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28 Pen Key Drive, Upper Matecumbe Key Islamorada, FL 33036
4 Beds
4 Baths
3,044 SqFt


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First time offered for sale... the most exclusive spot in Islamorada's most exclusive gated community! This open bayfront Old Florida home rests on nearly half an acre with the most enchantingly beautiful shoreline and crystal clear water in Islamorada. 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 that is directly on the open bay. It also has its own private dock (in need of repair) and a large private pool, in addition to enjoying use of the community boat basin and the community pool if desired. Another unique feature of Pen Key is that the club employs a full-time property manager living on site to help maintain the pristine 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. This original concrete home has a concrete roof and is ready for you to come in and make it your own. The unique floor plan features a spacious living area with coral rock fireplace that opens to a glassed-in Florida room with sliders directly to the pool. In the main home are two bedrooms with two adjoining full baths. Outside the front door on the opposite side of the carport are two private guest suites, both with ensuite full baths. Both of these guest suites have their own private entrances. Outside is a large shady grass yard with beautiful mature trees. This one-of-a-kind community is also perfectly situated in downtown near fine dining, bars, shops, art galleries, museums and of course, the monthly Art Walk and Full Moon Party. 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 Club.
  • Price:
  • $5,450,000
  • Bedrooms:
  • 4
  • Full Baths:
  • 4
  • Square Footage:
  • 3,044
  • Acreage:
  • 0.49
  • Year Built:
  • 1964
  • Listing ID #:
  • 599529
  • Street Address:
  • 28 Pen Key Drive
  • City:
  • Upper Matecumbe Key Islamorada
  • State:
  • Florida
  • Postal Code:
  • 33036
  • County:
  • Monroe
  • Subdivision:
  • Penn Key Club (83.0)
  • Listing Status:
  • Active
  • Listing Type:
  • Single Family Detached
  • Fireplace:
  • Yes
  • Flooring:
  • Carpet, Tile
  • Number Of Units:
  • 1
  • Total Building Square Footage:
  • 3044
  • Type Of Roof:
  • Concrete Tile
  • View:
  • Water
  • Year Built:
  • 1964
  • Conforms To Zoning:
  • R1 - Residential Single Family
  • Association Fee:
  • $6,500
  • Association Fee Payment Frequency:
  • Annually
  • Property Taxes:
  • $5,668
  • Tax Year:
  • 2021
  • Room Description:
  • 4 Bedrooms, 4 Full Baths
  • Parking Description:
  • Carport, Covered, Guest, Off Street, Open
  • Appliances:
  • Oven, Range, Refrigerator
  • Heating:
  • Fireplace
  • Waterfront:
  • Yes
30-year Conforming



30-year FHA



30-year VA



Last updated: 3/24/2023
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Source: CINC

  • Copyright © 2023 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.

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