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3 Beds
3 Baths
2,600 sqft

$3,900,000

18 Pen Key Club, Upper Matecumbe Key Islamorada FL, 33036

Price per sqft$1,500.00
Built in1962
Property size2,600 sqft
Property typeResidential

Overview

Active

Listed Oct 10, 2026

Updated 22h ago

Sunset views in Islamorada's most coveted location: PEN KEY CLUB. From the front doorstep, you can see straight through the house to the sparkling waters of Florida Bay, so the view will take your breath away before you put a foot inside the house! Established in the 1950s, Pen Key Club is a small, private, gated bayfront community on Upper Matecumbe Key, Islamorada's ''downtown'' island. The location is excellent by land and sea. Boating access is exceptional. In fact, it's why the club was founded here. Immediate access to Florida Bay and quick, easy access to the ocean through Whale Harbor Channel. Dockage for boats to 32 feet (plus engines) is available for club members only. Quiet and tucked away, it's close to many of Islamorada's favorite restaurants, including Chef Michael's, Kaiyo and Pierre's, as well as shops and local gathering places like the Cheeca Lodge. Owners share a pool, marina and sunset viewing areas, while the association cares for the landscaping. An onsite property manager receives packages and helps owners with day-to-day needs, making it easy to live here full time or to come and go. Overlooking the marina and bay, this one-level home has high ceilings and two large living areas lined with wide banks of impact glass doors. Expansive bay views extend throughout the main living areas and primary bedroom suite. The large covered patio offers plenty of space for morning coffee, dinner with friends and a front-row seat for the sunset. The comfortable layout puts everything on one floor, with three bedrooms, each with an en suite bath, plus a separate office, laundry room and garage. Concrete construction, impact windows and doors and a metal roof add strength and peace of mind. You really can have it all: big bay views, dockage, excellent boating access and favorite restaurants and shops nearby, with the ease of a single-level home in a peaceful community where living is easy.

$25,947/mo

Est. mortgage payment based on a $3,900,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
621575

Interior Features

Bedrooms
3
Bathrooms
3
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.24 Acres

Other Property Details

Taxes
$9,352
Tax Frequency
Annually
Association Fee Frequency
Monthly
Garage
Yes
View
Yes
Pets Allowed
Yes
Pool
Yes
Waterfront
Yes
55+/Senior Community
No
MLS provider logo

Listed by Christy Hughes with Coldwell Banker Schmitt Islamorada
Listing Contact: 305-393-6190 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 10/11/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Florida Keys Board of REALTORS® all rights reserved.

Data last updated on 10/11/2026 at 3:36 AM UTC

 

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