33 Pen Key Club Drive, Islamorada Village Of Islands, FL 33036

Islamorada Village Of Islands
Local realty services provided by:Better Homes and Gardens Real Estate Destinations
33 Pen Key Club Drive,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
Office: ocean sotheby's international realty
MLS#:621487
Source:FL_FKBOR

Price summary

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

About this home

Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected...

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Home facts

  • Year built:1987
  • Subdivision & Development:Penn Key Club (83.0)
  • Listing ID #:621487
  • Added:6 day(s) ago
  • Updated:October 09, 2026 at 03:07 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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