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$16,000,000
4 Beds 3 Baths A12069701 MLS
Own an entire private island in the Florida Keys, just ¼ mile offshore from Marathon! East Sister Rock Island offers extraordinary privacy surrounded by turquoise waters, yet is only minutes from the mainland. The property encompasses approx. 6.5 acres, including approx. 5.8 acres of surrounding seabed, creating an exceptional marine setting for snorkeling, swimming, kayaking, paddleboarding, fishing and watersports. The beautifully updated 3-bedroom, 2-bath main residence and detached guest house offer over 5,000 total SF of living and entertaining space. Recent renovations include an updated kitchen with gorgeous countertops and modern finishes. A 12-ft-wide wraparound veranda captures panoramic water views, sunrises and spectacular Keys sunsets. Amenities include a waterfront pool and spa, tropical landscaping, outdoor entertaining areas, and a 100-ft deep-water dock. Self-sufficient infrastructure includes solar and wind power, battery storage, backup generator, desalination system and freshwater cistern capacity. Private helipad provides additional access. Seller is open to select Joint Venture opportunities.

1 E Sister Rck Island, Marathon

$27,500,000
9 Beds 10 Baths A12067078 MLS
One of the Florida Keys' most significant newly completed trophy estates, now making its market debut fully completed and never occupied. This one-of-a-kind waterfront residence offers 18,736 SF of interior living space and more than 29,000 SF under roof on approximately 1.72 acres with 200 feet of ocean frontage. A property of this scale, quality and waterfront presence has become exceptionally difficult to replicate under today's development environment, making it as irreplaceable as it is exceptional. Designed for the most discerning owners, the estate features 9 bedrooms, 9.5 bathrooms, a detached guest residence, private elevator, 9-car garage, and an extraordinary indoor-outdoor living experience highlighted by a newly completed 100-foot infinity-edge pool, separate beach-entry pool, and expansive waterfront terraces, unveiling an outdoor environment never before presented to the market. Included in the offering is a deeded 60-foot boat slip at a nearby marina, located approximately two minutes from the residence, providing immediate access to world-class boating and fishing. Marathon International Airport is approximately five minutes away, allowing seamless arrival by private aircraft. Contemporary architecture, exceptional craftsmanship, absolute privacy, and one of the most exclusive waterfront settings in the Florida Keys define this truly irreplaceable trophy estate. One of the Florida Keys' most significant newly completed trophy estates, presented fully completed and never occupied. Situated on approximately 1.72 acres with 200 feet of ocean frontage, this extraordinary residence represents a level of scale, quality and waterfront presence that has become exceptionally difficult to replicate under today's development environment in the Florida Keys.Offering approximately 18,736 square feet of interior living space and more than 29,000 square feet under roof, the residence has been thoughtfully designed to deliver an exceptional indoor-outdoor lifestyle while maintaining the highest standards of privacy, craftsmanship and contemporary architecture.Highlights include 9 bedrooms, 9.5 bathrooms, a detached guest residence, private elevator, garage with nine doors, a spectacular 100-foot infinity-edge pool, beach-entry pool and expansive waterfront terraces designed for entertaining and enjoying the Florida Keys lifestyle.The property also includes a boat slip at nearby Marina, located approximately two minutes from the residence, while Marathon International Airport is approximately five minutes away, offering exceptional convenience for owners and guests arriving by private aircraft.Property Highlights• Newly completed and never occupied• Approximately 18,736 SF interior living area• More than 29,000 SF under roof• Approximately 1.72-acre waterfront estate• Approximately 200 feet of ocean frontage• Detached guest residence• Private elevator• Garage with nine doors• 100-foot infinity-edge pool• Beach-entry pool• Boat slip included• Marathon International Airport approximately five minutes away• Contemporary architecture• Exceptional craftsmanship• Designed for privacy, entertaining and the Florida Keys lifestyleAvailable Upon Request• Floor Plans• Survey• Property Presentation• Professional Photography• Cinematic Video• Drone Footage• Additional Property DocumentationPlease contact the Listing Agent for additional information, property presentation, supplemental documentation and private showing arrangements.This is not simply a luxury residence—it is a trophy asset in a market where opportunities to create comparable waterfront estates have become exceptionally limited

2405 Coco Plum Drive, Marathon

$1,850,000
3 Beds 3 Baths A12061248 MLS
Rare Florida Keys boater's paradise on the golf course! This Marathon waterfront gem offers deep, wide canal access with direct routes to the Gulf and Atlantic, plus a 100-ft composite dock outfitted with a fish cleaning station, 12,000 lb boat lift, and 5,000 lb davit — bring the yacht, the sportfish, and all the toys. Enjoy front-row views of the Florida Keys Country Club golf course, just minutes from Sombrero Beach, the crown jewel of Marathon's beaches.Outdoor living is unmatched: a heated 26' x 13' pool, screened porch, fully equipped outdoor kitchen, and outdoor shower create the ultimate entertaining setup year-round. The oversized 6" reinforced concrete driveway with rebar is engineered to handle heavy equipment, trailers, or yacht storage with ease.Inside, impact windows and doors provide peace of mind and efficiency throughout. A convenient downstairs half kitchen adds flexibility for guests or multigenerational living, complemented by a legal downstairs enclosure — rare, permitted living space that adds real value.Golf course views, beach proximity, and true yacht-ready waterfront — this Keys property checks every box. Schedule your private showing today!

2557 Sombrero Boulevard, Marathon

$899,000
3 Beds 3 Baths A12057185 MLS
Welcome to your dream escape in the Florida Keys. This spacious 3-bedroom, 3-bath oceanfront townhome in the highly sought-after Bonefish Yacht Club Townhomes offer the perfect blend of coastal and laid-back island living. Set within an intimate marina community of just 34 residences nestled among lush tropical landscaping, this home feels both private and resort-like and also conveys with a deeded boat slip in Bonefish Marina (B-34). Enter through the foyer and up to two levels of open living, with 1,769 sq. ft. thoughtfully oriented for comfort, water views, and easy entertaining. The chef's kitchen features generous cabinetry, ample counter space, and an inviting eat-in island that flows seamlessly into the main living area, where sliding glass doors open to a spacious waterfront balcony overlooking the Key Colony Channel. The primary suite is a serene retreat with its own private balcony, walk-in closet, and ensuite bath, while two additional bedrooms offer flexible space for guests, family, or a home office, each with access to well-appointed baths. On the ground level, a private garage and generous storage provide the perfect place for fishing gear, paddleboards, and all your Keys lifestyle essentials. Residents enjoy a temperature-controlled pool, expansive sun deck, tiki lounge with wet bar, tennis and pickleball courts, and a private sandy beach. New roof in 2023 and new A/C in 25 with 12 year warranty.

95 Coco Plum Dr & Slip B-34 Unit 4, Marathon

$3,650,000
4 Beds 4 Baths A12056681 MLS
Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key with expansive water views, white sand beach, and a true resort-style experience in the Florida Keys. An exceptional investment opportunity, Casa Feliz is a strong producing vacation rental with rental history and future bookings already in place. Set on over 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, this exceptional estate is designed for both relaxation and entertaining. An observation pier invites kayaking, paddleboarding, fishing, and endless enjoyment of marine life, while the unique orientation captures both breathtaking sunrise and sunset views over the water, a rare and coveted feature in the Keys. Outdoor living is elevated with a resort-style saltwater pool featuring cascading waterfalls, spillover spa, and fully equipped poolside cabana complete with wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit create the ultimate setting for entertaining or unwinding beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was thoughtfully redesigned to maximize sweeping ocean views from nearly every room. Offering four custom bedroom suites, each with private en-suite bath, the home comfortably accommodates guests in luxury.

58652 Overseas Highway, Marathon

$7,495,000
5 Beds 4 Baths A12060805 MLS
Nestled on the exclusive private gated island of Sunrise Isles in Marathon, Florida Keys, this magnificent 2019 oceanfront estate redefines luxury living. One of only 20 residences within this secure island enclave, it offers an exceptional blend of privacy and the serene beauty of the Keys.This exquisite 5-bedroom, 4-bathroom residence spans approximately 3,500 square feet of crafted living space designed to capture breathtaking ocean views. The open-concept single-level floor plan seamlessly connects gourmet kitchen, dining, and living areas, while floor-to-ceiling windows flood the home with natural light. Each bedroom features an en-suite bathroom, while the primary suite offers panoramic ocean views and a spa-inspired bath.Impact-resistant sliding glass doors open to approximately 700 square feet of covered terrace, creating exceptional indoor-outdoor living. Set on over 32,000 square feet of waterfront property, the estate boasts 110 feet of sandy beachfront and an additional 110 feet of protected canal dockage with two custom boat lifts and an L-shaped synthetic dock, providing effortless access to open water.Outdoor amenities include a resort-style pool with water features, creating the perfect island retreat for entertaining or relaxing. Just ½ mile from Sombrero Beach and minutes from shopping, dining, and Marathon Airport, this extraordinary Sunrise Isles estate presents a rare opportunity to own one of the Florida Keys' finest luxury oceanfront residences.

108 Sunrise Drive, Marathon

$898,000
2 Beds 2 Baths A12056663 MLS
The first thing you'll notice isn't the vaulted wood ceilings or the tropical landscaping. It's the feeling that you've already arrived home.Located in one of Marathon's most sought-after neighborhoods, just 0.3 miles from Sombrero Beach, this elevated 2-bedroom, 2-bath home offers 1,458 sq. ft. of comfortable living designed for the Florida Keys lifestyle. Inside, you'll find beautiful tongue-and-groove wood ceilings, tile flooring throughout, spacious bedrooms and baths, and an upstairs laundry room. Two additional conforming downstairs rooms provide flexible space for a home office, studio, gym, or hobbies.Outside, your own private tropical retreat awaits with mature landscaping, fruit trees, an herb garden, multiple outdoor living spaces, a custom covered bar and grilling area, a cozy fire pit, and room to add a pool. Covered parking provides plenty of space for vehicles, boats, and all the toys.Built with durable combination construction and a tile roof, with annual homeowners, wind, and flood insurance totaling approximately $8,810.Eligible buyers may qualify for Florida's Hometown Heroes Program. Contact us for a list of participating lenders and program information.

422 Calle Limon, Marathon

$700,000
4 Beds 2 Baths A12055919 MLS
Discover an incredible waterfront investment opportunity in the heart of the Florida Keys! Located in the desirable Grassy Key area of Marathon, this property offers the perfect blend of lifestyle and investment potential. The property comes fully furnished, making it even more convenient and ready to enjoy!Just minutes from world-class fishing, boating, waterfront dining, Sombrero Beach, Curry Hammock State Park, Dolphin Research Center, and all the best attractions the Keys have to offer. Whether you're looking for a family vacation home, a high-performing Airbnb investment, or your next luxury development project, this property checks every box. Includes APPROVED PLANS for a stunning modern waterfront residence, saving you valuable time! (5 bedroom / 5 Bathroom with Pool)Enjoy direct ocean access from your 22-foot private dock, making it ideal for boating enthusiasts. Situated on a peaceful canal-front lot in one of the Keys' most active development areas, this is a rare chance to build a luxury home in a market with strong demand.Comparable newly built waterfront homes in the area have achieved values of $3.8 million and higher, presenting an exceptional opportunity for significant return on investment. Don't miss your chance to own a premier waterfront property with endless potential in one of Florida's most sought-after destinations.

59733 Paradise Place, Marathon

$2,100,000
4 Beds 2 Baths B26053283 MLS Sombrero Beach BLDG.
4/2 renovated waterfront home boasts private pool-new cutting edge technology (heater/chiller) for your enjoyment all year long, boat slip for vessels up to 50 ft. & parking! A TikiHut custom bar for making and enjoying libations al fresco. A tropical tree shaded fire pit area only steps from Award Winning Sombrero Beach. Mature vegetation that produces delicious coconuts, mouth watering mangoes & sea grapes for artisanal jelly production. A renovated Kitchen ideal for a cook's delight that features state of the art Cafe Appliances for all your culinary creations. This location is private, enclosed and parcel is ideal for expansion. Hurricane Impact Glass for safety. Home has been a successful vacation rental and is now available furnished and turn key. Location! Location! Location!

309 W Calzada De Bougainvillea, Marathon

$739,500
2 Beds 2 Baths A12050864 MLS
Waterfront Paradise with Saltwater Canal & Quick Ocean AccessExperience the best of coastal living in this exceptional waterfront property, perfectly situated on a deep saltwater canal with quick, no-bridge access to the open ocean. Whether you're an avid boater, fisherman, or simply love life on the water, this home offers the ideal setting for your waterfront lifestyle.Step outside to your private dock, ready to accommodate your boat for effortless days on the water. Enjoy peaceful canal views, breathtaking sunsets, and the convenience of being just minutes from the ocean.Inside, you'll find a bright and inviting living space designed for both comfort and entertaining. Large windows and open living areas showcase the beautiful waterfront setting, while spacious indoor and outdoor spaces provide plenty of room to relax with family and friends.*** BOAT LIFT HAS BEEN REMOVED AS OF THIS POST ***

425 89th Street Unit Ocean, Marathon

$905,000
2 Beds 2 Baths A11986521 MLS
Welcome to your slice of paradise in Marathon, where island living meets exceptional investment potential. Tucked at the end of a quiet street in mid-town, this upgraded property captures sweeping Atlantic Ocean views and boasts a strong short-term rental history - ideal as both a private retreat and income-producing asset. Expansive parking accommodates boats, multiple vehicles, RVs, and even an EV charging station, a rare find in the Keys. Lush landscaping with palms, raised garden beds, and automated irrigation creates a true tropical oasis with effortless upkeep. Inside, the updated kitchen features new appliances (2021), a stylish island, refreshed countertops and backsplash, and a functional pantry, perfect for entertaining. Thoughtful upgrades include Spanish tile work, blackout shades, updated ceiling fans, and refinished custom woodwork. Enjoy ocean views from the primary suite’s walk-in shower or unwind in the jetted whirlpool tub. Designed for both durability and efficiency, the home includes hurricane-impact windows and doors, upgraded insulation, a new central air system (2021) with A/C compressor (2026), refurbished roof (2021), a dryer duct fan, and numerous system upgrades. Outdoor living shines with a wraparound porch, outdoor shower, privacy wall, and garden shed. Whether you're seeking a full-time residence, vacation escape, or high-performing rental, this Marathon gem delivers on lifestyle, function, and location.

6501 Oceanview Avenue, Marathon

$464,950
2 Beds 2 Baths A12027597 MLS
Welcome to one of the most compelling lifestyle opportunities in the Florida Keys. Perfectly positioned within one of Marathon’s most vibrant & amenity rich, waterfront communities, this beautifully appointed 2 bedroom, 2 bath residence offers the ideal blend of island living, convenience, and value; without the traditional Florida Keys price tag. From the moment you arrive, the setting feels elevated, vibrant and unmistakably island inspired. Ideally situated within the community offering beautiful open water views, this residence enjoys a premier location with sweeping vistas from the top-level balcony, perfect for morning coffee or sunset cocktails. Inside, the light-filled interior features a stylish granite and stainless-steel kitchen, central air, interior laundry, and thoughtfully designed living spaces. Enjoy covered parking, under-home space, and easy access to the dock and waterfront gathering areas. Resort-style amenities include a beautiful pool, kayak launch, fire pits, outdoor kitchen, sun deck, and community lounge spaces. Walk, bike, or golf cart to waterfront restaurants, bars, live music, kayak and jet ski rentals, the iconic Seven Mile Bridge, and the scenic pedestrian bridge.$22,500 in secured rental income already in place for 2027. One of the most affordable newer construction opportunities in the Keys offering this level of lifestyle, amenities, and location.Please note: ownership is subject to monthly lot rent.

101 11th Street Ocean, Unit lot 13, Marathon

$1,450,000
3 Beds 2 Baths A12009194 MLS
Your Florida Keys Oasis is Here! Welcome to your slice of paradise, where turquoise waters, warm breezes, and endless sunshine create the lifestyle you've always dreamed of. This home offers all the amenities and easy ocean access you need to fully embrace the Florida Keys way of life, on one of the only Gulf Side flow through canals in the Middle Keys. CBS construction on 60 feet of waterfront property with 40 feet of composite dockage and 14K lb boatlift. Enjoy immediate, direct access to the Gulf of Mexico, just minutes to Sombrero Beach, Marathon Jet Center, restaurants, shopping, and world-class diving and fishing. This property is not just a dream home it's a fantastic vacation rental with 7-day minimums and current rentals in place. Don't miss this prime investment opportunity!

2133 Yellowtail Drive, Marathon

$29,500,000
10 Beds 13 Baths A11977067 MLS
A Private Waterfront Estate at The Edge of the Gulf of America. Set on 3 secluded acres+/- along one of the mostprotected stretches of the Gulf of America, 57783 Morton Street is a newly completed estate of rare scale, privacy,and modern coastal design. Surrounded by water, sandscape, and tidal ponds alive with marine life, the propertyoffers more than 200’+/- of direct water frontage and uninterrupted views across the open Gulf. Completed in2025 by builder and developer Alderuccio Corporation, this resilient, elevated retreat is constructed entirely ofconcrete and impact glass and is designed for effortless indoor–outdoor living. With three distinct finished livingspaces totaling approximately 10,000 SF+/-, the estate functions as a private resort offering privacy, recreation,and exceptional access to the best of the Florida Keys.

57783 Morton Street, Marathon

$2,000,000
A11872082 MLS
This rare 9-acre waterfront parcel is located on secluded Boot Key, a largely undeveloped island within the city limits of Marathon in the heart of the Florida Keys. Accessible only by boat since the drawbridge connection to Vaca Key was removed in 2010, the property offers privacy, natural beauty, and exceptional potential. Zoned mixed use, it includes 24 existing docks, a building and radio towers from a former local radio station, and portions of the land currently leased to fishermen. There are no active utilities on site, making it a true blank canvas for future development or a private retreat. With motivated ownership and flexible possibilities, this is a unique opportunity to secure a piece of the Florida Keys.

1 Boot Key Road, Marathon

$1,100,000
A11889293 MLS
FOR SALE OR LEASE COMMERCIAL CONDOMINIUMSuite Size: ± 4,139 SFUnits are divisible and contain separate entrances• Unit 16: ± 700 SF• Unit 17: ± 3,440 SFZoning: MU - Mixed Use CommercialParking: 14 Spaces @ 1: 300 SFTotal Building Parking: 60 SpacesBuilding Area: ± 17,095 SFYear Built: 1978Property Taxes: $1,050 per yearOperating Expenses: $1,781.00 per month• Fully improved medical suite adaptable for a variety of medical specialties• Multiple exam rooms, lab & diagnostic rooms, offices, conference rooms, staff and guest areas• Suitable for professional offices and retail services in a high-traffic business location• Well-maintained by current ownership• Ready for immediate operation with only cosmetic improvements or minor changes, avoiding increasedmaterial costs and permitting delays

Marathon

$500,000
A11947574 MLS
Excellent opportunity to own a two-story duplex in the heart of Marathon. Each unit offers 1 bedroom and 1 bathroom, situated on a generous 10,591 SF lot. Ideal for redevelopment, expansion, or construction of a larger duplex, subject to local approvals. Prime location near popular restaurants, Sombrero Beach, Marathon Sandbar, Florida Keys Marathon Airport, and Curry Hammock State Park. A versatile property with strong upside potential in the Middle Keys.Verified with the City of Marathon: The property is zoned Residential-Medium, so setbacks are 20ft from the front and back and 5ft from the sides, with a requirement of 20% open space, and the building has a height limit of 42ft. No Rogo points needed for building.

329 63rd Court Unit Gulf, Marathon

$1,999,000
4 Beds 3 Baths A12036239 MLS
Set within Coco Plum area of Marathon, this waterfront residence presents a rare opportunity to own a premier canal-front property in the Florida Keys. Offering direct boating access to open water, this home embodies the ultimate island lifestyle for the avid boater and coastal enthusiast. The property features a desirable waterfront setting, elevated construction, and an exceptional layout that provides the perfect bones to transform it into your dream home. With endless potential for customization, this residence is ideal for creating a modern coastal retreat or luxury Keys estate tailored to your vision. Located on a quiet, highly sought-after street, it offers both privacy and convenience, just minutes from beaches, dining, and all that Marathon has.

2100 Avenue H, Marathon

$405,000
A11728506 MLS
Rare opportunity to own an oversized half-acre (21,808 SF) dry lot in the highly desirable Coco Plum neighborhood of Marathon. Ideally located directly across from Coco Plum Beach, this oversized parcel offers beautiful ocean views and endless possibilities in one of the Florida Keys’ most sought-after locations. Enjoy easy access to the beach, boating, fishing, dining, and all that Marathon has to offer. Large lots in this location are becoming increasingly difficult to find. Whether you’re looking to secure a future investment or explore development opportunities, this property offers a unique chance to own a prime piece of the Florida Keys lifestyle. Wake up to breathtaking views, salty breezes, and quiet serenity. Don’t miss this rare chance to build steps from the beach with panoramic water views. Buyer to verify all building and development requirements with the City of Marathon.

300 Coco Plum, Marathon

$1,095,000
3 Beds 3 Baths A11974801 MLS
**Stunning Marathon Florida Waterfront Home Allowing Weekly Rentals With IMMEDIATE Income ** Welcome to your dream coastal escape! This exceptional 3-bedroom, 3-bath, FURNISHED townhome offers breathtaking rooftop views of the sparkling Gulf of Mexico and Vaca Cut, providing the perfect backdrop for a relaxed lifestyle by the sea. Experience luxurious living with two hot tubs -- one thoughtfully located on the ground floor for easy access, and the other perched atop the rooftop, ideal for soaking under the stars or admiring spectacular sunsets and boats cruising through the seas. This three-story townhome is located just a stone's throw away from the beautiful Key Colony Beach, so you can enjoy sun-soaked days on the shoreline and enjoy dining on the Ocean or shopping in the eclectic nearby stores. Take a Kayak Ride right from the community dock or soak in the waterside pool. Don't miss the opportunity to own this slice of paradise, where coastal charm meets modern comfort. Whether you're looking for a primary residence, a vacation getaway, or an investment property, this home is sure to exceed your expectations! See it in person and start imagining your life in this Turnkey waterfront oasis.

Marathon

$414,000
1 Beds 1 Baths A11975802 MLS
This beautifully updated waterfront condominium captures the essence of the Florida Keys lifestyle along a serene 200-ft-wide deep-water canal with 6+ ft control depth and no bridge clearance restrictions—The residence includes an assigned boat slip accommodating vessels up to approximately 43 ft, providing effortless access to open water. Hurricane-panel-protected sliding glass doors fill the home with natural light and open to a private waterfront balcony, creating seamless indoor-outdoor living for morning coffee or evening relaxation. Inside, modern finishes and a clean coastal design, a turnkey presentation. The property offers flexibility as a primary residence, second home, or income-producing vacation rental. Short-term rentals are permitted with a 7-night minimum. Community amenities include a heated pool, waterfront tiki huts with grilling areas, boat trailer parking, and maintained dockage—perfect for owners and guests. Ideally located in the Middle Keys, the property is minutes from Marathon Airport and about 40 miles from both Key West and Miami via US-1, offering convenient access while preserving a peaceful island setting. Coco Plum Beach is less than a mile away for kayaking, shoreline walks, and unforgettable sunsets. Boat slip fee is $500 annually and has been paid for 2026. Showings accommodated around current bookings; please provide notice when possible. Offered furnished and equipped; a short exclusion list of personal items is available upon request.

105 Avenue D Unit 113, Marathon