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$2,195,000

Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.

3 Beds ⋅ 4 Baths ⋅ 621487 MLS

33 Pen, Islamorada

$29,000,000

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 quatrefoil windows, Juliette balconies, wrought-iron railings, copper rain gutters, and hand-carved marble corbels enhance the home's architectural character. The floor plan includes four bedrooms, with three guest suites on the main level and a private third-floor primary retreat featuring two fireplaces, an office, tea room, sitting room, custom walk-in closet, private laundry room, spa-inspired bath, and balconies overlooking the living spaces below. The chef's kitchen is appointed with Viking, Miele, U-Line, and Sub-Zero appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen with a Viking grill, refrigeration, ice maker, bar seating, and covered dining overlooking the pool, beach, and bay. Additional spaces include a formal dining room with a hand-painted ceiling fresco, wellness room, sauna, private theater with wet bar, and a billiards lounge with mahogany coffered ceilings and coconut wood flooring. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep-water dockage, white-sand beach, and crystal-clear waters provide immediate access to world-renowned fishing, diving, snorkeling, and boating. Additional features include an air-conditioned boat room, skiff ramp, 4,000+ SF collector's garage, elevator servicing all 3 levels, Control4 smart home integration, Sonos, and secure walled & gated grounds.

4 Beds ⋅ 6 Baths ⋅ 620394 MLS

75090 Overseas Hwy, Islamorada

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