Beach Homes Realty
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Waterfront

33 pen key

Upper Matecumbe Key Islamorada, FL 33036

$2,195,000

3 BEDS 4 BATHS
4,537 SQFT0.3 AC LOT
Residential - Single Family
Waterfront
Image 1: Pen Key Sunsets
Image 2: Front Door
Image 3: Veranda
Image 4: Entrance
Bedrooms 3
Total Baths 4
Full Baths 3
Square Feet 4537
Acreage 0.3
Status Active
MLS # 619577
County Monroe
More Info
Category Residential - Single Family
Status Active
Square Feet 4537
Acreage 0.3
MLS # 619577
County Monroe
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.
Location not available
Listing
Street
Satellite

Exterior Features

  • Style Single Family
  • Construction Single Family
  • Siding CBS
  • Exterior Rain Gutters, Sprinkler System, Lighting
  • Roof Metal Roof
  • Garage Yes
  • Garage Description No, No
  • Water FKAA, Propane, Satellite Dish, Cable Available, Buyer to Verify, Municipal Sewer
  • Sewer FKAA, Propane, Satellite Dish, Cable Available, Buyer to Verify, Municipal Sewer
  • Lot Dimensions X

Interior Features

  • Appliances Washer, Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • Heating Central, Ductless
  • Cooling Central Air, Ductless, Ceiling Fans(s)
  • Living Area 4,537 SQFT
  • Year Built 1987

Financial Information

  • Parcel ID 1495140
  • Zoning R1 - Residential Single Family

Additional Services

Internet Service Providers

Listing Information

Listing Provided Courtesy of Ocean Sotheby's International Realty
Listing Agent Eric Rizzo
Florida Keys, MLS
Listing data is current as of 07/06/2026.

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