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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
$629,000
3 Beds ⋅ 2 Baths ⋅ A12063421 MLS ⋅ Puerta Del Sol BLDG.
Charming 3-bedroom, 2-bath elevated home in the heart of Marathon. This beautifully maintained property captures the relaxed island lifestyle with open living spaces, vaulted ceilings, and coastal finishes throughout. Enjoy outdoor living under the covered entertaining area complete with lounge seating, dining space, bar, and grill. The low-maintenance yard features tropical landscaping, plenty of parking, and room for a boat or trailer. Perfect as a vacation home or full-time residence, located minutes from beaches, marinas, and local dining. Live the Keys dream!

230 66th Street Unit Ocean, 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
$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
$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
$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
$1,499,999
4 Beds ⋅ 3 Baths ⋅ A11973480 MLS
Beautifully situated in iconic Sombrero Beach, this open-water retreat showcases breathtaking ocean views with ever-changing shades of turquoise and deep blue. Offering 4 bedrooms and 3 bathrooms, the home is filled with charm and coastal character. A covered lanai provides the perfect setting for outdoor dining and relaxation, while the upstairs sun deck invites you to soak in sweeping water views and refreshing sea breezes. The spacious outdoor area is ideal for entertaining or simply unwinding in your own private oasis.Located in a golf-cart-friendly, you can easily bike or walk to the grocery store and several of Marathon’s top restaurants—making this one of the most desirable areas in the Keys. Just a quarter of a mile away, you’ll also find a local golf course, adding even more recreational appeal right at your doorstep. Enjoy community gatherings at Sombrero Beach, including the famous Fourth of July celebration and fireworks. Weekly vacation rentals are permitted, offering excellent flexibility and income potential. Whether you're looking for a luxury vacation retreat, an income-producing property, or a full-time island residence, this is more than a home — it’s a lifestyle.A rare opportunity in one of Marathon’s most sought-after neighborhoods, where privacy, panoramic ocean views, nearby golf, and the relaxed island lifestyle blend seamlessly. No Association.

227 Sombrero Beach Road, Marathon
$3,475,000
5 Beds ⋅ 6 Baths ⋅ A11886591 MLS ⋅ Oasis By The Bay BLDG.
Luxury 5-Bedroom Waterfront Home in the Florida Keys in Marathon, Florida! This stunning 5-bedroom, 5.5-bath residence sits on the desirable bay side, offering breathtaking water views and endless sunsets. Perfectly designed for comfort and entertaining, the home features an open-concept living space, gourmet kitchen, and spacious bedrooms with en-suite baths for ultimate privacy. Step outside to enjoy resort-style living with a sparkling pool, expansive patio, and direct access to the bay. Boating enthusiasts will love the assigned dock slip,making days on the water effortless. Whether you're seeking a full-time residence, vacation getaway, orinvestment property, this home delivers the ultimate Keys lifestyle—luxury, relaxation, and adventureright at your doorstep.

990 41st Gulf 9 Street, Marathon
$7,750,000
4 Beds ⋅ 5 Baths ⋅ A12028272 MLS ⋅ Sunrise Isles BLDG.
Experience the rare combination of protected dockage and direct oceanfront living at 128 Sunrise Drive. Situated within an exclusive gated enclave of just 20 lots, this newly constructed 2025 waterfront residence offers a level of privacy, luxury, and lifestyle rarely found in the Florida Keys. Positioned to capture unobstructed ocean views and a year-round ocean breeze, this home offers an elevated coastal lifestyle with exceptional attention to detail throughout. Each bedroom features a private ensuite bathroom and spacious walk-in closet, while a true foyer entry, elevator, and abundant storage create a floor plan that is as functional as it is beautiful. The open concept living offers the perfect home to entertain and enjoy tons of natural light. The interior design offers high end tile selections, designer light fixtures and wood accents throughout. The home also features 3 interior bars and window treatments throughout. The living spaces seamlessly transition outdoors, where an expansive entertainment area is designed to embrace the Keys lifestyle. Enjoy a resort-style pool and hot tub, outdoor kitchen, and multiple spaces to relax while overlooking the waters of the Atlantic. A rare wade-in beach offers effortless access to the ocean, while protected dockage on the canal side provides a secure spot for your boat. Additional features include a one-car garage, oversized air-conditioned storage space, and a generous covered carport ideal for vehicles, boats, and more!

128 Sunrise Drive, Marathon
$4,490,000
5 Beds ⋅ 5 Baths ⋅ A11981197 MLS
Experience exceptional waterfront living in this 2022 built home featuring 5 bedrooms and 4.5 bathrooms, perfectly positioned on the Gulf side with breathtaking water views. The main level offers a bright and open layout designed for both comfort and entertainment. A spacious modern kitchen showcases elegant cabinetry, quartz countertops with a striking waterfall edge, and premium stainless-steel appliances. Large dining and living areas, complete with a stylish wet bar, creating the perfect space for hosting and relaxing. This level also includes a convenient half bath and a utility room with laundry. Upstairs, the second-floor features five generously sized bedrooms and four full bathrooms. The expansive primary suite offers ample space, a beautifully designed modern bathroom, and a private porch where you can enjoy breathtaking sunset views over the water. Two additional bedrooms share a Jack-and-Jill bathroom and provide access to a balcony overlooking the pool and waterfront. A fourth bedroom, currently used as a home office, is located near another full hallway bathroom. The fifth bedroom is a private suite with its own ensuite bathroom. Featuring a large patio area ideal for entertaining, a spacious pool, and a 55-foot dock, making this property perfect for boating enthusiasts and waterfront relaxation. Additional highlights include a large two-car plus garage with ample storage space. Boat Lift plans have already been approved and permits granted and available.

865 50th Street Unit Gulf, Marathon
$424,999
2 Beds ⋅ 2 Baths ⋅ A11948112 MLS
The Keys are calling! Welcome to this beautifully appointed 2-bedroom, 2-bath residence offering the island lifestyle you’ve been dreaming of—without the steep price tag. This light-filled home features a stylish granite and stainless-steel kitchen, central air conditioning, and convenient interior laundry, making everyday living both comfortable and effortless.Step outside to the third-floor balcony, where open water and ocean views create the perfect backdrop for morning coffee or evening sunsets.Located within a true oceanfront community, residents enjoy an impressive array of amenities, including a resort-style pool, covered parking, kayak launch area, and a waterfront community lounge complete with a sun deck, fire pits, and an outdoor kitchen with stainless-steel grill—ideal for relaxing or entertaining.Perfectly situated in the heart of Marathon, just 2.5 hours from Miami and approximately one hour from Key West, this property delivers the best of the Florida Keys lifestyle with convenience and accessibility.With no HOA fees, property taxes included, and a full-time property management company maintaining the common areas, ownership here is truly low maintenance—just arrive and enjoy island living. This is the most affordable new-construction opportunity in the Keys, offering unmatched amenities for the price.Please note: the property is subject to monthly lot rent

101 11th Street Ocean, Unit 17, Marathon
$760,000
2 Beds ⋅ 2 Baths ⋅ A12040308 MLS
Welcome to your slice of paradise in the heart of Marathon! This beautifully updated canal-front retreat offers the ultimate Florida Keys lifestyle with direct boating access, private dockage, and a backyard designed for year-round enjoyment. Whether you’re seeking a full-time residence, vacation getaway, or income-producing investment, this property checks every box.Inside, you’ll find a bright and inviting open-concept layout featuring updated flooring, a modern kitchen, stylish finishes, spacious bedrooms, and beautifully renovated baths. The coastal-inspired interior is move-in ready and perfectly complements the relaxed waterfront setting.Step outside to your private tropical oasis complete with a sparkling above-ground pool, expansive entertaining areas, tiki-style bar, paver driveway, and approximately 50 feet of canal frontage. Boaters will appreciate the private dock, seawall, and quick access to open water for world-class fishing, diving, and island hopping.Additional features include a metal roof, hurricane protection, ample parking, low-maintenance exterior, and exceptional outdoor living spaces designed to embrace the Keys lifestyle.Ideally located near restaurants, marinas, shopping, beaches, and all that Marathon has to offer, this waterfront gem delivers the perfect blend of comfort, recreation, and island living. Don’t miss this rare opportunity to own a canal-front retreat in one of the Florida Keys’ most desirable boating communities.

837 91st Court Unit Ocean, Marathon
$1,725,000
A11841247 MLS
Stunning duplex on a generous 7,500 square foot lot with 75 feet of dock/sea wall. Each unit has 3 bedrooms and 2 bathrooms. Enjoy the Florida lifestyle with an above ground pool and fully fenced yard, ideal for entertaining. Short term rentals possible with the appropriate license. Live in one unit and receive rental income from the other, keep it as a duplex investment, or convert it into a single-family home facing deep water canal with no bridges. Strong rental market. Both units offer spacious layouts, ample parking, and separate utilities. The property's canal front location offers excellent access to the ocean/bay with minimal time. Very well protected with boot key harbor. The owner is a real estate agent WATERFRONT DUPLEX WITH ENDLESS POSSIBILITIES | Prime Investment Opportunity Full water front duplex on a generous 7,500 sq ft lot boasting 75 feet of seawall and private wooden dock. Each well-maintained unit features 3 beds/2 baths with modern updates. Enjoy the Florida lifestyle with an above-ground pool and fully fenced yard perfect for entertaining. Perfect for a large family or two families. Multiple investment strategies await: Live in one unit while collecting rental income from the other, maintain as a profitable duplex investment (short term 7 night rentals possible with the appropriate rental license) or convert to a luxurious single-family waterfront estate. Strong rental market in this sought-after location ensures steady cash flow potential.Both units offer spacious layouts, ample parking, and separate utilities. The property's waterfront location provides excellent boating access to both ocean & bay side of the keys and stunning city & sunset views. Don't miss this rare opportunity to own a versatile investment property with significant upside potential.

440-442 48th Street Unit Ocean, Marathon
$799,000
2 Beds ⋅ 1 Baths ⋅ A12046769 MLS
This charming 2-bedroom- 1-bath home in Marathon Keys offers the perfect blend of comfort and island living. With a spacious layout, modern amenities, and a prime location, it´s an ideal spot for those seeking a relaxing retreat or a cozy year-round residence. Whether you´re enjoying the tranquil surroundings or exploring nearby attractions, this property is a true gem in the heart of the Keys!

925 83rd Street Unit Ocean, Marathon
$995,000
2 Beds ⋅ 2 Baths ⋅ A12010398 MLS
Turnkey Investment Opportunity just 0.3 miles from iconic Sombrero Beach, generating an impressive $116,000 in short-rental income in 2025. Fully furnished and 100% rental-ready, this property includes local rental management & future bookings already in place- allowing a new owner to step in and start earning immediately! Enjoy the best of Keys living with a heated pool, lush private fenced yard and multiple porches including screened spaces for seamless indoor-outdoor living. Inside, the open-concept layout features abundant natural light and a modern kitchen ideal for entertaining. Built in 2016 to modern hurricane standards with impact windows, impact doors and durable Hardie board siding, plus covered parking and ample storage below, this home is as functional as it is inviting. Experience the best of island living near the beach while benefiting from consistent rental income- without the expense and upkeep of a seawall or dock.

320 Calzada De Bougainville, Marathon
$2,790,000
4 Beds ⋅ 4 Baths ⋅ A11978158 MLS
A rare waterfront estate along a 200-foot wide canal with a 110-foot dock and direct ocean access, capturing the essence of Florida Keys living. Spanning over 3,200 square feet, this residence features four bedrooms and three-and-a-half baths, ideal for hosting family and guests in true island style.Inside, a dramatic grand staircase and soaring two-story great room create an inviting yet refined atmosphere. Walls of windows frame tranquil water views and fill the space with natural light, providing the perfect setting for entertaining or relaxing after a day on the water. The kitchen offers granite countertops, stainless steel appliances, and an open layout that seamlessly connects the living and dining areas.Outside, your private waterfront retreat awaits. The 110-foot concrete dock with dual 40-foot finger piers provides exceptional deep-water dockage for multiple vessels, including large yachts, with quick Atlantic access. Boaters will appreciate the floating jet ski and kayak docks, davits, fish-cleaning station, and ice machine.Surrounded by lush tropical landscaping, the heated pool and spa create a secluded oasis where island breezes and sunshine define everyday living. Whether enjoying mornings on the water, afternoons poolside, or evenings under the stars, this property delivers the luxury and lifestyle of the Florida Keys.

14 Avenue F, Marathon
$2,890,000
5 Beds ⋅ 4 Baths ⋅ A12006854 MLS
Huge Direct Oceanfront Compound — One-of-a-Kind with 276-Foot Concrete DockAdjacent to World-Famous John Pennekamp, Coral Reef State Park & Molasses Reef.Discover a truly exceptional and private oceanfront compound designed for boating enthusiasts, investors, or multi-generational living. Spread across three expansive lots, this rare property includes two distinct homes and direct water access — a combination that’s nearly impossible to find in today’s market. Seller will consider all reasonable offers.The primary residence features 3 bedrooms and 2 full baths, offering bright, comfortable living spaces and sweeping ocean views. The second home, complete with 2 bedrooms and 2 baths on a separate meter, is ideal for guests, extended family, or short-term rental opportunities.Step outside to unparalleled oceanfront living with a 276-foot concrete dock, perfect for accommodating large vessels, fishing, and launching watercraft. The grounds offer generous room for entertaining, expansion, or simply enjoying the peaceful surroundings of this secluded coastal haven.Highlights:3 lots with two homes and a 276-ft dockDirect ocean access — idea for boating on the Ocean or Bay.Steps from John Pennekamp Coral Reef State ParkPerfect for entertaining, investing, or creating a family retreatUnmatched privacy and coastal lifestyle potential.

34 Atlantic Drive, Marathon
$2,799,000
5 Beds ⋅ 5 Baths ⋅ A12008188 MLS
Weekly rental income-producing property with open water access and dockage on desirable Sombrero Beach Road. This 5-bedroom, 5-bath coastal villa is a proven vacation rental offering immediate income potential in the heart of Marathon, just moments from Sombrero Beach. Thoughtfully designed across three levels, the home features light-filled interiors with a coastal palette of soft blues and crisp whites, creating a relaxed luxury feel. Modern finishes, spacious living areas, and seamless indoor-outdoor flow enhance the overall appeal. An elevator provides convenient access to all levels, and multiple balconies capture tropical breezes and water views. Private dockage with direct open water access makes this an ideal property for boating and fishing enthusiasts. The outdoor area includes a private pool and ample space for entertaining, adding to its strong rental performance. Located just a short walk or bike ride to Sombrero Beach, known for its sandy shoreline, calm waters, and beautiful sunsets. Ideal as an investment property, second home, or full-time residence with income potential.

443 Sombrero Beach Road, Marathon
$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
$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
$1,700,000
2 Beds ⋅ 3 Baths ⋅ F10543646 MLS ⋅ Key Colony BLDG.
Unapproved Short Sale for Non-Conforming 2 Bed/3 Bath Waterfront Home in Marathon. Large corner lot with 205 feet of water frontage. First floor has non-conforming addition of 2 bedrooms and living area. Second floor nicely updated with renovated kitchen, baths and impact windows throughout.

10999 Ave 3rd Avenue, Marathon