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$1,874,000
3 Beds ⋅ 3 Baths ⋅ 620674 MLS
Located on 1.85 acres of tropical and native landscaping, this mystical waterfront estate in Key Largo offers the perfect blend of privacy, comfort, and coastal living. Designed with both family life and entertaining in mind, this charming three bedrooms, two and a half bath residence features a spacious, light filled, open concept floor plan with clean architectural lines and seamless indoor- outdoor living. At the center of the home is a beautifully appointed kitchen anchored by an expansive island, creating the ideal gathering space for casual family meals and entertaining guests. Generous living spaces flow effortlessly to a covered central courtyard, extending the home's living area into a private outdoor sanctuary. Beyond the courtyard, the backyard unfolds into a breathtaking waterfront setting with direct ocean access. Surrounded by mature landscaping and exceptional privacy, this serene retreat feels like your own secluded oasis. Whether you are relaxing by the water, enjoying the tranquil surrounds, or setting out for a day on the ocean, this property captures the best of the Florida Keys lifestyle.

120 Coco Plum Rd Unit S, Key Largo
$729,000
2 Beds ⋅ 3 Baths ⋅ 620672 MLS
Wake up to wide-open Gulf views from this beautifully maintained residence in Gulfpointe Two, a sought-after waterfront community in the heart of Marathon. Designed to make the most of its coastal setting, the home offers multiple private balconies, bright open living spaces, and water views that create a relaxing backdrop throughout the day. The main living level features a spacious open-concept layout connecting the kitchen, dining area, and living room. Large windows and sliding glass doors fill the space with natural light while showcasing the Gulf beyond. The updated kitchen is designed for both everyday living and entertaining, with granite countertops, abundant cabinetry, stainless steel appliances, a generous breakfast bar, and plenty of workspace. Coastal furnishings and clean finishes complement the easygoing Keys atmosphere. Upstairs, the primary bedroom provides a peaceful private retreat with access to its own balcony and beautiful views across the water. From morning coffee to sunset cocktails, the outdoor spaces offer the perfect place to enjoy the sea breeze and watch boats pass in the distance. Gulfpointe Two is a well-maintained waterfront community offering a heated pool with a chiller for added comfort during the warmer summer months. Gulfside dockage with finger piers is available to owners on a first-come basis and can accommodate boats up to approximately 36 feet. Boaters will appreciate the convenient access to both the Gulf and Atlantic, with Vaca Channel just minutes away. Weekly vacation rentals are permitted, providing excellent flexibility for use as a full-time residence, seasonal getaway, or income-producing investment. Centrally located near Marathon's restaurants, shopping, marinas, beaches, and everyday conveniences, this inviting waterfront property delivers the views, boating access, and relaxed island lifestyle buyers come to the Florida Keys to enjoy.

12690 Overseas Highway Unit 413, Marathon
$659,000
3 Beds ⋅ 2 Baths ⋅ 620669 MLS
Take this opportunity to own a beautifully updated home on nearly half an acre! Located in the peaceful highly desired neighborhood of Grassy Key. Minutes from the best restaurants, roof top bar, market and water park, it truly is an oasis.

58110 Ferreire St, Marathon
$8,500,000
620668 MLS
BUSINESS INCLUDED: Very Profitable Marina & Unique Resort in Islamorada, FL. 2025 NET Income reported over $800,000/yr. !! Offered at over 9.5% Cap rate at Asking Price. Manager on site handles responsibilities with oversight from the absentee owner. Rare 1+ Acre Oceanside Lot with many uses possible. Deep water protected harbor with 18 large boat slips that can accommodate 50+ ft. yachts. Approach depth approximately 6 ft.+ at high tide with a clearly marked channel. Successful Boat Rental Business with 17 boats included in the sale. Lucrative Vacation Rental Business with (10) Aqua Lodges and 1 houseboat also included. Features include water, new 30 Amp and 50 Amp electric at each slip, fuel dock, concrete building with office, ship store, workshop, and garage/storage. 2 outdoor showers, 2 bath houses with indoor showers, stalls, and dressing area. New waste/pump-out station and fuel station. An additional separate concrete building used for storage on the North side of the property. New Concrete In-ground Pool, Deck and Fence just completed. Brand new floating docks. Private marina, must call for an appointment and sign an NDA/CA for more information.

200 Treasure Harbor Dr, Islamorada
$1,249,000
3 Beds ⋅ 2 Baths ⋅ 620667 MLS
Enjoy the best of Sombrero Beach living from this beautifully appointed 3-bedroom, 2-bath canal-front home, ideally located within walking distance of one of Marathon's most loved beaches. With a private 50-foot dock, generous parking, and weekly rentals permitted, the property offers an exceptional combination of boating access, beachside convenience, and investment flexibility. Inside, the bright open-concept floor plan is designed for relaxed Keys living and effortless entertaining. A wall of impact-resistant windows fills the main living areas with natural light, while coastal colors, crown molding, plantation shutters, and thoughtfully selected furnishings create a polished yet comfortable atmosphere. The spacious living and dining areas flow seamlessly into the kitchen, making it easy to gather with family and friends. The well-equipped kitchen features white cabinetry, stainless steel appliances, abundant counter space, a large island with bar seating, and stylish pendant lighting. Multiple dining and seating areas provide plenty of room for hosting, while the home's numerous windows bring in tropical views from nearly every direction. Outside, lush landscaping creates a private island setting leading to the canal and dock. There is ample room to store a boat trailer and keep fishing, diving, kayaking, and beach gear close at hand. The enclosed garage provides additional secure storage, while the metal roof and impact-resistant windows offer valuable peace of mind. Offered fully furnished and ready to enjoy, this home works beautifully as a full-time residence, weekend retreat, or income-producing vacation rental. Its central Marathon location places shopping, dining, marinas, boating, and everyday conveniences nearby, with world-famous Sombrero Beach just a short walk away. Private dockage, weekly rental flexibility, generous storage, and a premier Sombrero Beach location make this canal-front home an exceptional opportunity!

319 Sombrero Beach Road Unit 2, Marathon
$775,000
4 Beds ⋅ 4 Baths ⋅ 620666 MLS
Discover the potential of this spacious CBS home situated on an oversized corner lot in the highly desirable Largo Sound Village neighborhood of Key Largo. Located in an X Flood Zone, this property offers added peace of mind with no flood insurance typically required by lenders. The upper level features a generous living area with 2 bedrooms, 2 bathrooms, an elevator, and two versatile bonus rooms that can be used as an office, hobby room, guest space, or additional living area. The lower level has been thoughtfully configured into two 1-bedroom, 1-bathroom living spaces, providing excellent flexibility for extended family, guests. Residents have the option to join the private Largo Sound Village homeowners park for just $150 annually, which includes access to a boat ramp and waterfront park on Largo Sound with outstanding boating access to both the Atlantic Ocean and Florida Bay. Conveniently located less than an hour from Miami, this property offers endless possibilities in one of Key Largo's most sought-after family-friendly communities.

322 3rd Rd, Key Largo
$599,000
620663 MLS
Great opportunity to own a 60' x 20' deep-water boat slip in the highly sought-after Oceans Edge Resort & Marina on Stock Island. This premier marina offers approximately 8' controlled depth with easy access to both the Atlantic Ocean and the Gulf of Mexico. Owners enjoy access to the resort's exceptional amenities, including six swimming pools, a fitness center, open parking, a fuel dock, dog park, and an on-site waterfront bar and restaurant. The marina also features a professional on-site rental management program, providing an excellent opportunity to generate rental income when the slip is not in use.

5950 Peninsular Ave Unit 674, Stock Island
$4,750,000
6 Beds ⋅ 5 Baths ⋅ 620662 MLS
TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West
$4,750,000
7 Beds ⋅ 5 Baths ⋅ 620661 MLS
TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West
$1,050,000
3 Beds ⋅ 2 Baths ⋅ 608599 MLS
This east facing, solid concrete 3-bedroom, 2-bathroom vacation rental is furnished and designed for both relaxation and aquatic adventure. As you arrive, the paved driveway leads you to a home that is wrapped in the warmth of the Florida sun. This home is in excellent condition and offers a keyless system that ushers you into the living space where the natural light floods through plantation shutters. The living area, with its comfortable furnishings and inviting ambiance, flows seamlessly into a well-appointed dining space and fully equipped kitchen with stainless steel appliances. The metal roof is easy to maintain while the entire home maintains a cool, coastal vibe with its tile flooring throughout. Step outside, and you're greeted by a gated yard that's fenced for privacy, and generously sized, ideal for pets or hosting lively outdoor gatherings. But the true crown jewel of this property is its 60 feet of dockage, complete with a step-down kayak launch and a separate step-down boat launch, offering direct access to the Gulf for endless nautical excursions. For those who live for the water, the property's dock is a dream come true, equipped with power and water, a swim ladder for an effortless dip in the sea, and a fish cleaning station to prepare your fresh catch. Whether you're setting off for a day of fishing or simply basking in the beauty of the Gulf, this home caters to all your seafaring desires. Back on land, an exterior storage shed provides ample space for all your gear, from fishing rods to snorkeling equipment. The large yard, kissed by the morning sun, becomes a sanctuary in the afternoons, offering shade and a cool place to unwind after a day on the water. This home is a fully furnished escape that embodies the spirit of vacation living. With its blend of style, comfort, and waterfront features, this home is ready to be a vacation rental or your own private retreat in the enchanting Florida Keys. Experience direct Gulf access in this Marathon gem

2240 Yellowtail Dr, Marathon
$824,000
3 Beds ⋅ 2 Baths ⋅ 620660 MLS
Seller has this property listed with VRBO. Rental income for 2025 was over $100,000 for the year. Wide water views from this beautiful renovated furnished condo boasting a fantastic floor plan compared to other condos, is attractively decorated with an updated and modern coastal look. Many windows for natural light and a huge L-shaped balcony boasting pocket sliding doors for indoor/outdoor living space. Kitchen has white countertops, newer SS appliances, and a terrific bar/butler's pantry w/ wine refrigerator. Main bedroom opens to the balcony, has large step-in shower and dual sinks. Other features include impact glass windows & doors, natural stone floors, plantation shutters, a barn door, extra storage and covered parking (trucks & pets OK). Full-time residents can homestead this property and receive mail or use as a vacation home with the option to rent through on-site Hawks Cay or personally through rental outlet of your choice (Airbnb, VRBO, VACASA, etc.). Optional membership to resort fitness center, tennis, kids and adult activities. Seller will respond to all offers.

8302 Marina Villas Dr Unit 8302, Duck Key
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 620657 MLS
Rarely available end-unit townhome in the highly coveted, gated community of Indigo Reef! Because Unit 26 is a premium end-unit, it is bathed in abundant natural light and offers an expansive, airy feel that feels more like a private single-family home. This meticulously maintained 3-bedroom, 2.5-bathroom retreat features beautiful, durable LVT flooring throughout the downstairs living areas, complemented by tastefully updated, stylish furniture. Upstairs, you will find low-maintenance, clean tile flooring spanning all three bedrooms. Enjoy gorgeous Gulf views directly from the comfort of both your living room and your private primary suite--each complete with its own covered porch to drink in those spectacular Florida Keys breezes and sunsets. Delight in total peace of mind with mechanical and structural updates already taken care of, including an A/C system that is only 4 years old and a roof valley professionally replaced in 2024. Head down to your deeded 35-foot boat slip--perfect for quick access to world-class fishing and diving. The resort-style amenities are second to none, boasting a magnificent pool surrounded by lush tropical landscaping, a fitness center, and convenient covered parking. Weekly rentals are permitted, and this property is already an established vacation home with an excellent, proven rental history. Whether you are looking for a turnkey investment property, a dream getaway, or a permanent island home, Unit 26 offers the ultimate Florida Keys lifestyle. Schedule your private showing today!

11600 1st Ave Unit 26, Marathon
$1,325,000
2 Beds ⋅ 2 Baths ⋅ 620655 MLS
Deep water Canal front home, on large lot in nice neighborhood, it faces an environmentally protected 10-acre lake across the street affording forever views and privacy. Currently the property has a small wooden dock, and building a new customized concrete or wood T-dock with boat lifts should be possible. If purchasing this property solely for the land, having an existing home by-passes the long wait, costs and uncertainty of going through ROGO. In fact you could probably start building your dream home in months not years (check with the local building department to be sure). However, this waterfront sailboat access home offers a livable, sturdy, well insulated and functional 782 sq ft wood frame, site-built house on concrete columns; finish floor is at Elevation 11.71. The lot is large enough that thousands more square feet of living area can be added to the existing home. If remodeling the house, only the exterior walls are load bearing and all interior walls could be removed leaving an approximate 15'6'' x 44'6'' interior open area, large enough for a Big Game Room, and wide enough to accommodate a regulation sized Billiard Table, but probably too small for a skating rink. Or if you prefer, just knock the whole house down and build your dream home from the ground up, (you'll save money on impact fees, water and sewer hook-up). There are many mature trees providing shade and privacy. The canal is deep enough to accommodate most sailboats. The House is built strong, using 2x12 floor and roof joists 16'' o.c. 2x6 exterior wall studs 16''o.c. 3/4'' plywood on roof and floors. 3/4'' plywood on exterior walls with 5/8'' plywood fastened over it. Impact windows and door. 8' ceiling clearance under house. House could easily be wire lathed and stuccoed, sided with cement board, vinyl siding etc. or even completely enclosed with poured concrete or concrete block construction. Home sold As-Is, owner is a licensed real estate agent.

956 Shaw Dr, Key Largo
$1,099,000
2 Beds ⋅ 3 Baths ⋅ 620653 MLS
One of the greatest luxuries in Key West isn't extravagance--it's finding a home where life feels a little quieter, a little easier, and a little more connected to the island around you. That's exactly what you'll find at 97 Seaside North Court. Tucked inside the often-overlooked gated Seaside Residences community, this light-filled townhome offers something increasingly difficult to find in Key West--privacy, space, and a sense of calm.Natural light pours through eight additional windows found only in some end units, while mature palms and established mahogany trees create a backdrop of green from every room. Whether enjoying a quiet morning coffee, working from home, or entertaining friends, the four opposing balconies welcome the island breezes and connect the home to its peaceful surroundings. Built with solid masonry construction, impact-rated windows and doors, 16 solar panels paired with a Generac battery storage system, and an elevator that services every floor, this home was designed with comfort, durability, and resilience in mind. The ground-level screened enclosure with a garden offers exceptional flexibility as a home gym, yoga studio, covered dining area, or entertaining space.Residents enjoy a secure, well-maintained community with resort-style amenities including a swimming pool and fitness center, all within easy reach of Smathers Beach, Key West's longest stretch of sandy beach. Built in 2005 on a larger-than-average lot, with 1,824 square feet of air-conditioned living space, three full baths, an outdoor shower, garage, and even a rooftop stargazing deck. 97 Seaside Court North is now offered at an exceptional value within Seaside Residences--an opportunity to enjoy one of Key West's most desirable gated communities without compromising on space, quality, or lifestyle.

97 Seaside N, Key West
$374,000
2 Beds ⋅ 2 Baths ⋅ 620635 MLS
Turn key furnished condo in Islamorada! This beautifully appointed 2 bedroom, 2 bath condo features an open floor plan, abundant natural light and a rare balcony. Remodeled unit which includes impact windows and doors, crown molding, wood engineered laminate flooring, and a full size washer and dryer. The open-chef's kitchen boasts a spacious breakfast bar, extra tall hardwood cabinets, granite counter tops and backsplash, under-cabinet and recessed lighting, a dishwasher, and a newer refrigerator in 2022. The primary ensuite offers a walk-in closet with custom shelving. AC was replaced in 2023, Metal roof installed in 2024. The complex offers a heated swimming pool, and clubhouse. Founder's Park, Islamorada's Community Park, is on the same island. Admission into the park is free for Islamorada residents. The park offers an Olympic size swimming pool, tennis courts, pickleball courts, ball fields, marina, beach and boat ramp. Plantation Villas is close to Plantation Key Elementary School and Coral Shores High School, grocery store, shopping, restaurants and movie theater.

40 High Point Rd Unit 703, Islamorada
$195,000
620651 MLS
Build your dream home in the desirable Twin Lakes subdivision! This vacant homesite is nestled within an established residential community and offers a fantastic opportunity to create a beautiful home. Conveniently located near shopping, restaurants, dive shops, marinas, and local entertainment, you'll enjoy easy access to everything that makes the Florida Keys lifestyle so desirable.

657 Colson Dr, Key Largo
$540,000
3 Beds ⋅ 2 Baths ⋅ 620650 MLS
Spacious Key Largo Living! Welcome to this well-maintained double-wide mobile home located in a desirable Key Largo neighborhood. Offering a 3 bedroom and 2 bathroom home featuring a spacious primary bathroom and large closets in every room along with an open floor plan with a generously sized kitchen and living area, creating a comfortable space for everyday living and entertaining. Step outside to an impressive backyard designed for enjoying the Florida Keys lifestyle with outdoor kitchen and a spacious area. Conveniently located near delicious restaurants, shopping, and everyday conveniences. You will appreciate the close proximity to the public boat ramp at John Pennekamp Coral Reef State Park, providing easy access to world-class boating, fishing, diving, snorkeling, and all the recreational opportunities the Florida Keys are known for.

915 Plantation Rd, Key Largo
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 620649 MLS
Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

87851 Old Hwy Unit P3, Islamorada
$660,000
2 Beds ⋅ 2 Baths ⋅ 620648 MLS
This beautifully updated 2-bedroom, 2-bath D-model at Ocean Pointe is an exceptional opportunity. Featuring two private balconies-a rare and highly sought-after feature. You'll enjoy extra outdoor living space along with beautiful ocean views, tropical breezes, and breathtaking Keys sunrises. Offered fully furnished and turnkey, this condo is ideal as a vacation home, income-producing investment, or both. The open floor plan features an updated kitchen, granite countertops, stainless steel appliances, and a full-size washer and dryer. Both bathrooms have been renovated, and impact-resistant windows and sliding glass doors provide added security and peace of mind. The unit also boasts a strong history of successful short-term rentals. Ocean Pointe is a gated, resort-style waterfront community that allows nightly rentals with no restrictions on owner usage or property management. Amenities include a protected marina with direct ocean access, boat ramp, dry boat storage, heated Jr. Olympic-size pool, 14-person spa, pool bar, oceanfront café and lounge, private beach, boardwalk, observation pier, lighted pickleball and tennis courts, and 24-hour security. Whether you're boating to the reef, fishing, diving, relaxing by the pool, or simply taking in the incredible ocean views, this exceptional condo offers the perfect combination of luxury, flexibility, and the ultimate Florida Keys lifestyle.

500 Burton Dr Unit 4208, Tavernier
$450,000
2 Beds ⋅ 2 Baths ⋅ 620647 MLS
2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

3312 N Northside Dr Unit 607, Key West
$2,200,000
3 Beds ⋅ 2 Baths ⋅ 620645 MLS
Welcome to 273 W Seaview Dr, a private retreat in the heart of Duck Key, home to Hawks Cay Resort and some of the best boating and fishing waters in the Florida Keys. Built in 2020 on a 15,247 SF lot, this concrete home is elevated on concrete pilings and engineered to withstand hurricane force winds, with impact windows and doors throughout for lasting peace of mind and favorable insurance considerations. The main living level is reached by two separate entries, a front stairway and a rear balcony, and offers 3 bedrooms, 2 full bathrooms, and an in unit washer and dryer across a bright, thoughtfully finished floor plan with custom exterior finishes, drywall interiors, a flat clay tile roof, and forced air cooling. Below, the ground level provides extensive covered parking and storage space, along with a shaded open porch, ideal for boat gear or beach equipment. Outdoors, the property has been extensively upgraded. The owner just completed a brand new 288 SF pool with a paver deck, and recently added a paver brick driveway and multiple brick and tile patio areas for entertaining. The yard is enclosed with wrought iron fencing and gates for added privacy. A standout feature is the detached 2,046 SF garage on the south side of the property, built in 2023 with room for up to nine vehicles, a rare find for boat owners, car collectors, or anyone in need of serious storage space in the Keys. This property suits a vacation home or full time residence equally well. Duck Key offers a welcoming, close knit island community along with excellent public, private, and charter schools nearby. Enjoy the Florida Keys lifestyle: no state income tax, roughly 230 sunny days a year, and some of the most stunning beaches, fishing, and boating waters in the country. Live securely, comfortably, and luxuriously in paradise, and schedule your private showing today.

273 W Seaview Dr, Duck Key
$739,000
2 Beds ⋅ 2 Baths ⋅ 620643 MLS
Two Oceanfront Balconies comes with this updated D model at Ocean Pointe. Remarkable Kitchen remodeling job , both baths too with Impact windows and sliders. Wow factor Ocean Views with all the amenities owners and guest want. Jr. Olympic pool with 14 person Spa, Pool Bar, Direct ocean access Marina with dry boat storage. Lighted Tennis & Pickle ball courts. Oceanfront Cafe & Lounge. No restrictions on owners use and No restrictions on who an owners uses to manage their property. This Condo is being sold fully furnished with Housewares. Use it as much as you like and rent it out when its not in use , it's the owners choice.

500 Burton Dr Unit 4206, Tavernier
$1,139,000
3 Beds ⋅ 2 Baths ⋅ 620641 MLS
Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

1708 South Street, Key West
$259,000
620638 MLS
Live aboard boat slip offered in Sombrero Marina is 50' long accommodating up to 55' length boat; includes one allocated parking space. With beautiful views from your boat, enjoy all that Marathon has to offer. This slip is centrally located, and nearby you can play golf, go fishing and kayaking, spend a day at the beach, and more! End your days with a meal or a drink and some entertainment at The Dockside Bar and Grill located on premises. The Marina also has additional showers, restroom, and laundry available for use. Along with a dockmaster who can help with renting your slip out for additional income while you are not there. Current rental income for this slip size is $1,600/mo. Buyer is responsible for paying a 6% transfer fee to the state of Florida and there is a lease fee for the bay bottom. Don't miss out on this opportunity to live or invest in the Florida Keys at a low cost. *Boat is not sold with the slip- but owner is selling separately*

35 Sombrero Blvd Unit B31, Marathon
$549,500
1 Beds ⋅ 1 Baths ⋅ 620633 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 715, Islamorada
$600,000
2 Beds ⋅ 3 Baths ⋅ 620630 MLS
Don't miss this remodeled property with cheerful tropical touches that brighten every stay in the Florida Keys. This spacious two-story townhome offers 930 SF square of living space, approximately 30 additional SF than the typical 2 bedroom, 2 ½ bathroom properties in the area, making it an exceptional choice for a vacation getaway, investment property, or both. The home features a bright, open-concept first floor plan which includes a well-appointed kitchen equipped to satisfy even the pickiest chef, an expanded dining area, a comfortable living room, a convenient half bath, and a laundry closet with a washer and dryer. Upstairs the main bedroom with cathedral ceilings has an ensuite bathroom and porch, a second bedroom and a second bathroom have entrances on the hall. Enjoy the Florida Keys lifestyle from either the upstairs or downstairs private porches, where you can sip your morning coffee or unwind with a glass of wine while overlooking the sports fields and children's recreation area, which is currently being transformed into a water park. The enclosed backyard adds even more outdoor enjoyment and privacy. Centrally located in the heart of the Florida Keys on the grounds of Hawks Cay Resort, this townhome is within walking distance of restaurants, marina access, and a variety of water activities. Whether you're looking for a personal retreat, a vacation rental with excellent income potential, or the perfect combination of both, this property is ready to impress. Schedule your private showing today and discover all it has to offer!

7103 Harbor Village Dr, Duck Key
$549,500
1 Beds ⋅ 1 Baths ⋅ 620629 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This double queen bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 716, Islamorada
$1,059,000
2 Beds ⋅ 2 Baths ⋅ 620624 MLS
A true Marathon canal-front classic, thoughtfully renovated for easy Keys living. This updated waterfront home offers 75 feet of dockage, a solar-powered boat lift, and no-bridge access to Boot Key Harbor and the Atlantic Ocean, making it an ideal setup for boaters, anglers, and anyone ready to enjoy the Florida Keys lifestyle. Upstairs, the bright open-concept living area features 2 bedrooms and 2 full bathrooms, new flooring, a refreshed kitchen with new appliances, and updated bathrooms with new vanities and fixtures. Impact windows and doors provide added peace of mind, while fresh interior and exterior paint, a new upstairs A/C system, and new ductwork enhance the home's comfort and functionality. The spacious lower level offers the flexible storage space every Keys owner appreciates--perfect for fishing gear, diving equipment, tools, paddleboards, bikes, and everything that comes with life on the water. Outdoor spaces are designed for relaxing, entertaining, and low-maintenance island living. Enjoy a rethatched tiki hut, an open patio finished with vinyl wood-plank decking, a new aluminum staircase and railing, a remote-controlled fence, a fenced backyard, and an irrigation system. Set on a 7,500-square-foot lot, the property offers plenty of room for boat and RV storage, additional parking, and everyday convenience. The home is being offered with furnishings negotiable, giving buyers the flexibility to create a turn-key retreat or personalize the space to their own style. Centrally located near Marathon restaurants, shopping, Sombrero Beach, Fishermen's Community Hospital, and all the best of the Middle Keys, the property works beautifully as a year-round residence, weekend getaway, or rental investment opportunity. With seven-day minimum rentals allowed, strong boating features, generous outdoor space, and thoughtful updates throughout, this canal-front home offers the flexibility, comfort, and Keys lifestyle buyers are looking for.

305 50th St, Marathon
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 620623 MLS
Single Family Residential Key Largo property with canal view. With FEMA MAP actualized and currently active since 02/18/2005. C3 Kitchen updated, bathrooms updated. Satisfactory condition for the age and type of structure. With canal frontage with dockage and inmediate open water access. Three bedrooms and two bathrooms and covered rear deck with canal view.

119 Peace Ave, Tavernier
$300,000
620621 MLS
50' X 22' boat slip at the World famous Lor E Lei marina. Excellent in-town location, you know you're going to boat over here anyway so you might as well tie up for the night! Enjoy the sunsets, unwind, Uber home, or use for your fishing business, so many possibilities. A rare find.

96 Madeira Rd Unit # 10, Islamorada