Islamorada, Florida listings for sale


$29,500,000 - Islamorada, FL

82719 Old Hwy Islamorada, FL - An oasis of coastal elegance and timeless design, this exceptional estate offers over 40,000 square feet of stunning indoor and outdoor living. Blending Hamptons sophistication with Florida Keys charm, every detail has been artfully curated—from shimmering mosaic fountains and sweeping staircases to floor-to-ceiling windows and bespoke stained-glass elevator doors. Intricate wrought-iron balconies, glowing chandeliers, and a luminous fireplace add glamour throughout. Perfectly suited for both refined living and elegant entertaining. This Exquisite home boasts versatile spaces including a half basketball court that transforms into a ballroom, pickle-ball or volleyball court, and a massive rooftop deck ideal for entertaining large crowds.
1995 | 7 | 10 | 10,112 sqft.
$10,500,000 - Islamorada, FL

91 Iroquois Islamorada, FL - Discover this luxurious ocean view gated home on a point lot over 1/2 acre, featuring over 6,000 sq ft of living space, 6 bedrooms, 5 bathrooms, and 4 oceanfront rooms. Highlights include soaring ceilings, a large garage, putting green, an elevator, deep water access with 2 boat lifts (45,000 and 16,000 lb), beachfront and canal access, and a multi-million dollar renovation. Enjoy easement rights for tennis and pickleball courts. A rare blend of elegance and coastal bliss.
1989 | 6 | 5 | 6,100 sqft.
$2,800,000 - Islamorada, FL

141 El Capitan Drive Islamorada, FL - Stunning Waterfront Oasis in Port Antigua Welcome to your dream home in the Florida Keys-a rare canal-front gem perfectly positioned at the T-junction of two pristine, crystal-clear waterways in the highly sought-after community of Port Antigua, Islamorada. This turnkey 4-bedroom, 3-bathroom residence offers a seamless blend of luxury, comfort, and coastal charm, and is ready for immediate enjoyment. This fully updated property is built for both relaxed living and entertaining, with thoughtful design features throughout. Upstairs, the open-concept layout includes a spacious living area that connects effortlessly to the kitchen and dining spaces. The kitchen is a showstopper-featuring sleek quartz countertops, new cabinetry, stainless steel appliances, and a generous island for casual dining or prepping meals with ease. Wood-look porcelain tile flooring runs throughout, paired with fresh interior paint and all-new dimmable LED lighting for a modern and inviting atmosphere. The upstairs layout includes two large ensuite bedrooms located on opposite sides of the home, offering privacy and flexibility. Each suite features ample closet space and updated baths with elegant finishes. Step outside the living room to your screened balcony-perfect for morning coffee or evening cocktails with unobstructed views of the wide canal and your private dock just below. Downstairs is a fully renovated guest suite that feels like its own private retreat. With two bedrooms, one bathroom, and a full kitchen, it's ideal for visiting friends, extended family, or even potential rental income. The layout offers flexibility and privacy, while maintaining connectivity to the rest of the home. Step into the backyard and find your personal paradise. A brand-new pool with a tranquil fountain creates the ultimate setting for relaxation or poolside fun. The stylish louvered pergola provides the perfect balance of sun and shade, making it a comfortable spot for lounging throughout the day. The wraparound porch and fully screened upper balcony expand your outdoor living options, ideal for taking in the sea breeze, reading a book, or entertaining guests. Additional features include dual A/C units and dual water heaters, ensuring optimal comfort year-round for both levels of the home. The private dock offers direct access to the bay and beyond, making this home a boater's dream. As a resident of Port Antigua, you'll have exclusive access to a private white sand beach with tiki huts and picnic areas, a community boat ramp, and quick access to both the Atlantic Ocean and Florida Bay. Whether you're into fishing, boating, snorkeling, or just soaking in the island lifestyle, this neighborhood delivers it all. Don't miss this rare opportunity to own a move-in ready canal-front pool home in one of Islamorada's most desirable neighborhoods. Whether you're seeking a full-time residence, a vacation escape, or a versatile investment, this home checks every box.
1988 | 4 | 3 | 2,098 sqft.
$2,599,000 - Islamorada, FL

189 Gulfview Drive Islamorada, FL - Welcome to Port Antigua! This beautiful Key West-style home in Port Antigua boasts an open floor plan with a spacious kitchen featuring a large center island. The main living area on the second floor includes three bedrooms and two bathrooms, while the first floor offers an entertainment room that could serve as a fourth bedroom. Two sets of sliding glass doors lead to a screened-in porch overlooking the canal, perfect for enjoying the waterfront views. The home is equipped with high-impact-resistant windows and doors for added security and energy efficiency. Boaters will appreciate the 45-foot concrete dock with a 15,000 lb-rated boat lift, making it easy to enjoy life on the water. As part of Port Antigua's Homeowners Association, residents have exclusive access to a private beach with breathtaking year-round sunsets. This is a fantastic opportunity to embrace the Keys lifestyle-don't miss out!
2004 | 3 | 2 | 2,010 sqft.
$2,149,000 - Islamorada, FL

126 Columbus Dr Islamorada, FL - 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 10-12 FT. Unique layout offers 2 bedrooms & 2 baths on the second floor with a full kitchen & spacious living room area, washer & dryer. First floor offers 1 bedroom and 1 bath, washer & dryer, full kitchen (separate living units). New roof/hurricane impact windows. Easy storage space. Ample parking. Call us today for more info!
1974 | 3 | 3 | 1,066 sqft.
$2,100,000 - Islamorada, FL

157 Venetian Dr Islamorada, FL - Welcome to paradise! This inviting home features an open-concept living area, complete with a large loft that houses two cozy queen beds, a master bedroom, a guest bedroom, and two bathrooms. This well-maintained, three-story home offers ample storage, including a convenient ground-level storage area and workshop. Step outside to enjoy a new, expansive patio, lush turf, and a refreshing saltwater pool. Nestled on a cul-de-sac street, this home is set back from the Overseas Highway in a golf-cart-friendly community. From your 50’ dock its quick access to bay and ocean through the Channel #2 and Channel #5 bridges. Relish stunning sunsets at your private neighborhood beach, complete with relaxing chairs, tiki huts, and grills to cook your catch. We can't wait for you to experience it all!
1992 | 3 | 2 | 1,263 sqft.
$1,999,999 - Islamorada, FL

144 Anglers Way Islamorada, FL - ANGLERS REEF OCEANFRONT HOME WITH DEEDED DOCK in Islamorada.7 DAY RENTALS ALLOWED. Dock accommodates up to a 31' boat. A beautiful 2-bedroom, 2.5-bath, 2-story home with 2 porches & a balcony overlooking the Atlantic Ocean. Located in the gated community of Anglers Reef, half way between Miami & Key West. This property contains 2 large bedroom suites on the 2nd floor. Home looks out to the community pool & marina(see included video). Upgrades include impact windows/doors, metal roof, composite decks/railings, granite counters, wood cabinets, tile floors, bamboo floors, shutters/blinds, brand new dishwasher & refrigerator. The community features 2 sandy beaches, pool, gated entry, marina, kayaks & paddle boards. Perfect home for primary residence, vacation family home or investment.
2007 | 2 | 2 | 1,674 sqft.
$1,500,000 - Islamorada, FL

120 Anglers Way Islamorada, FL - Islamorada Exclusive Anglers Reef Resort! An oceanfront gated community with resort -style amenities, marina, & 2 sandy beaches; this fully furnished, two-story single-family home, w/ 2 Bedrooms, 2.5 Baths, is a treasure for ocean lovers & investors alike. Premium features include impact windows & doors, stainless steel appliances, wood cabinetry, & granite countertops. A Boater’s Paradise with direct oceanfront access & proximity to the famous Islamorada sandbar, & a deeded boat slip is also available for sale, accommodating a boat up to 31 feet. Proven Rental Success, in a well-established program, this home has a 7-Day rental license, with over 175 five-star reviews, making it an ideal investment opportunity or personal retreat. Pet friendly community.
2007 | 2 | 2 | 1,137 sqft.
$1,199,999 - Islamorada, FL

102 Anglers Way Islamorada, FL - ANGLERS REEF HOMEf, Islamorada's Upscale Oceanfront Gated Community, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking, metal roof & impact doors & windows. The community features 2 sandy beaches, a pool & marina on the Atlantic Ocean. Home has been in rental program for many years with a good following. Own your vacation home for free & more. Great investment. Call today for a showing!
2007 | 2 | 2 | 1,376 sqft.
$1,160,000 - Islamorada, FL

82260 Overseas Highway Islamorada, FL - Paradise Found: Renovated Jungle Treehouse! Welcome to your dream retreat in the heart of the Florida Keys. Nestled in the highly sought-after village of Islamorada, this exquisitely remodeled 3-bedroom, 3-bath estate redefines luxury living. Perfectly situated on a sprawling 15k+ square-foot lot, this SOLD CBS Bproperty offers an unparalleled combination of elegance, privacy, and tropical charm. NEW 2024 roof, and electrical, and state-of-the-art impact windows, providing peace of mind and protection while letting in abundant natural light. The interiors have been meticulously updated whilst keeping the Old Florida Charm alive. The kitchen is a true chef's dream. The expansive lot provides endless opportunities for outdoor living. Imagine hosting unforgettable gatherings in your oversize
1964 | 3 | 3 | 2,808 sqft.