Islamorada Homes with Open Water Waterfront features

Islamorada Homes with Open Water Waterfront features

Welcome to Islamorada, the enchanting Village of Islands nestled in the heart of the Florida Keys, Monroe County. Known for its breathtaking views and vibrant marine life, Islamorada is often referred to as the “Sportfishing Capital of the World.” This idyllic locale is a paradise for outdoor enthusiasts, offering an array of water sports, from fishing and diving to kayaking and paddleboarding. With its pristine beaches, lush landscapes, and stunning sunsets, Islamorada is not just a destination; it’s a lifestyle.

When it comes to real estate, the charm of Islamorada truly shines through its spectacular homes with open water waterfront features. Imagine waking up to the gentle sound of waves lapping against the shore and the soft glow of the morning sun reflecting off the water. Many of these properties boast direct access to the Atlantic Ocean, allowing you to embark on a fishing adventure or a leisurely day on the water right from your backyard.

These waterfront homes are designed to maximize the breathtaking views, featuring expansive decks, private docks, and spacious outdoor living areas perfect for entertaining or simply unwinding in paradise. Whether you’re seeking a cozy retreat or a luxurious estate, Islamorada offers a diverse range of properties that cater to every taste and lifestyle.

With its unique blend of natural beauty, vibrant culture, and endless recreational opportunities, Islamorada is more than just a place to live; it’s a place to thrive. Discover your dream home in this tropical haven and embrace the ultimate Florida Keys lifestyle!

Newest Islamorada Homes with Open Water Waterfront features

$999,000
3 Beds ⋅ 2 Baths ⋅ 621074 MLS
Discover easy bayfront living in this beautifully updated townhome at Executive Bay Club, where breathtaking views of Florida Bay take center stage. The open living area and kitchen enjoy beautiful, unobstructed bay views, while the upstairs primary bedroom offers its own spectacular waterfront perspective. The main living level features level tile flooring and a comfortable, inviting layout designed to take full advantage of the setting. Upstairs, you'll find three bedrooms plus a versatile loft and a spacious bath with a jetted tub and separate shower. Executive Bay Club has recently completed significant community improvements, including a replaced and expanded dock, an updated clubhouse, pool, pool deck and pool bathrooms, all completed within the past two years. With these improvements already made, there are no pending assessments. Move-in ready and ideally positioned on Florida Bay, this is a wonderful opportunity to own a waterfront townhome in one of the Keys' most desirable communities. Don't miss your chance to enjoy bayfront living, beautiful sunsets and the relaxed Florida Keys lifestyle at Executive Bay Club.

87200 Overseas Hwy Unit J 6, Islamorada
$2,400,000
3 Beds ⋅ 4 Baths ⋅ 621073 MLS
Simply the best location, exclusive & extremely private. This is a rare find and a single-family home that's rarely available. It's tucked away in the prestigious ''Plantation Lake Estates,'' a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach, tennis courts, a full-service marina, a dog park, sports fields, and Olympic-size lap pools. This home boasts a stunning great room with a gorgeous coral fireplace and soaring wood beam ceilings. They all overlook the glistening Atlantic Ocean, providing priceless views and sunrises. The home has a metal roof, a modern kitchen, updated baths, and impact windows and doors. The exterior has been reinforced with rebar and stucco. There are three inviting bedrooms, including a third-floor master en-suite with a private porch. A large ''rec room'' with a cabana kitchen is perfect for indoor-outdoor entertaining. You'll have world-class fishing and diving right in your own backyard.

316 North Dr, Islamorada
$15,000,000
621011 MLS
Discover an extraordinary opportunity on Florida Bay in Plantation Key, offering a rare combination of privacy, natural beauty and approximately 1,250 feet of waterfront with sweeping open-water views and spectacular sunsets. The property encompasses 21+ acres, with approximately 5 acres already cleared for the homesite and improvements. The remaining acreage creates an exceptional natural backdrop and sense of seclusion rarely found in the Florida Keys. A private drive winds through the tropical surroundings to the homesite, while a completed observation dock offers a beautiful setting to enjoy Florida Bay. Designed for this remarkable property is an exceptional 8-bedroom luxury residence created for sophisticated Keys living. Plans feature eight bedroom suites, expansive living and entertaining spaces, a chef-inspired kitchen with oversized island, private office, game room, elevator, extensive garage and storage areas, covered balconies and terraces, plus a pool and spa with generous outdoor living areas. For a buyer who purchases prior to completion, a unique opportunity awaits. The seller will pay the building costs for the planned residence, subject to the terms, specifications and allowances of the purchase agreement. Depending on the stage of construction, the buyer may also have the opportunity to personalize available finishes, selections and certain design elements. Ideally positioned near Snake Creek, enjoy convenient Bay-to-Ocean access with no fixed-bridge restriction and proximity to Founders Park. A remarkable opportunity to create a private Florida Bay retreat where luxury, privacy and the natural beauty of the Keys come together in one exceptional setting.

86600 Overseas Hwy, Islamorada
$427,000
2 Beds ⋅ 2 Baths ⋅ 620997 MLS
BEAUTIFUL CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000! LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY IN THE HIGHLY DESIRABLE PLANTATION BY THE SEA ON THE OCEAN IN THE BEAUTIFUL FLORIDA KEYS! LOCATED ON HIGHLY SOUGHT AFTER MILLIONAIRES ROW! UPON ENTERING THIS GATED COMMUNITY, THE OCEAN GREETS YOU AS YOU PARK IN YOUR DESIGNATED COVERED PARKING SPACE. UPON ENTERING YOUR CONDO, THIS PARTIALLY UPDATED CONDO WITH OPEN CONCEPT KITCHEN, WELCOMES YOUR HOME TO A CHEF'S DREAM KITCHEN WITH PLENTY OF CABINET SPACE. NEW WATER HEATER, SCREENED IN PATIO ON THE FIRST FLOOR AND GORGEOUS OCEAN VIEWS FROM THE SECOND FLOOR. CLUBHOUSE/COMMUNITY ROOM, FITNESS ROOM, SAUNA, KAYAK STORAGE, LONG AND WIDE FISHING PIER/DOCK ALLOWS YOU TO TIE UP YOUR BOAT FOR LOADING AND UNLOADING WALK TO WORLD CLASS RESTAURANTS, SHOPPING, AND FOUNDER'S PARK. ALL ARE CLOSE! TAKE ADVANTAGE OF THIS AMAZING OPPORTUNITY TO LIVE FULL TIME WHERE OTHERS VACATION, OR START A VACATION RENTAL BUSINESS HERE IN THE BEAUTIFUL FLORIDA KEYS!

87455 Old Hwy Unit 248, Islamorada
$6,195,000
4 Beds ⋅ 5 Baths ⋅ 620986 MLS
Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

144 N Rolling Hill Rd, Islamorada
$11,000,000
5 Beds ⋅ 5 Baths ⋅ 620965 MLS
Extraordinary opportunity to own one of the Florida Keys' most spectacular oceanfront residences. Set along a breathtaking stretch of pristine shoreline, this remarkable estate seamlessly blends exceptional architecture, sophisticated design and an unparalleled waterfront lifestyle. Set on nearly an acre with 100 feet of white-sand Atlantic Ocean frontage, this newly completed renovation by acclaimed D'Asign Source delivers exceptional design, craftsmanship and timeless elegance with breathtaking ocean views from virtually every room. This residence features 5 bedrooms, 4 full bathrooms and 1 half bath, a residential elevator, full-size tennis/pickleball court and spectacular infinity-edge pool with spa. The grand open-concept living space features custom shellstone flooring and seamless indoor-outdoor living. A stunning chef's kitchen is appointed with a complete suite of Miele appliances, including three ovens, two dishwashers, panel-ready refrigerator and freezer, built-in coffee maker and six-burner cooktop with integrated extractor. Additional highlights include a butler's pantry, dedicated laundry room and two expansive bonus rooms ideal for a gym or game room. The top floor offers a luxurious primary suite enhanced by cathedral ceilings, oceanfront terraces and spa-inspired bathroom along with two additional en suite guest rooms. Outdoor living is exceptional, with generous covered entertaining areas, a fully equipped summer kitchen and an infinity pool and spa that appear to merge with the endless turquoise waters of the Atlantic. The gated and fenced grounds provide privacy and include a two-car garage, car lift, whole-house generator and buried propane tank. With WEEKLY rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. This remarkable estate offers a combination of sophisticated luxury, resort-style amenities and unmatched beachfront living in Islamorada

75751 Overseas Hwy, Islamorada
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 620933 MLS
Villa 1 offers one of the most coveted locations within the exclusive 22-villa community at The Islands of Islamorada. Ideally positioned as the closest oceanfront villa to the private marina, this exceptional residence enjoys some of the community's most impressive ocean views and an incredible connection to the water. The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 1, Islamorada
$2,485,000
3 Beds ⋅ 3 Baths ⋅ 620704 MLS
Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket. This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms, and a tranquil porch ideal for enjoying sunset skies. The top floor is reserved for the expansive master suite, complete with a private balcony and sweeping waterfront views. Tarpon Flats offers an amenity-rich lifestyle tailored to the discerning buyer. Enjoy a waterfront pool and gazebo, private beachfront access, generous dockage for your skiff, a charming greenhouse, and a tennis court with shaded seating for guests. Adding to the ease of ownership, the community provides a full-time concierge service and an on-site handyman, ensuring both comfort and convenience year-round. Sophistication, privacy, and natural beauty converge in this exceptional Islamorada retreat--come discover what makes Tarpon Flats truly one of a kind.

81250 Overseas Highway Unit 2, Islamorada
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 620649 MLS
Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

87851 Old Hwy Unit P3, Islamorada
$549,500
1 Beds ⋅ 1 Baths ⋅ 620633 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 715, Islamorada
$549,500
1 Beds ⋅ 1 Baths ⋅ 620629 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This double queen bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 716, Islamorada
$13,750,000
5 Beds ⋅ 7 Baths ⋅ 620590 MLS
Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.

19 Avacado St, Islamorada
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