33 Pen Key, Islamorada, FL 33036

Islamorada
Local realty services provided by:Better Homes and Gardens Real Estate Destinations
33 Pen Key,Upper Matecumbe Key Islamorada, FL 33036
$2,195,000
  • 3 Beds
  • 4 Baths
  • 4,537 sq. ft.
  • Single family
  • Active
Listed by: eric m. rizzo, jamie daniels
Office: ocean sotheby's international realty
MLS#:619577
Source:FL_FKBOR

Price summary

  • Price:$2,195,000
  • Price per sq. ft.:$483.8
  • Monthly HOA dues:$646

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
  • Subdivision & Development:Penn Key Club (83.0)
  • Listing ID #:619577
  • Added:196 day(s) ago
  • Updated:August 07, 2026 at 02:59 PM

Rooms and interior

  • Bedrooms:3
  • Total bathrooms:4
  • Kitchen Description:Built-in Cabinets, Pantry, Quartz Countertops
  • Living area:4,537 sq. ft.

Heating and cooling

  • Cooling:Ceiling Fans(s), Central Air, Ductless
  • Heating:Central, Ductless

Structure and exterior

  • Year built:1987
  • Building area:4,537 sq. ft.
  • Lot area:0.3 Acres
  • Exterior Features:Boat Slip, Lighting, Rain Gutters, Sprinkler System

Finances and disclosures

  • Price:$2,195,000
  • Price per sq. ft.:$483.8
  • Tax amount:$17,068

Features and amenities

  • Amenities:Built-in Cabinets, Cathedral Ceilings, Drapes Included, Pantry, Smoke Alarms, Storage, Window Treatments

Parking

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

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