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For Sale

33 Pen Key

33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036

$2,195,000
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.

3
beds

4
baths

4,537 Sq.Ft. LIVING AREA

0.3 Acres lot

Eric Rizzo, PA

Eric Rizzo, PA

Features & Amenities

Interior

  • total bedrooms3
  • Total bathrooms4
  • full bathrooms3
  • half bathroom1
  • Laundry room Laundry Room
  • Flooring Wood, Tile, Carpet
  • APPLIANCES Dishwasher, Disposal, Dryer, Freezer, Gas Appliances, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
  • other interior Features Utility Room, Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Drapes/Blinds Incl, Elevator, Pantry, Quartz Countertops, Smoke Alarms, Split Bedroom, Storage, Window Treatments

Area & Lot

  • Status For Sale
  • Living Area4,537 Sq.Ft.
  • Total Area4,537 Sq.Ft.
  • Lot Area0.3 Acres
  • MLS® ID619577
  • TypeResidential
  • YEAR BUILT1987
  • NeighborhoodIslamorada
  • Architecture StylesAbove Flood, Other Bldg Style
  • Water FrontageNone
  • View DescriptionNo Waterview

Exterior

  • PoolConcrete, In Ground, Above Ground, Decked
  • roofMetal
  • parkingOpen, Guest, Off Street, Vehicle Restrictions, Attached, Garage Door Opener
  • HEAT TYPECentral, Ductless
  • AIR CONDITIONINGDuctless, Central Air, Ceiling Fans(s)
  • Disability FeaturesAccessible Elevator Installed, Parking
  • security FeaturesElectric Gate
  • other exterior FeaturesRain Gutters, Lighting, Sprinkler System, Boat Slip

Financial

  • Sales Price$2,195,000
  • Real Estate Tax $17,069/yr
  • Maintenance Fee $696/mo
  • HOA $50,000/mo
  • Zoning R1 - Residential Single Family
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Schedule a Showing

We would love to show you this beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Schedule a Showing

We would love to show you this beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Thank you for your interest in 33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036. We are reviewing your request and will be in touch shortly!
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OCEAN SIR

License # : CQ1039964

Phone

305.712.8888

Email

marketing@oceansir.com

Address

81888 Overseas Highway Islamorada FL 33036 12420 Overseas Highway Marathon FL 33050 1075 Duval Street Suite 15C Key West FL 33040

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