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4 Bedroom Homes for Sale in Islamorada, FL

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Welcome to your dedicated resource for 4 bedroom homes for sale in Islamorada, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Islamorada, FL agent, Marc Plotkin specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 4 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 4 Bedroom Homes for Sale in Islamorada, FL

4 Beds ⋅ 6 Baths ⋅ A12050889 MLS ⋅ Matecumbe Ocean Bay (75.0) BLDG.

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views. An arcaded hallway with a hand-tiled barrel-vaulted ceiling connects interiors featuring Italian finishes, exquisite marble details, five fireplaces, hand-painted ceiling frescoes, and a one-of-a-kind imported tile roof. Florentine windows, Juliette balconies, wrought-iron railings, copper gutters, and hand-carved marble corbels. The floor plan includes four bedrooms, with three guest suites on the main level and a private third-floor primary retreat. The chef's kitchen is appointed with top of the line appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen and covered dining. A formal dining room with a hand-painted ceiling fresco, wellness room, sauna, theater, and billiards lounge. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep dockage, sand beach, and clear waters provide immediate access to fishing, diving, snorkeling, and boating. An air-conditioned boat room, skiff ramp, 4,000+ SF collector's garage, elevator servicing all 3 levels, C4/Sonos smart home, secure walled & gated grounds.

75090 Overseas Highway, Islamorada

4 Beds ⋅ 5 Baths ⋅ A12032087 MLS ⋅ Plantation Beach BLDG.

Private Bayfront Estate in desirable Islamorada offering a serene ambiance on an oversized parcel of pristine bayfront with breathtaking sunsets and unobstructed panoramic views of the Florida Bay. This exceptional waterfront retreat features an irreplaceable protected boat basin, concrete jetty, and T-dock providing superior deep-water dockage. Encompassing 4,000 square feet of beautifully designed living space, this remarkable residence includes 4 spacious bedrooms and 4.5 bathrooms. This home showcases an inviting kitchen and multiple expansive living areas all thoughtfully designed for ultimate comfort and entertaining, ideal for hosting family and guests or enjoying a private coastal escape. Step outside to your own tropical sanctuary with unforgettable sunsets, year-round outdoor living, and the sparkling waters of Florida Bay creating the ultimate Florida Keys lifestyle. A rare opportunity to own in one of Islamorada's most exclusive waterfront settings.

88110 Overseas Hwy, Islamorada

4 Beds ⋅ 4 Baths ⋅ A12028354 MLS ⋅ White Marlin Beach Sec 1 BLDG.

TURN KEY Canal-Front Islamorada Home with Pool, Dock & Private Beach Access Luxury canal-front home in Islamorada offering spacious living, refined coastal design, and exceptional outdoor amenities. This meticulously maintained residence features a flexible split floor plan with a main-level living area, wet bar, bedroom, and full bath overlooking the outdoor kitchen and resort-style pool. Upstairs includes 3 additional bedrooms, 2.5 baths, an open living area, pristine kitchen, and walk-in laundry room/office. The fenced backyard is designed for easy living with turf, low-maintenance landscaping, and privacy! Concrete dock with 20,000 lb boat lift and space for multiple boats. Owners also enjoy access to the private White Marlin homeowners beach and close proximity to area amenities. The perfect Florida Keys getaway with strong monthly rental income potential! A rare opportunity for turnkey waterfront living in the heart of Islamorada.

145 Venetian Drive, Islamorada

4 Beds ⋅ 4 Baths ⋅ A12010138 MLS ⋅ Lower Matecumbe BLDG.

The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.

74049 Overseas, Islamorada

4 Beds ⋅ 2 Baths ⋅ A11897000 MLS ⋅ White Marlin Beach Sec 2 BLDG.

Boater’s dream home in White Marlin Beach, Islamorada. Unique 2-story single-family home with split layout, two 800 square feet 2BD/1BA units. Separate entrances and laundry in each unit, 70' dock with private boat ramp on a tranquil mangrove canal. This property is facing mangrove with maximum privacy, just 7 homes from the bay! Plenty of parking for RVs/trailers. Enjoy access to the White Marlin’s private homeowners park and beach, one of the only white sand beaches for miles. Perfect for extended family, guests and rental income potential. Don’t miss this rare opportunity in one of the Keys most sought-after neighborhoods.

164 Venetian Dr, Islamorada

4 Beds ⋅ 5 Baths ⋅ A11885559 MLS ⋅ Mat Ocean View BLDG.

Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise views. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys — an extraordinary pairing of true beachfront living and convenient boating access.

109 Columbus Dr, Islamorada

4 Beds ⋅ 4 Baths ⋅ A11626493 MLS ⋅ Mate Ocean Bay Subd Sec 1 BLDG.

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a cozy loft. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area — ideal for entertaining. The chef's kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys' most sought-after locations.

75761 Overseas Hwy, Islamorada

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