33 Pen Key Drive, Islamorada, FL 33036

Islamorada
Local realty services provided by:Better Homes and Gardens Real Estate Destinations
33 Pen Key Drive,Islamorada, FL 33036
$2,495,000
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  • 3 Beds
  • 4 Baths
  • 4,537 sq. ft.
  • Single family
  • Active
Listed by: eric m. rizzo, taylor globus
Office: ocean sotheby's international realty
MLS#:618190
Source:FL_FKBOR

Price summary

  • Price:$2,495,000
  • Price per sq. ft.:$549.92
  • Monthly HOA dues:$50,000

About this home

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...

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Home facts

  • Year built:1987
  • Listing ID #:618190
  • Added:90 day(s) ago
  • Updated:March 11, 2026 at 02:30 PM

Rooms and interior

  • Bedrooms:3
  • Total bathrooms:4
  • Full bathrooms:3
  • Half bathrooms:1
  • Kitchen Description:Built-in Cabinets, Dishwasher, Disposal, Freezer, Gas Appliances, Microwave, Oven, Pantry, Quartz Countertops, Range, Refrigerator, Wine Cooler
  • Bedroom Description:Split Bedroom
  • Living area:4,537 sq. ft.

Heating and cooling

  • Central air:Yes

Structure and exterior

  • Roof:Metal Roof
  • Year built:1987
  • Building area:4,537 sq. ft.
  • Lot area:0.3 Acres
  • Architectural Style:Single Family
  • Exterior Features:Open Porch/Balcony, Screened Patio, Screened Porch/Balcony, Sprinkler System, Windowed Porch/Balcony
  • Levels:2 Stories

Utilities

  • Sewer:Municipal Sewer

Finances and disclosures

  • Price:$2,495,000
  • Price per sq. ft.:$549.92
  • Tax amount:$17,069 (2025)

Features and amenities

  • Laundry features:Dryer, Washer
  • Amenities:Built-in Cabinets, Cable Wired, Cathedral Ceilings, Drapes Included, Electric Gate, Pantry, Satellite Wired, Smoke Alarms, Storage, Window Treatments
  • Pool features:Above Ground, Concrete, Decked, In Ground

Parking

  • Parking description:Attached, Auto Door Opener, Garage, Guest Parking, Off Street Parking, Open Parking, Vehicle Restrictions
  • Garage spaces:3

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