Islamorada Waterfront Homes For Sale on the Ocean Side

Welcome to Two White Turtles, a beautifully renovated, turnkey waterfront coastal paradise retreat - perfect for a vacation rental, second home, or primary residence. This stunning canal-front property offers homeowner access to a rare white sandy BEACH and is designed for the ultimate Florida Keys lifestyle. The grand French door entrance leads to open-concept areawhich features soaring wood-beamed ceilings, abundant natural light, a gourmet chefs kitchen with quartz countertops, French door refrigerator, all stainless appliances, a pantry with pullout drawers, ample storage, a dining spot and living space for entertaining or lounging while watching a 55 TV. Off the lounge are two ensuite bedrooms, each with their ownbathroom, wall mounted TV, abundant closet space, and dual sinks with a walk-in shower in the primary suite. Outdoors, relax in the tiki hut by the canal, rinse off in the outdoor shower, or unwind in the private backyard overlooking the mangroves. The 75 dock with a 7k boat lift and davits makes this a boaters paradise, offering direct ocean and quick bay access via Channel 2 and 5 bridges - just minutes from Alligator Reef Lighthouse. Additional features include a one-car garage with extra storage, ample parking for trailers, multiple vehicles, and an RV. Featuring a fenced, no-maintenance turf grass yard with pavers, a newer 5V crimp roof, with impact windows and doors. Peekaboo ocean views, starry nights, and ocean breezes enhance the homes serene setting. A bonus generator, extra fridge and freezer also add convenience. An easy walk to some nearby restaurants is a plus, making this location a perfect slice of paradise. Come watch the manatees float by and experience Keys living at its finest. Schedule your private showing today!

Venetian Shores location for under $2M! This spacious and solid concrete house has an excellent location right off Snake Creek for fast access to both Ocean & Bay, fuel, bait and provisions. Enjoy 70 of commercially zoned dockage in the best Islamorada location available! Upstairs features an open floor plan with gourmet kitchen and breakfast bar, office area, bonus room, roomy bedrooms and two full bathrooms. Downstairs guest suite with bathroom & kitchen plus screened patio to access the outside tiki hut and nice outdoor living on the canal.

Incoming producing property with future bookings already in place! Beautiful Florida Keys home, 1,827 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed and elevated in 2021. Boaters paradise with 75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift. Canal depth is estimated to be 10-12 FT. This unique layout offers 2 bedrooms and 2 baths on the second floor with a full kitchen and spacious living room area, washer and dryer. First floor offers 1 bedroom and 1 bath, washer and dryer, full kitchen and its own washer and dryer for your convenience (separate living units). New roof/hurricane impact windows throughout. Easy storage space. Ample parking.

Welcome to your dream home in the heart of Islamorada! This beautifully remodeled 3-bedroom, 3-bathroom Florida modern home offers the perfect blend of luxury and convenience. Located on a fantastic canal just moments from the ocean, this turn-key property is ready for you to move in and start living the ultimate Florida lifestyle.The spacious, open-concept floor plan is bathed in natural light, creating a bright and airy atmosphere throughout. The oversized gourmet kitchen is a chefs dream, featuring high-end stainless steel appliances, sleek countertops, and ample storage space, ideal for both entertaining and everyday living.The bathrooms are stunning, with modern fixtures and finishes that enhance the homes overall elegance. Impact-resistant windows and doors provide peace of mind, while adding to the contemporary feel of the home.For added versatility, the home includes a dedicated office or media room--perfect for remote work or relaxing in style. Outside, enjoy exceptional dockage and a charming gazebo, ideal for unwinding or entertaining by the water.Experience the best of the Islamorada lifestyle with this unique property. Whether youre boating, fishing, or simply relaxing by the canal, this home offers the ideal setting for living in paradise. Dont miss the opportunity to make this exceptional property yours!

ANGLERS REEF OCEANFRONT HOME WITH DEEDED DOCK. RARE OPPORTUNITY to own an oceanfront home in the prestigious Anglers Reef development in Islamorada. Deeded boat slip accommodating up to a 31 ft boat included in offering. A beautiful 2-bedroom, 2.5-bath, 2-story home with 2 porches and a balcony overlooking the Atlantic Ocean. Located in the gated community of Anglers Reef on Windley Key approximately half way between Miami and Key West. This property contains 2 large bedroom suites with bathrooms on the 2nd floor. A living room, kitchen, dining room and powder room on the main level. Looks out on the community pool and marina (see included video). Upgrades include impact windows/doors, metal roof, composite decks/railings, granite counter tops with wood cabinets, tile floors downstairs and bamboo floors upstairs, shutters/blinds, brand new dishwasher and refrigerator. The community features 2 sandy beaches, pool, gated entry, marina, kayaks and paddle boards. Perfect home for primary residence, vacation family home or investment property. Call today for a showing

Welcome to this charming Old Florida-style cottage, an ideal weekend retreat nestled on Lower Matecumbe Key in Islamorada! This property is set on nearly half an acre, boasting an impressive 100 ft of private beach frontage directly on the crystal-clear ocean. This cottage is a perfect fixer-upper opportunity, offering you the chance to renovate and personalize the existing structure or build your dream home on this stunning piece of prime real estate. Step inside to discover two spacious bedrooms and two full bathrooms. The interior features beautiful beamed and tongue-and-groove ceilings, adding a touch of character and warmth to the space. Imagine starting your mornings with a cup of coffee or unwinding in the evenings with a glass of wine, all while enjoying breathtaking views of the magnificent Atlantic Ocean. The gentle ocean breezes create a serene atmosphere, perfect for quiet contemplation and entertaining friends and family. With its prime location and charming features, this cottage is a rare find that invites you to embrace the laid-back Florida Keys lifestyle. Dont miss your chance to make this idyllic getaway your own!

Welcome to your slice of paradise in the sought-after Matecumbe Ocean View neighborhood! This beautifully upgraded concrete home (including the roof) is built for durability, comfort, and style. Fully fenced and thoughtfully designed, the exterior grounds features sleek new concrete and turf along the sides of the house for a clean, modern look.The backyard is an entertainers dream with a full outdoor kitchen, a sparkling pool, and a spacious 75 ft. concrete seawall complete with a 15,000 lb elevator boat lift. Enjoy quick and easy access to the ocean via a marked channel--perfect for boating enthusiasts who want to be on the water in just minutes. Great fishing and diving awaits! Inside, youll find an upgraded interior featuring stainless steel appliances, a wine fridge, a walk-in pantry, and generous living space. The large bedrooms offer comfort and privacy, while the expansive balcony invites you to relax and soak in the coastal breezes. Matecumbe Ocean View is a desirable community with its own boat ramp conveniently located at the beginning of the street, making launching a breeze. This home is close to great amenities located in Islamorada like Robbies, Worldwide Sportsman, a number of restaurants, Bud N Marys Marina and more! Whether youre looking for a full-time residence or a vacation escape, Cortez Dr is the ideal blend of luxury, function, and Keys lifestyle.

Welcome to Matecumba Ocean View! Ocean Views from this home, feel the ocean breeze.This recently up dated home is your Island Dream Home Come True. Newly updated kitchen with Island eat in kitchen counter, all new stainless steel appliances, all new floors throughout. All master suite on the 3rd floor with private balcony and ocean views.Extra large 2nd and 3rd bedrooms, with walk in closet, private open balcony and Ocean Views. A boater paradise 75ft of concrete dock with 20,000 lb. boat lift, A set of davits and built in pool with pool heater/chiller for the ultimate outdoor experience. Canal depth is estimated to be 10-12 ft. Direct Ocean Access for your boat. Just 5 minutes to the Ocean and Bay access too. Income producing property with future bookings. The property includes a great yard for entertaining with Automatic sprinkler system,Electric GateFully gated and fenced yardLocated on a very quiet dead end street

Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch, lower level covered patio, living room and 2 of the 3 bedrooms.Fully remodeled in 2021, this charming get-away has been entirely refreshed with new everything...including impact windows and doors, metal roof, flooring, new appliances, central air, pool equipment and electric gate. Furnishings and finishes reflect the coastal cottage style creating the epitome of relaxation and embodying the Florida Keys lifestyle.

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

LOOKING FOR THE PREMIER DEEP WATER OCEAN/BAY ACCESS COMMUNITY? Discover the epitome of waterfront living in the exclusive community of Venetian Shores in Islamorada. Renowned for its expansive 100-foot-wide canals, this neighborhood provides unparalleled access to both the Atlantic Ocean and Florida Bay via Snake Creek--ideal for boating enthusiasts. This meticulously updated residence boasts 4 spacious bedrooms and 4 bathrooms. The upper level features three en-suite bedrooms, ensuring privacy and comfort for all occupants. The main living area is highlighted by soaring tongue-and-groove vaulted ceilings and 8-foot impact-resistant French doors that open to a screened lanai overlooking the saltwater pool and canal. The gourmet kitchen is equipped with stainless steel appliances and a gas stove, catering to culinary enthusiasts.The ground floor offers a legal apartment complete with a bedroom and full bath, perfect for guests. Entertain effortlessly on the expansive covered porch, which provides a serene setting to enjoy the outdoors.The saltwater pool is designed for year-round enjoyment, featuring both heating and cooling capabilities, along with a retractable cover for added convenience. A dedicated, air-conditioned mancave offers ample space for storing boating, fishing, and diving equipment. For boating aficionados, a 20,000-pound boat lift was installed, and the property is fully fenced with a sliding gate, ensuring privacy and security.With nearly $80,000 invested in recent improvements, this home is move-in ready. Embrace the Florida Keys lifestyle with world-class fishing and diving just minutes away. Dont miss the opportunity to own this exceptional waterfront property-- Your Florida Keys Dream Home Awaits!

This brand-new tri-level home in the FL Keys perfectly captures the essence of sophisticated luxury & relaxed island living. With both bay & ocean access, 60 ft. of canal frontage + private concrete dock, its ideal for saltwater enthusiasts. The home flows seamlessly from the rec room & summer kitchen to pool area, all set in a fenced yard - perfect for kids & pets. The 2nd level offers open living & dining, kitchen island, sleek wet bar & laundry room. An expansive balcony is perfect for family dinners & unwinding. Upstairs, elegant finishes & water views offer a peaceful master retreat. Just blocks from Tavernier Marina & fuel station, close to the top dining spots in Islamorada & only 90 mins. from Miami, this home is an ideal vacation retreat w/no HOA & great rental income potential.

Located in a private, gated community in the heart of Islamorada, 109 South Drive is a rare waterfront retreat that perfectly blends luxury, comfort, and the ultimate Florida Keys lifestyle. The main home features 4 spacious bedrooms and 3.5 beautifully designed bathrooms upstairs, while a separate 1-bedroom, 1-bath apartment downstairs offers privacy for guests or rental potential. Enjoy a custom resort-style pool surrounded by lush, tropical landscaping and a brand-new designer kitchen by Allabastro Designs. Boaters will appreciate the protected dockage with an ipe dock and direct ocean access -- no bridges, no long idle canals. Relax on the rooftop balcony with panoramic ocean views or entertain on expansive outdoor patios. With its unmatched access, thoughtful upgrades, and serene island ambiance, this property is a true Islamorada gem.

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

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!

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!

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.

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.