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$999,000
3Beds
3Baths
1,548Sqft
Duck, Florida, 33050, United States
Looking for your Florida Keys dream home with space to spread out, soak up the sun, and maybe even tinker with a classic car or two? Welcome to 108 Jamaica Street on Duck Key, a tropical paradise on a double lot with a custom-built CBS home, screened pool, guest house, cistern for watering plants and washing cars, and epic garage. This place was built with love by the current owner and it shows.
Homes and Land
$999,000
108 Jamaica Street
3Beds
3Baths
1,548Sqft
Duck, Florida, 33050, United States
Looking for your Florida Keys dream home with space to spread out, soak up the sun, and maybe even tinker with a classic car or two? Welcome to 108 Jamaica Street on Duck Key, a tropical paradise on a double lot with a custom-built CBS home, screened pool, guest house, cistern for watering plants and washing cars, and epic garage. This place was built with love by the current owner and it shows. Inside the main house, you'll find gorgeous cypress tongue-and-groove ceilings, impact windows, a big kitchen with quartz counters, and a breakfast bar that seats six for friends and family to gather around. The primary suite has a cedar closet and loads of light. Between the main house and guest you will find your own private pool lounge, completely screened in so you can enjoy a clean pool all day or night, no bugs allowed! The detached guest house is perfect for in-laws, visitors, or a home office. Got toys? There's space for an RV and a garage that's built above flood level, a true rarity in the Keys. For more entertainment you can join Club Duck Key offering a large pool, tennis, pickleball, clubhouse and more. Live the island lifestyle in this peaceful home on one of the most desirable islands in the Keys.
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Homes and Land
$4,900,000
5Beds
5Baths
4,284Sqft
MARATHON, Florida, 33050, United States
Nestled within the coveted Coco Plum neighborhood, this remarkable estate epitomizes luxury waterfront living in the heart of the Florida Keys.
Homes and Land
$4,900,000
116 Avenue G
5Beds
5Baths
4,284Sqft
MARATHON, Florida, 33050, United States
Nestled within the coveted Coco Plum neighborhood, this remarkable estate epitomizes luxury waterfront living in the heart of the Florida Keys. Meticulously crafted by D'asign Source, this custom home boasts an unparalleled blend of sophistication, comfort, and functionality while also offering some of the best deep-water boating in the Keys from 110' of canal frontage and rare deeded canal bottom. Upon arrival, the estate captivates with its generous private lot and meticulously manicured flora. Renovated to perfection in 2024, the main house and new addition guest house seamlessly integrate modern amenities with tasteful seaside decor. Inside, the spacious open floor plan and towering cathedral ceilings give way to a wall of windows overlooking a generous deck and pool below. A gourmet kitchen is outfitted with top-of-the-line Sub Zero, Wolf, and Miele appliances, quartz countertops, and a walk-in pantry, and a 450-bottle walk-in wine closet with independent climate control caters to the discerning oenophile. After dining, retreat to the primary suite, where a balcony offers breathtaking views of the tranquil pool deck and canal below. Enjoy expansive outdoor living spaces, where a heated and chilled saltwater pool awaits alongside an aptly outfitted outdoor kitchen, providing the perfect setting for alfresco dining and soires under the stars. 80' of new dockage with dolphin cluster pilings to accommodate up to a 90' yacht plus a new 20K pound lift all on a 200' wide canal with 6' control depth yields unrivaled large vessel access to both the Atlantic Ocean or the Gulf. An outdoor shower provides a refreshing respite after a day on the water. 3 separate garages afford parking in excess of 4 vehicles, and storage for an abundance of toys and tools. 45 KW Generator to power the entire house with 1,000 gallon propane tank. Owner occupied and never rented this Coco Plum Estate offers a rare opportunity to indulge in the quintessential Florida Keys Lifestyle.
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Homes and Land
$14,500,000
3Beds
4Baths
4,065Sqft
Duck, Florida, 33050, United States
Nestled within the confines of exclusive Plantation Island, at the end of a quiet cul-de-sac, lies a monumental Oceanfront estate of unparalleled proportion. Enveloped in lush tropical landscaping, and sprawling across an oversized 17,900 Sq. Ft.
Homes and Land
$14,500,000
201 W Seaview Drive
3Beds
4Baths
4,065Sqft
Duck, Florida, 33050, United States
Nestled within the confines of exclusive Plantation Island, at the end of a quiet cul-de-sac, lies a monumental Oceanfront estate of unparalleled proportion. Enveloped in lush tropical landscaping, and sprawling across an oversized 17,900 Sq. Ft. Point Lot, boasting stunning Open Water Views, every detail has been considered at this coastal retreat in coveted Hawks Cay! Enjoy Direct Ocean Access with approximately 200' of concrete seawall, with additional dock featuring jetski and boat lifts, this exceptional property allows for frequent boating with ease. Cool off in the resort-style, saltwater infinity pool, or sink into a luxurious hot tub at days' end while taking in stunning Sunset Views. Venture inside this colossal masterpiece through a sleek, glass elevator. The show-stopping Great Room features soaring ceilings, well-appointed wet bar, and walls of impact-resistant doors and windows which open to unobstructed Ocean Views. Ideal for entertaining, the open-concept main living space flows seamlessly into an expertly-equipped Chef's Kitchen, complete with premium Jenn Air appliances, ample prep- and storage space, and generous peninsula with counter seating. Guests will enjoy elevated accommodations in a separate wing, with elegant en suite bathrooms, and access to a spacious veranda overlooking the well-manicured yard and Open Ocean beyond. The primary suite epitomizes luxury, boasting an expansive walk-in closet with custom built-in storage, opulent en suite bathroom, with Ocean Views, deep soaking tub, walk-in shower adorned with walls of onyx stone, and veranda access. The primary bedroom features impact-resistant, pocket sliding glass along two walls, which open entirely for enjoying sublime sunsets and ocean breezes; relax and unwind in this exceptional retreat. The property offers a plethora of parking and storage with detached garage, open- and street parking. Peace and tranquility abound at this extraordinary property!
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Homes and Land
$14,500,000
201 W Seaview Drive
3Beds
4Baths
4,065Sqft
$14,500,000
Duck, Florida, 33050, United States
$557,900
1Beds
2Baths
850Sqft
MARATHON, Florida, 33050, United States
Welcome to Ocean Isles Fishing Villagea gated, seven-acre oceanfront community in the heart of the Florida Keys. Offering brand-new concrete block construction built above flood and allowing seven-day rentals, Ocean Isles combines modern living with resort-style amenities. Townhome #31 is a desirable end unit, located just two rows from the gated entrance with distant views of the Atlantic.
Homes and Land
$557,900
10877 Overseas Highway 31
1Beds
2Baths
850Sqft
MARATHON, Florida, 33050, United States
Welcome to Ocean Isles Fishing Villagea gated, seven-acre oceanfront community in the heart of the Florida Keys. Offering brand-new concrete block construction built above flood and allowing seven-day rentals, Ocean Isles combines modern living with resort-style amenities. Townhome #31 is a desirable end unit, located just two rows from the gated entrance with distant views of the Atlantic. This two-story residence offers approximately 800 sq. ft. of modern living space. The main level features a bright living area, sleek kitchen with stainless steel appliances, and a full bath. Upstairs, the private primary suite includes its own full bath and captures the essence of relaxed Keys living. Every detail has been designed for peace of mind and convenience, including impact windows and doors. Step outside and enjoy resort-style amenities: a spectacular oversized oceanfront pool, clubhouse, tiki huts, and fish cleaning stations for the avid angler. For boating enthusiasts, Ocean Isles delivers unmatched value with a private boat ramp and convenient reserved dockage for owners to use, the newly updated marina, protected by Jack Tar Flats, features a seawall, bulkhead, and docksensuring smooth access to world-class fishing and diving waters. Adding to its appeal, Ocean Isles is located just moments from Marathon Airport, which caters to private jets and smaller planesnearly within walking distancemaking this community especially convenient for those seeking a lock-and-leave Florida Keys retreat with effortless travel access. Perfectly situated in Marathon, Ocean Isles provides easy access north to Islamorada or south to Key West, along with local dining, shopping, and attractions just minutes away. Whether you're looking for a weekend escape, an income-producing property, or your own piece of paradise, this is an opportunity not to be missed.
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Homes and Land
$557,900
10877 Overseas Highway 31
1Beds
2Baths
850Sqft
$557,900
MARATHON, Florida, 33050, United States
$825,000
2Beds
2.5Baths
1,602Sqft
MARATHON, Florida, 33050, United States
Available for the first time in 25 years, this exceptional fully furnished, turnkey residence offers a rare blend of privacy, serenity, and sweeping marina vistas with northerly views to the Gulf's horizon.
Homes and Land
$825,000
6201 Gulf of Mexico Boulevard 201
2Beds
2.5Baths
1,602Sqft
MARATHON, Florida, 33050, United States
Available for the first time in 25 years, this exceptional fully furnished, turnkey residence offers a rare blend of privacy, serenity, and sweeping marina vistas with northerly views to the Gulf's horizon. From its elevated vantage point, the home captures an ever-changing waterfront backdropboats moving through the marina, shifting light over the mangroves, and gentle Gulf breezes throughout the day. The north-facing orientation keeps the main balcony exposure comfortable and highly usable, without harsh direct sun straight on. Morning and late-afternoon light is softer and comes from the side of the curved balcony, while golden hour brings beautiful warmth and glow across the water. The interior is thoughtfully oriented to maximize water views and is offered fully furnished for immediate enjoyment. Recent updates include a 2025 HVAC and water heater, high-end impact sliders and corner windows, and improvements following Seawatch's major concrete restoration. The modern kitchen features stainless steel appliances, generous cabinetry, and an inviting layout for both entertaining and everyday living. Both suites are spacious and private, each with its own bath. Set on 17 gated acres, Seawatch offers resort-style amenities including a recently rebuilt pool facility, spa, cabana, fitness center, tennis and pickleball courts, a half basketball court, and a large storage barn for boats, RVs, kayaks, paddleboards, and golf carts. Lush landscaping and winding paths enhance the private island-retreat atmosphere. While this residence does not include a private slip, slips are often available for purchase, lease, or complimentary use. At 825,000, it is positioned well below the units above and below in its stackyet offers superior privacy, finishes, and one of the community's most compelling view experiences.
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Homes and Land
$825,000
6201 Gulf of Mexico Boulevard 201
2Beds
2.5Baths
1,602Sqft
$825,000
MARATHON, Florida, 33050, United States
$999,000
2Beds
2.5Baths
1,352Sqft
MARATHON, Florida, 33050, United States
Enjoy elevated Gulfside living in this well-maintained 2-bedroom, 2.5-bath condo located within Gulfpointe Complex Two in Marathon. This spacious residence offers covered parking for up to three vehicles and is thoughtfully designed with an open-concept main level and private bedroom suites upstairsideal for full-time living, a Florida Keys retreat, or an income-producing investment.
Homes and Land
$999,000
12690 Overseas Highway 112
2Beds
2.5Baths
1,352Sqft
MARATHON, Florida, 33050, United States
Enjoy elevated Gulfside living in this well-maintained 2-bedroom, 2.5-bath condo located within Gulfpointe Complex Two in Marathon. This spacious residence offers covered parking for up to three vehicles and is thoughtfully designed with an open-concept main level and private bedroom suites upstairsideal for full-time living, a Florida Keys retreat, or an income-producing investment. The main living level features a bright, open floor plan with living room, kitchen, dining area, and a convenient half bath, opening to a private balcony with beautiful Gulf views. Upstairs, the primary bedroom includes an ensuite bath and its own balcony with serene water views, while the guest bedroom is complemented by a full hall bath. Built with solid concrete construction, a durable metal roof, and new hurricane impact windows and doors, this residence offers peace of mind along with island comfort. Balconies on both levels enhance indoor-outdoor living and provide stunning sunset views over the Gulf. Gulfpointe Two is a well-maintained waterfront community featuring a heated pool with a chiller for comfort during the warmer summer months and Gulfside dockage with finger piers. Dock access is first-come for owners, with accommodations for boats up to 36 feet and quick access to both the Gulf and AtlanticVaca Channel is just minutes away. Weekly vacation rentals (7-day minimum) are allowed, offering flexibility and strong investment potential. Whether you're seeking a primary residence, fishing retreat, or rental opportunity, this Gulfside condo delivers location, lifestyle, and value in the heart of the Florida Keys.
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Homes and Land
$999,000
12690 Overseas Highway 112
2Beds
2.5Baths
1,352Sqft
$999,000
MARATHON, Florida, 33050, United States
$2,199,000
3Beds
2.5Baths
1,720Sqft
MARATHON, Florida, 33050, United States
Seller Financing Available Pre-Construction Waterfront Retreat Deep Water Sunrise Views Located right across from the island of Boot Key, this exceptional pre-construction offering combines protected deep-water living, open-water views, and one of the most desirable boating locations in Marathon.
Homes and Land
$2,199,000
1252 24Th Street Ocean
3Beds
2.5Baths
1,720Sqft
MARATHON, Florida, 33050, United States
Seller Financing Available Pre-Construction Waterfront Retreat Deep Water Sunrise Views Located right across from the island of Boot Key, this exceptional pre-construction offering combines protected deep-water living, open-water views, and one of the most desirable boating locations in Marathon. Explore scenic kayak trails for beginners and advanced paddlers, surrounded by rich nature and wildlife where dolphins and manatees are frequently seen. The property faces east for breathtaking sunrises, while Boot Key provides natural protection during stormscreating an ideal, secure harbor environment. With approx 60 feet of deep-water dockage, enjoy ample space for large or multiple vessels, excellent maneuverability, and direct access to world-class boating. Inside the harbor, convenience is unmatched with 5 restaurants and 3 gas docks just minutes away. Commencing soon on this with construction, the custom home is designed with modern coastal style and true Keys practicality. The residence will feature 3 bedrooms and 2.5 bathrooms, offering elevated living spaces perfectly oriented toward panoramic Boot Key Harbor views. Whether you're a dedicated boater, nature lover, investor, or seeking a peaceful Keys escape, this rare property delivers the ultimate blend of location, protection, and lifestyle. Seller will finance with half down!
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Homes and Land
$2,199,000
1252 24Th Street Ocean
3Beds
2.5Baths
1,720Sqft
$2,199,000
MARATHON, Florida, 33050, United States
$1,399,000
1.34Sqft
Duck, Florida, 33050, United States
Discover a rare opportunity in the heart of Duck Key at 1 Trinidad Street a premier parcel spanning over an acre in one of the most desirable neighborhoods in the Florida Keys. This exceptional property offers remarkable potential for new construction, redevelopment, or long-term investment.
Homes and Land
$1,399,000
1 Trinidad Street
1.34Sqft
Duck, Florida, 33050, United States
Discover a rare opportunity in the heart of Duck Key at 1 Trinidad Street a premier parcel spanning over an acre in one of the most desirable neighborhoods in the Florida Keys. This exceptional property offers remarkable potential for new construction, redevelopment, or long-term investment. With its generous size, privacy, and prime location directly across from the Duck Key Clubhouse and just steps from the pool, tennis courts, and social amenities this site combines lifestyle appeal with investment value. Whether you're envisioning a luxury Keys estate, a multi-structure retreat, or a strategic hold for future growth, the possibilities are endless. The property carries density for up to 7 homes, and according to Monroe County, it aligns with the majority of criteria required for ROGO (Rate of Growth Ordinance) building right transfers. While formal approval must follow the county's established process, preliminary guidance supports the feasibility of securing those rights offering a compelling path for developers and investors. Large parcels of this caliber are increasingly rare build your vision and create something extraordinary on Duck Key.
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Homes and Land
$2,899,000
0.92Sqft
MARATHON, Florida, 33050, United States
Build your dream oceanfront home in the prestigious gated community of Sunrise Isle, a coastal island of just 20 properties located next to beautiful Sombrero Beach in the heart of Marathon. Build anytime you like as the property comes with a deeded City of Marathon Transferrable Building Right subject to the conditions of the City of Marathon. Generous 40,249 sq. ft.
Homes and Land
$2,899,000
94 Sunrise Drive
0.92Sqft
MARATHON, Florida, 33050, United States
Build your dream oceanfront home in the prestigious gated community of Sunrise Isle, a coastal island of just 20 properties located next to beautiful Sombrero Beach in the heart of Marathon. Build anytime you like as the property comes with a deeded City of Marathon Transferrable Building Right subject to the conditions of the City of Marathon. Generous 40,249 sq. ft. ocean and canal front lot (a rare find in the Keys) boasts approximately 104 ft. beach frontage and approximately 467 ft. deep water canal frontage with the option for boat dockage on two separate sides of the canal. A brand new concrete seawall offers superb boating access to both the Ocean and Gulf for world-class fishing and diving. Fly into Marathon's Jet Center just minutes away and once home walk to beautiful Sombrero Beach or enjoy golf, dining and shopping just seconds away. Can be purchased with the adjacent waterfront lot giving you the whole end of the peninsula for a total of 1.7 Acres with 190' of beachfront and 565' of dockage (see 96 Sunrise Dr MLS #616113). Don't miss this opportunity to build your custom waterfront home in the Fabulous Florida Keys.
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Homes and Land
$4,699,000
3Beds
4.5Baths
4,000Sqft
MARATHON, Florida, 33050, United States
Nestled on a secluded 2-acre lot in Grassy Key, Marathon, this gated waterfront estate boasts 4,000 sq. ft. and is highlighted with a ton of amenities including two docks, 4 post boat lift, private sandy beach and an infinity-edge elevated pool blending seamlessly with the gulf and featuring a built-in table and chairs for relaxing or entertaining.
Homes and Land
$4,699,000
58213 Morton Street
3Beds
4.5Baths
4,000Sqft
MARATHON, Florida, 33050, United States
Nestled on a secluded 2-acre lot in Grassy Key, Marathon, this gated waterfront estate boasts 4,000 sq. ft. and is highlighted with a ton of amenities including two docks, 4 post boat lift, private sandy beach and an infinity-edge elevated pool blending seamlessly with the gulf and featuring a built-in table and chairs for relaxing or entertaining. Expansive covered areas by the pool offer shaded spots for lounging and has direct access to the living areas. Double entry doors with intricate carved wood details welcome you into a light-filled home. The open-concept living area is graced by large windows and sliding glass doors that frame panoramic views and create a seamless connection between indoors and outdoors. A striking marble fireplace serves as the focal point. Every element of this home reflects thoughtful design, from the impact-rated doors and windows, in-house elevator plus marble floors, exquisite cabinetry, and refined finishes enhancing the home's timeless appeal. The main kitchen is a chef's delight, featuring granite countertops, two wine coolers, and abundant cabinetry. A cozy dining nook encased in windows offers stunning gulf views, creating the perfect setting for every meal. The primary suite is a sanctuary of luxury, featuring panoramic gulf views, a two-sided fireplace, and direct access to the pool. The en-suite bathroom offers a private sauna, jetted tub, walk-in shower, and makeup counter, creating a spa-like retreat. The guest quarters are designed for comfort and independence, offering a morning kitchen and two guest suites. Each suite includes its own en-suite bathroom and generous closet space, ensuring privacy and convenience for visitors. The large office can also serve as a 4th Bedroom. Additional amenities include a home theater room complete with reclining seats and bar plus an oversized 3-car garage with lift.
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Homes and Land
$4,699,000
58213 Morton Street
3Beds
4.5Baths
4,000Sqft
$4,699,000
MARATHON, Florida, 33050, United States
$849,000
2Beds
2.5Baths
1,352Sqft
MARATHON, Florida, 33050, United States
Welcome to Gulfpointe II, a Gulf front community offering lots of amenities including great dockage, large heated and chilled pool and lots of parking. This spacious 2 Bedroom 2 Bath condo offers an open floor plan with panoramic views of the gulf from all angles. Enjoy morning coffee or evening cocktails watching the sunset over the water from one of your.
Homes and Land
$849,000
12690 Overseas Highway 310
2Beds
2.5Baths
1,352Sqft
MARATHON, Florida, 33050, United States
Welcome to Gulfpointe II, a Gulf front community offering lots of amenities including great dockage, large heated and chilled pool and lots of parking. This spacious 2 Bedroom 2 Bath condo offers an open floor plan with panoramic views of the gulf from all angles. Enjoy morning coffee or evening cocktails watching the sunset over the water from one of your. two porches that face different angles so you can capture shade and breezes all day long while enjoying Gulf views. Inside, the open-concept living room is spacious and flooded with natural light, creating a bright and airy feel. The kitchen is functional, with ample counter space for cooking and meal prep and stainless steel appliances. A large island with peninsula seating provides extra seating, perfect for dining or entertaining. The primary bedroom is a private retreat with its own half wrap-around balcony, offering a serene spot to enjoy the views. The room is spacious, with an en suite bathroom featuring double sinks and a generous closet. The guest Bedroom is equally large and comfortable with room for queen and twin beds. Offered furnished and rental ready. Located in Marathon, this condo allows 7 days rentals and offers easy access to local beaches, restaurants, and outdoor activities. With a heated and AC cooled pool, first-come dock, 8 boat slips great for family fishing with dock lights, and community pool and Gulfside views this condo is the perfect place to enjoy the best of the Florida Keys.
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Homes and Land
$849,000
12690 Overseas Highway 310
2Beds
2.5Baths
1,352Sqft
$849,000
MARATHON, Florida, 33050, United States
$1,299,000
4Beds
3Baths
1,888Sqft
MARATHON, Florida, 33050, United States
Experience the ultimate in Florida Keys living at this canal front 4-bedroom, 3-bath 1,888 sq. ft. half-duplex pool home located in the heart of Marathon. Ideally located just down the street from stunning Sombrero Beach, this waterfront retreat offers deep water dockage with ocean acces, a private heated pool, and desirable weekly rental zoning with good rental history.
Homes and Land
$1,299,000
231 Sombrero Beach Road 1
4Beds
3Baths
1,888Sqft
MARATHON, Florida, 33050, United States
Experience the ultimate in Florida Keys living at this canal front 4-bedroom, 3-bath 1,888 sq. ft. half-duplex pool home located in the heart of Marathon. Ideally located just down the street from stunning Sombrero Beach, this waterfront retreat offers deep water dockage with ocean acces, a private heated pool, and desirable weekly rental zoning with good rental history. Inside, enjoy an open-concept layout with coastal-inspired finishes, abundant natural light, and seamless indoor-outdoor flow. The inviting living room opens to a spacious balcony overlooking the canal, while the dining area and kitchen blend modern convenience with island charm. Downstairs, a covered patio with ceiling fan and grill area sets the stage for alfresco entertaining, all framed by swaying palms and tropical landscaping. Boaters will love the easy ocean access, while guests will appreciate proximity to the Marathon Jet Center, shopping, dining, and all that the Florida Keys lifestyle has to offer. Whether you're looking for a personal escape, an investment property, or both this is the piece of paradise you've been waiting for.
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Homes and Land
$1,299,000
231 Sombrero Beach Road 1
4Beds
3Baths
1,888Sqft
$1,299,000
MARATHON, Florida, 33050, United States
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