Islamorada Homes with Ocean Front Waterfront features

Islamorada Homes with Ocean Front Waterfront features

Welcome to Islamorada, a tropical paradise nestled in the heart of the Florida Keys, within Monroe County. Known as the "Village of Islands," this enchanting destination boasts a unique blend of natural beauty, vibrant culture, and an array of recreational activities that make it a sought-after location for both vacationers and residents alike. With its stunning oceanfront views, Islamorada is a haven for those who appreciate the charm of coastal living.

Imagine waking up every morning to the gentle sound of waves lapping against the shore, with the sun rising over the horizon, painting the sky in hues of gold and coral. Homes in Islamorada with oceanfront waterfront features offer not just a residence, but a lifestyle defined by tranquility and adventure. Whether you're a boating enthusiast, a fishing aficionado, or simply someone who enjoys lounging by the beach, these properties provide unparalleled access to the crystal-clear waters of the Atlantic Ocean.

Islamorada is also known for its rich marine life, making it a prime location for snorkeling, diving, and fishing. The area hosts numerous festivals and events that celebrate its vibrant culture, including art shows, culinary delights, and live music. With a tight-knit community and a welcoming atmosphere, you’ll find that Islamorada is more than just a place to live; it’s a place to thrive.

Explore the diverse range of oceanfront homes available, each offering unique features and breathtaking views. Discover your dream property in Islamorada and embrace the coastal lifestyle you've always envisioned!

Newest Islamorada Homes with Ocean Front Waterfront features

87455 Old Hwy Unit APT 234, Islamorada
$399,000
2 Beds ⋅ 2 Baths ⋅ 621854 MLS
Enjoy a tropical retreat at Plantation By The Sea, an oceanfront community in Islamorada. Relax beside the sparkling oceanfront pool or cast a line from the community fishing pier, then head out for waterfront dining, live music, and eclectic local shops. This inviting 2-bedroom, 1.5-bath condo offers a two-level layout with living spaces downstairs and both bedrooms upstairs. Bamboo flooring adds warmth to the living and dining areas and bedrooms. The updated kitchen features white cabinetry and generous counter and storage space. The open living and dining area flows onto a covered balcony nestled among tropical greenery - a pleasant spot for morning coffee or unwinding after a day exploring the island. Both upstairs bedrooms feature sliding glass doors opening to balcony spaces. An updated full bathroom with a tiled walk-in shower, a convenient downstairs half bath, and an in-unit Bosch washer and dryer add everyday comfort. Assigned covered parking and a ground-level storage room provide added convenience. Community amenities also include an oceanfront clubhouse with a kitchen, a pool table, and a ping-pong table - a great place to entertain friends and family. Take in ocean views while working out in the fitness center, or unwind in the men's and women's saunas. Gated entry and kayak and paddleboard storage add to the community's appeal. Nearby Founders Park offers a beach, Olympic-size swimming pool, tennis and pickleball courts, ball fields, and an amphitheater. Whether you're seeking a seasonal getaway or a year-round home, this welcoming condo puts the best of Islamorada within reach.

87455 Old Hwy Unit APT 234, Islamorada
79901 Overseas Highway Unit 217, Islamorada
$399,000
1 Beds ⋅ 1 Baths ⋅ 621774 MLS
Discover this 1 bedroom / 1 bath condo at The Palms of Islamorada, ideally located in the heart of Islamorada on Upper Matecumbe Key. Offering 827sf of living space, this condo features a spacious open porch, covered parking, and convenient kayak and paddleboard storage. The Palms is a gated oceanfront community situated directly on the Atlantic Ocean, with views of Alligator Lighthouse. Residents enjoy a variety of amenities, including a waterfront swimming pool, jacuzzi, tiki hut for entertaining and grilling, fitness facilities, and a community room. Conveniently located near Mile Marker 80, The Palms is adjacent to Lazy Days Restaurant and just minutes from local favorites such as Papa Joe's and Bud N' Mary's Marina. Nearby marinas offer boat storage options, while numerous restaurants, shops, and recreational activities are just a short distance away. Whether you're looking for a primary residence or a seasonal getaway, this condo offers a wonderful opportunity to enjoy the Florida Keys lifestyle in a central Islamorada location.

79901 Overseas Highway Unit 217, Islamorada
74501 Overseas Hwy, Islamorada
$4,850,000
5 Beds ⋅ 4 Baths ⋅ 621750 MLS
Discover a rare oceanfront paradise in the Florida Keys, situated on 1.35 acres of private oceanfront property featuring an extraordinary stretch of natural sandy beach, a feature seldom found in the Keys. Perfectly positioned next to iconic Sea Oats Beach, known for its pristine shoreline and seasonal sea turtle nesting, this exceptional estate offers privacy, coastal elegance, and breathtaking turquoise waters, just minutes from Islamorada's renowned dining and shopping. Enter through a private electric gate with ample parking for vehicles, boats, and trailers, plus an oversized three-car garage with pull-through access. An expansive ground-level storage area, currently utilized as a private gym, provides additional space for recreational equipment and boating gear. Built with concrete construction, the residence features impact-resistant windows and doors, along with a 25kW propane generator. Inside, marble floors, granite countertops, stainless steel appliances, a wine refrigerator, built-in ice maker, and spectacular open living spaces create an inviting coastal retreat. Four sets of double sliding impact glass doors frame panoramic ocean views and abundant natural light. The residence features five bedrooms and four full bathrooms, including two guest suites with private baths. The oceanview primary suite offers a walk-in closet, dual vanities, soaking tub, and walk-in shower. Outside, a lagoon-style pool, Jacuzzi, and wraparound balcony create an exceptional setting for entertaining and enjoying the ocean breezes. Offered below its 2026 appraised value, this remarkable oceanfront estate presents a rare opportunity to own 1.35 acres of private oceanfront property with a natural sandy beach, stunning open-water views, and convenient access to Islamorada's restaurants, shopping, and marinas.

74501 Overseas Hwy, Islamorada
79901 Overseas Highway Unit 410, Islamorada
$695,000
2 Beds ⋅ 2 Baths ⋅ 621648 MLS
Located in the heart of Islamorada, this 2 bedroom, 2 bath condo at The Palms of Islamorada offers beautiful Atlantic Ocean views and a spacious covered porch accessible from both the living room and primary bedroom. The primary suite features an en suite bathroom, while the covered porch provides an inviting outdoor space to enjoy the ocean breeze. Residents can enjoy a variety of resort style amenities within this gated oceanfront community, including a waterfront swimming pool, jacuzzi, tiki hut, fitness facilities, a community room, and covered parking. Situated on Upper Matecumbe Key near Mile Marker 80, The Palms is conveniently located near local favorites such as Lazy Days Restaurant, Papa Joe's, and Bud N' Mary's Marina, along with numerous other dining, shopping, and recreational options. A great opportunity for a primary residence or seasonal getaway in a central Islamorada location.

79901 Overseas Highway Unit 410, Islamorada
75931 Overseas Hwy, Islamorada
$7,400,000
5 Beds ⋅ 6 Baths ⋅ 621646 MLS
Discover an extraordinary oceanfront retreat in the Florida Keys, where 1.38 acres of lush tropical grounds, 150 feet of private sandy beachfront, and sweeping Atlantic Ocean views create an exceptional setting for island living. Designed to embrace its spectacular surroundings, this 4,770-square-foot estate offers five bedrooms and five-and-a-half baths, including separate guest quarters for added privacy. Soaring 30-foot ceilings and expansive windows fill the interiors with natural light while showcasing breathtaking ocean views. Elegant furnishings and thoughtfully appointed living spaces complement the home's sophisticated yet relaxed coastal atmosphere. Offered fully furnished and turnkey, the property is ready for immediate enjoyment. Outdoors, a resort-style infinity-edge pool and spa overlook the turquoise Atlantic waters, creating a seamless connection between luxury living and the natural beauty of the Keys. The expansive private beach invites endless days of kayaking, fishing, swimming, or simply relaxing beneath the palms. A spacious two-car garage adds convenience to this exceptional property. With zoning that permits weekly rentals, the estate also presents an attractive opportunity for those seeking a luxury vacation retreat with income-producing potential. Whether envisioned as a private family compound, an unforgettable vacation escape, or a full-time residence, this remarkable estate captures the essence of Florida Keys living--privacy, natural beauty, and effortless oceanfront luxury.

75931 Overseas Hwy, Islamorada
82719 Old Hwy, Islamorada
$24,995,000
7 Beds ⋅ 11 Baths ⋅ 621626 MLS
Experience unparalleled oceanfront living at the Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship. Set on just under an acre of pristine coastline, the property offers 19,784 SF of total living and entertaining space, including 10,182 SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors with natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, a Baccarat-inspired grand ballroom, and a custom Glamour Suite. Outdoors, a mosaic pool and spa overlook the Atlantic Ocean, complemented by alfresco dining, a firepit lounge, putting green and multiple terraces with sweeping coastal views. A 300 inch outdoor LED theater and rooftop terrace elevate the experience. A 100ft private dock provides direct ocean access. Approved plans include 6 additional suites, including 2 oceanfront residences, allowing expansion into a multi-structure compound. A rare legacy estate defined by privacy, scale, and presence

82719 Old Hwy, Islamorada
75055 Overseas Hwy, Islamorada
$2,790,000
3 Beds ⋅ 2 Baths ⋅ 621394 MLS
Wake up to endless ocean views and the effortless simplicity of life on the beach. This pristine three-bedroom, two-bath oceanfront retreat offers a private, gated setting with a pool, spacious covered patio, and beautiful beach and ocean views from the upper porch, lower-level patio, living area, and two of the three bedrooms. Fully remodeled in 2021, this charming getaway was thoughtfully refreshed throughout, including impact windows and doors, a metal roof, new flooring, appliances, central air conditioning, pool equipment, and an electric entry gate. Coastal cottage-inspired furnishings and finishes create a casual, welcoming atmosphere designed for effortless island living. From mornings overlooking the ocean to afternoons by the pool, this beautifully maintained home captures the relaxed simplicity of the Florida Keys lifestyle.

75055 Overseas Hwy, Islamorada
88181 Old Hwy Unit APT G31, Islamorada
$699,000
3 Beds ⋅ 2 Baths ⋅ 621332 MLS
Looking for a private 3-bedroom condo with dockage that feels like home? Coral Harbour Club's distinctive open-sided building design provides windows on multiple exposures--including in the kitchen and in every bedroom and bath--filling the home with natural light and tropical views. Shared community boat slips and an excellent on-site marina make boating part of everyday life, with fuel and ice available on the property. Head out for fishing, diving, sandbar days or exploring the Florida Keys, then return to your peaceful retreat. Unlike most waterfront condos squeezed onto a narrow strip of shoreline, Coral Harbour Club spans approximately 14 lush acres with mature landscaping and remarkably spacious, private grounds. Two pets any size are welcome, with shaded walks and access to the Atlantic. Nearby covered parking provides convenient access to the building's central elevator up to the third floor, which is shared with only four other residences. Inside, this spacious split-plan condo has been thoughtfully updated for timeless Keys living. The kitchen features a classic Tuscan-style renovation with newer appliances, while both baths have been updated in elegant island style. One bedroom currently serves as a custom built-in office and can easily convert back. Additional features include new central A/C, full-size washer and dryer, generous closets and additional hall storage. A large wrap-around screened porch extends from both side bedrooms across the living area--perfect for morning coffee or unwinding after a day on the water. Impact windows and doors offer peace of mind, while accordion shutters protect the porch while you're away. Amenities include an oceanfront pool, expansive clubhouse, saltwater lagoon with sandy beach, tennis, pickleball and bocce ball courts, and extensive waterfront grounds with shady seating spots for enjoying shimmering sunrises and ever-changing ocean views.

88181 Old Hwy Unit APT G31, Islamorada
75433 Overseas Hwy, Islamorada
$3,999,000
4 Beds ⋅ 4 Baths ⋅ 621270 MLS
Wake up to the sunrise over the Atlantic from this private oceanfront retreat offering two separate residences, a sandy beach, and direct access from Highway to Ocean. This unique property offers a 3BD/3BA main residence plus a separate 1BD/1BA guest house, ideal for extended family, visiting friends, private home, or income producing estate. Enjoy a sandy beach, pool, two beachside tiki huts, observation pier, concrete boat ramp and rock jetties for tide protection, creating the ultimate setting for entertaining and waterfront living. Extensive upgrades include impact windows and doors, metal roof, A/C, stucco, paint, appliances and more. With abundant parking for cars, boats, trailers, toys and guests, there is room for everyone. Just minutes by boat to Alligator Lighthouse and nearby Caloosa Marina for fuel, ice, boat storage and food. A rare opportunity to own a true oceanfront Keys compound with space, privacy and a stunning view!

75433 Overseas Hwy, Islamorada
316 North Dr, Islamorada
$2,350,000
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
75751 Overseas Hwy, Islamorada
$10,000,000
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
136 Aregood Ln, Islamorada
$780,000
2 Beds ⋅ 3 Baths ⋅ 620945 MLS
Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, peaceful oceanfront community of just 10 townhomes, you'll have a beach, pool and your own slip for boat up to 30'. Spend the day on the water, relax by the pool or head up to the rooftop deck for ocean breezes & a peekaboo water view. There are four balconies - so you can enjoy some shade at any time of day. Although this seller never rented, the home is eligible for a coveted weekly rental license, giving a new owner the flexibility to enjoy it personally while also taking advantage of the strong Keys vacation rental market. The 2 bedroom, 2.5 bath townhome has a comfortable layout, with a private bath for each bedroom, a half bath on the main living level, and *straight interior* stairs rather than a spiral staircase. It's also refreshingly low maintenance, with concrete construction, a concrete roof, impact windows and doors, and an HOA that takes care of the grounds. Because this is a townhome rather than a condo, owners choose how much insurance to carry, and current insurance costs are surprisingly low. It's even in an X flood zone, so no flood insurance is required. Covered parking and an entry from underneath the home are two more practical touches that make coming and going easy, rain or shine. Trailer/boat storage is allowed under the home. The location works just as well by water as it does by land, with fantastic fishing and diving just steps from home and a great Old Highway location close to Founders Park, restaurants and everything you come to Islamorada to enjoy. Breezy and relaxed when you're here, with the ability to generate income when you're not. It's a rare and excellent combination.. good for your heart and your wallet.

136 Aregood Ln, Islamorada
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