33 Pen Key, Islamorada, FL 33036
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33 Pen Key, Islamorada, FL 33036
33 Pen Key, Islamorada, FL 33036
33 Pen Key, Islamorada, FL 33036
33 Pen Key, Islamorada, FL 33036
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Laurie Keiling

Laurie Keiling

+1(305) 363-9484
$ 2,195,000
Est. payment /mo
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33 Pen Key Islamorada, FL 33036

3 Beds

4 Baths

4,537 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Residential - Single Family

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 Single Family

Bedrooms 3

Full Baths 3

Half Baths 1

Construction Status CBS

HOA Fees $50,000/mo

HOA Y/N Yes

Rental Info No

Year Built 1987

Annual Tax Amount $17,068

Tax Year 2025

Lot Size 0.300 Acres

Acres 0.3

Property Sub-Type Residential - Single Family

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

Area 23 - Upper Matecumbe

Zoning R1 - Residential Single Family

Rooms

Other Rooms Laundry Room, Utility Room

Interior

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

Heating Central Air, Ductless, Ceiling Fans(s)

Cooling Central Air, Ductless, Ceiling Fans(s)

Flooring Tile, Carpet, Wood

Furnishings Negotiable

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

Exterior

Exterior Feature Rain Gutters, Sprinkler System, Lighting

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

Pool In Ground, Decked, Concrete, Above Ground

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

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

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

View No Waterview

Roof Type Metal Roof

Handicap Access Yes

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

Private Pool Yes

Building

Story 2 Stories

Sewer Yes

Construction Status CBS

Others

SqFt Source Tax Records

Security Features Electric Gate

Acceptable Financing No Seller Finance, Conventional, Cash

Listing Terms No Seller Finance, Conventional, Cash

Special Listing Condition Updated/Remodeled

Pets Allowed Pets Allowed

Listed by Ocean Sotheby's International Realty

NEARBY SCHOOLS & PROPERTIES

Laurie Keiling

Laurie Keiling

Advisor | License ID: SL559865

+1(305) 363-9484

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33 Pen Key