Find Your Dream Home in Islamorada

Listed in Islamorada:

Discover all the newest listings in Key Largo in one place so that you can stay updated on the latest real estate market trends!
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
16 Avacado St, Islamorada
$23,500,000
9 Beds ⋅ 11 Baths ⋅ 621766 MLS
Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

16 Avacado St, 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
High Point Rd, Islamorada
$400,000
621733 MLS
Opportunity awaits to bring your vision to life! This 14,300-square-foot parcel encompasses approximately one-third of an acre, with 130 feet of frontage and 110 feet of depth. Situated on the bayside of Plantation Key in the established High Point neighborhood, this oversized Florida Keys vacant land opportunity offers the space to envision your own island retreat. Partially cleared and fenced, the property is conveniently located near schools, restaurants, shopping, boating, fishing, and all that Islamorada has to offer. Preliminary communications with the Village of Islamorada Building and Planning Departments indicate that the parcel is buildable; however, no formal building approval or permits are currently in place. No protected species restrictions or conservation easements are currently known. Buyers are to independently verify all.

High Point Rd, 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
179 Azalea St, Islamorada
$2,450,000
4 Beds ⋅ 4 Baths ⋅ A12106064 MLS ⋅ Plantation Key Colony 1st BLDG.
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 St, 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
133 Anglers Way, Islamorada
$1,700,000
2 Beds ⋅ 3 Baths ⋅ 621627 MLS
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
59 W Plaza Del Sol, Islamorada
$3,275,000
5 Beds ⋅ 3 Baths ⋅ A12105412 MLS ⋅ Port Antigua Plat No 3 & BLDG.
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
Start Your Search

How much is your home worth?

Get instant property value now!