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Wade M. Berlin

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  4. 33 Pen Key Drive, ISLAMORADA, FL 33036
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33 Pen Key Drive
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PRICED AT ONLY: $2,495,000

Address: 33 Pen Key Drive, ISLAMORADA, FL 33036

Description

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.

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  • MLS#: 618190 ( Single Family )
  • Street Address: 33 Pen Key Drive
  • Viewed: 1
  • Price: $2,495,000
  • Price sqft: $550
  • Waterfront: No
  • Waterfront Type: Bay Front,Gulf Front
  • Year Built: 1987
  • Bldg sqft: 4537
  • Bedrooms: 3
  • Total Baths: 4
  • Full Baths: 3
  • 1/2 Baths: 1
  • Days On Market: 69

Description

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.
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Features
Building and Construction
  • Absolute Longitude: 80.620996
  • Construction: CBS
  • Exterior Features: Rain Gutters, Sprinkler System, Lighting
  • Floor: Tile, Wood
  • Porchbalcony: Open Porch/Balcony, Screened Patio, Windowed P/B, Screened P/B
  • Roof: Metal Roof
  • Sqft Source: Tax Records
  • Total Number Of Units: 0.00
Property Information
  • Property Condition: Updated/Remodeled
  • Property Group Id: 19990816212109142258000000
Garage and Parking
  • Vehicle Storage: Garage, Vehicle Restrictions, Off Street Parking, Guest Parking, Open Parking, Auto Door Opener, Attached
Eco-Communities
  • Off Shore Island: No
  • Pool Info: In Ground, Decked, Concrete, Above Ground
  • Water View: No Waterview
Utilities
  • Cooling: Central Air, Ductless, Ceiling Fans(s)
  • Gf Interior Features: Dual Flush
  • Handicap Access: Yes
  • Heating: Central, Ductless
  • Pets: Pets Allowed
  • Pub Sewer Hkup: Yes
  • Security: Electric Gate
  • Utilities: FKAA, Propane, Satellite Dish, Cable Available, Buyer to Verify, Municipal Sewer
  • Windowsdoors: Impact Rstnce Window, Impact Rstnce Doors
Amenities
  • Neighborhood Feature: Community Pool, Other Area Features, Beach, Manager on Premises, Community Dockage
Finance and Tax Information
  • Association Info Association Fee: 50000.00
  • Association Info Assocmnt Fee Per: Monthly
  • Association Info Maintenance Fee: 695.83
  • Fee Includes: Common Area Mnt, Other, Security
  • Tax Year: 2025
Rental Information
  • Rentals Allowed: No
Other Features
  • Accessibility Feat: Accessible Elevator Installed, Parking
  • Alternate Key Num: 1495140
  • Appliances: Washer, Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • As Is Rght To Inspct: Yes
  • Association Info 1st Right Of Refusal: Yes
  • Association Info Assoc Approval Req: Yes
  • Association Info Condo Doc S: Yes
  • Association Info Mandatory Home Owners Asc: Yes
  • Association Info Voluntary Home Owners Asc: No
  • Deed Restrictions: Yes
  • Dockage Dock: Wood
  • Dockage Seawall: Cut/Natural
  • Dockage: Dock Privileges, Basin, Boat Slip, Assigned Dock
  • Flood Zone: AE, AE
  • Furnished: Negotiable
  • Interior Features: Drapes/Blinds Incl, Built-in Cabinets, Quartz Countertops, Window Treatments, Walk-in Closet(s), Storage, Smoke Alarms, Elevator, Pantry, Split Bedroom, Cathedral Ceilings
  • Legal Description: LOT 33 AND SE 1/2 LOT 32 PEN KEY CLUB SEC 2 PB4-54 UPPER MATECUMBE KEY OR917-2027/28 OR1399-307/08 OR1456-1149/51 OR145
  • Mile Marker: 83.00
  • Pre Wired: Cable, Satellite
  • Side: Bay/Gulf
  • Species List: No
  • Style: Single Family
  • Zoning: R1 - Residential Single Family
Nearby Subdivisions
Anglers Reef   Anglers Reef (85.0)   Bay Hammock (83.2)   Galen Beach (85.0)   Hammock (83.5)   Lower Mat Bch (74.0)   Lower Mat Harbor (75.0)   Mat Ocean Bay (75.0)   Mat Ocean Beach (75.0)   Mat Ocean View (76.5)   Mat Sandy Bch (75.0)   Matecumbe Ocean Bay (75.0)   Matecumbe Ocean Bay Sec 2   Misc Plantation Key (85.0)   Misc Upper Matacumbe (82.0)   Not Applicable   Pearl City (89.0)   Penn Key Club (83.0)   Plant Beach (87.5)   Plant Ridge (87.0)   Plantation Lake Estates (87.0)   Port Antigua (74.5)   Russell Estates (83.2)   Safety Harbor   Safety Harbor (74.0)   Strattons (82.5)   Tarpon Flats (81.5)   Tea Table (79.5)   Toll Gate Shores (73.5)   Toners Nautical Sh (87.0)   Treasure Harbor (86.5)   Upper Matecumbe Key   Venetian Shores (86.0)   White Marlin Bch (74.5)  

Contact Info

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  2. The Real Estate Professional You Deserve
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Wade M. Berlin

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