Welcome to your legacy retreat in Islamorada's premier gated

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Home For Sale

33 Pen Key Drive

Upper Matecumbe Key, Florida 33036

Monroe County

Waterfront: Yes

Water View: Yes

Community: Penn Key Club (83)

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$2,495,000 3 br, 4.0 bath 4537 sq. ft. 0.300 acres

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.

Interior:
  • Bedrooms: 3
  • Baths: 4.0
  • Sq Ft: 4537
  • Year Built: 1987
  • Utilities: 
  • Fireplaces: 
  • Stories: 2
  • Heat/AC: 
  • Garage: Garage, Guest, Open
Exterior:
  • Lot Size: 0.300 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: Water
  • Yard: 
  • Siding: 
  • Roof: Metal
  • Property Taxes: $17,069
  • MLS #: 618190
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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: 7175842
Viewed 14 times.
Updated: Jan 23, 2026

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, 4.0 baths, 4537 sq ft.