Legacy Retreat in Islamorada - Gated Waterfront Estate with

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Home For Sale

33 Pen Key Drive

Upper Matecumbe Key, Florida 33036

Monroe County Water View: Yes

Community: Penn Key Club (83)

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$2,495,000 3 br, 3.0 bath 4537 sq. ft. 0.300 acres

Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where privacy, elegance, and world-class amenities converge. This expansive Key West-style residence is nestled within one of the Florida Keys' most prestigious gated communities, offering full-time property management, a protected marina, and a lifestyle defined by serenity and sophistication.From the moment you pass through the palm-lined entrance, you're surrounded by manicured tropical beauty. The home's vibrant exterior, wraparound porches, and timeless craftsmanship evoke classic island charm, while interiors are bathed in natural light and framed by lush garden views.Designed for effortless indoor-outdoor living, the spacious three-bedroom layout opens to expansive patios ideal for entertaining or quiet reflection. Towering palms, mature trees, and vibrant bougainvillea create a secluded sanctuary, while the scent of salt air and golden sunsets set the tone for unforgettable evenings.Enjoy exclusive access to a resort-style pool, private beach, kayak launch, the sunset point, and a full-service marina with direct access to world-class sport fishing and boating. Full-time on-site property managers ensure peace of mind, whether you're in your residence or away for the season.Located in the heart of Islamorada, this property offers unmatched proximity to fine dining, boutique shopping, and the legendary waters of the sport fishing capital of the world.Whether you're seeking a seasonal escape or a legacy investment, this home offers the perfect blend of luxury, leisure, and long-term value. Schedule your private tour today and experience the rare combination of privacy, prestige, and paradise.

Interior:
  • Bedrooms: 3
  • Baths: 3.0
  • Sq Ft: 4537
  • Year Built: 1987
  • Utilities: 
  • Fireplaces: 
  • Stories: 2
  • Heat/AC: 
  • Garage: Garage, Guest, Open
Exterior:
  • Lot Size: 0.300 acre
  • Lot Dimensions: 
  • View Types: Water
  • Yard: 
  • Siding: 
  • Roof: Metal
  • Property Taxes: $10,526
  • Yearly HOA Fee: $8,349
  • MLS #: 616008
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Contact Information:
Beach Home For Sale in Upper Matecumbe Key, Florida
Listing Agent: Eric M. Rizzo, Ocean Sotheby's International Realty, 305-394-3062, 305-712-8888 Listing Site, Listing Status: Active
Copyright © 2025 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 6476507
Viewed 47 times.
Updated: Oct 15, 2025

This property is a Home located at 33 Pen Key Drive, Upper Matecumbe Key, Florida 33036, and is currently For Sale at $2,495,000. This Home has 3 bedrooms, 3.0 baths, 4537 sq ft.