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301 Sombrero Blvd Unit 202, Marathon
$389,900
1 Beds ⋅ 1 Baths ⋅ 621616 MLS
Enjoy the relaxed Florida Keys lifestyle in this beautifully remodeled one-bedroom, one-bathroom harborfront condo, offering captivating Boot Key Harbor views. Located on the second floor, this inviting retreat features a clean, simple style with tasteful furnishings that create a comfortable and welcoming atmosphere. Step out onto your screened-in porch to take in the waterfront scenery, with boats cruising by and paddleboarders and kayakers enjoying the peaceful surroundings. When it's time to unwind, take a refreshing dip in the sparkling blue waterfront pool, where you can relax and soak up the sunshine while enjoying the beautiful harbor setting. Whether you're sipping your morning coffee, unwinding with a good book, or watching the ever-changing waterfront views, this condo offers the perfect place to embrace the coastal lifestyle. Boating enthusiasts will appreciate the convenience of 30-foot assigned boat dockage, making it easy to explore everything the Florida Keys waters have to offer. Perfect as a weekend getaway, seasonal retreat, or full-time residence, this charming waterfront condo offers the ideal blend of comfort, convenience, and laid-back island living.

301 Sombrero Blvd Unit 202, Marathon

2143 Yellowtail Dr, Marathon
$1,549,000
3 Beds ⋅ 2 Baths ⋅ 621615 MLS
Discover the Florida Keys lifestyle in this beautifully maintained 3-bedroom, 2-bath waterfront pool home offering 1,540 sq. ft. of living space on a wide boating canal with direct Gulf access. Designed with a unique multi-level layout, the home welcomes you with a floating staircase leading to a bright and airy Great Room featuring wood floors and impact glass doors overlooking the water. The charming Kitchen showcases soaring wood ceilings, glass-front cabinetry, stainless steel appliances and a breakfast bar opening to the Living and Dining Areas. The main level offers a guest Bedroom with wood-beamed ceilings and water views, along with a full Bath. A short staircase leads to the second Bedroom with cathedral wood ceilings and an ensuite Bath, while the uppermost level features a cozy loft-style third Bedroom. Step outside to your private waterfront retreat with a heated and chilled pool complemented by expansive decking, new artificial turf and an outdoor shower. Boating enthusiasts will appreciate 60' of concrete dockage with a 13,000 lb. boat lift, dedicated angler's prep station and easy Gulf access for world-class fishing, diving and exploring the surrounding waters. Additional highlights include impact windows and doors, a metal roof, newer A/C, updated decking and fresh paint. A garage and generous ground-level storage provide ample space for vehicles, boating equipment and all your Keys essentials. This inviting waterfront home is ideal as a full-time residence, vacation getaway or investment opportunity in the heart of the Florida Keys.

2143 Yellowtail Dr, Marathon

389 N Anglers Dr Unit 107, Marathon
$524,995
2 Beds ⋅ 2 Baths ⋅ 621573 MLS
Morning coffee overlooking the water. A bike ride to Sombrero Beach. Afternoons spent boating, fishing, or relaxing by the pool. This is the Florida Keys lifestyle, and at Coral Club, it's ready to enjoy from day one. Located in a peaceful Marathon neighborhood just one mile from Sombrero Beach, this beautifully updated and furnished 2-bedroom, 2-bath canal-front condo combines waterfront living, comfort, and convenience. This first-floor residence features a bright, open layout, tasteful coastal finishes, and an enclosed patio overlooking the canal. Watch boats cruise by, enjoy your morning coffee, or unwind with an evening cocktail as the waterfront setting makes every day feel like a getaway. Inside, thoughtful updates, stainless steel appliances, an in-unit washer and dryer, and impact-resistant windows and doors offer style and peace of mind. Furnished and move-in ready, all that's left to do is arrive and enjoy. Coral Club amenities include boat slips (subject to availability), a heated and chilled pool, waterfront tiki hut, and clubhouse with a full kitchen and bathroom. Anglers will appreciate the community ice machine, fish freezers, and private storage for fishing gear, kayaks, and beach essentials. Just one mile away, Sombrero Beach offers sandy shores, swimming, volleyball, playgrounds, and picnic areas. Grocery stores, shopping, and waterfront restaurants are conveniently nearby. Whether you're seeking a primary residence, vacation retreat, or investment property, this turnkey Coral Club condo offers the location, amenities, and coastal lifestyle that make the Florida Keys special. Bring your flip-flops, grab your fishing rods, and start living the Keys lifestyle!

389 N Anglers Dr Unit 107, Marathon

1153 70th St, Marathon
$14,999,000
6 Beds ⋅ 7 Baths ⋅ 621538 MLS
Set across three parcels totaling approximately 10.46 acres, this extraordinary Gulf-front estate offers 6,661 sq. ft. of living space, 6 bedrooms and 6.5 baths in a setting defined by privacy, craftsmanship and panoramic water views. Designed by D'Asign Source and completed in 2016, the residence was constructed to exceptional standards with 120 concrete pilings to bedrock, galvanized steel framing, impact-rated openings and a standing seam metal roof. Inside, soaring ceilings, intricate tray ceilings, solid mahogany doors and expansive Weiland sliders create a seamless connection to the Gulf. The chef's kitchen features Blue Louise granite, an onyx backsplash, Wood-Mode cabinetry, Wolf and Sub-Zero appliances and a butler's pantry. Additional highlights include a temperature-controlled 1,000-bottle wine cellar, commercial-grade elevator, smart-home technology and an impressive McIntosh home theater with 130'' screen and Sony laser projector. Outdoors, a heated and chilled zero-edge saltwater pool and spa overlook the Gulf, complemented by a swim-up bar, waterside fire pit, putting green and saltwater basin stocked with local marine life. Boaters will appreciate the illuminated dock, 100,000-lb lift accommodating vessels up to 55' and additional 10,000-lb lift. A private walking trail winds through the additional acreage, while the rooftop deck captures sweeping water views from sunrise to sunset. Extensive infrastructure includes a 135 kW whole-house generator, buried propane storage, reverse-osmosis drinking water, whole-house water softening, irrigation and Coastal Source outdoor lighting and audio. Rarely does an estate of this scale combine expansive Gulf frontage, exceptional boating, substantial acreage and uncompromising craftsmanship in the heart of the Florida Keys.

1153 70th St, Marathon

303 Sombrero Blvd Unit 207, Marathon
$569,000
2 Beds ⋅ 2 Baths ⋅ 621527 MLS
YOUR OWN BOAT SLIP, BEAUTIFUL HARBOR VIEWS AND TURNKEY FLORIDA KEYS LIVING! Waterfront living meets effortless island style at this beautiful 2-bedroom, 2-bath residence overlooking Boot Key Harbor in the heart of Marathon. Positioned to capture expansive harbor views, colorful Keys skies, and the peaceful surroundings of the neighboring golf course, this furnished condominium offers an inviting retreat with boating right outside your door. The thoughtfully remodeled interior features a spacious, comfortable floor plan designed for easy coastal living. An enclosed balcony adds approximately 90 square feet of additional living space and creates a wonderful setting to relax while taking in the waterfront scenery. Offered fully furnished and complete with an in-unit washer and dryer, the residence is ready to enjoy from day one. For those drawn to the water, an assigned boat slip makes getting out on the harbor remarkably convenient, while dedicated kayak storage offers another way to explore the surrounding waterways. Additional features include an exterior owner's storage closet and a recently renovated waterfront community pool. Set along a quiet, low-traffic stretch of Sombrero Boulevard, the location offers a welcome sense of privacy while keeping the best of Marathon close at hand. Sombrero Beach, boating, golf, shopping, dining, and everyday conveniences are all just minutes away. Whether envisioned as a full-time Keys residence or an easy-to-enjoy island getaway, Unit 207 offers a compelling combination of waterfront views, boating access, updated interiors, and an exceptional Marathon location.

303 Sombrero Blvd Unit 207, Marathon

10877 Overseas Highway Unit 82, Marathon
$699,000
1 Beds ⋅ 2 Baths ⋅ 621492 MLS
Ocean Isles Fishing Village is a one-of-a-kind answer to your Florida Keys paradise lifestyle. And this condo is something special. This unique 1-bedroom, 2-full-bath design gives you a true front-row, MILLION-dollar view of the Atlantic Ocean and the beautiful waterfront swimming pool. Morning coffee may never taste the same again! Built in 2022, this 850 sq. ft. oceanfront condo gives you incredible water views from both levels. Better yet, the elevator is right next to the unit, making life a little easier for anyone who prefers to skip the stairs. Step inside to an open living area, a fully equipped kitchen with granite countertops, coastal-style flooring, a full bathroom, and a balcony looking straight out over the Atlantic. Upstairs, the spacious primary suite is your own private getaway with a second full bathroom and private balcony. Open the door, feel the ocean breeze, and remember why you came to the Keys in the first place. Built high above flood elevation with solid CBS construction, impact windows, and a metal roof, this condo is being offered turnkey. Bring your flip-flops and toothbrush. The gated 7-acre community offers plenty to keep you busy, or happily doing nothing at all. Enjoy the large elevated waterfront pool, updated marina, private boat ramp, assigned boat slips, fish-cleaning stations, tiki huts, grilling areas, and air-conditioned clubhouse. Come for the million-dollar view. Stay for the Florida Keys lifestyle.

10877 Overseas Highway Unit 82, Marathon

58030 Overseas Hwy, Marathon
$3,500,000
3 Beds ⋅ 2 Baths ⋅ 621475 MLS
Great opportunity in the Middle Florida Keys! Owner financing available. Seller financing is available with a 20% down payment, 6.5% interest in a 5-year balloon. Other additional terms are subject to seller approval. This beautifully remodeled luxury oceanfront home is ideal as a full-time residence, vacation retreat, or income-producing investment. The property has a weekly vacation rental license and is currently used by the owner as a second home and part-time vacation rental. The home features three bedrooms, plus an additional room currently used as a fourth bedroom. Enjoy a beautiful, heated oceanfront pool, a smokeless fire-pit area, and breathtaking, unobstructed Atlantic Ocean views from all three levels. The property also includes boulders seawall. Recent improvements include a new roof and new air-conditioning unit, both installed in 2025. Completely remodeled with high-quality finishes, this exceptional property offers comfort, luxury, spectacular views, and excellent vacation-rental potential. Please note: The listing agent has a personal interest in this property.

58030 Overseas Hwy, Marathon

217 Bruce Ct, Marathon
$2,450,000
3 Beds ⋅ 2 Baths ⋅ 621465 MLS
ALMOST A HALF A MILLION DOLLAR PRICE DROP IN 30 days. VERY motivated seller! All offers considered!! Exquisite Tropical keys living in this natural setting with sunset views in the warmth of a coastal home along this beautiful bayside waterfront corner lot, surrounded by 155 feet of seawall & a fabulous 35+ foot dock equipped with a 13000 lbs. boat lift & Quick easy access to the Gulf. Ease in navigating the bay waters for docking & terrific for even the ''monster'' boats! Multiple docking configurations possible! This home provides tranquil privacy & easy living. A large covered out door living area along with an enclosed flex space offers endless opportunities. Plus a double car garage that is large enough for a full size truck! Staying home for the day? Cool off in your pool or sit in the shade of the coconut trees. Want to take a water break? Private steps to the bay with easy launching for your kayaks or paddle boards. Enjoy the views of the gulf & sunsets from your patio & backyard. This open floor plan, high ceilings 3 bedroom, 2 bath home has amazing appointments & finishes throughout. A beautiful kitchen designed for the most discerning chef with: expansive island, stunning granite counters, nicely upgraded 1 year new SS appliances, double Pantry cabinetry & storage galore. Plus a morning coffee bar with upper & lower cabinets , sink & beverage fridge. The Primary ensuite provides a spacious room, natural light, a walk-in shower, a soaking tub & double sinks with drawer/cabinetry vanity, pendent lights plus a TV. Both bathrooms have tile decorative features along with stunning granite counters in primary & Quartz in Guest room + framed mirrors. Additional storage in separate laundry room & linen closets. The expansive patio, dock & stairs recently redone with maintenance free composite; Never have to paint or replaced. Almost new construction, barely been lived in, used as a part-time getaway & Never been a rental. Built 2 feet above flood elevation.

217 Bruce Ct, Marathon

815 39th St, Marathon
$2,490,000
4 Beds ⋅ 4 Baths ⋅ 621438 MLS
Welcome to Emerald Flats, an exclusive gated waterfront community in the heart of Marathon, where sophisticated coastal design and the Florida Keys lifestyle come together effortlessly. Designed & Built by D'Asign Source, this beautifully furnished 4-bedroom, 4-bath residence was completed in 2025 and offers 2,805 square feet of refined living space, thoughtfully designed for both relaxed everyday living and memorable entertaining. High ceilings, abundant natural light, impact-rated windows and doors, and a metal roof complement the home's fresh, modern construction. The interiors are light, airy, and beautifully curated in an elevated coastal palette. At the heart of the home, the designer kitchen pairs quartz countertops, KitchenAid stainless steel appliances, crisp white cabinetry, statement lighting, and an oversized waterfall-edge island with generous seating. A separate bar and entertaining area adds another layer of functionality, while the open-concept layout flows seamlessly into the dining and living spaces. Expansive glass doors invite the outdoors in and open to spacious covered balconies overlooking the Gulf, creating an exceptional setting for morning coffee, sunset cocktails, or simply enjoying the tropical surroundings. The bedrooms are equally inviting, with private balcony access in select rooms and beautifully appointed baths featuring quartz surfaces, glass-enclosed showers, and custom tile details. Boating is an effortless part of the lifestyle with Boat Slip #29 included, measuring approximately 45 feet long by 14.75 feet wide, providing convenient private docking just moments from home. Fully furnished and move-in ready, this exceptional Emerald Flats residence offers the perfect blend of luxury, waterfront living, modern comfort, and easy access to everything that makes Marathon so special. Bring your suitcases, your boat, and start living the Keys lifestyle from day one.

815 39th St, Marathon

818 39th St, Marathon
$2,390,000
5 Beds ⋅ 4 Baths ⋅ 621439 MLS
Welcome to Emerald Flats, a gated waterfront enclave in the heart of Marathon where refined coastal design meets the Florida Keys lifestyle. Designed & Built by D'Asign Source, this beautifully furnished 5-bedroom, 4-bath residence was completed in 2025 and offers 2,565 square feet of thoughtfully designed living space, with high ceilings, an open-concept layout, impact-rated windows and doors, and a metal roof. Elevated on concrete pilings, the home is designed for both style and durability while creating generous covered space beneath the residence. Inside, the light-filled living areas showcase a sophisticated coastal aesthetic with seamless flow between the kitchen, dining, and gathering spaces. The kitchen is a true centerpiece, featuring quartz countertops, KitchenAid stainless steel appliances, crisp white cabinetry, a striking waterfall-edge island, and generous seating and prep space. Expansive glass doors open to covered balconies, extending the living space outdoors, while a separate bar and entertainment area adds another polished touch for hosting family and friends. Outdoor living is equally impressive, with a private heated pool, tropical landscaping, expansive paver areas, and multiple covered spaces ideal for relaxing or entertaining. Boaters will appreciate the included Boat Slip #30, reported to measure approximately 45 feet long by 14.75 feet wide, offering convenient private docking within the Emerald Flats Marina community. The slip is separately identified by Monroe County as a marina condominium boat-slip parcel. Fully furnished and move-in ready, this home offers an exceptional combination of luxury, boating access, modern construction, and effortless island living in one of Marathon's desirable waterfront communities.

818 39th St, Marathon

143 Dorsett Dr, Marathon
$4,950,000
4 Beds ⋅ 3 Baths ⋅ 621424 MLS
Introducing - Casa Del Mar Estate - this exceptional new home offers a rare level of privacy, scale, and waterfront living on an expansive 26,000+ square foot lot accessed by a private road. Designed to take full advantage of its spectacular setting, the property enjoys unobstructed ocean views and an effortless connection between the residence and the surrounding water. The main living quarters offer four bedrooms and three bathrooms, complemented by substantial finished storage space on the lower level. Built with quality and longevity in mind, the residence features impact-resistant windows and doors, a durable metal roof, concrete construction, and premium finishes throughout, offering the ideal combination of style, security, and peace of mind for waterfront living in the Florida Keys. Beyond the residence, the grounds have been thoughtfully designed for refined outdoor living and entertaining, with a resort-style pool positioned directly toward the ocean and a beautifully appointed gazebo creating the perfect setting for sunset gatherings and private celebrations. An outdoor kitchen, pool table, and table tennis area further extend the living space outdoors, creating an environment equally suited to relaxed afternoons with family or elegant entertaining with guests. The waterfront experience is equally impressive, with generous dockage and a new 20,000-pound boat lift, providing exceptional convenience for boating. Two substantial outdoor sheds offer additional storage for boat side essentials, tools, fishing equipment, and water toys, while the expansive grounds provide something rarely found in the Keys: meaningful room for future expansion. A generous portion of the property remains available for new owners to reimagine and potentially add a guest house, A rare combination of privacy, expansive oceanfront grounds, unobstructed views, exceptional boating amenities, and future expansion potential, offering the ultimate Florida Keys lifestyle.

143 Dorsett Dr, Marathon

499 Sombrero Beach Rd, Marathon
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 621413 MLS
Welcome to 499 Sombrero Beach Road, a fantastic opportunity to own a piece of the Florida Keys lifestyle in Marathon! Ideally situated just off U.S. Highway 1 at approximately Mile Marker 50, this property offers a convenient location with easy access to Sombrero Beach, local restaurants, shopping, boating, fishing, and everything that makes Marathon such a sought-after Keys destination. This property provides a great balance of accessibility and the laid-back atmosphere the Middle Keys are known for. One of the few sand beaches of the Keys- Sombrero Beach is just down the bike path, a wonderful place to enjoy a day in the sun, take a swim, or catch a spectacular Keys sunset. Marathon is renowned for its world-class recreational opportunities, including boating, offshore and backcountry fishing, diving, snorkeling, and waterfront adventures. From this location, you'll be conveniently positioned to explore the surrounding islands while still being close to everyday amenities, restaurants, marinas, and local attractions. On site 56' dock was replaced in 2023 and features fish cleaning station, water and electric. The wide canal and premium 5' deep water access allows for larger boats than the average Keys property. Whether you're looking for a full-time residence, a vacation getaway, or an investment opportunity, 499 Sombrero Beach Road is a perfect opportunity. Established, professionally managed, licensed, weekly vacation rental. Come experience the relaxed pace, tropical surroundings, and endless outdoor recreation that make Marathon such a special place to call home. Updates include remodeled kitchen and baths, impact French doors, a metal roof (2021), and AC (2023). It's fully turnkey, with furnishings and future bookings included.

499 Sombrero Beach Rd, Marathon

10877 Overseas Highway Unit 31, Marathon
$529,000
1 Beds ⋅ 2 Baths ⋅ 621411 MLS
A rare two-full-bath layout gives Townhome #31 an edge, adding extra comfort and flexibility for owners, guests, or short-term renters. Located in Ocean Isles Fishing Village, a gated seven-acre oceanfront community in Marathon, this brand-new concrete block townhome offers modern construction, resort-style amenities, and seven-day rental capability. Townhome #31 is a desirable end unit positioned just two rows from the gated entrance, with distant Atlantic views. The two-story residence offers approximately 800 square feet of well-planned living space. The main level includes a bright living area, a sleek kitchen with stainless steel appliances, and a full bath. Upstairs, the private primary suite features its own second full bath, creating a layout that is especially convenient for both everyday living and guests. Impact windows and doors add peace of mind, while the community itself is designed around the Florida Keys lifestyle. Residents enjoy an oversized oceanfront pool, clubhouse, tiki huts, fish-cleaning stations, a private boat ramp, and reserved dockage for owner use. The updated marina is protected by Jack Tar Flats and features a seawall, bulkhead, and docks, offering convenient access to some of the area's best fishing, diving, and boating waters. Ocean Isles is also just minutes from Marathon Airport, making it especially convenient for owners traveling by private or smaller aircraft and adding to the appeal as a lock-and-leave Keys retreat. With an ideal Marathon location, easy access north toward Islamorada and south toward Key West, and close proximity to dining, shopping, and local attractions, Townhome #31 offers a versatile opportunity for a personal getaway, full-time residence, or income-producing vacation rental. Its rare two-full-bath layout, boating access, end-unit position, and resort-style amenities make it a standout within the community.

10877 Overseas Highway Unit 31, Marathon

15 Sombrero Blvd Unit 212W, Marathon
$460,000
2 Beds ⋅ 2 Baths ⋅ 621392 MLS
****BRAND NEW 2.5 TON RHEEM SPLIT SYSTEM 15.2 SEER2 ENERGY EFFICIENT A/C SYSTEM!!**** Discover your perfect Florida Keys getaway at 15 Sombrero Blvd, Unit 212 in Marathon! This beautifully updated 2-bedroom, 2-bath condo comes fully furnished with brand-new furnishings, offering a stylish, turnkey retreat ready for you to enjoy from day one. Located in Marathon Country Club Condominium, this inviting unit is just blocks from Sombrero Beach, with convenient access by bike or on foot. Boaters will appreciate the rare opportunity for dockage accommodating boats up to 25 feet with no waiting list,along with quick access to both the ocean and Gulf via a wide, deep canal. Enjoy the community pool and relaxed, resort-style atmosphere while being just minutes from Marathon's shopping, dining, and endless Keys adventures. Whether you're looking for a turnkey vacation escape, a full-time residence, or a place to enjoy the best of the Florida Keys, this fully furnished condo delivers comfort, convenience, and location. Bring your suitcase and start enjoying the Keys--this one is ready for you! Schedule your private showing today.

15 Sombrero Blvd Unit 212W, Marathon

12400 Overseas Hwy Unit Villa 3, Marathon
$769,000
3 Beds ⋅ 3 Baths ⋅ 621323 MLS
PRIVATE ROOFTOP TERRACE, PANORAMIC WATER VIEWS AND WEEKLY RENTAL FLEXIBILITY! Welcome to Villa #3, a turnkey, fully furnished 3-bedroom, 3-bath villa offering 1,493 sq. ft. in a private gated bayfront community in Marathon. With 7-day rentals allowed and rental income already being produced, this property offers excellent flexibility as a vacation rental, second home, or Florida Keys getaway. Beautifully decorated in warm coastal style, the villa features an open-concept living, dining, and kitchen area with bar seating, stainless steel appliances, and a fully equipped kitchen. The spacious layout includes two primary suites with en-suite baths, a third bedroom and full bath, washer and dryer, owner's closet, and multiple private balconies. Impact-resistant windows and doors and a pre-built elevator shaft add additional value. A standout feature is the expansive private concrete rooftop terrace with panoramic views of the Gulf, Vaca Cut and Marathon--perfect for sunset cocktails and entertaining. Outdoor amenities include covered parking for at least two vehicles, a grill, seating area, bait freezer, kayaks, and sunshades. The community offers a pool, dockage, and waterfront common areas with beautiful bay views. Association services include water, sewer, trash, landscaping, and pool maintenance. Fully furnished and ready to enjoy from day one, Villa #3 combines the Florida Keys lifestyle with the added advantage of weekly rental flexibility and income potential.

12400 Overseas Hwy Unit Villa 3, Marathon

355 Stirrup, Marathon
$3,300,000
4 Beds ⋅ 4 Baths ⋅ 621321 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 turnkey home offers exceptional privacy, protected dockage and sweeping Gulf views with spectacular sunsets. Extensively updated, the home features a brand-new kitchen with custom cabinetry, a custom bar, updated flooring, new impact windows and doors, and new A/C units. New Hardie board siding accents the front exterior, adding texture and architectural character. The main level features the primary suite with a newly expanded and completely renovated bathroom. An additional guest bedroom enjoys marina views with a full bath nearby. A newly extended covered back porch off the living and dining rooms offers outdoor seating and dining overlooking the pool and Gulf. Upstairs, a secondary primary suite features a private full bath and walk-out balcony with stunning bay views, while another guest bedroom and half bath also enjoy expansive open-water views. Downstairs, a spacious covered patio and newly built tiki bar create additional entertaining space poolside. The pool has been beautifully re-tiled and refinished with new equipment, including a heater and chiller. A redone waterfront observation deck provides easy kayak access, views over the sandy bay bottom, and a front-row vantage point for spectacular sunsets. Protected dockage is just across the street in Stirrup Key's private marina. Boat slip D41 includes a new concrete walk-out dock and a 15,000-lb boat lift, with instant bay access and quick ocean access via Vaca Cut or Seven Mile Bridge. Additional features include a metal roof, garage, ground-floor storage, a fenced dog run, and mature tropical landscaping highlighted by a grove of gumbo limbo trees. Sunset Anchorage brings together open-water views, protected boating, privacy, and unforgettable Florida Keys waterfront living-offered turnkey and ready to enjoy from day one.

355 Stirrup, Marathon

851 104th St, Marathon
$4,675,000
3 Beds ⋅ 3 Baths ⋅ 621314 MLS
Welcome to Your Private Oasis in the Heart of the Florida Keys! Discover this hidden gem, a secluded gated estate nestled amidst the stunning landscape of the Florida Keys. Located directly on the sparkling waters of the Atlantic Ocean with 120' of protected deep-water dockage on canal, this property is perfect for boating enthusiasts. This half-acre estate exudes charm and casual elegance, with wide, sweeping porches at both the front and back, providing the perfect setting for outdoor relaxation and entertaining. Inside, you'll find three spacious bedrooms, three luxurious baths, and a cozy den that offers versatile living space. Beautifully landscaped with mature tropical plants, this home features a stunning pool set amidst lush gardens, creating your own slice of paradise. Plus, you're just a short walk from the Millionaire FBO Jet Center, making travel to and from this exquisite location a breeze. Don't miss the opportunity to own this exceptional estate in the Florida Keys! Schedule your private showing today!

851 104th St, Marathon

117 Coco Plum Dr Unit D2, Marathon
$675,000
2 Beds ⋅ 3 Baths ⋅ 621306 MLS
Welcome to 117 Coco Plum Dr #D2, a beautifully updated and fully furnished townhouse in The Shores of Coco Plum, one of the Middle Keys' most desirable oceanfront communities. This spacious two-story residence blends modern comfort with relaxed coastal living in an intimate beachfront setting. The main level features soaring ceilings, abundant natural light, and an open living area that flows easily to a screened balcony, creating a comfortable spot for outdoor dining, morning coffee, or simply enjoying the ocean breeze. Upstairs, the primary suite offers its own private open-air balcony, along with a spacious layout and beautifully finished en-suite bath. Both upstairs bedrooms include private en-suite bathrooms, providing privacy and convenience for owners and guests alike. A half bath on the main level adds extra functionality for everyday living and entertaining. The remodeled kitchen features quality wood cabinetry, natural stone countertops, and stainless steel appliances, while wood-look tile flooring runs throughout the home for a clean, cohesive feel. Additional features include impact windows and doors, an indoor laundry closet with a full-size washer and dryer, and covered parking. The Shores at Coco Plum is an intimate 16-unit oceanfront community offering a heated swimming pool, tennis and pickleball courts, on-site storage, and direct access to one of the few long, walkable beaches in the Middle Keys. Whether you're swimming, snorkeling, paddling, walking the shoreline, or simply relaxing by the water, the best of Keys living is right outside your door. With its updated interior, private outdoor spaces, beachfront location, and fully furnished convenience, this townhome is well suited as a full-time residence, second home, or investment property.

117 Coco Plum Dr Unit D2, Marathon

108 Ave D, Marathon
$5,499,000
6 Beds ⋅ 6 Baths ⋅ 621304 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 Ave D, Marathon

835 & 837 Copa D Oro, Marathon
$5,399,000
8 Beds ⋅ 8 Baths ⋅ 621248 MLS
Looking for a truly unique opportunity in the Florida Keys? Check out these 2 Custom Luxury CBS Pool Homes that are side by side! Live in one, and rent the other, corporate retreats, weddings, vacation rentals, tons of options! Can be sold furnished and turn key too. Experience luxury waterfront living in these custom-built, new construction two-story concrete homes featuring 4 bedrooms and 4 private en-suite baths. Designed for entertaining, the open-concept layouts seamlessly blends indoor and outdoor living. The chef's kitchens boasts top-of-the-line stainless steel appliances including double convection ovens, Smart refrigerator, dishwasher, vented range hood, prep sink, wine chiller, quartz countertops, custom cabinetry, and a large island. Porcelain tile flooring, custom fixtures, LED lighting, and abundant natural light enhance every space. A first-floor en-suite bedroom offers balcony access overlooking the pool, dock, and water. The dramatic floating staircase with custom LED chandelier leads to three additional en-suite bedrooms upstairs. The primary suite features a floating soaking tub, double vanity, custom porcelain tile shower, and MOEN programmable multi-head shower system with smartphone controls. Additional features include impact windows and doors, web-enabled security camera system, 4K Smart TVs in every room, 8-foot interior doors, two 3-ton 16 SEER A/C units, standing seam metal roof, aluminum railings, and expansive balconies on both levels. Located in the desirable Flamingo Island neighborhood of Marathon, just minutes from Sombrero Beach, dining, shopping, and entertainment. Enjoy quick access to open water, world-class fishing, boating, diving, and the crystal-clear turquoise waters of the Florida Keys. Built to impress and built to last, these exceptional waterfront retreats offer the ultimate Florida Keys lifestyle. Set up your preview today!

835 & 837 Copa D Oro, Marathon

57457 Morton St, Marathon
$2,695,000
2 Beds ⋅ 2 Baths ⋅ 621246 MLS
A rare combination of land, privacy, boating, and open-water living awaits on approximately half an acre of Gulf-front paradise in Grassy Key. With panoramic water views, a private beach, waterfront dock with a 20,000-pound boat lift, heated concrete pool, and lush tropical grounds, this property captures the very best of Florida Keys living. Surrounded by mature landscaping, the two-bedroom, two-bath residence enjoys a peaceful, private setting with beautiful Gulf views. Light-filled living spaces embrace the waterfront surroundings, while the kitchen features granite countertops and stainless steel appliances. Both bedrooms offer private baths for owners and guests alike. Step outside and the Keys lifestyle comes alive. Walk to your private sandy beach, lower the boat from your 20,000-pound lift for a day on the water, relax beside the heated pool, or watch the sun disappear over the Gulf from your own shoreline. Expansive grounds and tropical landscaping provide a level of space and privacy that can be difficult to find in the Keys. The property also boasts an exceptional rental history, consistently renting approximately 50 weeks per year and generating roughly $175,000 in annual rental revenue--a testament to the tremendous appeal of this waterfront setting. Whether you're searching for a private Keys retreat or a proven vacation rental investment, this Grassy Key property offers an extraordinary combination of lifestyle and opportunity. Private beach. Open Gulf views. Boating. Pool. Half an acre of tropical privacy. This is the Florida Keys lifestyle people dream about.

57457 Morton St, Marathon

96 Ave C, Marathon
$1,250,000
2 Beds ⋅ 3 Baths ⋅ 621219 MLS
Bonefish Yacht Club Townhomes, a Middle Keys premiere boating community cloistered around the 50 slip Bonefish Marina. Resort style living in this sought after oceanfront complex of only 34 homes. This unit can conveys with A-16, a deep water, direct ocean access, 40' liveaboard boat slip. Buyer approval for the boat slip will be required through Bonefish Marina. Other amenities featured are; swimming pool, tiki, meticulously maintained tropical landscaping, tennis and private beach access. Unparalleled views of the marina and Key Colony Channel. Two story townhome with covered parking and secure angler's room on the lower level, kitchen, living, dining on the main level and two spacious bedrooms with full baths on the third floor. Private, open air balconies to enjoy both sunrise and sunset. Concrete construction, impact windows and metal roof. Excellent for a full time residence, Keys fishing getaway or investment property as a income producing weekly rental. A true pleasure to show.

96 Ave C, Marathon

875 50th St, Marathon
$5,499,000
5 Beds ⋅ 5 Baths ⋅ 621212 MLS
At the very tip of a private peninsula in the heart of the Florida Keys, this stunning Gulffront property delivers the ultimate waterfront lifestyle. Built in 2022, this 4,146 sq. ft. Coastal Modern residence was crafted by one of Marathon's premier builders with meticulous attention to detail, blending clean architectural lines with the relaxed elegance of island living. From the moment you arrive, the Gulf is your constant backdrop. Expansive walls of glass flood the interiors with natural light and frame endless turquoise waters. Every living area, from the two spacious lounges to the gourmet kitchen, was designed to maximize the view and the connection to the outdoors. The chef's kitchen is both beautiful and functional, featuring waterfall-edge quartz counters, premium stainless appliances, and abundant prep space. Whether hosting a casual brunch or an elegant dinner, this open-concept space flows seamlessly to indoor and outdoor gathering areas. Five ensuite bedrooms provide private sanctuaries for family and guests. The primary suite is a haven unto itself, offering a sitting area, spa-inspired bath, and a private porch where morning coffee comes with dolphin sightings and golden sunrises. Step outside to a personal resort: a shimmering pool with sun shelf, expansive patios for lounging, and a palm-lined peninsula with a fire pit at its tip. A deep-water dock, private boat basin, and 4-post lift make boating effortless, with 5' control depth ensuring smooth access to open water. This home offers the convenience of an elevator, an oversized 2-car garage, and low-maintenance construction designed for coastal living. Located 5 minutes from Marathon Jet Center, you can go from tarmac to tiki torch in record time. Whether it's a weekend escape, seasonal retreat, or full-time residence, this Gulf Front estate offers something truly rare: privacy, luxury, and the beauty of the Keys wrapped into one extraordinary address. Fantastic Rental History. Offer Turnkey.

875 50th St, Marathon

2000 Coco Plum Dr Unit 302, Marathon
$379,000
1 Beds ⋅ 2 Baths ⋅ 621184 MLS
Perched above the shimmering Coco Plum Channel, this beautifully reimagined one bedroom, one- and-a-half bath residence at Bonefish Towers offers ocean views from every window -- a rare opportunity to own in one of Coco Plum 's most coveted addresses. Thoughtfully renovated throughout, the residence showcases a crisp, coastal-inspired aesthetic complemented by raised ceilings in the master bath, kitchen, and foyer. Every detail has been elevated, from the brand-new impact windows and sliding glass doors to the updated air conditioning, kitchen, flooring, electric blinds and so much more. This home is being offered furnished. As one of only thirteen residences in the building with two balconies, it offers an exceptional setting for indoor-outdoor living and unobstructed water views. Resort amenities in the community include a heating swimming pool, update fitness center, tennis/pickleball court, waterfront tiki hut/fishing station, waterfront BBQ area, 24 hour security and plenty of parking. The building is in great shape with two new elevators, a new roof and new exterior paint.

2000 Coco Plum Dr Unit 302, Marathon

111 Ave D, Unit 2, Marathon
$2,899,000
5 Beds ⋅ 5 Baths ⋅ 621167 MLS
Now offered turnkey furnished, this brand-new waterfront home in Marathon's Coco Plum neighborhood features 5 bedrooms, 5 bathrooms, and two 40+ ft boat slips. Enjoy a private pool, covered terraces, and a summer kitchen overlooking the canal. The first floor offers a ranch-style entrance with a bedroom, full bath, family room, and laundry--ideal for guests or mother-in-law quarters. Upstairs, open-concept living, a beautifully appointed kitchen, and a primary suite with a private waterfront terrace complete the home. Built with rentals in mind, dual washer and dryer stations make hosting easy. CBS construction, impact windows and doors, and a metal roof add lasting appeal to this ready-to-enjoy Keys retreat.

111 Ave D, Unit 2, Marathon

171 Ave D, Marathon
$2,395,000
4 Beds ⋅ 3 Baths ⋅ 621168 MLS
New construction waterfront living in the heart of Coco Plum. This beautifully designed 4-bedroom, 3-bath residence combines modern coastal style, exceptional outdoor living, and direct boating access in one of Marathon's most desirable waterfront neighborhoods. Thoughtfully positioned to take advantage of the setting, the home offers expansive open-water views from nearly every room and a bright, open-concept layout designed for both everyday living and entertaining. The main living level features a spacious living and dining area surrounded by natural light and water views, along with two guest bedrooms and a full bath. Upstairs, two generously sized primary suites each feature private en-suite baths and elevated panoramic views, creating peaceful private retreats above the water. Outdoor living is a true highlight, with three covered terraces spanning both levels, a large resort-style pool, and a convenient poolside prep station with sink and storage. Whether hosting guests, relaxing by the pool, or enjoying a quiet morning overlooking the water, the home is designed to embrace the Florida Keys lifestyle. Boaters will appreciate approximately 50 feet of deep-water dockage with quick ocean access, along with a fish-cleaning station, bait freezer, and covered parking for added convenience. Ideally located near Coco Plum Beach and just minutes from Marathon's dining, shopping, and attractions, this newly constructed waterfront residence offers an exceptional combination of modern comfort, boating access, privacy, and island living, perfect as a full-time residence, vacation retreat, or investment property.

171 Ave D, Marathon

235 Tropical Ave, Marathon
$1,150,000
4 Beds ⋅ 3 Baths ⋅ 621156 MLS
Tucked into the natural landscape of Grassy Key, 235 Tropical Avenue offers a unique combination of space, privacy and the unhurried character that defines life in the Middle Keys. Set on a 15,000-square-foot lot in Crains Subdivision, this concrete stilted residence offers more than 3,600 square feet of living space, impact windows and doors, and generous indoor-outdoor areas designed around the Florida Keys lifestyle. An expansive open layout creates room to gather, entertain and settle in comfortably, with multiple living spaces and an easy connection to the outdoors. Lush native vegetation surrounds the property, creating a remarkable sense of privacy and seclusion. The partially fenced backyard centers around an inviting in-ground pool with waterfall, tanning shelf and water features, setting the stage for long afternoons outside and evenings under the palms. Ample parking provides room for multiple vehicles and boat trailers, an especially valuable feature for enjoying life on the water. Above it all, a rooftop observation deck captures ocean views and a beautiful perspective across Grassy Key. Watch the light change over the horizon and native birds gather around the natural salt ponds behind the property. Crains Subdivision also offers a community sunset park, while a public boat ramp is just minutes away for convenient access to the surrounding waters. Centrally positioned between Marathon, Duck Key and Islamorada, the home is convenient to Curry Hammock State Park, Dolphin Research Center, waterfront dining, marinas, fishing, diving, paddling and the Florida Keys Overseas Heritage Trail. Whether envisioned as a full-time residence or a private Florida Keys retreat, 235 Tropical Avenue feels connected to its surroundings, offering a spacious and secluded setting from which to experience the water, wildlife and easy rhythm of Grassy Key.

235 Tropical Ave, Marathon

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