$2,495,000

FOR SALE

33 Pen Key

Upper Matecumbe Key Islamorada, Fl, 33036

MLS #618190

Subdivision: Penn Key Club (83.0)

Building: -

3 Beds

3/1 Baths

4537 sqft

$ 549.92 /sqft

Property Details

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.

Property Features

-

Property Type
Single Family
HOA Fee/Monthly
-
HOPA
-
Membership Fees
-
Appliances
Washer,Wine Cooler,Gas Appliances,Freezer,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer
Restrictions
Yes
Furnished
-
Flooring
Tile,Wood
No. of Floor
-
Terms Considered
No Seller Finance,Conventional,Cash
Year Built
1987
Cooling
Central Air,Ductless,Ceiling Fans(s)
Pets Allowed
-
Amenities
-
Interior
Drapes/Blinds Incl,Built-in Cabinets,Quartz Countertops,Window Treatments,Walk-in Closet(s),Storage,Smoke Alarms,Elevator,Pantry,Split Bedroom,Cathedral Ceilings
Maintenance Fee Includes
-
Governing Bodies
-
Construction
CBS
Security
Electric Gate
Heating
Central Air,Ductless,Ceiling Fans(s)
Garage/Carport
-
Dining Area
-
Exterior
Rain Gutters,Sprinkler System,Lighting
Pet Restrictions
-
Parking
No
Application Fee
-
Water Access
-
Pool
Yes
Gated Community
-
Status
A
Listing Office
Ocean Sothebys International Realty

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Listing Courtesy of: Ocean Sothebys International Realty