Refine Search
Map
Sort by
$3,850,000
4 Beds ⋅ 4 Baths ⋅ 620893 MLS
Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level includes 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen, making it ideal for guests, multi-generational living, or maximizing short term rental income.Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie's Marina and Theater of the Sea, you'll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.

74049 Overseas Hwy, Islamorada
$1,490,000
3 Beds ⋅ 3 Baths ⋅ 620353 MLS
Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of newly decked dockage along the tranquil ''Sleepy Lagoon'', this exceptional property combines relaxed island living with effortless boating access to both the ocean and bay. The light-filled second floor features an open-concept living, dining, and kitchen area with soaring cathedral ceilings and new vinyl flooring throughout. The recently remodeled kitchen showcases new cabinetry, stainless steel appliances, and an inviting layout ideal for entertaining. Two bright bedrooms with laminate flooring are located on this level, including a spacious primary with en-suite bath. Step outside onto the expansive second-floor balcony and enjoy breathtaking lagoon views while watching manatees glide by and fish jump in the tranquil waters below. The first floor offers additional flexible living space with an open bedroom/living area and full bath, featuring sliding glass doors that lead directly to the tropical backyard, pool, and dock. Designed for comfort and convenience, this fully turnkey home includes well-maintained accordion shutters on all non-impact windows, generous storage space for water toys and gardening equipment, and a securely anchored storage shed. Outdoor living is truly exceptional. Relax beneath the airy chickee hut, cool off in the in-ground pool after a day on the water, or entertain family and friends with freshly grilled BBQ favorites in the private backyard oasis. Additional features include a JetDock, fish cleaning station, spacious outdoor shower, fenced backyard for pets, and ample parking for boats, trailers, RVs, and recreational equipment. Residents may enjoy access to a beautiful sandy beach within the subdivision through a voluntary HOA membership. The beach is a protected turtle nesting habitat.

140 Iroquois Dr, Islamorada
$7,600,000
4 Beds ⋅ 5 Baths ⋅ 619928 MLS
Discover paradise in Islamorada, with beautiful ocean views, protected canal dockage, and resort-style amenities that you'll never want to leave! Blending luxury living with the Florida Keys lifestyle, this home is designed with both entertaining and relaxation in mind. You'll find modern touches throughout this fully-furnished 4 bed, 5 bath home with an abundance of natural light enhancing it's coastal charm. The main level showcases ocean views from the large kitchen, living and dining areas, a French door sunroom and a massive elevated patio for seamless indoor/outdoor entertaining. Head downstairs and bring your resort experience to life. Relax under the poolside beach cabana, complete with an outdoor kitchen and furnished interior bonus room with a full bath connected by interior stairs or elevator. Sunbathe on your sandy beach complemented by a well-manicured backyard with privacy landscaping, mangroves, palm trees and a turf lawn. Take a dip in the resort-style pool/spa, play a little putt-putt golf, or use the access steps to the canal and explore the oceanside bonefish flat. Located in the heart of the sportfishing capital of the world, this home has the avid fishermen and watersport enthusiasts covered. With 200' of waterfrontage and 90' of dockage, safely secure your boats on the 40,000# or 15,000# lifts in the deep protected canal. Within minutes you could head offshore chasing big game fish or run bayside to fish the backcountry or explore the Everglades park. Just steps away from your dock is a dedicated tackle room complete with a chest freezer, commercial ice machine, rigging bench, rod racks and tool storage. Accompanied by an oversized 2 car garage, you'll have plenty of room to store all your toys and cars. Concrete construction, newer Interlock Aluminum Slate Roofing and equipped with impact windows & doors, this home was built to withstand anything. Start living your dream today in this true Florida Keys retreat on beautiful Lower Matecumbe.

91 Iroquois Dr, Islamorada
$960,000
4 Beds ⋅ 3 Baths ⋅ 619208 MLS
This fully furnished waterfront townhome 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 multigenerational living or hosting family and friends, with two bedrooms and two bathrooms on the main living level, and a large separate guest suite 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 Dr Unit 5, Islamorada
$999
1 Beds ⋅ 1 Baths ⋅ 609143 MLS
Welcome to our prime rental property in Lower Matecumbe, conveniently located between both the ocean and the gulf, unit 5. Unit 5 offers a 1/1 in the the stretch of the Upper Keys. Our versatile building offers a range of leasing options, including storage units, commercial spaces, and convenient docks. Whether you're seeking storage solutions, a strategic commercial location, or waterfront access for maritime activities, our property caters to diverse needs. Embrace the unique charm of the Florida Keys while enjoying the practicality and flexibility our building provides for both businesses and workforce housing. Utilities are an additional $395/month

74560 Overseas Highway Unit 5, Islamorada
$1,650,000
4 Beds ⋅ 2 Baths ⋅ 615180 MLS
Waterfront Pool Home, with 90' of Dockage on Lower Matecumbe. Discover island living at its finest in this meticulously maintained concrete home, situated on one and a half lots in the desirable Lower Matecumbe Beach neighborhood of Islamorada. With 90 feet of dockage, a spacious heated/chilled in-ground pool, and open water views from your private Tiki hut, this property offers the ultimate Keys lifestyle. The light-filled open-concept layout connects the living, dining and kitchen areas under a cathedral ceiling - perfect for entertaining or relaxing in style. The home offers four bedrooms, including a primary suite and guest suite, both with modern en-suite bathrooms. One bedroom is currently used as an office, and another as an additional sitting room, offering flexibility to suit your needs. Enjoy tranquil sunrise views from the large screened patio, furnished with a comfortable outdoor set that stays with the home. Classic plantation shutters throughout the home add to the warm island feeling, while impact-resistant sliders and windows facing the water ensure peace of mind against severe weather. Street-facing and side windows are protected by well-maintained accordion shutters. All glass surfaces are treated with sun shield film or in-glass color protection to enhance energy efficiency. The newly redone, oversized dock includes a 15,000 lb boat lift, providing quick and easy access to both the Atlantic Ocean and Florida Bay. Whether you are watching manatees and various sea life swim by, rinsing off your catch at the large fish-cleaning station, or enjoying the ocean breeze under the Tiki hut, this home is a heaven for boaters and outdoor enthusiasts. First time on the market in nearly 30 years - truly a rare Keys gem! Additional highlights include: Shiplap wall in Living Room, adding to the coastal look. Fenced backyard for privacy, perfect for pets. Voluntary HOA gives beach access to a wide sandy beach. Plenty of storage.

119 Iroquois Dr, Islamorada
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 618050 MLS
Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada. A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas--perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full bathrooms, including a luxurious primary suite with a sleek modern en-suite bathroom and a large walk-in closet. A versatile bonus room offers endless possibilities as a media room, den, office, or children's retreat. The oversized gourmet kitchen is a chef's dream, showcasing brand-new high-end stainless steel appliances, elegant quartz countertops, and generous storage. Impact-resistant windows and sliding glass doors provide peace of mind while enhancing the home's clean, contemporary style. Step outside to your private backyard and enjoy peaceful sunrise views or savor coffee and cocktails beneath the shaded gazebo. Boaters will love the newly decked 60-foot dock, offering immediate access to both the Atlantic Ocean and Florida Bay. From watching manatees glide by to cleaning the day's catch at the large fish station, every detail is designed for waterfront living. An added bonus is the voluntary HOA, which provides access to a wide sandy beach, known as a turtle-nesting haven. Welcome to your place in paradise. 🌴

159 Iroquois Dr, Islamorada
$1,342,000
2 Beds ⋅ 2 Baths ⋅ 613869 MLS
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 area which features soaring wood-beamed ceilings, abundant natural light, a gourmet chef's 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 own bathroom, 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 boater's 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 home's 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!

176 Iroquois Dr, Islamorada
$825,000
616719 MLS
This exceptional canal-front vacant lot on Lower Matecumbe Key represents a truly prime piece of cleared real estate. The permit for this property is in hand and ready for building. Seize this rare opportunity to build your dream home in a highly sought-after Keys location.

149 Iroquois Dr, Islamorada
$775,000
3 Beds ⋅ 3 Baths ⋅ 610870 MLS
This is a must see fully furnished waterfront townhome, with a 21 foot dock that should be able to accomodate a 25' boat. The canal leads out to the ocean and a short run to Channel 2 or Channel 5 bridge brings you to the bay side. There are 2 main bedrooms and both have ensuite baths, an updated kitchen and appliances, with a bedroom and a bath as well as living space downstairs for family or visiting friends. There is storage for tools and toys.

100 Iroquois Dr Unit 3, Islamorada
$3,003,000
4 Beds ⋅ 3 Baths ⋅ 612438 MLS
The Ospreys are back! Welcome to The Osprey's Nest; your perch by the Ocean in one of Islamorada's 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

133 Sunset Dr, Islamorada
$1,375,000
3 Beds ⋅ 3 Baths ⋅ 611507 MLS
Incoming producing property with future bookings already in place! This two story-waterfront property in the Florida Keys within Lower Matecumbe Key (near mile marker 74) 3 bedrooms and 3 baths total (2 bed/1bath on the second floor, 1bed/1bath on first floor, and 1 full bath on exterior) on the ocean side with 1,920 sq ft of living space. Second floor has 2 bedrooms, 1 bath and first floor has 1 bedroom and 1 bath with an additional full bathroom on the exterior of the property. This unique canal front property offers a 6,600 sq ft total lot size with access to the open ocean and bay within minutes. 60 FT concrete dock offers space for your boats, jets ski's and more. 2 boat lifts included in the purchase, one can hold up to 10,000 lbs and other 15,000 lbs. Plenty of parking for multiple cars within the actual property. Furniture can be included in the sale. Call us today for in-person/virtual showings.

158 Iroquois Dr, Islamorada