Browse All Penn Key Club (83.0) Properties for Sale

3 Beds ⋅ 4 Baths ⋅ 619577 MLS

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 residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined by serenity and sophistication. A palm-lined entrance leads to a vibrant exterior with wraparound porches and sun-filled interiors framed by lush garden views. The spacious three-bedroom layout is designed for effortless indoor-outdoor living, with multiple gathering spaces opening to expansive patios ideal for entertaining, unwinding, or savoring golden sunsets. Mature palms, bougainvillea, and the scent of salt air create a secluded sanctuary that feels worlds away. Residents enjoy exclusive access to a resort-style pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to world-class sport fishing and boating, while full-time on-site property management ensures peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. Whether you're seeking a seasonal escape or a long-term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.

33 Pen Ky, Islamorada

$3,800,000

4 Beds ⋅ 4 Baths ⋅ 599529 MLS

Prime location! Rare bayfront property in a private gated community located in the heart of downtown Islamorada with gorgeous sunset views, private pool and dockage! This original 4 bed/4 bath concrete home has a concrete roof and is ready for you to come in and make it your own, or take advantage of the existing building right to create your dream home in Islamorada's most exclusive community. Tucked into its own private corner of prestigious Pen Key Club, this ground level home is one of only seven in the 31-home community directly on the open bay and is on one of the largest lots with nearly half an acre of upland and another half an acre of baybottom. It also has a large private pool and had its own private dock on the property (in need of repair), in addition to enjoying use of the community boat basin and the community pool if desired. The current home is 2/2 in the main house and has 2 separate 1/1 guest suites, each with its own private entrance. Outside is a large shady grass yard with beautiful mature trees, including a stunning Haden mango. Another unique feature of Pen Key is that the club employs a full-time property manager living on site to maintain the grounds and common areas. After a day out fishing or boating, come home and watch the sunset from your own back yard and then stroll through the meticulously landscaped neighborhood and out the secure front gates to enjoy fine dining just steps away at Ziggie & Mad Dog's. This community is also perfectly situated in downtown near fine dining, bars, boutiques, salons, shops, art galleries, museums and of course, the monthly Art Walk and famous monthly Full Moon Party. The Village of Islamorada also offers Freebee Electric Vehicle Ridesharing for added convenience. If you are ready to live the good life in the heart of downtown Islamorada, then it's time to discover the peace, security and lush tranquility of Pen Key.

28 Pen, Islamorada

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