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

The Ospreys are back! Welcome to The Ospreys Nest; your perch by the Ocean in one of Islamoradas most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20 dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive. Listing includes canal parcel with dock across the street RE#00389220-000100

Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Cafe, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, youll discover sweeping bay views and a rare tiki hut at the end of the dock--your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area--ideal for guests or extended family. Whether youre looking for your forever getaway in the Keys or a smart investment when youre not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

Welcome to Paradise in Port Antigua, one of Islamoradas best-kept secrets! This spacious 4-bedroom, 4-bath home, built in 2019, offers the ultimate Florida Keys lifestyle with modern coastal design, deep-water dockage, and exceptionally low insurance premiums with the possibility of assuming a 2.8% interest rate! Located in the highly sought-after Port Antigua community, residents enjoy unique deepwater dockage and over 1,000 feet of private, exclusive beach frontage.This thoughtfully designed home features a well-planned layout with two primary suites--one on each level--providing privacy and comfort for residents and guests. Each floor includes a separate living space, connected by an interior staircase (all above flood!). A kitchenette on the first level adds convenience, making this home ideal for multi-generational living or hosting visitors. Upstairs, the open-concept layout boasts a spacious kitchen island, high-end appliances, and a seamless flow into the dining and living areas. Balconies on both levels provide stunning canal views, offering perfect spots for outdoor relaxation.The upper level offers three bedrooms and two full baths, while the lower level includes an additional primary suite, two full guest baths, a wet bar, and a secondary living area with easy access to outdoor spaces. The generously sized bedrooms feature large closets, enhancing the homes comfort and functionality.Built for durability, this home includes a standing seam metal roof, all impact windows and doors, and tile floors throughout.Outside, the property boasts two garages--one with AC--a commercial-grade ice machine, and 56 feet of concrete dockage on a desirable 90-foot canal with deepwater access. A 20,000-pound boat lift is included, along with ample parking for vehicles and trailers. Theres even room for expansion if you wish to add more dockage or a pool. This home checks all the boxes and is move-in ready! Call today for more information.

Waterfront Elegance in Venetian Shores - A Turnkey Coastal GemDiscover the pinnacle of Florida Keys living in this impeccably remodeled waterfront oasis, located in the highly sought-after Venetian Shores. This sophisticated 4-bedroom, 3-bathroom retreat spans over 3,000 square feet of thoughtfully designed living space, blending contemporary luxury with island-inspired charm.From the moment you step inside, youll be captivated by the refined finishes and custom upgrades throughout -- including a gourmet chefs kitchen, spa-quality bathrooms, and expansive open-concept living areas ideal for relaxing or entertaining.This home is truly move-in ready, featuring a brand-new roof, sparkling new pool, all-new impact windows and doors, a state-of-the-art 27,000 lb boat lift, and premium craftsmanship in every detail.Boaters will appreciate 70 feet of deepwater dockage with instant access to Snake Creek -- offering seamless navigation to both the Atlantic Ocean and Florida Bay.Whether youre searching for a permanent residence or a high-end vacation escape, this home offers the perfect blend of luxury, comfort, and unbeatable location.Exclusively offered in Venetian Shores -- where world-class boating and refined coastal living come together.

Now priced under appraisal! Introducing the Sea Pearl: a rare and refined coastal masterpiece nestled just four parcels from the Gulf. This ultra-modern smart home constructed in 2016 redefines luxury Keys living, offering five spacious bedrooms, five and a half bathrooms, and over 4,100 square feet of meticulously designed and furnished interior space. Boaters will delight in 70 feet of concrete dockage with water and electric, 15,000 lb boat lift, and panoramic sunset views over a protected nature preserve across the canal--ensuring privacy and tranquility that can never be built upon. This concrete haven is fully equipped with a whole-home generator, Control4 smart system (for AC, music, lights, alarm, security cameras, TVs and more), impact windows/doors, metal roof, and a sleek glass elevator connecting all three levels. Nearly 1,500 square feet of open-air porches and patios invite you to unwind and soak in the Gulf breezes. Step inside the ground level to a welcoming foyer that opens to a sitting area, custom wet bar, Anglers room, and guest ensuite bedroom. Just beyond, enjoy a resort-style pool and built-in spa surrounded by shell stone decking that stays cool even in the height of summer. On the second level, a show-stopping modern kitchen features custom cabinetry, Brittanica Cambria quartz countertops, expansive island with waterfall edge, seating for 8, GE Monogram appliances, Viking 6-burner induction cooktop, and wine cooler--perfect for entertaining. This level also offers three additional bedrooms, including a Jack-and-Jill suite, full laundry, and half bath. The entire top floor is reserved for the primary suite: a true sanctuary with sweeping water views and open air porch, spa-like bathroom with soaking tub, glass shower, bidet, and a custom walk-in closet. With optional White Marlin Beach access, this home is the epitome of modern island elegance--where every detail has been curated for comfort, style, and the ultimate Florida Keys lifestyle.

Seize the rare opportunity to build your dream home in one of Islamoradas most coveted locations! Located directly across from the iconic Alligator Reef Lighthouse. Across the street from a protected preserve that will never be developed, and featuring a deep water channel capable of accommodating boats up to 40 feet, this property offers unmatched privacy and access.Imagine living just a short stroll from the legendary Square Grouper, Midway Cafe, Robbies. Down the road from some of the best restaurants in Islamorada like Ziggies, Mad Dogs, and Chef Michaels. This oversized lot, just shy of an acre, provides the perfect canvas for a builder, developer, or savvy end user to craft a stunning, custom-designed home in an unparalleled location. Dont miss your chance to secure this exceptional piece of paradisean extraordinary opportunity to live where others only dream!

This remarkable 34,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay. One of the key highlights of the lot is its exceptional dockage (65 ft), which has previously accommodated a 36-foot Bertram, making it perfect for boating enthusiasts. The property also offers ample space for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds, creating a tranquil atmosphere for evening relaxation. The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aquatic species, like fish, birds, manatees, and a multitude of different birds. Its a perfect canvas for your dream residence or vacation retreat. With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this property is one of the best on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation. May also purchase the vacant lot up front that has a Market Rate TDR on it. Combined you would have ability to build 2 large homes on a combined 49,000 of land. This would make an exceptional family compound in the heart of Islamorada. Possible owner financing. Owner / Agent

Not one, but TWO dwellings on an oversized parcel from Highway to Ocean! With an ultimate Florida Keys resort feel, this private 4 BD/ 4 BA home has endless ocean views and opportunities! Whether you are looking for a primary residence or a home with strong rental income, this property has it all! Boasting a pool, 2 brand new tiki huts, observation dock, boat ramp, beach AND 2 rock jettys for storm protection. This property has been completely remodeled with brand new impact windows and doors, kitchen appliances, washer and dryer, metal roof, exterior stucco, paint and finishes. Plenty of room for car parking, toys, trailers and friends! Bring your clothes and enjoy paradise with plenty of room to entertain and just enough privacy!

A truly spectacular waterfront home with 150 feet of prime bay frontage, offering breathtaking views of some of the clearest waters in the Florida Keys. This property has undergone a complete top-to-bottom renovation with exceptional attention to detail. Solid concrete bunker with a concrete roof and impact windows & doors. Boaters will appreciate the deep-water dockage, accommodating nearly any vessel, with easy ocean access through Channel 5.The main living area upstairs features three bedrooms, two bathrooms, and a beautifully designed kitchen with high-end appliances--all framed by stunning turquoise water views from nearly every room. Downstairs, a separate guest suite includes a private bedroom, bathroom, living room, and kitchen, perfect for visitors or additional living space.A pool permit is already in place, or you can take a refreshing swim right in the bay. This home is truly one-of-a-kind--dont miss the chance to own a special piece of paradise!

Panoramic Bay and Sunset Views! Breathtaking Bayfront Home in Safety Harbor.Experience the stunning beauty of panoramic bay views from this exquisite bayfront home in the premier Safety Harbor neighborhood on Lower Matecumbe. This home is in pristine condition and features an irreplaceable cut-in boat slip with a composite dock on the bay ensuring that your views are not obstructed, and providing immediate bay access and quick ocean access via the two bridges at Channels 2 and 5.Inside, youll find four spacious bedrooms and three bathrooms, perfect for comfortable living. An enclosed garage for all of your fishing and diving gear. The home is equipped with a new whole house generator, ensuring uninterrupted power.Step outside and immerse yourself in resort-style living with a luxurious pool and spa, lush low maintenance landscaping, perfect for relaxation and entertaining. Enjoy breathtaking sunsets year-round from your own private oasis either at the tiki bar, the dock, or one of the two bayfront screened porches. Dont miss the opportunity to own this exceptional bayfront home in Safety Harbor. Schedule your private showing today!

BRAND NEW DOCKAGE COMING SOON!! UPDATED PICTURES ONCE COMPLETED!! Discover coastal luxury in this stunning 4-bedroom, 4-bathroom bayside paradise. With 4,144 square feet of luxurious living space, this home offers breathtaking sunset views and direct access to the sparkling waters of the Florida Keys. Indulge in spacious, open-concept living areas, perfect for entertaining guests. Retreat to one of two primary suites, each featuring a large walk-in closet and private en-suite bathroom. Ascend to the rooftop deck and be rewarded with unobstructed, open-water bay views. The property features a separate living space, ideal for in-laws or guests, offering privacy and independence. The modern kitchen boasts sleek stainless steel appliances, double oven, gas appliances and ample counter space, perfect for culinary enthusiasts. The homes durable construction with a metal roof, and impact-resistant windows and doors, ensures peace of mind. For added security and privacy, the property is fully fenced and features an electric gate. Enjoy panoramic water views and unforgettable sunsets from your private oasis. With large boat dockage, youll have plenty of room for multiple boats, jet skis and easy access to the open water for boating, fishing, and other water activities. This completely updated home offers the ultimate experience in comfort and convenience. Whether youre seeking a serene retreat or an active water lovers paradise, this home has it all. Dont miss this opportunity to own a piece of paradise.

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout.Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation.On the main floor, the gourmet kitchen is a chefs dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock.This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating open water views and is situated on 1.3 acres of land. Complete with three bedrooms and two bathrooms, this ground-level, and updated residence is the perfect place to entertain while basking in all of the beauty the Keys offers. Zoned residential estate, this income-producing home qualifies for weekly rentals, which provides ample opportunities for a discerning buyer.

This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this residence offers ample space for family and guests. Enjoy stunning ocean views from various vantage points within the home, enhancing the comfort and breathtaking natural beauty. The observation dock provides a perfect spot for relaxation, while the saltwater pool equipped with heater/chiller, ensures year-round enjoyment. Added features are quartz countertops, top-of-the-line appliances and the Residential Estate zoning allows weekly vacation rentals with a high-income stream.This combination of amenities creates an inviting atmosphere that reflects the privacy and charm of the Florida Keys lifestyle.

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chefs kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys most sought-after locations.

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

Welcome to your private tropical retreat in the heart of Islamorada, Florida Keys. This stunning gated oceanfront estate showcases unparalleled beauty with a private walk-in sandy beach, offering direct access to crystal-clear waters. Designed for both relaxation and recreation, the property features 5 spacious bedrooms, 6.5 luxurious bathrooms, a resort-style pool, a pickleball court, and a putting green, all set amidst lush, tranquil landscaping.Wake up to spectacular ocean views from nearly every room, and enjoy the serenity of your tropical surroundings. This property is offered turn-key, fully furnished and equipped, making it an ideal primary residence, second home, or lucrative vacation rental opportunity in one of the Keys most desirable locations.Your dream oceanfront lifestyle awaits in Islamorada -- where every day feels like a vacation.

$400,000 PRICE REDUCTION !! ... Welcome to Serenity Cove, a remarkable, comfortably luxurious estate set along the shores of the Florida Bay. This custom-designed property, stretching from the highway to the bay is almost 1.75 acres. It is perfect for those who value peace, relaxation, and the simple joys of what the Florida Keys has to offer.This home offers four bedrooms and four bathrooms and 110 of dock with multiple slips accommodating up to a 45 boat with 5 draft and 16k lift. This home has been thoughtfully designed with tasteful moldings, and warm, inviting finishes. The kitchen, is equipped with top-tier appliances, custom cabinetry, and a roomy island - perfect for those who love to cook and entertain. It smoothly transitions into the formal dining room, making it an ideal space for both quiet family dinners and larger celebrations.The second-floor suite, with its spacious layout, welcoming fireplace, and private balcony, is the ultimate retreat. The en-suite bathroom, has a dual vanity, a claw-foot soaking tub, and a walk-in shower, guarantees moments of relaxation.The first floor offers a smart design with separate living areas and bedrooms. The 1st floor suite includes a steam shower and a reinforced safe room that doubles as a walk-in closet. The additional two bedrooms and a den with surround sound and a wet bar are comfortably located on the opposite side of the home.Enjoy quiet moments on the covered patio or engage in lively gatherings around the spacious poolside patio, which leads directly to the sandy beach for amazing sunsets. Here, youll find ample seating, a fire pit, a Boat House and steps leading to the basin for swimming and exploring the Bays unique ecosystem.Serenity Cove is comfortably tucked away from the hustle of US1, offering a sense of privacy and security, while maintaining easy access to schools, shopping, dining that make Islamorada so desirable.

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.