Islamorada Real Estate

Islamorada Real Estate

Welcome to Islamorada, a tropical paradise nestled in the heart of the Florida Keys! Known as the "Village of Islands," this stunning destination offers a unique blend of natural beauty, vibrant culture, and a relaxed island lifestyle that captivates residents and visitors alike.

With its crystal-clear waters, lush landscapes, and breathtaking sunsets, Islamorada is a haven for outdoor enthusiasts and nature lovers. The area is renowned for its world-class fishing, making it a top choice for anglers eager to catch tarpon, bonefish, and sailfish. Dive into the vibrant underwater world at the nearby coral reefs or embark on a kayaking adventure through the serene mangroves—there’s no shortage of activities to keep you engaged.

Beyond its natural allure, Islamorada boasts a rich history and a charming community spirit. Explore the local art galleries, indulge in fresh seafood at waterfront restaurants, or partake in the lively festivals that celebrate the island’s culture. The community is tight-knit, welcoming newcomers with open arms and fostering a sense of belonging that is hard to find elsewhere.

Real estate in Islamorada varies from luxurious waterfront estates to cozy cottages, providing options for every lifestyle. Whether you’re searching for a vacation home or a permanent residence, you’ll find properties that offer stunning views and easy access to the best of island living.

With its idyllic setting and vibrant community, Islamorada is more than just a place to live; it’s a lifestyle. Come discover the magic of this enchanting village and find your slice of paradise today!

Newest Listings in Islamorada

179 Azalea Street, Islamorada
$2,450,000
4 Beds ⋅ 4 Baths ⋅ A12106064 MLS
Captain's Delight! Beautifully updated home in tranquil Plantation Key Colony. Great location for a boater or simply someone that enjoys Keys living. Four bedrooms and four and a half bathrooms. New pool with heater and chiller. Watch the sunset or the sunrise from the rooftop observation / sun deck. No bridges to the bay and take Tavernier Creek to the ocean.

179 Azalea Street, Islamorada
59 W Plaza Del Sol, Islamorada
$3,275,000
5 Beds ⋅ 3 Baths ⋅ A12105412 MLS
Spectacular turnkey luxury meets the ultimate boater's paradise, nestled in Islamorada's coveted Port Antigua community! Built with solid concrete construction, this exceptional waterfront residence offers a rare Florida Keys feature: a full lower level, seamlessly connected by an interior staircase. Offering nearly 3,000 SF, 5 bedrooms, 3 bathrooms. The lower level features 3 spacious bedrooms, a secondary kitchen, and custom rear deck, while upstairs showcases soaring ceilings, a gourmet kitchen, and 2 additional bedrooms. Completely remodeled from top to bottom with no expense spared! Premium flooring, custom Hunter Douglas shades, Big Ass Fans, upgraded bathrooms, and a new driveway. Offered fully furnished with luxurious Restoration Hardware pieces, flush-mounted Samsung Frame TVs, and a professional-grade pool table that converts into an expansive dining table. Enjoy a 75-foot concrete dock with 2 boat lifts and a dedicated fish-cleaning station. Port Antigua's exceptionally wide canals offer quick, direct access to both the Atlantic Ocean and Florida Bay for world-class offshore and backcountry fishing. Situated on a generous 7,500 SF lot with ample room for a custom swimming pool and outdoor oasis. Major upgrades include a new metal roof, full impact-resistant windows and doors, 2 new A/C systems, and a garage, and additional storage offering peace of mind. Residents also enjoy exclusive access to Port Antigua's private white-sand beach and community boat ramp.

59 W Plaza Del Sol, Islamorada
133 Anglers Way, Islamorada
$1,700,000
2 Beds ⋅ 3 Baths ⋅ A12098949 MLS ⋅ Anglers Reef BLDG.
Beautiful 2BR/2.5BA home in Anglers Reef, Islamorada’s upscale gated oceanfront community. Features a 31' deeded BOAT SLIP with direct Atlantic access and no bridges, making it ideal for boating and fishing enthusiasts. Offered turnkey furnished with hardwood floors, granite countertops, stainless steel appliances, impact windows and doors, 2 private carports, two bedroom balconies, a front porch, and a rear porch. Enjoy a private community beach, pool, and oceanfront marina. Approved for weekly vacation rentals, offering an excellent investment opportunity or the perfect Florida Keys retreat!

133 Anglers Way, Islamorada
115 Villa Bella, Islamorada
$4,899,000
4 Beds ⋅ 4 Baths ⋅ A12095140 MLS
Experience turnkey luxury in the renowned Venetian Shores community with this exceptional 4-bedroom, 4-bath concrete waterfront residence, completely rebuilt from top to bottom with designer finishes and thoughtful details throughout. Offered fully furnished and completely outfitted, this home is ready to enjoy from day one, including linens, bathroom essentials, a fully stocked kitchen, and three mini-bar setups. Currently operating in a successful vacation rental program, the property is equally suited for personal use, entertaining, or continued rental operation. Beautifully finished interiors create a sophisticated coastal feel, while a versatile downstairs versatile space offers the flexibility of a 5th bedroom, private office, game room, or lounge. Outdoor living is equally impressive with a resort-style pool that can be heated or chilled for year-round enjoyment. Extensive landscape and architectural lighting create a stunning atmosphere after sunset, while under-dock lighting illuminates the water for nighttime fish watching. An outdoor shower provides added convenience after swimming or boating. A customized golf cart makes cruising through Venetian Shores effortless. With its complete rebuild, designer interiors, turnkey furnishings, flexible living spaces, resort-style amenities, and established rental operation, this property offers the ultimate Florida Keys lifestyle. Simply arrive, unpack, and start enjoying.

115 Villa Bella, Islamorada
161 Palermo Drive, Islamorada
$1,950,000
3 Beds ⋅ 2 Baths ⋅ A12098342 MLS
Perfect fishing retreat/home. A boater's and angler's paradise in Venetian Shores! This 3-bedroom, 2-bath home at 161 Palermo Drive offers deep water and immediate access to the bay and ocean. Enjoy an open floor plan and screened porch, plus concrete construction, a concrete roof, impact windows & doors. A lift makes carrying heavy items upstairs easier. A spacious downstairs rec room with storage, covered parking, and a separate A/C shed for your fishing gear make it easy to enjoy life on the water.

161 Palermo Drive, Islamorada
80902 OLD Highway, Islamorada
$2,950,000
4 Beds ⋅ 3 Baths ⋅ B26081372 MLS
RARE OPPORTUNITY IN CORAL COVE! Welcome to Island Hopper, an award-winning tropical plantation-style home in one of Islamorada's most private gated communities. Set on an oversized double lot, this beautifully updated 4-bedroom, 3-bath home offers 3,550 sq. ft. of living space plus 1,200 sq. ft. of covered outdoor living. A spectacular wraparound porch, soaring windows, and abundant natural light capture the relaxed elegance of Keys living. The private top-floor primary suite features a walk-in closet, Jacuzzi tub, and adjoining office. Recent upgrades include impact windows and doors, four new A/C units, approximately 5,000 sq. ft. of new marble pavers, 7,500 sq. ft. of new turf, and lush tropical landscaping with mature orchids and privacy hedging. RARE OPPORTUNITY IN CORAL COVE! Welcome to Island Hopper, an award-winning tropical plantation-style home in one of Islamorada's most private gated communities. Set on an oversized double lot, this beautifully updated 4-bedroom, 3-bath home offers 3,550 sq. ft. of living space plus 1,200 sq. ft. of covered outdoor living. A spectacular wraparound porch, soaring windows, and abundant natural light capture the relaxed elegance of Keys living. The private top-floor primary suite features a walk-in closet, Jacuzzi tub, and adjoining office. Recent upgrades include impact windows and doors, four new A/C units, approximately 5,000 sq. ft. of new marble pavers, 7,500 sq. ft. of new turf, and lush tropical landscaping with mature orchids and privacy hedging. Enjoy the privacy of a dry-lot home with the benefits of waterfront living. Coral Cove's amenities include community boat dockage with water and power, fish-cleaning station, oceanfront pool, and tiki huts. Four covered parking spaces plus dedicated golf-cart parking complete the property. Ideally located in the heart of Islamorada, within walking distance of restaurants, shopping, and entertainment. With only 9 homes in Coral Cove, opportunities to own in this special community are exceptionally rare.

80902 OLD Highway, Islamorada
111 ANGLERS Way, Islamorada
$1,199,999
2 Beds ⋅ 3 Baths ⋅ B26080616 MLS ⋅ Anglers Reef BLDG.
Experience the Florida Keys lifestyle at Anglers Reef, Islamorada's upscale gated oceanfront community. This beautifully appointed 2 bedroom, 2.5 bath home features a covered carport & four inviting porches, perfect for enjoying the tropical surroundings. Inside, you'll find Brazilian cherry hardwood floors, a spacious kitchen with granite countertops, stainless steel appliances, two breakfast bars, & abundant cabinetry. Additional features include a durable metal roof & impact windows & doors. Vacation rentals are permitted, making this an excellent opportunity for both personal enjoyment & investment. The home has been part of a successful rental program for many years & enjoys an established following of returning guests. Anglers Reef offers resort style amenities including two sandy be

111 ANGLERS Way, Islamorada
87429 Old Highway, Islamorada
$18,499,000
6 Beds ⋅ 8 Baths ⋅ A12092985 MLS
The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand porte-cochère, the single-level main residence unfolds with soaring ceilings, white oak floors and 12-foot retractable glass walls that dissolve the boundary between interior and oceanfront living. At its center, a chef's kitchen pairs a cascading Calacatta marble island with Thermador appliances and a walk-in pantry, opening seamlessly to expansive living and dining spaces. The main residence includes four bedrooms and six full baths, with an impressive primary suite featuring a fireplace, dual walk-in closets, safe room and spa bath with steam shower. Additional suites offer en suite baths, private balconies and ocean views. A detached two-bedroom, two-bath guest residence brings the estate to six bedrooms while preserving privacy between owners and guests, with substantial grounds offering extraordinary flexibility for the future. Outside, the property assumes the scale of a private resort. Two resort-style pools with spas and sun decks are joined by a summer kitchen and multiple terraces. A fitness center with sauna, soundproof theater and golf simulator complete the lifestyle offering.

87429 Old Highway, Islamorada
82719 Old Highway, Islamorada
$24,995,000
7 Beds ⋅ 11 Baths ⋅ A12091663 MLS
Experience unparalleled oceanfront living at 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 10,182SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors w/ natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, putting green, 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, and multiple terraces w/sweeping coastal views. A 300" 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. This is more than a home, it is a rare legacy estate.

82719 Old Highway, Islamorada
100 IROQUOIS Drive Unit 5, Islamorada
$999,999
3 Beds ⋅ 3 Baths ⋅ B26070805 MLS
This waterfront home offers 36 feet of dockage and a beautifully renovated interior designed for effortless Keys living. Thoughtfully updated and tastefully decorated, the home is move-in ready and ideal for full time living or weekend getaway. The layout is exceptionally well-suited for hosting and entertaining, with two bedrooms and two bathrooms on the main living level, and a large separate guest suite and bonus area on the lower level providing privacy and flexibility. Enjoy peaceful views from the screened-in porch, perfectly positioned to capture a straight, open view down the canal, while the spacious backyard offers plenty of room to relax, entertain, and a blank canvas to further enhance your outdoor living experience to your liking. Boaters will appreciate quick access to the ocean, with a beautiful sandbar/beach nearby, perfect for anchoring up for a day of sun, as well as convenient routes to the bay via Channel 2 or Channel 5 bridges. Additional features include a rare garage space, ideal for storing a golf cart, jet skis, and gear while keeping everything protected from the elements.Located on Lower Matecumbe Key, this property provides a walkable Keys lifestyle. Stroll down to the fishing pier to catch dinner and take in a sunset view or hop in the golf cart and ride down to the locals favorite, Habanos restaurant and their new tapas bar right on the ocean for dining and drinks. This is a must-see waterfront opportunity combining comfort, functionality, and the best of island living.

100 IROQUOIS Drive Unit 5, Islamorada
102 Venetian Drive, Islamorada
$1,600,000
3 Beds ⋅ 2 Baths ⋅ A12080331 MLS
Boaters paradise in Isla Morada Florida the Sport Fishing Capital of the World, this 3 bedroom 02 bath home is ready to enjoy. Own a piece of paradise in the Florida Keys a Marine Sanctuary. This home is located is the sought after community of Marlin Beach adjacent to Port Antigua. It has private dockage for your boat as well as access to the Atlantic Ocean within minutes from your backyard.

102 Venetian Drive, Islamorada
316 N Dr, Islamorada
$2,350,000
3 Beds ⋅ 4 Baths ⋅ A12076505 MLS
Simply the best location, exclusive & extremely private. 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 modern kitchen and updated baths, as well as impact windows and doors. The exterior has been reinforced with rebar and stucco. There are three inviting bedrooms, including a third-floor primary en-suite with a private porch.

316 N Dr, Islamorada
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