$2,195,000
 $11,783 est/mo Sourced by Back At You

33 Pen Key,ISLAMORADA, FL 33036

ISLAMORADA, FL 33036

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Description

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.

Details

MLS #619577
Listing TypeFor Sale
StyleHouse
HOA Dues$645
Sub-TypeResale
StatusActive
Year1987
Days On Site127
Listing Provided ByOcean Sotheby's International Realty | Eric M. Rizzo

Features

Bed(s)3
Bath(s) 4 Total
SQ Feet4,537
PoolYes
ZoningR1 - Residential Single Family
Acreage0.30
Water FrontNone
Property ViewNo Waterview

Taxes

Property17068

Area Information

StateFL
CountyMonroe
CityISLAMORADA
Zip Code33036
Area23 Upper Matecumbe
Community NamePenn Key Club (83.0)
Listing VS Median (in Penn Key Club (83.0))
Price:
$2,195,000
low | high
Med:
$2,195,000
50% of Average
sqft:
4,537
low | high
Med:
4,537
50% of Average
$ / sqft:
$484
low | high
Med:
$484
50% of Average
On site:
127
low | high
Med:
127
100% of Average
Sourced by Back At You

Market Activity 33036

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Learn More About This Property

StateFL
CountyMonroe
CityISLAMORADA
Zip Code33036
Area23 Upper Matecumbe
Community NamePenn Key Club (83.0)
Listing VS Median (in Penn Key Club (83.0))
Price:
$2,195,000
low | high
Med:
$2,195,000
50% of Average
sqft:
4,537
low | high
Med:
4,537
50% of Average
$ / sqft:
$484
low | high
Med:
$484
50% of Average
On site:
127
low | high
Med:
127
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/4 mile)
Price: $1.646M - $2.743M
sqft: 3,000 - 5,500
Nearby Listings Property ImageNearby Listings Details
19 Avacado Street Property Photo 1
$13,750,000
19 Avacado Street
Islamorada, FL 33036
Listing Updated: August 6, 2026 at 12:32:04 PM PDT