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$5,195,000
Shark Key
Shark Key   - MM: 11.00
5 Bed, 5 Baths, 4,176 SqFt Days Listed: 17
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Tucked behind swaying palms and lush tropical landscaping, this elegant and timeless waterfront estate captures the essence of Florida Keys living--from breathtaking sunset views to exceptional outdoor spaces. Whether youre lounging on your private beach or entertaining by the pool, every moment here is a reminder of why you chose island life.Inside, sun-drenched living areas showcase wide-open Gulf views and an abundance of natural light. The gourmet kitchen is thoughtfully designed with custom cabinetry, high-end appliances, and a spacious island--ideal for both everyday living and entertaining. Upstairs, the master suite features panoramic water views and a generous walk-in closet. Three additional bedrooms are located on the upper level, with a fifth bedroom and full bath on the main level offering added flexibility.Designed for seamless indoor-outdoor living, the home opens to a private deck, sparkling pool, and an observation dock--perfect for catching every sunset. Additional features include a copper patina roof, a 3-car covered carport, full generator, ample storage and a wave runner lift.Located in the prestigious, gated community of Shark Key, just minutes from Key West, this estate offers access to resort-style amenities including a clubhouse, inland swimming lagoon and beach, plus pickleball and tennis courts.24 Cannon Royal Drive is everything you love about the Keys--all wrapped into one exceptional waterfront property.

$5,245,000
Long Key
Long Key Ocean Bay Colony   - MM: 66.00
7 Bed, 7 Baths, 7,941 SqFt Days Listed: 8
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Costal Elegance - Live the Dream in this Resort Style, Luxurious Beachfront, Pool Home. Wake up to stunning sunrises with Spectacular Oceanfront Views! 100 ft. of Private Sandy Beach. The sprawling indoor and outdoor spaces provide the perfect setting for large gatherings and entertaining. Gourmet Kitchen with double ovens. 15 mins. from the best dinning and shopping options. Seabird Marina is only 3.5 miles away. More than just a home, its a lifestyle. Let this piece of paradise be yours and experience the ultimate private retreat. Owner is Agent.

$5,299,000
Marathon
Woodburns Subdivision   - MM: 49.50
3 Bed, 3 Baths, 2,428 SqFt Days Listed: 59
-4.78% ($266,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage90ft.

Private Waterfront Estate in the Florida KeysThis gated, one-acre estate offers the ultimate blend of privacy, nature, and waterfront living in the heart of the Florida Keys. Nestled among lush, mature tropical landscaping, the property feels like a secluded island retreat. As you pass through the gates, you are welcomed by a beautifully manicured paradise with a coral-cut shoreline, a firepit at the waters edge, and panoramic sunset views over the open water. Just offshore, two small uninhabited islands provide a unique opportunity for exploration.The 3-bedroom, 3-bathroom home is designed for comfort and indoor-outdoor living, with an open concept living room, kitchen, and dining area that seamlessly flows into multiple outdoor living spaces. The upper level includes two spacious bedrooms and two bathrooms, while the conforming lower level offers an additional bedroom, bath, sitting area, and a separate entrance--perfect for guests or an in-law suite. A tool/storage room on the ground floor adds to the convenience of this beautiful estate. The wraparound balcony that surrounds the entire home includes several screened-in areas, enhancing the flow of indoor-outdoor living.Updated with a new metal roof in 2024, the home features stainless steel appliances and breathtaking water views. The property boasts approximately 520 feet of shoreline and a custom dock, including an 84-foot by 4-foot dock with a 21-foot by 8-foot extension and a double floating dock for two jet skis--perfect for boating enthusiasts. Covered parking for four cars is available under the elevated home, with additional parking along the entrance way leading to a circular driveway.Set on three originally platted lots (12, 13, and 14), the property offers the flexibility to separate, redevelop, or keep as a private compound. Located just a short walk from fine dining, shopping, and more, this rare waterfront offering combines serenity, convenience, and endless possibilities.

$5,299,000
Upper Matecumbe Key Islamorada
Venetian Shores   - MM: 86.00
6 Bed, 6 Baths, 4,964 SqFt Days Listed: 42
-3.64% ($200,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift100f

Exquisite Tri-Level Waterfront Estate in Islamorada!Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence boasts an open-concept floor plan with soaring ceilings, a fireplace and a grand living area.Enjoy seamless indoor-outdoor living with an expansive wraparound veranda, perfect for soaking in the breeze and relaxing water views. The beautifully landscaped 10,000sqft lot provides privacy and tranquility, while the swimming pool offers the ultimate relaxation.For boating enthusiasts, this property is a dream come true! Featuring 100 of deep-water concrete dockage equipped with a 20,000lb catamaran width elevator boat lift and a 5500lb set of davits you will enjoy immediate access to both the Atlantic Ocean and Florida Bay for excellent offshore and backcountry fishing. A two-car garage with a new A/C unit, plus additional covered carport parking, ensures ample space for vehicles and storage along with a beautifully paved driveway.Come experience the best of the Florida Keys lifestyle in this exceptional waterfront retreat!Updates....1. NEW 2-car Air Conditioning Split with 10-year warranty2. New Dock and Stair Brick Pavers3. New third-floor Impact Windows4. Two New third-floor Impact French Doors5. Two New third-floor electric Rolladen Hurricane Shutters6. Swimming poll resurfacing with new glass edge surround7. Dock has a 220-volt pedestal to service dock-side marine electric needs

$5,495,000
Marathon
Boot Key View   - MM: 49.00
8 Bed, 8 Baths, 6,618 SqFt Days Listed: 257
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits90ft.

Fabulous Investment Property with a beautiful Villa with passive income of Half Millionper year! Great opportunity to live in on property in 2-bedroom Carriage House whilemake millions with high earning vacation Villa in the Florida Keys.Solid investment property for short-term rental while living in paradise in the FloridaKeys.Smart investors will buy this destination location home in the islands to optimize youryear-round income no other location in the nation (USA) brings in this high returnincome. 10-12% return annuallyOwner will consider financing possible depending on credit score down payment andminimum down payment is 40% of asking price of $5,750,000. You can either managethis yourself or we can manage it for you for passive income!Welcome to the world of azure blue waters, tropical warm weather gently oceanbreezes and the island sun of the Florida Keys. The Florida Keys is one of the mostsought-after destinations for anyone wanting to get-away from the mainland and relax orgo fishing. Once you arrive, youll feel a laid-back Island Time atmosphere where timeseems to stand still, and everyone feels more relaxed.Great Family Reunion Large Vacation Rental has 6 bedrooms 5 bath steps away fromthe most famous of the best beaches in the Florida Keys - Sombrero Beach.Sombrero Beach is 3 blocks walking distance - where you can rent kayaks atthe beach, and you can enjoy fishing off our new dock. Great for fishermen - 85 ft. Deep Water Dock 10 min. ride through the famedSisters Creek to the open ocean, 15 min. to the 7-mile bridge, six NM toSombrero Reef.Spacious accommodations with over 6,600 sq. ft. luxury living and a 90dock DETACHED CARRIAGE HOUSE RENTS FOR 3,000 A MONTH

$5,495,000
Key Largo
Blue Wtr Trailer Vill   - MM: 92.50
5 Bed, 5 Baths, 3,499 SqFt Days Listed: 143
-8.34% ($500,000) 1 Price Change : Last Change 78 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 749ft.

Massive, massive, massive dock on this peninsula. This is a Boaters Dream with Unmatched Dockage!Situated on a private peninsula, this incredible property boasts over 740 feet of concrete dockage, perfect for boaters and water enthusiasts. Offering the ultimate convenience and luxury for your boating lifestyle. Whether you own a yacht or a smaller boat, theres ample space to accommodate all your watercraft.While the 5-bedroom, 5-bath concrete home is impressive, its the dockage that truly sets this property apart. Imagine hosting a yacht party, enjoying easy access to the open water, or simply relaxing on your private dock with spectacular marina views. Live on your own peninsula with over 700 feet of concrete dockage on deep water access straight out to the ocean. This magnificent Tavernier home is nestled on nearly an acre of land, this exquisite property offers a rare amount of waterfront situated on its own peninsula, providing privacy and great marina view. Gather your best friends and create your private yacht club. Live on your own peninsula! Deep water access straight out to the ocean. This magnificent Tavernier home is nestled on nearly an acre of land, this exquisite property offers a rare amount of waterfront situated on its own peninsula, providing privacy and great marina view. Imagine inviting all your friends to your yacht party on your peninsula. Deep-water access leading directly to the open ocean or easy bay access too --perfect for the avid boater or water enthusiast.This stunning concrete 5-bedroom 5 bath home is thoughtfully designed with:Main Level: Two ensuite bedrooms, two additional guest bedrooms, and two guest baths, offering ample space for family and guests.Guest Quarters: A separate one-bedroom, one-bathroom suite on the ground floor with direct

$5,499,000
Marathon
Crains Subdivision   - MM: 58.00
3 Bed, 3 Baths, 5,220 SqFt Days Listed: 123
-7.58% ($451,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin

Nestled on a secluded 2-acre lot in Grassy Key, Marathon, this gated waterfront estate boasts 5,220 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 homes timeless appeal. The main kitchen is a chefs 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.

$5,500,000
Summerland Key
Summerland Estates   - MM: 25.00
3 Bed, 3 Baths, 2,088 SqFt Days Listed: 131
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 180ft.

Exceptional Investment Opportunity in the Lower Florida Keys!Owner and private financing are available. This is one of the very few vacation rental properties licensed for daily, weekly, or monthly rentals. Boasting an impressive occupancy rate and generating up to $400,000 annually, this property offers stress-free, passive income in Summerland Key, a premier location.Discover a rare gem in the heart of the Lower Keys! Recently remodeled to perfection, this luxurious three-bedroom beach house includes a sunroom with a palatial ocean view, currently used as a fourth bedroom. Just 20 miles from vibrant Key West, this coastal retreat features a private natural beach, breathtaking ocean views, and access to a private airport for island residents less than two blocks from the property.Dont miss this unparalleled investment opportunity!Please note that I have a personal interest in this property.

$5,500,000
Marathon
Fat Deer Key   - MM: 53.00
10 Bed, 10 Baths, 6,128 SqFt Days Listed: 17
Multi-Units - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Live and/or work in this RARE 100 of waterfront re-development opportunity with DEEP WATER DOCKAGE APPROVED! 200 HIGHWAY FRONTAGE! Huge 74,890 SQ FT site with an ACTIVE Conditional Use PERMIT for 10 unit and 4 affordable staff group home units, price INCLUDES 6 MARKET RATE TBRs, which could be sold off separately if desired. This MIXED USE ZONING has many commercial-residential possibilities...for example: could go to 10 market rate units on site, or higher density with affordable housing, or boutique HOTEL if you bring transient rights, etc. Includes a two-story raised CBS 6,128 SQ FT building that could be used in so many different ways, includes 2,340 SQ FT of extra outdoor porches. This would make an amazing live-work setup, or re-hab the huge building into whatever your imagination could create. BEST LOCATION near Vaca Cut for easy Ocean-Bay access, easy airport access, SHORT-TERM RENTAL FRIENDLY! Contact Peter and Ewa Schwarz for more info and a private viewing of this amazing opportunity to get into THE KEYS LIFESTYLE...live, work, business, family compound...you can do it all right here on the water!

$5,600,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
4 Bed, 4 Baths, 5,608 SqFt Days Listed: 1100
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,BasinConcr

Spectacular Open Water location, with fabulous views from this well-built Oceanfront concrete home. Direct Ocean access from the step down concrete seawall/dock that wraps around the waterside of the property, including the boat basin with two boat lifts and a fish cleaning station. Relax in large pool with over-spill hot tub & a big pool patio area and a covered patio for entertaining, which drinks in the Ocean view. Interior features abound: wood cabinetry, granite, marble, and more. Double bronze doors adorn the entrance and foyer. There is a formal dining room off the kitchen. The master bedroom opens onto a porch, facing the Ocean. Soaring ceilings in the living room, with Casablanca style rotating fans. The upstairs level has a lovely deck that faces the Ocean, perfect to relax, enjoy the sunsets, and where you can see for miles and miles. Gated and fenced.

$5,650,000
Key Largo
Key Largo Beach Addition   - MM: 100.00
5 Bed, 5 Baths, 4,306 SqFt Days Listed: 64
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip

Enjoy endless ocean views with this ultra-sleek and modern 4,306 Sq. Ft. home. Exquisite indoor and outdoor living areas are complete with floor-to-ceiling windows and breathtaking ocean views. A gorgeous chefs kitchen has a custom island and top of the line appliances. The main suite retreat has a large, custom walk-in closet, private balcony and a generously sized bathroom with dual vanities, frameless shower and Jacuzzi. The remaining 4 bedrooms all have walk-in closets and en-suite bathrooms. With a private roof top deck ideal for entertaining and relaxing, a beautiful L-shaped pool, covered terrace, and private dock with direct ocean access, this home is Florida living at its finest. Photos included are of conceptual renderings of the home.

$5,650,000
Key Largo
Sunset Point   - MM: 95.00
4 Bed, 4 Baths, 1,872 SqFt Days Listed: 301
-8.13% ($500,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat SlipC

THE BEACH HOUSE ON SUNSET ROAD! Enjoy both sunrise & sunset from your own backyard in the Florida Keys! Welcome to a unique point of land on Florida Bay, offering two lots with almost an acre of land, a quarter-acre bay bottom and features over 200 feet of waterfront, a remodeled multi-story concrete home, a resort-style pool, dockage for multiple boats, and a sandy beach with sea oats creating an idyllic setting for enjoying the parade of boats and marine wildlife meandering by. The remodeled beach residence is situated on the southernmost lot, while the resort-style pool, framed by palm trees, is positioned on the northern lot. A gated entry and driveway lead guests to panoramic open water views across the pool and from the two-story, 4-bedroom, 2-bathroom home on two living levels. The main living level includes a kitchen, dining area, two guest bedrooms, and a full bathroom, plus three sets of French doors opening to an outside covered entertaining area. Interior stairs lead to the second living level with a vaulted tongue-and-groove open beam ceiling, a living/media room, side sitting parlor, third guest bedroom, primary suite, and an expansive upper deck for an even greater birds-eye view of the Bay. The waterfront area includes a concrete seawall, two concrete piers, a cut-in boat slip/basin for added protection, a large Chickee Hut with picnic table, two smaller boat ramps for launching paddleboards/kayaks, and a sandy beach with wade-in beach entry. A myriad of mature palms encircles the home and pool. At night, enjoy the lighted palms as they sway in the tropical breeze, providing the ultimate backdrop for your own personal resort. This one-of-a-kind point of land on the island of Key Largo is perfectly situated to not only enjoy the most colorful sunsets by night but also the captivating early morning sunrises. Enjoy your beachfront paradise or create your vision by constructing a larger estate - the choice is yours! Duplicate Listing, MLS #613012.

$5,700,000
Shark Key
Shark Key   - MM: 11.00
4 Bed, 4 Baths, 5,300 SqFt Days Listed: 63
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Welcome to one of Shark Keys landmark estates--a custom-built, beautiful Mediterranean-inspired home. This exclusive property offers timeless architecture, open water views, and an unparalleled island lifestyle.Nestled on the northern end of Shark Key and set back from the road for privacy, this 5,300-square-foot estate sits on a 21,075-square-foot lot with breathtaking open water views. Designed for comfort and entertaining, the home features 4 bedrooms, 4.5 bathrooms, a private office, a home theater, an elevator, a full bar, and expansive balconies and elegant terraces that invite you to take in stunning sunrises and peaceful water views.Each of the bedrooms has an ensuite bathroom and private balcony, while the primary suite boasts incredible water views. The outdoor living spaces are equally impressive, featuring a pool, hot tub and ample room for entertaining and lounging. Theres also space to add an observation dock for a flats boat.Enjoy the exclusive amenities of Shark Key, including pickleball, tennis courts and a private sandy beach. Located just minutes from Key West, yet offering a private retreat, this estate is truly one of a kind.This lovingly maintained home presents an exciting opportunity to update and make it your own while preserving its classic Mediterranean charm.Dont miss this rare offering--schedule your private showing today!

$5,750,000
Key Largo
Key Largo Beach Addition   - MM: 100.00
5 Bed, 5 Baths, 4,473 SqFt Days Listed: 66
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip50ft.

Extraordinary 6,043 Sq.Ft. waterfront home with the finest quality and finishes set in a private enclave of Buttonwood Circle. This entertainers dream home offers impressive ocean views, spacious living and dining areas and a gourmet kitchen. Highlights include a gorgeous main suite with a spacious balcony offering spectacular views and luxurious bath to be equipped with spa tub, separate shower and custom walk-in closet. Enjoy the desirable Florida indoor-outdoor lifestyle with seamless access to landscaped grounds which will include a sparkling pool and barbeque area. Featuring four additional bedrooms with ensuite bathrooms and a roof top deck ideal for entertaining, this will be a true retreat! Photos included are of renderings of the home.

$5,750,000
Duck Key
Plantation Island   - MM: 61.00
4 Bed, 4 Baths, 3,304 SqFt Days Listed: 332
-4.17% ($249,999) 1 Price Change : Last Change 138 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 78ft.

Step into paradise with this stunning retreat in Duck Key, Florida! This 4-bedroom, 4-bathroom haven offers an escape from the ordinary, with 72 feet of deep-water dockage, a 10,000 lb and 20,000 lb boat lift. The house is wrapped in shell stone, calacatta stone, le cornu stove, and features furniture from Restoration Hardware, marble floors, and baseboards.Florida is renowned for its incredible quality of life, with no state income tax and a consistently warm climate perfect for year-round enjoyment. Enjoy more than 230 days of sunshine each year and average temperatures ranging from the mid-70s in winter to the low 90s in summer. The state boasts a range of pristine beaches and turquoise waters that beckon for relaxation and adventure.Duck Key is not only a haven for water enthusiasts, but it also provides access to exceptional educational opportunities, with a mix of highly-rated public, private, and charter schools. Additionally, the area is known for its strong sense of community and character, contributing to a desirable and secure island lifestyle.Spend your days exploring vibrant marine life, diving into crystal-clear waters, or unwinding on pristine beaches. Nearby, discover a wealth of waterfront dining options where you can indulge in fresh seafood while soaking in breathtaking sunset views.Dont miss this opportunity to live in the second house from the entrance to Duck Key. This secure and luxurious island living opportunity is waiting for you!

$5,750,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 3,597 SqFt Days Listed: 186
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. A recently sold $3.5M, 4000 sq. ft. home was torn down just to obtain a buildable lot on Hilton Haven. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock while overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75 by 300 bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living rooms custom hand built beamed wood cathedral ceiling and a majestic staircase. The current sunroom, converted into a dining room, features French doors that open to views of the pool and harbor. The expansive deck leads down to the lower entertaining level. The chefs kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to the rear private deck and dock. Completing the first floor are the laundry room, a half-bath, a full bath, and a charming guest bedroom. The sunroom with a wet bar and bathroom provides access to the one car garage, and second staircase leading to the second-floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. https://show.tours/e/4vNFpvG

$5,950,000
Key Largo
Tarpon Acres   - MM: 102.00
5 Bed, 5 Baths, 2,364 SqFt Days Listed: 253
-11.06% ($740,000) 2 Price Changes : Last Change 19 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Basin

Welcome to the ultimate tropical sanctuary in Key Largo! An extraordinary waterfront estate with two homes, spanning over 2.5 acres along Tarpon Basin. This breathtaking property offers unparalleled sunset vistas, a coral jetty framed by a lagoon, a boat ramp, lush mangroves, and a canopy of majestic mahogany trees.Green sloping land is elevated for privacy and optimal protection . The estate features two impeccably remodeled homes with high-end finishes. The main house includes three bedrooms, four elegantly appointed bathrooms, a full kitchen, and spacious living areas. The second home offers two beautifully crafted bedrooms, two luxurious bathrooms, and a full kitchen. Both homes are adorned with lavish spa-like bathrooms and hand-carved, imported Bali doors and casings.The Suburban/Commercial Zoning offers limitless investment possibilities, or a private sanctuary, a high-end vacation rental, an exclusive event venue, or a family compound. Imagine creating an oversized dream home surrounded by tropical splendor.Just 65 minutes from Miami International Airport, this one-of-a-kind estate is perfect as a peaceful hideaway, a lucrative income property, or a stunning family compound. Create your private sanctuary and embrace the essence of the Florida Keys lifestyle.

$5,990,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 16
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

$5,990,000
Key Largo
Monroe Park   - MM: 112.50
4 Bed, 4 Baths, 5,007 SqFt Days Listed: 263
-7.85% ($510,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Other Dock

Exceptional waterfront living with amazing open water views over looking Barnes Sound. A quick jaunt to Miami yet this tropical oasis feels like youre on your own private island estate. 60 concrete dock on a protected inlet for your boats and other watercrafts . Over 4100 sq ft of living area over 3 levels in a thoughtfully laid out floor plan with elevator access, wrap around decks, plus a rooftop terrace for sunning and entertaining with jaw dropping views. 3 suite Bedrooms, Study (or 4th BR) 3.5 Baths, Exercise Room, 2 extra deep garages, an expansive screened lanai on the ground level and terraces on the 2nd & 3rd levels.

$5,990,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 16
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock,Basi

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 04-24-2025.
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