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For Sale

33 Pen Key Drive

33 Pen Key Drive, Upper Matecumbe Key Islamorada, FL 33036

$2,495,000
Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where privacy, elegance, and world-class amenities converge. This expansive Key West-style residence is nestled within one of the Florida Keys' most prestigious gated communities, offering full-time property management, a protected marina, and a lifestyle defined by serenity and sophistication.From the moment you pass through the palm-lined entrance, you're surrounded by manicured tropical beauty. The home's vibrant exterior, wraparound porches, and timeless craftsmanship evoke classic island charm, while interiors are bathed in natural light and framed by lush garden views.Designed for effortless indoor-outdoor living, the spacious four-bedroom layout opens to expansive patios ideal for entertaining or quiet reflection. Towering palms, mature trees, and vibrant bougainvillea create a secluded sanctuary, while the scent of salt air and golden sunsets set the tone for unforgettable evenings.Enjoy exclusive access to a resort-style pool, private beach, kayak launch, the sunset point, and a full-service marina with direct access to world-class sport fishing and boating. Full-time on-site property managers ensure peace of mind, whether you're in your residence or away for the season.Located in the heart of Islamorada, this property offers unmatched proximity to fine dining, boutique shopping, and the legendary waters of the sport fishing capital of the world.Whether you're seeking a seasonal escape or a legacy investment, this home offers the perfect blend of luxury, leisure, and long-term value. Schedule your private tour today and experience the rare combination of privacy, prestige, and paradise.

3
beds

3
baths

4,537 Sq.Ft. LIVING AREA

0.3 Acres lot

Eric Rizzo, PA

Eric Rizzo, PA

Taylor Globus

Taylor Globus

Features & Amenities

Interior

  • total bedrooms3
  • Total bathrooms3
  • full bathrooms2
  • half bathroom1
  • Flooring Tile, Wood
  • APPLIANCES Washer, Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • other interior Features Drapes/Blinds Incl, Window Treatments, Quartz Countertops, Built-in Cabinets, Walk-in Closet(s), Storage, Smoke Alarms, Elevator, Pantry, Split Bedroom, Cathedral Ceilings, Cable, Satellite, Laundry Room, Utility Room, Impact Rstnce Window, Impact Rstnce Doors

Area & Lot

  • Status For Sale
  • Living Area4,537 Sq.Ft.
  • Lot Area0.3 Acres
  • MLS® ID616008
  • TypeResidential
  • YEAR BUILT1987
  • NeighborhoodIslamorada
  • Water FrontageNone
  • View DescriptionNo Waterview
  • School DistrictYes

Exterior

  • STORIES2
  • utilitiesFKAA, Propane, Satellite Dish, Cable Available, Buyer to Verify, Municipal Sewer
  • PoolIn Ground, Decked, Concrete, Above Ground
  • roofMetal Roof
  • parkingGarage, Off Street Parking, Guest Parking, Open Parking, Auto Door Opener, Attached
  • HEAT TYPECentral, Ductless
  • AIR CONDITIONINGCentral Air, Ductless, Ceiling Fans(s)
  • Disability FeaturesAccessible Elevator Installed
  • HOA AmenitiesCommon Area Mnt, Other, Security
  • security FeaturesElectric Gate
  • other exterior FeaturesRain Gutters, Sprinkler System, Lighting

Financial

  • Sales Price$2,495,000
  • Real Estate Tax $10,526/yr
  • HOA $696/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 Drive, 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 10055 Overseas Highway Marathon FL 33050 1075 Duval Street Suite 15C Key West FL 33040

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