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Islamorada Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Total Listings 65
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$10,750,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
6 Bed, 6 Baths, 6,866 SqFt Days Listed: 157
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,BasinConcr

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

$10,900,000
Lower Matecumbe
Mat Sandy Beach   - MM: 75.00
4 Bed, 4 Baths, 4,512 SqFt Days Listed: 347
-5.22% ($600,000) 1 Price Change : Last Change 73 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip,

Unravel your dreams through this gated Estate Residence encompassing entire peninsula with over 500feet of bayfront and protected crystal clear waters. This pristine private luxury resort style property and residence includes designs by DAsign Source and provides ultimate privacy while exposing the surrounding majestic waters. Avid boaters will appreciate this dockage for multiple large boats, plus onsite boat ramp Y private boat lift. Marked features of this Estate include professionally designed infinity pool & waterfalls, jacuzzi, and salt water pond overlooking the bay, manicured lawns with 28 zone irrigation, extensive tropical landscaping, paver brick driveway, detached 2 car garage plus additional undercover parking, separate multipurpose CBS building, expansive outdoor porches and entertainment areas, German inspired indoor & outdoor fireplace, stand alone carport with car washing facilities, full home generator, home security system, advanced stereo system for interior & exterior of home. This custom designed concrete Residence consists of two buildings attached by large open covered breezeway. Enter into the foyer leading to a grand interior living and entertaining area offering views in every direction, all of which lead out to expansive wrap around porches. Custom gourmet kitchen with dual refrigerator, dual dishwashers, dual ranges, all Viking appliances, wet bar with wine cooler, & multiple sinks. Private office, walkin pantry, & guest bath. The sleeping quarters located in separate building offers private third floor master suite & bath with steam shower, jacuzzi tub, dual sinks, & a dream walkin closet. Two additional guests rooms, bathroom & living area on main level. Additional ground level cabana bar, plus private guest suite. This grand Estate home was completely rebuilt in 2006 and 2009 with two separate buildings attached by exceptional breezeway and all overlooking the beautiful gulf front waters. So much more...call for full details.

$13,995,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
7 Bed, 7 Baths, 6,696 SqFt Days Listed: 101
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift50ft.Concre

Discover the essence of elegance at Southern Paradise, a coastal masterpiece nestled along the Atlantic Ocean. Located at Mile Marker 83, this property offers direct Old Road access, perfect for walking, biking, or carting. With over 200 ft of beachfront on 1.5 acres, the main residence boasts sunny verandas, 5 bedrooms, 6.5 baths, and more than 5,600 sq ft of air-conditioned living space. A separate guest cottage provides an additional 2 bedrooms and 2 baths, ideal for visitors seeking comfort and privacy. A paved old brick driveway leads up to both entrances and garage. From the moment you step into the inviting french door entrance your eyes are fixated on blue sky, beach and water. The 1st floor living space opens to a cool, grassy lanai, leading to the beach, a lap pool, and a hot tub. Spacious patios offer ample room for guests to savor the Caribbean breezes, while the pier, skiff lift, and kayak launch provide easy ocean access. The main residence is designed for entertaining, featuring expansive ceilings and a layout that includes both an East and a newly added West wing. Each generously appointed bedroom comes with its own ensuite bath, ensuring ultimate comfort and privacy for family and guests. On the 1st floor, East-facing french doors open to over 1,900 sq ft of covered terrace. The open-concept great room encompasses a kitchen equipped with a Wolf gas range, double SubZero refrigeration, and an attached wine cellar, all centered around an expansive island counter. A wet bar and powder room adjoin the kitchen, enhancing convenience for gatherings. The West wing includes an exercise room with a full ensuite spa bath and a luxurious primary suite. The master bath features an ocean-view soaking tub, double vanities, a separate shower, bidet, and water closet.This wing also offers a well-equipped laundry room, storage cabinetry, an office alcove, and direct garage access. 2nd floor presents 2 guest rooms that share a sitting room, wet bar, & terrace.

$14,500,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 9,011 SqFt Days Listed: 517
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 80ft.Concrete

Nestled in the panoramic setting of Islamorada, Florida, the brand new construction at 87895 Old Hwy offers a premium blend of luxury, privacy, and elegant island living. Sprawled over two acres on the azure Atlantic, this opulent abode stretches a massive 9,011 sq ft under air, extending to over 15,000 sq ft under roof. The expansive property includes five spacious bedrooms, five state-of-the-art baths, along with three additional half baths. The home features Thermador /Uline appliances including ice makers & upgraded eco-insulated commercial CGI windows and doors, an additional investment of $200k over the original allowance, that enhance the comfort and luxury of the interiors. Experience unmatched waterfront vistas with the houses 160 ft concrete jetty wrapped in a retaining wall and an 80 ft dock with electric and water facilities. Preserve your luxury vessels on the 20k 4 post elevator lift, adding convenience to lifestyle. The residence also includes an exercise room w/ possible conversion to 6th bedroom, theater room w/ possible conversion to 7th bedroom , office/den, & a laundry room on each level. An elevator ensures smooth movement across the floors. Indulge in outdoor living with the private pool, jacuzzi & around 1735 sqft of porches for lavish entertainment & serene lounging.The property comes protected by a concrete retention wall along the entire perimeter of the shoreline, ensuring complete tranquility. A private gated entrance exudes grandeur while providing security. This estate is zoned (Residential Estate), allowing the owner to apply for vacation rentals, if desired. Currently under construction with an estimated completion date in February or March 2024, the property is perfect for those seeking a custom luxury experience. Enjoy a world-class island living experience in this architecturally significant estate filled with premium luxuries nestled right on the turquoise-blue waters of the Atlantic. Agents please check agent remarks

$22,500,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 75.00
10 Bed, 10 Baths, 3,772 SqFt Days Listed: 694
-24.37% ($7,250,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift,Dav

Fall in love at first sight as you step into this natural beauty with over a quarter mile of pristine white sand beach that kisses the edge of the Atlantic Ocean. Now being offered for the very first time, this one of a kind legacy property beckons you to bask in original elements of the Florida Keys way of life at Kids Cay. Three charming homes; a timeless 4 bedroom main house, an expansive 4 bedroom guest house and a lovely 2 bedroom caretakers cottage. This tropical and tranquil estate has nearly 8.5 acres of upland plus 7.98 acres of ocean bottom plus ample and protected concrete dockage (104 feet and 34 feet) and oceanfront observation pier. Extra wide and spacious porches adorn every corner of the classic homes and are a seamless blend of indoor and outdoor living maximizing the infinite open water views and constant ocean breezes. Enjoy complete privacy lounging by the resort-style pool or stroll barefoot along your private beach, and nature preserve; a sanctuary for plethoras of beautiful native birds. This estate is the epitome of true island living and serenity and beautifully lends itself to photo shoots, movies, weddings and luxury weekly rentals.

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 12-26-2024.
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