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Rat, Key West
$850,000
2 Baths ⋅ 619620 MLS
FOR SALE: Mellow Ventures LLC - Premier Eco-Tour & Luxury Houseboat Rental Company in the Florida Keys Step into one of the most unique lifestyle and income-producing businesses in the Florida Keys. Mellow Ventures LLC is a turnkey, multi-stream eco-tour and hospitality operation with a proven track record, established brand presence, and rare waterfront assets perfectly positioned for continued growth. Operating out of Key West, this boutique adventure company has built a reputation for intimate, sustainable experiences on the water—guided eco tours, private charters, island excursions, and custom adventures designed to showcase the natural beauty of the Lower Keys. In addition to its successful charter business, the sale includes two custom-built luxury houseboats, currently operating as high-demand short-term rentals. These floating suites offer a one-of-a-kind Airbnb experience that consistently generates strong occupancy and premium nightly rates. Each vessel blends modern comfort with an immersive waterfront setting, providing an unforgettable stay for guests seeking something truly special. Highlights Include: -Well-established eco-tour & charter business with brand recognition in Key West -24' Twin Vee -Two fully custom houseboats designed for nightly rentals -Strong Airbnb track record with exceptional occupancy -Multiple revenue streams: eco tours, private charters, overnight rentals -Turnkey operation with booking systems, media assets, furnishings & equipment -Excellent online reviews and repeat clientele -Ideal opportunity for owner-operator or investor seeking passive/managed income -Rare waterfront lifestyle business in a world-renowned destination This is a unique chance to acquire a thriving, experiential Keys business blending adventure tourism with boutique hospitality—a lifestyle investment that generates real returns.

Rat, Key West

1220 Georgia St, Key West
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 619619 MLS
Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

1220 Georgia St, Key West

21640 Overseas Hwy, Cudjoe
$2,800,000
4 Beds ⋅ 3 Baths ⋅ 619615 MLS
SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

21640 Overseas Hwy, Cudjoe

2515 Staples Ave Unit Unit B, Key West
$449,000
2 Beds ⋅ 1 Baths ⋅ 619604 MLS
Why buy in a condo complex? This charming renovated 2-bedroom, 1-bath residence offers an exceptional opportunity to own in the heart of Key West without sacrificing privacy or outdoor living. Thoughtfully updated throughout, the home features a modern kitchen with stainless steel appliances, dishwasher, and the convenience of an in-unit washer and dryer (an amenity not always found in Key West). Sharing just one common wall, the home lives much like a private cottage with its own entrance, parking, and a fenced backyard currently with a deck, designed for relaxing, entertaining, or enjoying island life. Recent renovations include hurricane-impact windows, updated plumbing, newer air conditioning, and stylish finishes that make this property truly move-in ready. Ideally located in Mid-Town along Key West's cross-town bike path, you'll enjoy quick access to beaches, shopping, dining, and Old Town. At $449,000, this is an outstanding alternative to condo living with the added benefits of private outdoor space, no shared hallways, and the comfort of a home that is ready to enjoy from day one. (condo docs to be filed). Call today for your personal tour.

2515 Staples Ave Unit Unit B, Key West

810 Carey Ln, Key West
$2,150,000
3 Beds ⋅ 2 Baths ⋅ 619599 MLS
Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, light-filled kitchen with updated finishes--ideal for entertaining or relaxed island living. The home works beautifully as a two-primary suite layout, with the flexibility to convert one suite into a third bedroom or private study. Step outside to your own tropical retreat, complete with a refreshing plunge pool surrounded by lush landscaping. Located in the heart of Old Town, you're just moments from dining, shops, and the vibrant local scene, yet enjoy the peace and privacy of a hidden setting. Additional highlights include off-street parking--a rare and valuable convenience in this sought-after neighborhood. Whether you're seeking a full-time residence, vacation home, or investment property, this cottage captures the essence of Key West living. Possible Seller financing. .

810 Carey Ln, Key West

88747 Old Hwy, Islamorada
$8,000,000
3 Beds ⋅ 3 Baths ⋅ 619592 MLS
Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ultimate getaway for relaxation and adventure. Unwind in the oversized heated pool or customized hot tub after a day of sun and fun. The Tiki Hut provides convenient storage for all your water toys, making your boating and beach days effortless. Enjoy practicing your swing on the private putting golf course, all while surrounded by breathtaking ocean scenery. With a lucrative 7-day rental option and an easily obtainable license, this gem is perfect for both personal enjoyment and investment. Don't miss your chance to own this slice of paradise--schedule a viewing today!

88747 Old Hwy, Islamorada

21090 5th Ave, Cudjoe
$2,999,999
4 Beds ⋅ 3 Baths ⋅ 619589 MLS
Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of your gear. Inside, the spacious 4 Bedroom, 3 Bath 3,056 sq. ft. home comfort and style blend with ease. The kitchen stands out with 6-burner Viking Range, Viking dishwasher, cabinet-front refrigerator, stainless appliances, pantry and generous space for entertaining, flowing seamlessly into the main living areas. Soaring ceilings fills the home, creating a bright and inviting atmosphere throughout. Upstairs a loft-style office and a dedicated theatre room offering a bar with beverage center provides the perfect setting for movie nights or game-day gatherings. The primary suite serves as a private retreat, complete with a lavish bath with bidet, separate shower and a relaxing jet tub, ideal for unwinding at the end of the day. Porches on both sides of the home overlook the canals and lead to a unique sandy point at the corner, offering a peaceful setting to take in water views and stunning sunset skies. After a day on the water relax by your waterfront heated salt pool or enjoy sipping cocktails on the screened lanai. Additional amenities include impact windows and doors, whole house generator and ice machine. Cudjoe Gardens is an upscale waterfront community known for its ground-level concrete homes thoughtfully built above the floodplain. The neighborhood is home to Cudjoe Gardens Marina, a convenient full-service stop for fuel, bait, and refreshments on your way to world-class fishing and diving. Residents also enjoy The Bent Prop, a beloved waterfront restaurant offering a true taste of the Keys lifestyle.

21090 5th Ave, Cudjoe

5555 College Rd Unit Grunt 9, Key West
$245,000
619583 MLS
OWNER FINANCING AND QUICK CLOSE AVAILABLE. Lowest cost liveaboard 45'X 16' slip in Key West. Live in Paradise for only $245,000 with HOA fee and property tax of less than $600 per month (plus utilities). This 120 slip marina is deeded real property where you own the bay bottom, desired floating concrete design, located in well-protected area and on leeward side of the island. Pool and fitness additional $75 mo. Mailboxes $25/mo. $5 pump-out. Cable/Internet available. Security cameras throughout. Immediate access to gulf and easy access to Atlantic. Showers, laundry, dog walk, bike racks, convenience store, fuel and use of 1 parking space. Separate water and electric meters with (2) 30 amp portals. Owners may have pets with restrictions. Visit https://www.sunsetmarinakw.com for more information on marina.

5555 College Rd Unit Grunt 9, Key West

1306 51st St, Marathon
$495,000
2 Beds ⋅ 1 Baths ⋅ 619582 MLS
Updated, elevated, and centrally located, this 2-bedroom, 1-bath half duplex offers an appealing combination of durable construction, modern finishes, and flexible Keys living. Located in the heart of Marathon and surrounded by mature native landscaping, the residence features CBS construction, an elevated design, a concrete roof, impact-resistant windows, and a newer HVAC system. Inside, the thoughtfully remodeled interior offers an open, comfortable layout with gray faux wood plank flooring, granite countertops, stainless steel appliances, and clean coastal finishes. Two covered parking bays beneath the home provide convenient space for vehicles, a boat, trailer, bicycles, fishing equipment, paddleboards, and the recreational gear that comes with Florida Keys living. Additional open parking and RV or trailer parking add to the property's everyday functionality. With seven-day minimum rentals permitted, the residence offers versatility as a primary home, seasonal retreat, employee-housing solution, or investment property, subject to applicable regulations. Separate electric and water meters provide additional convenience. Ideally positioned near shopping, dining, marinas, beaches, the community boat ramp, and daily conveniences, this move-in-ready property places the best of Marathon within easy reach. The adjoining half duplex is also available for purchase, creating a rare opportunity to acquire the entire property for expanded housing, multigenerational living, or investment potential.

1306 51st St, Marathon

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

2805 Flagler Ave, Key West
$874,999
3 Beds ⋅ 2 Baths ⋅ 619565 MLS
This sophisticated residence features off-street parking for two vehicles or a boat and is just a block away from the community boat ramp. Recent upgrades include hardie board siding, acoustic, and hurricane-rated doors and windows. An independent storage shed that offers additional storage space. The backyard provides a serene outdoor area perfect for enjoying the island lifestyle. The focus on high-quality finishes, expansive outdoor living, and an inviting design radiates luxury and comfort, making it ideal for entertaining friends and family. The location provides convenient access to exceptional dining, coffee shops, shopping, as well as recreational amenities such as sports venues and schools. Its proximity to the beach and downtown, coupled with low-maintenance landscaping, enhances its appeal and renders it a perfect choice for embracing the island lifestyle with luxury and comfort.

2805 Flagler Ave, Key West

214 Eanes Ln, Key West
$3,300,000
4 Beds ⋅ 4 Baths ⋅ 619548 MLS
Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X flood zone, this property offers added peace of mind and potential savings on insurance--an increasingly valuable feature in today's market. This unique property is configured as two separate units, featuring a main two-story residence and a detached guest quarters, with a combined total of 2,573 square feet of living space. The detached unit is separately licensed and equipped with its own electric and water meters, providing true independence and strong income-producing potential. The main home offers a spacious and functional layout designed for island living. The first floor includes multiple living areas, with a generous living room, separate dining space, family room, and a well-appointed kitchen that opens to outdoor patio and deck areas--perfect for entertaining. Upstairs, you'll find three bedrooms, including a primary suite, along with multiple bathrooms and private balconies that capture the charm of Key West. The detached unit provides a private retreat complete with a bedroom, bathroom, kitchenette, and living space--ideal for guests, extended family, or rental income. Additional highlights include off-street parking for two vehicles, a rare and valuable feature in Old Town, as well as inviting outdoor spaces designed for relaxing and entertaining. Whether you're looking for a primary residence with additional income, a second home with flexibility, or a pure investment opportunity, 214 Eanes Lane delivers versatility and value in one of Key West's most sought-after neighborhoods.

214 Eanes Ln, Key West

12399 Overseas Highway Unit 41, Marathon
$182,500
618026 MLS
Looking for the perfect home for your boat? This 40' side-tie slip at the Boat House Marina provides a stress-free docking experience. Up to 40' LOA and the slip is 13.42' wide. You can stay on board 5 consecutive nights and up to 10 nights per month. Electric is metered and water is included in the association fees, making this a convenient and cost-effective choice for any owner. Please note that the slip is currently rented through 8/31/2027, offering immediate rental income for an investor or a future-planned spot for your own vessel. The Boat House Marina is known as one of the nicest marinas in the Middle Keys and offers a protected basin with quick access to both the Atlantic and the Gulf. Don't miss this opportunity to own a premier dockage spot in the heart of the Keys!

12399 Overseas Highway Unit 41, Marathon

5950 Peninsular Ave Unit 708, Stock Island
$325,000
619234 MLS
A beautiful 45' liveaboard slip at Oceanside Marina in Oceans Edge Resort offers direct deep-water access to the Atlantic Ocean, making it the perfect Key West retreat for passionate boaters. Whether you're seeking a vacation escape, a full-time waterfront lifestyle, or an ideal home base for a charter business, this slip delivers exceptional versatility. Owners enjoy full access to the resort's premium amenities, including six swimming pools, a state-of-the-art fitness center, a full bathhouse with laundry facilities, a dog park, complimentary pump-outs, fuel docks, and more. The property also features an excellent onsite restaurant and bar, along with outdoor movies and occasional live music for a true resort experience. Unlike most marinas in the Keys, this property includes owned bay bottom-making it deeded real estate that is financeable and not subject to a Florida Bay Bottom lease. To top it off, this is widely considered the easiest slip to navigate in the entire marina, offering effortless docking and departure. Come experience one of the finest boating locations in Key West.

5950 Peninsular Ave Unit 708, Stock Island

35 Sombrero Blvd Unit B1, Marathon
$365,000
618579 MLS
SELLER IS OPEN TO OFFERS! Experience the quintessential Florida Keys lifestyle at Sombrero Marina, a casual and welcoming community in the heart of protected Boot Key Harbor. This slip is OWNED BAYBOTTOM. Per the survey, the slip is 87' long, 20.56' wide at the dock and 21.64' wide at the outside pilings. Up to 75' LOA and max 18'9'' beam, per the dockmaster. Slips capable of accommodating vessels up to 75' LOA are exceptionally rare to find in Keys, making this a unique opportunity for owners of larger yachts. This expansive slip also offers the security of baybottom ownership, allowing for full-time liveaboard status. Additionally, convenient financing is available through a local bank to make your island transition seamless. This slip is as versatile as it is spacious, serving as a perfect seasonal home for your vessel or a reliable permanent residence. When you aren't using the slip yourself, the on-site dockmaster can rent the slip out for you, providing a hands-off way to offset ownership costs. Life here is defined by ease; you are just steps away from the iconic Dockside restaurant for live music, meals and a great social atmosphere. The slip includes 30/50 amp service and a deeded land footprint directly in front--ideal for a golf cart. Don't miss this chance to secure one of the few large-scale liveaboard slips in the heart of the Keys.

35 Sombrero Blvd Unit B1, Marathon

100 Ave I, Unit 6, Marathon
$375,000
610716 MLS
Discover a rare opportunity to own an oversized boat slip with live-aboard approval in the desirable Cocoplum neighborhood of Marathon. Offering an impressive 22' width, 80' length, and 6' draft, this slip easily accommodates larger vessels, and a recently removed piling maximizes your available space. Nestled on the ocean side, you'll enjoy direct, fast, no-bridge access to the open water, perfect for avid boaters and anglers. Positioned at the end of the marina in a secure, gated section, the slip offers added privacy and quicker navigation straight to the ocean. A spacious Tiki hut extends your living area onto land, creating an inviting space for relaxing, entertaining, and embracing the island lifestyle. Stylish faux-wall panels on each side provide privacy while still capturing refreshing tropical breezes. It's a versatile, blank canvas ready for your personal touch. The marina features a community pavilion, bath house, and laundry facility, and this slip includes multiple storage units for all your gear and equipment. With a strong monthly rental potential and an unbeatable location, large slips with dedicated land-living amenities like this are truly hard to find. Don't miss the chance to experience this exceptional boat slip in paradise. Your ideal Keys retreat awaits!

100 Ave I, Unit 6, Marathon

1466 Overseas Hwy Unit Slip 6, Marathon
$185,000
617753 MLS
Slip 6 will accommodate up to a 48' LOA. New decking just installed on the finger pier. Its location in the basin keeps you protected. This 24-slip liveaboard marina will win you over alone with all of the amenities! Not to mention how it's immaculately maintained. Deep water access with 7' controlling depth per the dockmaster, buyer to confirm. Situated on the gulf side, you can enjoy beautiful sunsets in the covered pavilion right behind your slip. In the community building, there is an adorable 1 bedroom, 1 bath apartment upstairs that is available for you when you haul-out or for your guests when they come to visit. A community living, dining and full kitchen is downstairs, along with a laundry room with 2 sets of washer/dryers and two bathrooms with showers. The icing on the cake is the well-equipped workshop that is at your disposal. An ice machine and BBQ grills are also available. There is a small boat basin, next to the boat ramp, for boats up to 23.5' LOA, available at a fee. Kayak and paddleboard racks and boat trailer storage too (as available). As soon as you come through the gate at Harbour Cay Club, you will be sold on this gem of a marina in the Florida Keys! Seller will consider financing with 50% down. The buyer and their boat do need to be approved by Harbour Cay Club. Buyer must have a boat when they submit an offer.

1466 Overseas Hwy Unit Slip 6, Marathon

3029 N Roosevelt Blvd Unit APT 11, Key West
$679,500
2 Beds ⋅ 2 Baths ⋅ 619544 MLS
Welcome to your slice of paradise in the highly sought-after Key Cove community in Key West, FL, where island living meets enjoyable comfort. This beautifully designed townhome offers the perfect blend of coastal charm and modern convenience. Featuring a bright, open-concept layout, the living and dining spaces flow seamlessly with the well appointed kitchen. Ideal for entertaining or unwinding after a long day. Enjoy outdoor living with the covered balcony off of the living room. The Living Room & Foyer has updated Engineered Hardwood - European French Oak Flooring in March 2023. Kitchen Tile updated in August 2025. The stairs and Hallway have Hardwood flooring as well updated in June 2021. New Hot Water Heater in August 2025 along with updated Kitchen Light and Faucet in March 2026. Most of the rooms in the home have been freshly repainted with Sherwin Williams Paint. Upstairs features two spacious bedrooms with high ceilings. A gorgeous bathroom with plenty of light. There's also a hall laundry room for easier lifestyle duties. This home features covered parking with a garage door. Plenty of space underneath for extra storage. Key Cove residents love the laid-back lifestyle. Convenient location for food shopping, dining and entertainment. Also, there's a Community Pool to hangout and enjoy your day. Whether you're searching for a full-time residence or a second home, this home delivers the Key West lifestyle you've been waiting for and more.

3029 N Roosevelt Blvd Unit APT 11, Key West

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