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$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
$4,499,000
3 Beds ⋅ 4 Baths ⋅ 620861 MLS
Set along the Gulf on 2 lots within the sought-after gated Stirrup Key community, this beautifully appointed CBS residence captures panoramic open-water views, unforgettable sunsets, and a rare sense of privacy. Electronic gated entry and tropical surroundings create an immediate sense of arrival while extensive upgrades reflect elevated living and effortless enjoyment. Contemporary design and relaxed coastal living come together through an open, light-filled floor plan. Expansive impact windows and sliding glass doors frame the water from every angle, bringing the ever-changing Gulf backdrop into the interior. The chef's kitchen features quartz countertops, Bosch stainless appliances, custom cabinetry, and a seamless connection to the dining and living areas. Solar panels further enhance the home's thoughtful, energy-conscious design. The thoughtfully designed layout includes two spacious primary suites, each offering private balcony access and sweeping water views. A third guest bedroom, guest bath, private gym, and an additional full bath add comfort and versatility. Outdoors, the property unfolds as a private tropical escape. A waterfront pool, covered entertaining area, outdoor shower, and multiple gathering spaces create the perfect setting for relaxed afternoons and memorable evenings. Mature fruit trees surround winding garden pathways leading to peaceful seating areas and a waterfront fire pit. A deeded boat slip with lift in the private marina is located just steps from the front door, offering exceptional convenience on the water. Along the open-water shoreline, a private kayak dock with lift provides direct access to exceptional kayaking and paddleboarding from your own backyard. Just minutes from shopping, dining, and The Marathon International Airport, this exceptional residence offers a rare combination of open-water beauty, boating access, privacy, and effortless island living

108 Sunset Dr, Marathon
$777,000
2 Beds ⋅ 2 Baths ⋅ 620695 MLS
Desirable 2 bedroom, 2 bath on a Private Street with Waterfront Access! Welcome home to this well maintained concrete block home, ideally located on a quiet private residential street. Enjoy exclusive access to a community park and private boat ramp reserved for owners, making it perfect for boating and outdoor enthusiasts. The property features lush tropical landscaping with mature fruit trees, a beautiful rock garden, and plenty of out door space to relax and entertain. Inside, you'll find a comfortable layout with spacious living areas, while the oversized two car garage offers ample room for vehicles, storage or a workshop. Plus an extra storage, office or artisan space. Whether you're a first time home buyer, looking to down size, or searching for the perfect family home, this property offers comfort, privacy, and a desirable neighborhood in a peaceful setting. Don't miss this opportunity to own a slice of PARADISE!

91 Dorsett Dr, Marathon
$15,000,000
5 Beds ⋅ 5 Baths ⋅ 620594 MLS
Welcome to Palacio Coco Plum. Discover Your Florida Keys Oasis! Spectacular Ocean Front home in Marathon, the heart of the Florida Keys. This stunning property boasts luxury finishes throughout, including elegant marble floors, granite counters and volume coffered ceilings. Key Features include: His and Her ocean facing office, ideal for remote work or study, ocean views from most all rooms, white sand beach. privacy landscaping and massive car and equipment storage for multiple vehicles and hobbies. Boat Dockage Permitting is in Progress. Additionally, there is a whole house generator for back-up power, elevator from garage to top floor, heated and chilled pool and spa. The lovely gardens include mature mangoes and avocado trees and orchid trellis. 10 Minutes to Marathon International Airport. ADT Camera Security System on site

119 Coco Plum Dr, Marathon
$1,450,000
2 Beds ⋅ 3 Baths ⋅ 620503 MLS
Introducing 8401 Gulf of Mexico Blvd #8401, an exceptional waterfront penthouse with Boat Slip #23, located in the prestigious Seawatch community of Marathon, Florida. Renovated in 2023 and meticulously maintained since, this top floor residence offers an impressive combination of comfort, style, boating access and one of the most captivating open water views in the community. From the moment you step inside, expansive impact windows frame breathtaking Gulf views and fill the living space with natural light. The spacious layout features two generous suites, an open living and dining area and a clean coastal feel designed for relaxed Florida Keys living. The 2023 renovation included thoughtful updates to the kitchen, bathrooms, flooring and interior finishes. The kitchen offers updated cabinetry and appliances, while the remodeled bathrooms feature updated tile and showers, creating a move in ready residence that has been carefully improved and maintained. Seawatch is known for one of the most impressive amenity packages in the Middle Keys, including a gated entrance, marina, resort style pool and spa, cabanas, fitness center, clubhouse/event room, tennis & pickleball courts, elevators, tropical landscaping, natural habitat areas, lake and generous open space rarely found in a condo community. Complete with protected dockage and a premier waterfront setting, this Seawatch penthouse is ideal as a full time residence, seasonal retreat, or low maintenance Florida Keys getaway. Enjoy boating, views, privacy and resort style amenities all in one of Marathon's most desirable waterfront communities.

8401 Gulf Of Mexico Blvd Unit #401, Marathon
$14,995,000
11 Beds ⋅ 9 Baths ⋅ 620489 MLS
Welcome to Morton Manor, an exceptional gulf-side waterfront estate set on 2.82 private acres where luxury, privacy, and resort-style living come together in this extraordinary Florida Keys compound. Encompassing 8,515 sq. ft. of living space, this property features a 5-bedroom, 4.5 bath CBS main residence accompanied by two detached guest homes and a garage apartment, offering a total of 11 bedrooms and 8.5 baths designed to comfortably accommodate family and guests alike. The main home showcases an open-concept floor plan with expansive living and dining areas, two wet bars, elevator access, multiple laundry areas, and spacious guest accommodations, creating an ideal setting for both everyday living and large-scale entertaining. The detached bungalows and garage apartment provide additional flexibility for extended family, visitors, or exceptional rental opportunities while maintaining privacy throughout the estate. Impact-rated windows and doors, a durable metal roof, and quality construction provide lasting peace of mind. The outdoor amenities rival those of a private resort. Relax beside the pool, gather beneath multiple tiki huts, challenge friends to a game on the pickleball court or putting green and enjoy beautifully landscaped grounds. Boating enthusiasts will appreciate the 100' dock complete with 30-amp and 50-amp shore power, yacht dockage and 10K & 20K lb boat lifts. Positioned on the gulfside, the property offers easy access to world-class fishing, boating, snorkeling coves, sandbars, and unforgettable sunset cruises. Dining, marinas, and shopping are less than ten minutes away, and the Florida Keys Marathon International Airport is approximately 4 miles from the property for seamless private aviation access. Whether you're searching for a private family compound or an exceptional investment opportunity, Morton Manor offers a rare combination of acreage, waterfront living, luxury amenities, and versatility that is seldom found in the Florida Keys.

57733 Morton St, Marathon
$2,749,000
3 Beds ⋅ 4 Baths ⋅ 620237 MLS
A waterfront home that is truly the kind of place that makes people stop scrolling, not because it is flashy or overdone, but because it feels rare and real. Set in the highly desired Sombrero Golf Course neighborhood, this property offers a combination that is hard to find in the Florida Keys, a beautiful home, a prime waterfront setting, strong elevation, and a layout that makes everyday life easy while still feeling special. Inside, you will find three bedrooms, each with a private en suite bathroom, plus an additional half bath off the living room for guest convenience. The spacious open floor plan is built for easy living and entertaining, with the kitchen as the true centerpiece. Custom designed with hickory cabinetry, granite countertops, Wolf cooking appliances, a full size Sub Zero fridge and freezer, a 105 bottle wine cooler, and a Miele espresso machine, it is both beautiful and functional. The oversized island seats four and includes smart built in storage to keep everything organized and clutter free. Outside, enjoy a fully screened in pool deck with a built in outdoor kitchen, plus 125 feet of recently repoured dockage with a 15,000 pound boat lift, davits, and two 50 amp shore power stations, along with immediate Ocean and Gulf access for the ultimate Florida Keys boating lifestyle. One of the biggest advantages of this home is its rare ground level, above flood construction. That alone makes it stand out, but the high and dry elevation makes it even more desirable. With new impact windows and doors, a metal roof, and a whole house generator, the major upgrades are already done, offering comfort, confidence, and true peace of mind for Keys living.

2919 Sombrero Blvd, Marathon
$2,100,000
3 Beds ⋅ 2 Baths ⋅ 620036 MLS
Welcome to 499 Avenida Primiceria in Marathon FL. This unique home is perfectly located just 7 houses from beautiful Sombrero Beach and only minutes away from open water for boating. Enter into the central hub of the home that offers cathedral open beam ceilings and a generous, updated open floor plan for common living areas and direct access to the screened porch that overlooks the pool and dock. The split floor plan for the bedrooms offers additional privacy with the Primary suite located in the opposite wing from the guest rooms. Everything has been updated from the plank tile flooring, the impact resistant windows and doors, the open custom kitchen and update bathrooms. There is a while house generator. The lower level hosts a garage, workshop, covered entertaining area, and tons of additional storage space. The custom concrete pool is heated and chilled and the dock is 100' of concrete seawall with a 14k lb. boat lift. The grounds are covered with pea rock and mature tropical landscaping making for ease of maintenance and a lush private tropical setting. Call today for more information and schedule your private tour of this wonderful Florida Keys retreat.

499 Avenida Primiceria, Marathon
$2,950,000
3 Beds ⋅ 2 Baths ⋅ 619945 MLS
An Exquisite Tropical keys living experience awaits. A natural setting with sunset views in the warmth of a coastal home located along this beautiful bayside waterfront corner lot. This home is surrounded by 155 feet of seawall & a fabulous 35+ foot dock equipped with a 13,000 lb boat lift with 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 stilted home provides tranquil privacy & easy living. A concrete pad below provides lots of covered out door living space along with an enclosed a flex space area plus a double car garage that can handle 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 into the bay give you easy access to launch 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. This almost new construction has barely been lived in used as a part-time getaway & Never been a rental. The construction is built 2 feet above flood elevation. A tru

217 Bruce Ct, Marathon
$3,495,000
4 Beds ⋅ 4 Baths ⋅ 619913 MLS
Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key offering expansive water views, a white sand beach, and resort-style living. A strong-producing vacation rental with established history and future bookings in place, this exceptional estate presents an attractive investment opportunity. Set on more than 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, Casa Feliz is designed for relaxation and entertaining. An observation pier provides access for kayaking, paddleboarding, fishing, and enjoying abundant marine life. Dockage is available nearby at Duck Key Marina or Grassy Key Marina, if desired. The property's unique orientation captures both sunrise and sunset views, a rare feature in the Keys. Outdoor amenities include a saltwater pool with cascading waterfalls, spillover spa, and a fully equipped poolside cabana featuring a wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit offer inviting spaces to gather beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was redesigned to maximize ocean views throughout. Four custom bedroom suites, each with a private en-suite bath, comfortably accommodate guests. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Accordion impact-glass doors create a seamless connection between indoor and outdoor living. The gourmet kitchen features Café appliances, an induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, and a mural by a local artist. Come discover why Grassy Key is the place to be.

58652 Overseas Hwy, Marathon
$684,000
2 Beds ⋅ 3 Baths ⋅ 619770 MLS
Perfectly positioned just steps from the pristine shores of Sombrero Beach, premier shopping, and vibrant nightlife, Lemon Cove stands in a class entirely its own. No other condominium residence in the area offers such a rare combination of generous private parking, breathtaking canal frontage, impeccably manicured grounds, and a resort-style pool -- all seamlessly curated for the discerning buyer. This exceptional 2-bedroom, 2.5-bathroom canal-front residence commands sweeping views of both the sparkling pool and tranquil canal, framed by generously proportioned living spaces and refined, upscale finishes throughout. Every detail has been thoughtfully considered, offering an effortless lifestyle where luxury and low-maintenance living exist in perfect harmony. For those who have envisioned waking each morning to the serene beauty of waterfront living -- without compromise -- this is your moment to live near the beach!

591 Sombrero Beach Rd Unit APT 1B, Marathon
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 619765 MLS
Welcome to Casa Sirena, a refined waterfront retreat in Marathon offering comfort, privacy, and strong investment appeal. Seller Financing available! This five bedroom, three bath home includes a convenient outdoor pool bath and is ideally positioned with water frontage on two sides. Boaters will appreciate 100 feet of durable composite dockage, a jet ski lift, and a private boat ramp shared with just one neighbor. The home enjoys close proximity to Boot Key Harbor, with easy access to waterfront dining by boat, as well as a straightforward route to the Gulf via Knight Key Channel and immediate Ocean access. The surrounding Vaca Key and Boot Key provide a natural buffer, offering added protection from the elements. Outdoor living is central to the property, with lush tropical landscaping, a saltwater pool, tiki hut, and expansive wraparound patios accessible from all rooms. Inside, the open floor plan connects the living, dining, and kitchen areas, creating a comfortable and functional space. The kitchen is equipped with high end appliances suited for everyday use or hosting. Additional features include a spacious two car garage with ample storage, an extra washer and dryer, refrigerator, freezer, and workbench. The home is offered fully furnished and turnkey, ready for personal use or as a vacation rental. Privacy fencing, a security system, and gated dock and ramp access complete the offering.

103 52nd St, Marathon
$8,299,999
3 Beds ⋅ 4 Baths ⋅ 619460 MLS
Tucked on the private shores and gated community of Tingler Island, this one-of-a-kind dual-waterfront estate is where the Florida Keys lifestyle reaches its fullest expression. Design/Build by D'Asign Source, meet Bella Vista, a coastal-modern renovation. Experience the ultimate coastal dichotomy: wake to the breathtaking panorama of the Atlantic Ocean, while enjoying the calm, effortless convenience of protected canal-front docking. A rare luxury configuration w/ Main Home on the Open Atlantic Ocean to Guest Home on Canal Frontage. Spend your mornings fishing, afternoons floating in your multi-level infinity pool as it disappears into the ocean horizon & evenings gathered around the gas fire pit beneath swaying palms & stars. The 8' wide by 107' concrete dock accommodates two boat lifts (3,000 & 17,000 lbs) w/ water, electric, & lighting along the full seawall, everything a serious boater needs. The single-bedroom Main Home stuns w/ soaring 18-ft vaulted ceilings, exposed wood beams, & a wall of six floor-to-ceiling glass panels that open to frame the Atlantic as your daily backdrop. The gourmet kitchen features Sub-Zero & Wolf appliances, a Miele coffee system, a 10-ft island, Brittanica quartz countertops, & a temperature-controlled glass wine wall. A sea-inspired chandelier, custom wall paneling & thoughtful finishes flow throughout. The expansive Primary Suite anchors the home w/ ocean views, a floating soaking tub, glass rain shower, dual sinks, & a built-in home office tucked into the layout. The private Guest Home above the double garage offers 2 beds, 2 baths, a kitchenette, private balcony, & its own washer/dryer-ideal for guests or family. Outside, resort-style grounds include a gazebo w/ marble dining table, outdoor kitchen w/ Lynx premium grill & fridge, beach sand, fruit garden, Tuuci marine-grade parasols, tiki torches, Coastal Source audio, 1,000 gallon gas tank & full home generator. Bella Vista isn't just a home, it's your Keys life, fully lived.

100 Tingler Ln, Marathon
$4,400,000
3 Beds ⋅ 4 Baths ⋅ 619002 MLS
Now priced UNDER recent appraised value of $4,500,000! Embrace the RARE opportunity to own 1.75 acres of open water paradise in the prestigious, gated community of Stirrup Key. Over 600' feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Five protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary.

111 Windy Point Cir Unit & Lot 78, Marathon
$535,000
2 Beds ⋅ 2 Baths ⋅ 618736 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 Ave, Marathon