay or rent it out! This unit's potential rental income ranges from $4,165 to $6,195 for the week, Week 36 (2026: September 5th-12th) offers an ideal getaway, featuring warm weather, fewer crowds, and a relaxed island atmosphere! Photos and view of a closely similar unit, but not exact

617 Front Street, Key West

$949,000
3 Beds 2 Baths B26013545 MLS
Bring your boats to this beautifully furnished canal front home. This home is secluded on a large corner lot with 190 ft. of concrete seawall. Large and open living, dining, and kitchen areas. Lovely updated kitchen and bathes. New beautiful floors, along with impact windows, doors, and metal roof. Enjoy swimming in the above ground pool, relaxing on the deck, cocktails at the bar, or meeting the adorable key deer roaming the neighborhood. Great yard with room for all your toys. Three vacant lots next door are county owned for preservation. Lots of privacy! This home is totally furnished with lots of extras. TURN KEY READY! Successfully rents for$9000 during season. This house is MAGICAL! ROOF 2017 AC 2019

1540 Lantana Lane, Big Pine Key

$59,000
2 Beds 2 Baths 1073847 MLS
PENTHOUSE! Beautiful straight-on views of the Gulf, Pool, Beach, Sunsets, and Tiki Bar. Enjoy week 32 in this Timeless Timeshare and celebrate Lobster Week and the Rum Festival. The Galleon resort has Elevators, a rooftop deck, a gated parking garage, a sauna, an exercise room, and the Pirates Cove Cafe and Outdoor gas grills, which are located on the Marina side of the Galleon. Stay or rent it out! This unit's potential rental income ranges from $4,165 to $6,195 for the week. New 2026 furnishings! The penthouse has tall, vaulted ceilings and extra windows, allowing for natural light. This unit sleeps six with 2 beds, 2 baths, and a sleeper sofa. These photos are of a similar unit taken next door. Two sets of French doors with plantation shutters lead you out to your private balconies--5-piece primary suite with a jetted soaking tub and a walk-in shower. Enjoy the active waterways and boats as they sail by--photos and views of a closely similar unit, but not an exact .

617 Front Street, Key West

$42,000
2 Beds 2 Baths 1073845 MLS
Views of the famous Key West Sunset, Gulf of Mexico and pool await you when you arrive at this 4th-floor end- deeded timeshare unit. The live music from the Tiki bar saunters up to the balconies. This highly desirable winter week is magical enjoy the warm weather and Christmas boat parades while Key West is all dressed up for the holidays. Enjoy the private beach, pool, hot tub, sauna, outdoor gas grills located on the marina. Tiki Bar, Privates Cove cafe, exercise room or just steps away walk out the the Historic Key West Seaport Village for a delicious dinner or happy hour and just 2 blocks away is Famous Duval Street. The fully furnished unit has been updated with new furnishings. With 2 beds and 2 baths,, plus a sofa couch, this unit sleeps 6. Stay or rent it out! This unit's potential rental income ranges from $5,705 to $7,595 for the week. Highly rated resort - enjoy panoramic Key West views from the rooftop! Photos and Views are closely similarthe to unit but not exact.

617 Front Street, Key West

$59,900
2 Beds 2 Baths 1073844 MLS
On the Gulf of Mexico this 4th floor end unit Timeshare is on the water and overlooks the Key West Marina. 2 bed 2bath with sofa couch sleeps 6. Week 50 is a very sought after week that offers ideal winter weather, a relaxed island atmosphere and peak rental demand. Enjoy the decorative Christmas boat parades from your own personal view balconies and experience Key West all dressed up for the holidays. Enjoy the private beach, heated pool and hot tub, Tiki Bar, fitness center on onsite Pirates Cove cafe. In addition there are gas grills out on the marina. The C building in one of the most desirable buildings. Elevators, gated parking garage and lot. Brand new furnishings. The roof has a top deck to enjoy the most glorious Key West sunsets. Just steps away from the Historic Key West Seaport and 2 blocks from famous Duval Street. Photos and views are of a similar unit; the exact unit's layout is similar. Stay or rent it out! This week has rental potential of approx. $ 5,565-$ 7,595.

617 Front Street, Key West

$62,000
2 Beds 2 Baths 1073028 MLS
Penthouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year, Week 52- one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Celebrations, including live music, fireworks, and iconic Duval Street events. The Penthouse boasts expansive, straight-on views of the Gulf. Pool, hot tub,, private beach and Tiki bar, where a local guitarist performs nearly every day or night. There are elevators and one unassigned parking space. There is a sauna and exercise room, and the Pirates Cove cafe. Gated community. This Penthouse is located just two blocks from Famous Duval Street, and steps away from the marina and Key West's Historic Seaport. Daily Stay your week or rent it out. Rental rates for this unit range from $5,705 to $ 7,875 for the week.Photos and the view are of a similar unit, but not an exact

617 Front Street, Key West

$1,550,000
5 Beds 3 Baths B26002035 MLS
THE BEST DEAL In KEY COLONY! Rare opportunity to own a legal duplex being sold as A Single Family Home in the heart of Key Colony Beach in the beautiful Florida Keys. Located just one street off the Atlantic Ocean, 340-350 E Ocean Drive offers exceptional space, boating access, and an amazing investment opportunity with flexibility at a competitive price designed to sell. With 5 beds, 3 baths, and over 2,900 sq ft of living space, this property provides the rare opportunity to own a large waterfront home while still benefiting from the layout of a legal duplex. Sold together as a single property, it offers incredible versatility for full-time living, vacation use, or income-producing investment. Boaters will appreciate 50 ft of dockage with dual docks, allowing space for multiple vessels. Buyer and buyers agent to verify all info

350 E Ocean Drive, Key Colony Beach

$3,999,999
2 Beds 2 Baths B26001957 MLS
Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living.

77340 Overseas Highway, Islamorada

$2,249,000
4 Beds 3 Baths R11162784 MLS
Over 3400 sqft of Luxury Living is featured with this 2007 custom built CBS in the gated community of Stirrup Key Sub in Marathon. Elevated water views, a deeded boat slip, protected community marina, multiple outdoor living areas and a private pool. Designed for both everyday comfort and entertaining, this multi-level home offers generous interior space, flexible living areas, and a thoughtful indoor-outdoor layout. The ground level features a three-car garage, ample storage, and direct access to the pool area, creating an easy flow for relaxing, hosting, and enjoying the Keys lifestyle. The second floor serves as the main living level with two bedrooms, two full baths, a full kitchen, and open living and dining areas that extend onto a large screened lanai. This level is ideal for casual gatherings, quiet mornings, and evening breezes. The third floor offers a private primary suite, sitting area or fourth bedroom, bar/kitchenette, fireplace, spa-style bath, and an expansive lanai with peaceful elevated views. A spiral staircase leads to the fourth-floor widow's walk, finished with travertine flooring and a water hookup. From this vantage point, panoramic views stretch across Marathon and toward the Gulf, creating a quiet setting for sunrise, sunset, and open-air relaxation. A private nature path winds through preserved surroundings and leads to a Gulf-front observation dock, ideal for wildlife viewing and enjoying the surrounding natural setting. Additional features include a lift to the second floor for added convenience. Centrally located in Marathon, the home offers convenient access to shopping, dining, & daily necessities. With a deeded marina slip, elevated water views, pool, garage space, storage, multiple lanais, and a flexible custom layout, this property offers a rare combination of privacy, space, and boating access in Marathon. Schedule a private showing to experience this custom home and deeded marina slip in person.

205 Stirrup Key Boulevard, Marathon

$3,495,000
5 Beds 5 Baths W7882829 MLS
LOCATION LOCATION LOCATION DIRECTLY ON THE GULF W/ GULF OF AMERICA AND MARINA VIEWS! Welcome to an extraordinary opportunity to own a newly constructed, luxury waterfront residence in the heart of the Florida Keys. Located in the exclusive Emerald Landings community in Marathon, this exceptional home offers breathtaking open-water views, a private 50' boat slip included, and a rare private beach, kayak launch, blending high-end coastal living with unmatched boating convenience. Thoughtfully designed for both luxury and functionality, this stunning property features 5 bedrooms and 5 bathrooms, including two spacious primary suites with private balconies overlooking the water. An open-concept floor plan showcases a chef's kitchen with quartz countertops and waterfall island, seamlessly flowing into the living and dining areas--ideal for entertaining or relaxing with panoramic sunset views. Outdoor living is elevated with a heated resort-style pool, expansive patios, and multiple spaces designed for al fresco dining and sunset gatherings. Premium finishes, coastal-inspired design, and modern technology are found throughout the home, offering a turn-key experience for owners and guests alike.This property is the perfect investment opportunity, boasting a proven short-term rental history and strong income potential, while also serving as an ideal future personal residence for those dreaming of a private retreat in the Keys. Whether used as a high-performing vacation rental, a seasonal escape, or a full-time waterfront home, this property offers unmatched versatility. Centrally located near world-class boating, dining, shopping, and beaches, this rare offering combines luxury, location, and lifestyle--a true Keys dream home with income-producing potential. Being offered furnished.

805 39th Street Gulf, Marathon

$16,900,000
6 Beds 7 Baths F10548717 MLS
Escape to your own tropical paradise with this dreamy, ultra-luxurious 6-acre estate on Key Largo Bay, just one hour south of Miami. This extraordinary private retreat features a main residence w/in-law suite, plus three accessory dwelling units, offering a total of 6 bedrooms, 6 full bathrooms, and 1 half baths, perfect for hosting family and friends or creating a secluded personal sanctuary. The estate delivers true resort-style living with a stunning brand-new heated /chilled pool and a natural pool with a tranquil fountain, all set within a lush tropical landscape. With 300 feet of private waterfront, including 100 feet of sandy beach overlooking the Gulf, the property enjoys unobstructed panoramic views and some of the most breathtaking sunsets in the Florida Keys. Designed around a wellness-focused lifestyle, the property includes a sauna, cold plunge, outdoor shower, and dedicated workout and yoga areas, ideal for meditation, fitness, and holistic living surrounded by nature.Boating enthusiasts will appreciate the exceptional waterfront infrastructure, featuring multiple dock spaces, a covered boat house, a private basin, and an approved 99’6” private dock & tiki hut with an approximately 6-foot draft. The new dock adds flexibility to accommodate larger vessels and comfortably welcome multiple boating guests. This estate is positioned near Snake Creek and Tavernier Creek and provides quick access to both the Atlantic Ocean and the Florida Bay, making it a premier launch point for backcountry flats fishing, offshore adventures, sandbar days, and sunset cruises.The location also places you by iconic Florida Keys destinations, including the Islamorada Sandbar, Alligator Reef Lighthouse, and several popular waterfront restaurants easily accessible by boat, offering the ultimate Keys lifestyle of dining, cruising, and coastal exploration.The estate is home to hundreds of tropical plants and trees, ensuring unmatched privacy and natural beauty. An urban garden with organic herbs and vegetables supports a true farm-to-table lifestyle. Outdoor living is elevated with tiki huts, outdoor kitchens, expansive entertaining areas, and ample parking, making the property ideal for intimate retreats, wellness gatherings, or peaceful island living.This one-of-a-kind Key Largo estate is more than a home, it’s a lifestyle. Truly unforgettable and irreplaceable, it must be experienced in person to fully appreciate its scale, serenity, and extraordinary details.*Information is believed to be accurate but not guaranteed. Buyer & Buyer agent/broker to verify all details.

95410 Overseas Highway, Key Largo

$3,690,000
3 Beds 3 Baths W7882338 MLS
Stunning Furnished Coastal Modern 3-bedroom, 3-bath modern waterfront estate built by the Florida Keys' premier builder, D'Asign Source. This three-story solid concrete home offers exceptional design, craftsmanship, and strength, perfectly positioned on over a quarter acre with 110 feet of deep-water frontage along a 300-foot-wide canal. Boaters will love the 10,000 lb boat lift, 85 feet of dockage, and direct deep-water access to the Gulf and Atlantic. A fish cleaning station with water, bait freezer, and commercial ice machine make this property a dream for anglers and water enthusiasts. Inside, expansive glass doors and windows flood the living space with natural light and showcase panoramic canal views. The chef's kitchen features Viking appliances, quartz countertops, wine cooler, and premium finishes, while the open-concept design connects seamlessly to multiple balconies and outdoor living areas. The master suite includes an oversized rainfall shower and a private balcony overlooking the water, while two guest bedrooms provide bright, inviting retreats. Outdoor living is the heart of this home, featuring a custom 440 sq. ft. pool with hot tub and sunshelf, surrounded by soft sand, hammocks, and lush tropical landscaping. Entertain in style at the covered outdoor bar and grilling area, or unwind with sunsets from the private rooftop lounge overlooking the Gulf of Mexico. Additional features include four+ parking spaces, trailer parking, high-speed WiFi, multiple smart TVs, and a fully fenced yard that's pet-friendly. Tis property combines luxury, durability, and a true Keys lifestyle — offering modern design, deep-water access, and spectacular views in one of Marathon's most sought-after waterfront neighborhoods.

118 Avenue E, Marathon

$399,000
2 Beds 2 Baths R11147301 MLS 19 BLDG.
Ocean Breeze makes island living easy in this Florida Keys waterfront enclave. This fully furnished, newly constructed manufactured home is outfitted with tasteful coastal decor across the sunny 2 bed, 2 bath space. The upstairs private balcony overlooks the ocean for morning coffee. All modern appliances including washer and dryer and dishwasher complete the package. Enjoy full amenities in this well-maintained community including swimming pool, marina access, kayak launch, BBQ area, and proximity to all Marathon has to offer including watersports, dining, the local airport and quick access to the Gulf and Ocean. This residence is organized on a leasehold principle making home ownership stress-free.

101 11th Street Unit 19, Marathon

$1,800,000
2 Beds 2 Baths R11107393 MLS
Welcome to Paradise! this home sits on almost 3/4 of an acre along a direct access canal with 100 ft of waterfront! Want to park your RV and Boat under your home, done! Want to build your own luxury oasis, here you go. Want to just enjoy easy access to open water and majestic Sunsets from your private observation deck, got that covered! Fully screened wrap around porches allow you to open up and let the East - West trade winds breeze right through the entire home. Professionally landscaped perfection from your private dock with davits, boathouse and garden paths to the exterior elevator and massive shop/storage area downstairs. Close to Adams Cut for easy oceanside access. 1 hour from Miami international airport.

1514 Shaw Drive, Key Largo

$939,500
2 Beds 2 Baths R11139241 MLS
2-bed, 2-bath waterfront home, perfectly positioned on a corner lot in neighborhood of Marathon. CBS construction, this home seamlessly blends modern comfort, coastal elegance, and exceptional boating access. Situated on a wide, flow-through canal that leads directly to open water, this property provides effortless navigation to both the Gulf and the Atlantic Ocean, making this property a true boater's paradise. The 55-foot dock invites you to step aboard and set out for a day on the water or simply unwind with panoramic canal views framed by swaying palms and unbelievable sunsets. Step inside to find bright, open living spaces, in this beautifully updated home with new roof (2022), new A/C system, and new impact-resistant windows and doors. Back on market due to buyer financing

11725 3rd Avenue Ocean, Marathon