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2110 Dolphin Drive, Marathon
$1,599,000
2 Beds ⋅ 2 Baths ⋅ A12107785 MLS
Enjoy the Florida Keys at its best in this solid concrete, 2BR/2BA home in an established, quiet Marathon neighborhood. The fully renovated, open-concept interior spans 1,280 sqft of updated living space with tile floors and an A/C UV-light system. The gourmet kitchen boasts granite countertops, a multicolored glass tile backsplash, modern cabinetry with fossilized shell knobs and top-tier stainless steel appliances, including a Bosch induction range. The bathrooms feature high-end premium finishes. This stilted, 2-story concrete floor home has indoor stairs, features a durable metal roof, providing maximum structural integrity. Capitalize on outstanding vacation rental potential of $100k+ annually, or enjoy it as your private dream home. Located on a deep flow-through canal just 2 minutes from the open Gulf, this boater's paradise features a 60 ft dock with a heavy-duty 15,000-lb boat lift. An approved permit for a 10x20 ft swimming pool is ready to complete your backyard oasis. The lower level provides an additional 936 sq ft of enclosed ground-level storage, a covered carport, a Level 2 EV charging station, and a private waterfront entertaining area. Mechanical upgrades include a whole-house generator, an upgraded electric panel, and a 4-camera security system. Outside, a waterfront tiki hut overlooks the canal, surrounded by low-maintenance landscaping and two fenced areas for dogs. Kayak, paddle board, or boat to world-class fishing and reef diving in minutes!

2110 Dolphin Drive, Marathon

57652 Overseas Highway, Marathon
$2,600,000
3 Beds ⋅ 3 Baths ⋅ A12102621 MLS
Discover this exceptional oceanfront property on Grassy Key in Marathon, Florida! Fully remodeled, this solid-concrete home offers breathtaking ocean views and the ultimate Florida Keys lifestyle. Featuring 3 bedrooms and 3 bathrooms, the versatile layout includes one bedroom and one bathroom on the first level, with two bedrooms and two bathrooms upstairs.The open-concept living area showcases a brand-new kitchen with quartz countertops and stainless steel appliances. Enjoy a newly constructed concrete swimming pool with jacuzzi and water heater, impact windows and doors, and a wraparound balcony, brand-new AC system and more! The spectacular rooftop deck is perfect for entertaining, relaxing, and enjoying panoramic ocean views.A rare opportunity to own a beautifully upgraded waterfront property with excellent vacation rental potential. Weekly rentals offer an opportunity to generate income while enjoying your own private island retreat. Whether you're looking for a personal getaway or an income-producing investment, this remarkable property delivers breathtaking views, modern upgrades, and the best of Florida Keys living!

57652 Overseas Highway, Marathon

422 Harbour Drive, Marathon
$4,500,000
4 Beds ⋅ 3 Baths ⋅ NS1089477 MLS
There are places where the water is part of the view. And then there's Duck Key, where it shapes the entire way of life. Set in the heart of the Florida Keys, this two-story waterfront residence brings together thoughtful living spaces, beautiful open-water scenery, and everything that makes island life so distinctive. The home offers four bedrooms and three bathrooms, surrounded by lush landscaping and designed to make the most of its waterfront setting. Outside, the property really comes into its own. A private pool, beach area, and dock put the water at the center of every day. And for boaters, the details matter: A 30,000-pound boat lift, a jet ski lift, a fish cleaning station, and steps leading right into the water. A morning offshore, an afternoon exploring the keys, or a quiet evening back at the pool. Here, those aren't special occasions. They're simply options. Upstairs, the open living kitchen areas are made for gathering, but the water remains the focal point with sliding glass doors that open to an expansive balcony that wraps around the upper level. The upper floor also includes the master bedroom with an ensuite bath, second bedroom and full bath in the hallway. Downstairs, a second living area, kitchenette, two additional bedrooms, and another full bathroom create a flexible layout for family and guests. From the lower level, step outside to the balcony, pool, beach and dock. Beyond the property, Duck Key has its own distinctive appeal. Join the optional Duck Key clubhouse for a pool, tennis, pickleball, and events, or Hawks Cay Resort for its Michelin-rated Salt and Ash restaurant, saltwater lagoon, Dolphin Connection, and pools.

422 Harbour Drive, Marathon

233 Sombrero Beach Road, Marathon
$2,720,000
3 Beds ⋅ 3 Baths ⋅ A12103953 MLS
Experience luxury Florida Keys living at its finest! Built in 2022, this stunning 3-bedroom, 2.5-bath waterfront home sits on a main canal in Marathon’s desirable Sombrero Beach area, featuring a 70-foot composite dock and BRAND-NEW 20,000-lb boat lift! Enjoy quick boating access to the Atlantic Ocean and Gulf, with world-class fishing and diving at your fingertips. Walk or bike to beautiful Sombrero Beach, with grocery stores, shopping, and restaurants conveniently nearby. Inside, discover contemporary coastal elegance with oversized porcelain tile flooring, an open-concept layout, custom cabinetry, quartz countertops, stainless steel appliances, and an impressive oversized kitchen island. The spacious primary suite offers a spa-inspired bathroom with a freestanding soaking tub, oversized glass shower, dual vanities, and custom closets. An expansive upstairs loft with wet bar and beverage refrigerator is easily convertible into a 4th bedroom, guest suite, or office. Outside, enjoy your private saltwater pool, covered entertaining areas, multiple balconies, garage, and additional covered parking. Whether boating, fishing, entertaining, or relaxing in paradise, this exceptional property delivers the ultimate Florida Keys lifestyle!

233 Sombrero Beach Road, Marathon

355 Stirrup Key Boulevard, Marathon
$3,300,000
4 Beds ⋅ 4 Baths ⋅ A12092952 MLS
Welcome to Sunset Anchorage, a beautifully renovated open-water home in the exclusive gated community of Stirrup Key. Set on an expansive lot and a half, this three-story CBS home offers exceptional privacy, protected dockage, a private pool, and sweeping Gulf views with spectacular sunsets. Thoughtfully updated throughout, the home features a brand-new kitchen with custom cabinetry, custom bar, updated flooring, new impact windows and doors, new A/C units, and Hardie board siding accents. The main level features the primary suite with a newly expanded and completely renovated bath, plus a guest bedroom with marina views and a full bath nearby. An extended covered porch off the living and dining areas overlooks the pool and Gulf. Upstairs, a secondary primary suite offers a private bath and walk-out balcony with stunning open-water views, while an additional guest bedroom and half bath complete the level. Outdoor living includes a spacious covered patio, newly built tiki bar, and beautifully refinished and re-tiled pool with new equipment, heater, and chiller. A redone waterfront observation deck provides easy kayak access and an ideal place to enjoy the sunset. Across the street, protected dockage in Stirrup Key's private marina includes concrete boat slip D41 with a walk-out dock and new 15,000-lb Hurricane Hoist boat lift. Mature tropical landscaping and towering gumbo limbo trees complete this exceptional Florida Keys property.

355 Stirrup Key Boulevard, Marathon

101 11 Street Ocean Unit 3, Marathon
$399,999
2 Beds ⋅ 2 Baths ⋅ A12096187 MLS
This is the one! Welcome to 101 11th Street Ocean, Unit 3, a perfect 2 bedroom and 2 bathroom home with ocean views. Well maintained home awaits you, with a resort like surroundings. Great boating from just a walk away or just dip in the pool all day long, this home has it all.Also just priced perfectly and the grounds are all well taken care of, all you have to do is bring yourself. Walk right in to this raised home, with all the modern features that you can ask for. Kitchen, living room, bathroom with guest bedroom are all on first floor, all for great entertaining. Walk right up stairs to a primary second floor with a great sized bedroom and bathroom with a breakfast nook for you to feel like you never need to leave, until you walk right out to your balcony for those endless ocean views.Plenty of parking and right next to all the great restaurants that Marathon Key has to offer. Call today for your private showing.Please note, this is property is subject to a land lease agreement.

101 11 Street Ocean Unit 3, Marathon

101 11th Street Ocean, Unit lot 12, Marathon
$459,900
2 Beds ⋅ 2 Baths ⋅ A12089406 MLS
For those seeking an easier way to experience the Florida Keys—with breathtaking water views, boating access, community amenities, and rental potential—this exceptional end-unit residence offers something truly special. Positioned to capture expansive open-water views stretching to Isla Bella and beyond, this newer-construction, elevated two-bedroom, two-full-bath home enjoys a highly desirable end-unit location with an added sense of openness and privacy. An upper-level flex space opens to an expansive deck—an idyllic setting for morning coffee, sunset cocktails, or simply taking in the beauty of the Keys. Offered fully furnished and turnkey, with covered parking, the home is equally suited as a personal island retreat, low-maintenance second home, or income-producing rental property. Community amenities include a swimming pool, clubhouse, fish-cleaning station, sun deck, outdoor kitchen, boat slips, and more. World-class fishing, snorkeling, and diving are at your fingertips, with immediate access to open water and the renowned fishing grounds of the Humps approximately 30 miles offshore. Waterfront dining is just minutes away, while the iconic Seven Mile Bridge and pedestrian bridge to historic Pigeon Key are moments from home. Key West is approximately 45 minutes south, with Miami roughly two hours north. Arrive, unpack, and begin enjoying the Keys from day one—with an end-unit setting and breathtaking views that are truly difficult to replicate.

101 11th Street Ocean, Unit lot 12, Marathon

108 Avenue D, Marathon
$5,499,000
6 Beds ⋅ 6 Baths ⋅ A12088770 MLS
Experience exceptional waterfront living in this impressive Spanish-inspired concrete residence, built in 2019 and offering approximately 8,107 square feet of construction and 16,500 square feet lot size. Thoughtfully elevated and designed with an emphasis on space, quality, and comfort, this remarkable home showcases a highly customized interior with refined finishes throughout.Solid wood interior doors, generous room proportions, and carefully designed living spaces reflect the attention to detail found throughout the residence. Expansive recreational and entertainment areas on both the first and second floors provide exceptional flexibility for hosting, relaxing, and enjoying everyday family living.The home’s substantial concrete construction and elevated design complement its commanding presence, while the spacious interior offers an ideal combination of elegance and functionality.Positioned along an exceptionally Deepwater, wide-canal home with direct ocean access, the property provides an impressive waterfront setting and a sense of privacy and tranquility. A distinctive luxury residence offering exceptional scale, generous entertainment spaces, and outstanding waterfront appeal. Ideally located near the airport and surrounded by a variety of restaurants, dining options, and everyday conveniences, the home offers an excellent balance of privacy, accessibility, and lifestyle.

108 Avenue D, Marathon

11231 2nd Avenue Unit Ocean, Marathon
$535,000
2 Beds ⋅ 2 Baths ⋅ A12088607 MLS
Welcome to your slice of paradise in beautiful Marathon! Perfectly situated near the airport for easy access, this thoughtfully remodeled CBS 2-bedroom, 2-bath home blends modern finishes with cozy coastal charm. Recently renovated with attention to detail, the interior features stylish updates, a warm and inviting ambiance, and a functional layout designed for comfort and relaxation. New Metal roof July 2024. Step outside to your private, fenced backyard oasis complete with a brick-paved patio and lush tropical landscaping -- including your very own banana tree. It's the perfect setting for morning coffee, evening cocktails, or entertaining under the island sky. Whether you're seeking a 7-day rental income opportunity or your own personal retreat in the Keys, this property offers flexibility, privacy, and island living at its best. Don't miss this opportunity to own a piece of paradise at an affordable price!

11231 2nd Avenue Unit Ocean, Marathon

2240 HARBOR Drive, Marathon
$775,000
2 Beds ⋅ 2 Baths ⋅ B26075899 MLS
Welcome to 2240 Harbor Drive in Marathon, a beautifully maintained home situated in a highly desirable family neighborhood. This spacious corner lot offers nearly 10,000 square feet and is fully fenced, providing privacy, security, and plenty of room to enjoy the outdoors—with ample space to add a pool. Mature, lush landscaping creates a peaceful setting with abundant shade and privacy. Exceptional parking includes a paved driveway and a convenient double-wide gate, providing easy access for secure in-fence boat or trailer storage. For outdoor entertaining, enjoy the expansive bricked patio, cedar pergola, outdoor dining area, and built-in grill—perfect for relaxing or hosting family and friends. Inside, the home features tile flooring throughout, an ensuite primary bedroom with a walk-in shower and walk-in closet, Bahama shutters, and hurricane-rated double doors. Bonus room can be used as a den or office. Additional exterior features include two storage sheds and a detached laundry room, offering plenty of practical storage and workspace. Boating enthusiasts will appreciate the public community boat launch just 3/10 of a mile away, available free for residents. With its desirable family-friendly location, generous corner lot, boat/trailer storage, beautiful outdoor living spaces, and room for a pool, this Marathon property offers an exceptional Florida Keys lifestyle.

2240 HARBOR Drive, Marathon

8302 Marina Villas Drive Unit 8302, Marathon
$824,000
3 Beds ⋅ 2 Baths ⋅ M20039356 MLS ⋅ Marina Villas At Hawks Cay BLDG.
VRBO annual rental income is over $100,000 for the year 2025. Wide water views from this beautiful renovated furnished condo w/fantastic floor plan & is decorated w/updated & modern coastal look. Lots of natural light & huge L-shaped balcony w/pocket sliding doors for indoor/outdoor living space. Kitchen w/white countertops & newer SS appliances. Main bedroom opens to balcony, has large step-in shower & dual sinks. Impact glass windows & doors, natural stone floors, plantation shutters, a barn door, extra storage & covered parking (trucks & pets OK). Full-time residents can homestead this property & receive mail or use as a vacation home w/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 & adult activities

8302 Marina Villas Drive Unit 8302, Marathon

556 Sombrero Beach Road, Marathon
$1,625,000
A12087262 MLS
PRIME SOMBRERO BEACH WATERFRONT | TBR + FLOOR PLANS + ACTIVE PERMITRare opportunity to own a build-ready waterfront parcel in a prime Marathon location, just minutes from Sombrero Beach. This approximately 7,500 sq. ft. property offers the perfect setting to create a luxury Florida Keys retreat, with waterfront living and easy access to one of the area's most desirable beaches.The property comes with the major groundwork already completed, including TBR, floor plans, an active building permit, survey, and a cleared, build-ready site. The plans are designed for an impressive 3,924 sq. ft. CBS estate with 6 bedrooms, 6.5 bathrooms, a private pool, and spacious indoor and outdoor entertaining areas.Whether you're looking for a luxury primary residence, second home, or vacation rental investment, this property offers exceptional flexibility, with 7-day rentals permitted. There is also potential to add a 70-foot concrete dock, providing room for multiple boats and water toys.Prime location. TBR. Floor plans. Active permit. Everything is in place to move forward with your vision and create an exceptional waterfront home in the Florida Keys.Opportunities combining waterfront, proximity to Sombrero Beach, approved plans, and a build-ready site are increasingly hard to find.Build your dream. Enjoy the Keys. Invest in one of Marathon's most desirable locations.

556 Sombrero Beach Road, Marathon

211 S Anglers Drive S, Marathon
$2,395,000
4 Beds ⋅ 3 Baths ⋅ A12077214 MLS
Fantastic opportunity in Marathon's desirable Sombrero Beach area! Built in 2020, this beautifully designed 4-bedroom, 3-bath waterfront pool home offers 2,464 sq. ft. of comfortable living space and 100 ft of composite dockage with direct ocean access for ultimate boating and island living.Fully furnished and thoughtfully appointed—the open kitchen, dining, and living area create an easy gathering space, while spacious waterfront balconies on both levels invite you outside to enjoy tropical breezes. The main level includes a guest bedroom, full bath, and laundry room.On the top floor, the primary suite features an en-suite bath, walk-in closet, and private covered balcony, alongside two additional guest bedrooms and a hall bath.Downstairs, a covered entertainment area extends living outdoors, perfect for relaxing around the heated in-ground pool. Secure water toys and boating gear in the garage, and enjoy ample parking on the 10,218 sq. ft. lot.Located just a short walk from sandy Sombrero Beach and close to dining, shopping, and attractions. Currently operating as an active weekly vacation rental, offering a seamless turnkey investment, vacation retreat, or full-time Keys home. Experience the easy pace, boating, and beach days that make living in the heart of the Florida Keys so special!

211 S Anglers Drive S, Marathon

1157 91ST COURT OCEAN, Marathon
$3,150,000
4 Beds ⋅ 3 Baths ⋅ B26069099 MLS
Brand-new 2026 construction in Marathon! This elevated waterfront home offers nearly 2,500 SF under air plus 455 SF of balconies, for just under 3,000 SF total — 4 beds/3 baths, Atlantic Ocean views, and a refurbished dock fitting a ~40' vessel. Built to withstand 180-mph winds on auger-cast pilings, with covered parking/storage below. Inside: 9'6" ceilings, LVP flooring, granite counters, stainless appliances, dual HVAC. Brand-new pool & spa with saltwater system and smart automation. Impact windows/doors, metal roof, composite decking. Extended Property and Location Information: Welcome to this brand-new waterfront residence, completed July 2026, offering exceptional boating access, Atlantic Ocean views, and construction engineered specifically for the Florida Keys. This two-story home offers nearly 2,500 SF under air plus 455 SF of covered balconies, for just under 3,000 SF total living and outdoor space, with 4 bedrooms and 3 bathrooms. Built for the Keys Engineered for 180-mph wind conditions and Exposure D, the home is supported by 18-inch reinforced concrete auger-cast pilings extending into rock, along with reinforced concrete columns and grade beams. The elevated design places the main living areas well above base flood elevation while creating a large covered parking and storage area beneath the home — ideal for vehicles, boats, fishing gear, kayaks, and bikes. Interior Highlights Inside, 9'6" ceilings create a bright, open feel throughout. Quality finishes include solid interior doors, upgraded LVP flooring, crown molding, and recessed lighting with dimmers. The kitchen features extensive cabinetry, granite countertops, and stainless-steel appliances, while the bathrooms showcase custom tile work, stone-topped vanities, and frameless glass shower enclosures. A dual HVAC system with two separate condensers and air handlers provides dedicated cooling throughout. Exterior & Structure The exterior features a 5V crimp metal roof, cement-board siding, impact-rated windows and doors, high-grade composite decking, stainless-steel stair components, and multiple covered balconies overlooking the tropical surroundings and Atlantic Ocean. Pool & Spa The brand-new pool, spa, and landscaping were completed alongside the residence in July 2026 for a true turnkey property. Built on its own steel-reinforced auger-piling system, the pool features premium Jandy equipment: dual variable-speed pumps, cartridge filtration, a TruClear saltwater system, spa blower, 116,000-BTU VersaTemp heating/chilling system, and iAquaLink automation. Boating & Location The property offers canal frontage with a refurbished concrete dock and extended waterfront configuration accommodating a vessel of approximately 40 feet. The Atlantic Ocean is just moments away, putting world-class offshore fishing, diving, boating, and watersports right at your doorstep. Marathon's central Middle Keys location keeps restaurants, marinas, shopping, beaches, and everyday necessities close at hand. Florida Keys Marathon International Airport is also nearby, with Monroe County actively working toward the return of scheduled commercial passenger service by 2027. Square footage: 2,489 SF under air per professional floor plan measurement (KPV), plus approximately 455 SF of balcony space. Buyer to verify all measurements.

1157 91ST COURT OCEAN, Marathon

354 96th Street Unit Ocean, Marathon
$525,000
2 Beds ⋅ 1 Baths ⋅ A12072507 MLS
Discover the charm of this updated 2-bedroom, 1-bath home, ideally located in the heart of Marathon. Built in 1957, this classic Keys home offers character, comfort, and plenty of outdoor space. The open-concept living area creates an inviting flow for everyday living and entertaining, while the original terrazzo floors add timeless Florida charm. Situated on a large, beautifully shaded lot, the backyard possibilities are endless. There is plenty of space to create your own private outdoor oasis, including room for a pool, entertaining area, garden, or additional outdoor living space. A screened-in back porch provides the perfect spot to relax and enjoy the island breeze. The spacious storage shed offers abundant room for tools, bikes, fishing gear, or could easily become your own private man cave or hobby space. With its convenient location in the heart of Marathon, generous lot, mature shade trees, updated interior, and classic terrazzo flooring, this property offers a wonderful opportunity to enjoy the laid-back Florida Keys lifestyle with plenty of room to make it your own.

354 96th Street Unit Ocean, Marathon

1 E Sister Rck Island, Marathon
$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

2405 Coco Plum Drive, 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

58652 Overseas Highway, Marathon
$3,495,000
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

108 Sunrise Drive, Marathon
$7,495,000
5 Beds ⋅ 5 Baths ⋅ A12060805 MLS
** Seller Financing Available With 50% Down Subject To Acceptable Terms **Nestled on the private gated island of Sunrise Isles in Marathon, Florida Keys, this 2019 oceanfront estate redefines luxury living. One of only 20 residences within this secure island enclave, it offers a rare blend of privacy and the serene beauty of the Keys.This 5-bedroom, 4-bathroom residence spans 3,500 square feet of crafted living space designed to capture breathtaking ocean views. The open-concept single-level floor plan 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 for exceptional indoor-outdoor living. Set on over 32,000 square feet of waterfront property, the estate boasts 110 feet of sandy beachfront plus 110 feet of protected canal dockage with two custom boat lifts and an L-shaped synthetic dock, providing effortless open-water access.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

59733 Paradise Place, Marathon
$650,000
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) Seller is open to seller financing contact me for more details.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

101 11th Street Ocean, Unit lot 13, Marathon
$459,900
2 Beds ⋅ 2 Baths ⋅ A12027597 MLS
For someone looking for an easier way to enjoy the Florida Keys—with boating access, water views, community amenities, and rental income—this is an opportunity worth exploring.Land-lease communities offer a unique and often more approachable path to owning in the Florida Keys—and for the right buyer, the lifestyle and value can make tremendous sense.This newer-construction, elevated two-bedroom, two-full-bath home offers beautiful marina views, along with glimpses of the Gulf and open water from the balcony. An additional flex space on the upper level opens to an expansive deck, creating even more room to relax and enjoy the surrounding scenery.Offered fully furnished and turnkey, with covered parking, it is equally suited as a personal Keys retreat, low-maintenance second home, or income-producing rental property. January, February, and March 2027 are already booked, representing $22,500 in gross rental income.The monthly lot fee is $1,377/mo and $300/mo for dockage. Community amenities include a swimming pool, clubhouse, fish-cleaning station, sun deck, outdoor kitchen, boat slips, and more.The location places you close to waterfront dining on both the ocean and Gulf sides, with easy access to the two-mile pedestrian bridge leading to historic Pigeon Key. The iconic Seven Mile Bridge is moments away, with Key West approximately 45 minutes south and Miami roughly two hours north.Arrive, unpack, and begin enjoying the Keys from day one.

101 11th Street Ocean, Unit lot 13, Marathon

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