33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036
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Listed by Eric M. Rizzo Ocean Sotheby's International Realty
$ 2,195,000
Est. payment | /mo

3 Beds

4 Baths

4,537 SqFt


Save
$ 2,195,000
Est. payment | /mo
Save

3 Beds

4 Baths

4,537 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 4,537 sqft

Price per Sqft $483

Subdivision Penn Key Club (83.0)

MLS Listing ID 619577

Style Above Flood,Other Bldg Style

Bedrooms 3

Full Baths 3

Half Baths 1

HOA Fees $50,000/mo

HOA Y/N Yes

Year Built 1987

Annual Tax Amount $17,068

Tax Year 2025

Lot Size 0.297 Acres

Acres 0.3

Lot Dimensions X

Property Sub-Type Single Family Residence

Land Area 4537

Property 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.

Location

State FL

County Monroe

Community Other Area Features, Manager On Premises, Community Dockage, Beach, Pool

Area 23 - Upper Matecumbe

Zoning R1 - Residential Single Family

Direction Call listing agents to arrange access through the gate.

Interior

Interior Features Utility Room, Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Drapes/Blinds Incl, Elevator, Pantry, Quartz Countertops, Smoke Alarms, Split Bedroom, Storage, Window Treatments

Heating Central, Ductless

Cooling Ductless, Central Air, Ceiling Fans(s)

Flooring Wood, Tile, Carpet

Furnishings Negotiable

Window Features Impact Rstnce Doors,Impact Rstnce Window

Appliance Freezer, Dryer, Washer, Dishwasher, Disposal, Microwave, Gas Appliances, Oven, Wine Cooler, Range, Refrigerator

Laundry Laundry Room

Exterior

Exterior Feature Lighting, Rain Gutters, Sprinkler System

Parking Features Open, Guest, Off Street, Vehicle Restrictions, Attached, Garage Door Opener

Pool Concrete, In Ground, Above Ground, Decked

Community Features Other Area Features, Manager on Premises, Community Dockage, Beach, Pool

Utilities Available Cable Available, FKAA, Municipal Sewer, Satellite Dish, Buyer To Verify, Propane

Waterfront Description Bay Front, Open Water, None, Gulf Front

Roof Type Metal Roof

Porch Windowed P/B, Screened Patio, Open Porch/Balcony, Screened

Garage No

Building

Architectural Style Above Flood, Other Bldg Style

New Construction No

Others

HOA Fee Include Other,Common Area Mnt,Security

Senior Community No

Tax ID 00402800-000000

Security Features Electric Gate

Pets Allowed Yes

Nearby Locations

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33 Pen Key