Ad #7603365
MLS #619577
Welcome to your legacy retreat in Islamorada's premier gated
33 Pen Key, Upper Matecumbe Key, Florida, 33036
$2,195,000
3Beds
4Baths
4,537Sqft
0.300Acres
About this property
Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resortstyle 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 palmlined entrance leads to a vibrant exterior with wraparound porches and sunfilled interiors framed by lush garden views. The spacious threebedroom layout is designed for effortless indooroutdoor 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 resortstyle pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to worldclass sport fishing and boating, while fulltime onsite 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 longterm 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.
Property Features
3 Beds
4 Baths
4,537 Sqft
Built in 1987
0.300 Acres
Beachview
On Beachfront
Open
Siding: CBS
Metal Roof
Has Swimming Pool
Central, Ductless (Heating)
$17,069 / yr property tax
Monroe County
Penn Key Club (83) Community
Additional Photos
Contact Information
Eric M. Rizzo
Ocean Sotheby's International Realty
305-394-3062
Location
Listing Agent: Eric M. Rizzo (License #: 3347022) 305-394-3062
Broker: Ocean Sotheby's International Realty 305-712-8888 Listing Site
Copyright © 2026 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.
Broker: Ocean Sotheby's International Realty 305-712-8888 Listing Site
Copyright © 2026 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.
BeachHouse.com
Printed Jul 20, 2026
Photo Gallery
$2,195,000
3
Beds
4
Baths
4,537
Sqft
33 Pen Key, Upper Matecumbe Key, Florida, 33036
By contacting this agent you agree to these Terms and Conditions.
MLS# 619577
Welcome to your legacy retreat in Islamorada's premier gated
$2,195,000
33 Pen Key, Upper Matecumbe Key, Florida, 33036
3
Beds
4
Baths
4,537
Sqft
0.300
Acres
$2,195,000
33 Pen Key, Upper Matecumbe Key, Florida, 33036
3 Beds
4 Baths
4,537 Sqft
0.300 Acres
Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resortstyle 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 palmlined entrance leads to a vibrant exterior with wraparound porches and sunfilled interiors framed by lush garden views. The spacious threebedroom layout is designed for effortless indooroutdoor 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 resortstyle pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to worldclass sport fishing and boating, while fulltime onsite 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 longterm 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.
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Property Details
HOME DETAILS
3 Beds
4 Baths
4,537 Sqft
Built in 1987
0.300 Acres
BEACH & VIEW
Beachview
On Beachfront
EXTERIOR
Open
Siding: CBS
Metal Roof
Has Swimming Pool
INTERIOR
Central, Ductless (Heating)
FINANCIAL & COMMUNITY
$17,069 / yr property tax
Monroe County
Penn Key Club (83) Community
See More Details
Location
Mortgage Calculator
Ad Statistics
Ad Number
7603365
Viewed
66 times
Listing Status
Active
Added
Apr 21, 2026
Last Refresh
Jul 19, 2026 11:35:16 PM
Listing Information
Data Source
Florida Keys Board of REALTORS®
Source Property ID
619577
Listing Agent: Eric M. Rizzo (License #: 3347022) 305-394-3062
Broker: Ocean Sotheby's International Realty 305-712-8888 Listing Site
Copyright © 2026 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.
Broker: Ocean Sotheby's International Realty 305-712-8888 Listing Site
Copyright © 2026 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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