33 Pen Key Club Drive
Islamorada, FL 33036
3
Bed
4
Bath
4,537Sqft
Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys.Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasona
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,Whirlpool Bath Tub,Walk-in Closet(s),Storage,Smoke Alarms,Elevator,Pantry,Split Bedroom,Cathedral Ceilings Dual Flush Appliances: Washer,Wine Cooler,Ice Machine,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: Yes None 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: Homestead,Widow/Widower
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Virtual Tour
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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: $645.83 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 |
|---|---|---|---|---|---|
| Residential, Islamorada, FL, 33036 | $22,500,000 | 7 | 9 | -- | -- |
| 82891 Overseas Highway, Islamorada, FL, 33036 | $2,100,000 | 3 | 4 | 2,036 | 7,500 Sq. Ft |
| 88351 Old Highway HIGHWAY, Islamorada, FL, 33036 | $14,990,000 | 6 | 9 | 7,590 | -- |
| 144 N Rolling Hill Road.., Islamorada, FL, 33036 | $6,195,000 | 4 | 5 | 3,284 | -- |
| 87895 Old Highway HIGHWAY, Islamorada, FL, 33036 | $24,995,000 | 5 | 8 | 9,011 | -- |
| 87950 Overseas Highway .., Islamorada, FL, 33036 | $3,800,000 | 5 | 3 | 2,464 | -- |
| 87429 Old Highway HIGHWAY, Islamorada, FL, 33036 | $18,999,000 | 6 | 8 | 6,692 | -- |
| 87429 Old Highway, Islamorada, FL, 33036 | $18,999,000 | 6 | 8 | 6,692 | 124,146 Sq. Ft |
| 130 Palm Lane LANE, Islamorada, FL, 33036 | $2,250,000 | 3 | 3 | 2,796 | -- |
| 316 N Dr, Islamorada, FL, 33036 | $2,400,000 | 3 | 4 | -- | -- |
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ByOwner last updated this listing 10/03/2026 @ 03:51
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