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3 Beds
4 Baths
4,537 sqft

$2,195,000

33 Pen Key Club Drive, Upper Matecumbe Key Islamorada FL, 33036

Price per sqft$483.80
Built in1987
Property size4,537 sqft
Property typeResidential

Overview

Active

Listed Oct 2, 2026

Updated 5 days ago

Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.

$14,603/mo

Est. mortgage payment based on a $2,195,000 home price.

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

Additional information

MLS® ID
621487

Interior Features

Bedrooms
3
Bathrooms
4
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.3 Acres

Other Property Details

Taxes
$17,069
Tax Frequency
Annually
Association Fee Frequency
Monthly
Garage
Yes
View
Yes
Pets Allowed
Yes
Pool
Yes
55+/Senior Community
No
MLS provider logo

Listed by Eric M. Rizzo with Ocean Sotheby's International Realty
Listing Contact: 305-394-3062 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 10/3/2026. 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 10/3/2026 at 5:43 AM UTC

 

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