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3 Beds
4 Baths
4,537 sqft

$2,195,000

33 Pen Key, Upper Matecumbe Key Islamorada FL, 33036

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

Overview

Active

Listed Apr 20, 2026

Updated Apr 22

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.

$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
619577

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
Pool
Yes
MLS provider logo

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

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 4/22/2026. 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 4/22/2026 at 3:39 AM UTC

 

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