33 Pen Key
Islamorada, FL 33036
3
Bed
4
Bath
4,537Sqft
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 palm
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total Bedrooms: 3 Laundry Room,Utility RoomBathroom Information
Total Baths: 4 Full Baths: 3 Half Baths: 1 -
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 Dual Flush Appliances: Washer,Wine Cooler,Gas Appliances,Freezer,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer -
Roofing Information
Metal RoofFlooring Information
Tile,Carpet,WoodHeating & Cooling
Cooling: Central Air,Ductless,Ceiling Fans(s) Heating: Central,Ductless Water Front: No Bay Front,None,Open Water,Gulf Front No WaterviewWindow Information
Window Treatments: Impact Rstnce Window,Impact Rstnce Doors
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Building Information
Year Built: 1987 Total Units: 0.00 Floor Location: 12927 Construction: CBS Security System: Electric Gate Roof: Metal Roof -
Exterior Features
Rain Gutters,Sprinkler System,LightingPool Information
In Ground,Decked,Concrete,Above Ground -
Guest House Information
Legal
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Lot Information
Lot Dimensions: X Lot SqFt: 12,927 Lot SqFt Source: Tax Records 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 OR1456 -
Property Information
SQ ft (Living Area): 4,537 View: No Waterview Subdivision: Penn Key Club (83.0) Stories: 2 Stories
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Listing Price Information
List Price: $2,195,000 -
Listing Information
No Seller Finance,Conventional,Cash
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Tax Information
Taxes: $17,069 Tax Year: 2025 Parcel Number: 00402800-000000 Tax Exemptions: None
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Multi-Unit Information
Pets Allowed: Pets Allowed -
Homeowners Association Information
Mandatory Home Owners Asc: Yes Condo Doc's: Yes Voluntary Home Owners Asc: No 1st Right of Refusal: Yes Assoc Approval Req: Yes Association Fee: $50000.00 Maintenance Fee: $695.83 Assoc/Mnt Fee Per: Monthly
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Utility Information
FKAA,Propane,Satellite Dish,Cable Available,Buyer to Verify,Municipal Sewer
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 102 Anglers Way, Islamorada, FL, 33036 | $1,150,000 | 2 | 3 | 1,376 | 1,376 SqFt |
| 88351 Old Highway HIGHWAY, Islamorada, FL, 33036 | $15,990,000 | 6 | 9 | 7,590 | 7,590 SqFt |
| 87895 Old Highway HIGHWAY, Islamorada, FL, 33036 | $24,995,000 | 5 | 8 | 9,011 | 9,011 SqFt |
| 88110 Overseas Highway, Islamorada, FL, 33036 | $6,999,000 | 4 | 5 | 2,797 | 2,797 SqFt |
| 87950 Overseas Highway .., Islamorada, FL, 33036 | $3,800,000 | 5 | 3 | 2,464 | 2,464 SqFt |
| 87445 Old Highway HIGHWAY, Islamorada, FL, 33036 | $3,995,000 | 5 | 4 | 4,014 | 4,014 SqFt |
| 87429 Old Highway HIGHWAY, Islamorada, FL, 33036 | $18,999,000 | 6 | 8 | 6,692 | 6,692 SqFt |
| 87429 Old Highway, Islamorada, FL, 33036 | $18,999,000 | 6 | 6 | 6,054 | 6,054 SqFt |
| 316 North Drive DRIVE, Islamorada, FL, 33036 | $2,400,000 | 3 | 4 | 2,309 | 2,309 SqFt |
| 316 N Dr, Islamorada, FL, 33036 | $2,400,000 | 3 | 4 | -- |
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ByOwner last updated this listing 07/26/2026 @ 03:22
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