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$2,495,000

3
Beds
4
Baths
4,537
Sqft

33 Pen Key Drive, Upper Matecumbe Key, Florida, 33036

By contacting this agent you agree to these Terms and Conditions.
Home Florida Upper Matecumbe Key
Welcome to your legacy retreat in Islamorada's premier gated
Welcome to your legacy retreat in Islamorada's premier gated
Welcome to your legacy retreat in Islamorada's premier gated
Welcome to your legacy retreat in Islamorada's premier gated
Welcome to your legacy retreat in Islamorada's premier gated
MLS# 618190
Home For Sale

Welcome to your legacy retreat in Islamorada's premier gated

$2,495,000

33 Pen Key Drive, Upper Matecumbe Key, Florida, 33036

3
Beds
4
Baths
4,537
Sqft
0.300
Acres
$2,495,000
33 Pen Key Drive, Upper Matecumbe Key, Florida, 33036
3 Beds
4 Baths
4,537 Sqft
0.300 Acres

Accessibility Features

Accessible Elevator Installed
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.
39 days
on BarrierFreeHome.com
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Property Details

3 Beds
4 Baths
4,537 Sqft
Built 1987
0.300 Acres
No Patio
Garage, Guest, Open
Metal Roof
$17,069 Property Tax
Penn Key Club (83) Community
Monroe County
$600,000 Yearly HOA Fee
See More Details

Location

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Ad Statistics

Ad Number
7175842
Viewed
21 times
Added
Jan 23, 2026
Updated on
Jan 23, 2026

Listing Information

Data Source
Florida Keys Board of REALTORS®
Source Property ID
618190

Compliance

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.

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By proceeding, you consent to receive calls and texts to the number you provided, including email, marketing and auto notifications from DHN (linked to page that may discreetly list DHN Realty as an option), its affiliates and real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners about your inquiry and other home-related matters, but not as a condition of any purchase. You also agree to our Terms of Use, and to our Privacy Policy. Msg/data rates may apply. This consent applies even if you are on a corporate, state or national Do Not Call list. We may share information about your recent and future site activity with your agent to help them better understand what you’re looking for in a property.

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By proceeding, you consent to receive calls and texts to the number you provided, including email, marketing and auto notifications from DHN (linked to page that may discreetly list DHN Realty as an option), its affiliates and real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners about your inquiry and other home-related matters, but not as a condition of any purchase. You also agree to our Terms of Use, and to our Privacy Policy. Msg/data rates may apply. This consent applies even if you are on a corporate, state or national Do Not Call list. We may share information about your recent and future site activity with your agent to help them better understand what you’re looking for in a property.
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SERVICES
Buy Advertise
COMPANY
Testimonials About Us Office Locations
SUPPORT
Help Contact Us
ADDITIONAL MARKETS
LakeHouse.com MountainHomes.com BeachHouse.com GolfHomes.com
SUBSCRIBE
Receive notifications for new listings
Subscribe

Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 Wheelchair-accessible Housing & Universal Design Homes at Barrier Free Home
Part of Dream Home Network, Inc.
Last updated on 2026.03.03
Terms & Policy