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$3,650,000
4 Beds ⋅ 4 Baths ⋅ A12056681 MLS ⋅ Crains Sub BLDG.
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
$7,995,000
5 Beds ⋅ 4 Baths ⋅ A12060805 MLS ⋅ Sunrise Isle BLDG.
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 Dr, Marathon
$700,000
4 Beds ⋅ 2 Baths ⋅ A12055919 MLS ⋅ Jg Estates BLDG.
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. 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 Pl, 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
$1,999,000
4 Beds ⋅ 3 Baths ⋅ A12036239 MLS ⋅ Coco Plum Beach BLDG.
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
$675,000
4 Beds ⋅ 3 Baths ⋅ A12028981 MLS ⋅ Buttonwoods Acres BLDG.
New on the market in the heart of Marathon, FL! This property offers a great opportunity to own in one of the most convenient areas of the Florida Keys, just minutes from local shops, dining, marinas, beaches, and island attractions. Conveniently located across from the airport, this home features a brand-new metal roof, a fully fenced yard, and zoning that allows short-term vacation rentals with a 7-night minimum. Whether you are looking for a personal Keys getaway, a second home, or an income-producing vacation rental, this property offers great potential. Enjoy the relaxed island lifestyle while also taking advantage of the strong rental demand in Marathon. RV and metal shed are not included in the sale.

780 95th Street Ocean, Marathon
$7,750,000
4 Beds ⋅ 5 Baths ⋅ A12028272 MLS ⋅ Sunrise Isle 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
$2,875,000
5 Beds ⋅ 5 Baths ⋅ A12008188 MLS ⋅ The Reserve At Sombrero BLDG.
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 Rd, Marathon
$2,890,000
5 Beds ⋅ 4 Baths ⋅ A12006854 MLS ⋅ Knowlson Colony BLDG.
Huge Direct Oceanfront Compound — One-of-a-Kind with 276-Foot Concrete Dock Adjacent 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 dock Direct ocean access — idea for boating on the Ocean or Bay. Steps from John Pennekamp Coral Reef State Park Perfect for entertaining, investing, or creating a family retreat Unmatched privacy and coastal lifestyle potential.

34 Atlantic Drive, Marathon
$4,490,000
5 Beds ⋅ 5 Baths ⋅ A11981197 MLS ⋅ Latitude 24 (Replat Of Po BLDG.
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 Gulf, Marathon
$2,795,000
4 Beds ⋅ 4 Baths ⋅ A11978158 MLS ⋅ Coco Plum Beach BLDG.
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
$29,500,000
10 Beds ⋅ 13 Baths ⋅ A11977067 MLS ⋅ Crains Subd BLDG.
A Private Waterfront Estate at The Edge of the Gulf of America. Set on 3 secluded acres+/- along one of the most protected 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 property offers more than 200’+/- of direct water frontage and uninterrupted views across the open Gulf. Completed in 2025 by builder and developer Alderuccio Corporation, this resilient, elevated retreat is constructed entirely of concrete and impact glass and is designed for effortless indoor–outdoor living. With three distinct finished living spaces 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 ⋅ Anglers At Sombrero BLDG.
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 Rd, 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
$3,549,000
14 Beds ⋅ 19 Baths ⋅ A11782185 MLS ⋅ 9999 BLDG.
RARE 100' of waterfront re-development opportunity w/ DEEP WATER DOCKAGE APPROVED! 200' HIGHWAY FRONTAGE! Huge 74,890 SQ FT site with ACTIVE Conditional Use PERMIT for 10 unit & 4 affordable staff group home units. 6 TBR's available plus more. No TDR's required for pure commercial use! MIXED USE ZONING - many commercial-residential possibilities, e.g.: up to 10 market rate units, higher w/ affordable housing, or boutique HOTEL, etc. Includes 2 story raised CBS 6,128 SQ FT building that could be used in many different ways, plus 2,340 SQ FT of outdoor porches. Near Vaca Cut for easy Ocean-Bay access, near airport, SHORT-TERM RENTALS! Contact Peter for info and tour of this amazing opportunity. THE KEYS LIFESTYLE - live, work, business, family compound - do it all right here!

14 125th Street Gulf, Marathon