33 Pen Key Drive, Islamorada, FL 33036

Local realty services provided by:Better Homes and Gardens Real Estate Destinations
33 Pen Key Drive,Islamorada, FL 33036
$2,495,000
  • 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

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with a BHGRE®  affiliated agent to contact me about my real estate needs. By clicking Send message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a BHGRE®  affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (CENTURY 21® , Coldwell Banker® , Corcoran® , ERA® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1987
  • Listing ID #:618190
  • Added:1 day(s) ago
  • Updated:January 23, 2026 at 02:05 PM

Rooms and interior

  • Bedrooms:3
  • Total bathrooms:4
  • Full bathrooms:3
  • Half bathrooms:1
  • Living area:4,537 sq. ft.

Structure and exterior

  • Roof:Metal Roof
  • Year built:1987
  • Building area:4,537 sq. ft.
  • Lot area:0.3 Acres

Utilities

  • Sewer:Municipal Sewer

Finances and disclosures

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

New listings near 33 Pen Key Drive