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$3,900,000
620460 MLS
A truly once in a generation opportunity to build your dream estate in the heart of Islamorada's coveted Lower Matecumbe. This exceptional vacant homesite is one of the few remaining parcels of its size available in all of Islamorada, offering an incredibly rare combination of breathtaking ocean views and expansive wide canal views. Encompassing over 32,000 square feet, this extraordinary property provides the perfect canvas for a custom waterfront residence designed to capture spectacular sunrises, refreshing ocean breezes, and the unmatched beauty of the Florida Keys. Its unique setting offers the best of both worlds--open water vistas in the front and a wide canal in the rear, creating an unparalleled lifestyle for boating enthusiasts and those seeking privacy, space, and unforgettable scenery. Opportunities to acquire a property of this caliber have become increasingly scarce in Islamorada, where large vacant parcels are exceptionally limited. Whether you're envisioning a private family compound or a legacy waterfront estate, this one-of-a-kind offering represents a chance to create something truly extraordinary in one of the Florida Keys' most desirable destinations.

74900 Overseas Hwy, Islamorada
$1,149,000
619655 MLS
Waterfront commercial investment opportunity with 100 feet of dockage on a 13,500 sq ft lot, offering both canal frontage and open ocean views--an increasingly scarce combination in the Upper Keys. Ideally located just outside Port Antigua and White Marlin Beach, the property benefits from strong visibility and proximity to established boating and residential communities. The site features convenient eastbound ingress and egress, supporting efficient operations and customer access. Zoned Commercial Fishing, it allows for a diverse range of income-producing uses, including charter services, boat rentals, marine repair, seafood distribution, restaurant or other waterfront commercial ventures. With direct water access, substantial dockage, and flexible zoning, this parcel is well-positioned for long-term appreciation and immediate revenue potential in a supply-constrained coastal market.

74520 Overseas Hwy, Islamorada
$6,500,000
3 Beds ⋅ 3 Baths ⋅ 619209 MLS
The prettiest, most perfect Keys home you ever did see. Discover one of the most beautifully updated homes in the Florida Keys, set on two spacious lots on Sapodilla Drive. This exceptional property has been completely reimagined with high-quality upgrades throughout, including a brand-new metal roof, a stunning pool and spa, and a private dock with boat lift offering protected dockage and peaceful bay views. Thoughtfully designed for both everyday living and entertaining, the home features tasteful, modern finishes and a striking shell stone privacy wall that enhances its sense of seclusion. Positioned at the end of the street, the setting offers rare privacy and a quiet, tucked-away feel. Two garages provide ample room for vehicles, watercraft, and gear, making this property as practical as it is refined. A truly turnkey home with standout features in a highly desirable location.

158 Sapodilla Dr, Islamorada
$1,900,000
4 Beds ⋅ 3 Baths ⋅ 615669 MLS
Coastal Living at Its Finest on Sandy Cove Basin. Nestled along the serene shores of Sandy Cove Basin, this unique property offers expansive water views, exceptional dockage, and flexible living options — perfect for multi-generational families, guests, or rental potential. This home is thoughtfully designed with independent living spaces on each floor. Upstairs features a bright and breezy 2-bedroom, 2-bath layout with an open living area and full kitchen, all flowing seamlessly toward panoramic views of the Basin. Downstairs offers an additional private 2-bedroom, 1-bath suite complete with its own living area and kitchenette — ideal for extended stays or private guest quarters. Boaters will appreciate the impressive dockage on two sides of the property, with room to expand for additional boats and water toys. The boat ramp offers easy launching of kayaks, paddleboards or personal watercraft. The fire pit is the perfect place to unwind as the sun sets over the tranquil waters. Ample parking and relaxed outdoor living spaces round out this one-of-a-kind coastal getaway. Whether you're seeking a peaceful personal sanctuary or a versatile investment opportunity, this Sandy Cove gem delivers timeless waterfront living with effortless style.

117 Sandy Cove Ave, Islamorada
$3,300,000
3 Beds ⋅ 3 Baths ⋅ 618699 MLS
74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence, and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. The existing structure features expansive wraparound windows framing sweeping Atlantic views, plus a top-floor penthouse suite suited for owner occupancy, executive housing, or premium rental use (subject to approvals). The building configuration can also accommodate a rooftop helipad. Commercial Fishing zoning allows for uses such as a destination restaurant, seafood market, marine outfitter, charter or backcountry fishing headquarters, marina-support retail, or other enterprises aligned with the working waterfront. This is a high-visibility, commercial platform where housing, marine access, and US-1 frontage intersect to create compelling long-term value.

74560 Overseas Hwy, Islamorada
$6,150,000
5 Beds ⋅ 6 Baths ⋅ 618481 MLS
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 direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

137 Sapodilla Dr, Islamorada
$2,900,000
4 Beds ⋅ 4 Baths ⋅ 616038 MLS
Welcome to 109 Sapodilla Dr., Islamorada, FL This waterfront gem is nestled on the serene Sandy Cove Basin, offering a rare blend of privacy and deep-water access in a protected lagoon. This home is built entirely of concrete, including the roof, providing unmatched durability and peace of mind. Thoughtfully remodeled with a keen eye for detail, the residence effortlessly combines modern elegance with coastal charm. The oversized lot is beautifully landscaped, creating a tranquil oasis that's perfect for outdoor living. Boating enthusiasts will appreciate the private dock and boat ramp, providing seamless access to the open waters. Relax in the sparkling pool and jacuzzi, soaking in the Florida sunshine. A two-car garage adds convenience and ample storage, making this home as functional as it is luxurious. Whether you're seeking a permanent residence or a weekend retreat, 109 Sapodilla Dr. offers the best of Florida Keys living.

109 Sapodilla Dr, Islamorada
$2,500,000
2 Beds ⋅ 2 Baths ⋅ 607261 MLS
So many possibilities here! Listing includes 74550 Overseas Highway for a total of 200' of commercial waterfront on Lower Matecumbe, formerly Sandy Cove Marina. Additional commercial building right with one market rate dwelling unit from lot included, letter in hand. Commercial Fishing Zoning district.

74540 Overseas Hwy, Islamorada
$1,150,000
611290 MLS
LSSD. Statistical Purposes.

74520 Overseas Hwy, Islamorada