Luxury Properties for sale in Islamorada, Florida

A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a...

Presented by Gloria Walters | Ocean Sotheby's International Realty

Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada—just a short stroll to the area's most celebrated restaurants,...

Presented by Pierre Bellion | Ocean Sotheby's International Realty

A once-in-a-lifetime opportunity to own one of South Florida's most iconic properties. Welcome to Tea Table Key, a breathtaking 15-acre private island estate, accessible by car or...

Presented by Pierre Bellion | Ocean Sotheby's International Realty

A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over ½ acre lot with panoramic water views from every room. Offering 220+...

Presented by Sarah Ewald | Ocean Sotheby's International Realty

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort‑style living awaits in this Key West-inspired...

Presented by Eric Rizzo | Ocean Sotheby's International Realty

Set within a private gated enclave, this top-floor, corner unit captures the essence of Islamorada living. Quietly elevated, effortlessly refined, and deeply connected to the...

Presented by Gloria Walters | Ocean Sotheby's International Realty

Set on 1.38 acres of pristine oceanfront in the Florida Keys, this private estate offers the perfect blend of luxury, serenity, and tropical beauty. With an enormous 150-foot...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Commanding 170 feet of private Florida Bay frontage and situated on over an acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the...

Presented by Sarah Ewald | Ocean Sotheby's International Realty

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...

Presented by Sarah Ewald | Ocean Sotheby's International Realty

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered...

Presented by Sarah Ewald | Ocean Sotheby's International Realty

Coastal Elegance Meets Timeless Craftsmanship in Safety Harbor- Welcome to 'Piece of Quiet', a winner of the Miami Herald 'Fame' award for custom homes with unique architecture....

Presented by Eric Rizzo | Ocean Sotheby's International Realty

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. Seller Financing Available.Experience luxury coastal living at its finest in this exceptional Gated...

Presented by Globalty Investment

Make all of your Florida Keys fantasies come true at Fantasy Harbor! We're willing to bet you never even knew this gated community on Islamorada's Lower Matecumbe existed. This...

Presented by Sarah Ewald | Ocean Sotheby's International Realty