Discover Your Private Tropical Oasis in Islamorada.Welcome to

swipe instructions
Tap to see more photos

Home For Sale

33 Pen Key Drive

Upper Matecumbe Key, Florida 33036

Monroe County Water View: Yes

Community: Penn Key Club (83)

map
$2,800,000 3 br, 4.0 bath 4537 sq. ft. 0.300 acres

Discover Your Private Tropical Oasis in Islamorada.Welcome to your dream retreat in the heart of the Florida Keys in the sport fishing capital of the worlda'a stunning Key West-style home nestled amidst lush greenery in an exclusive gated bayfront private club community. This residence is more than just a home; it's a lifestyle defined by serenity, elegance, and the natural beauty of Islamorada.From the moment you pass through the palm-lined gated front entrance, you will notice the manicured tropical beauty of this community as you make your way to the classic architectural gem that will captivate you. Vibrant hues, large sitting porches, and timeless craftsmanship create a warm, inviting ambiance. Inside, open living spaces are bathed in natural light, blending seamlessly with the lush surroundings visible through every window.Step outside and find yourself in your very own tropical sanctuary. Towering palms, old growth trees, vibrant bougainvillea, and lush greenery surround the property, offering privacy and tranquility. Relax by the pool, host unforgettable gatherings on the expansive patio, or simply unwind as the breeze carries the scent of salt air.Nestled within a private club community, this home offers access to a range of world-class amenities, including a marina, sunset point, beach, and community pool. Plus, the vibrant culture and stunning waters of Islamorada are yours to explore from the protected marina.Whether you're seeking a permanent residence or a vacation escape, this property provides the perfect balance of seclusion and connection. From sunrise strolls on pristine beaches to evenings under the stars, every moment here feels like a slice of paradise.Don't just dream of the Keys, live it. Schedule your private tour today and experience firsthand what makes this home and private community so extraordinary.

Interior:
  • Bedrooms: 3
  • Baths: 4.0
  • Sq Ft: 4537
  • Year Built: 1987
  • Utilities: 
  • Fireplaces: 
  • Stories: 2
  • Heat/AC: 
  • Garage: Garage, Open
Exterior:
  • Lot Size: 0.300 acre
  • Lot Dimensions: 
  • View Types: Water
  • Yard: 
  • Siding: 
  • Roof: Metal
  • Property Taxes: $10,315
  • Yearly HOA Fee: $8,350
  • MLS #: 613198
Get More Info
static map
Contact Information:
phone Call now 1-855-943-4259
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: 5716572
Viewed 7 times.
Updated: Jan 17, 2025

This property is a Home located at 33 Pen Key Drive, Upper Matecumbe Key, Florida 33036, and is currently For Sale at $2,800,000. This Home has 3 bedrooms, 4.0 baths, 4537 sq ft.