About 33 Pen Key Drive
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 three-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.
Features of 33 Pen Key Drive
| MLS® # | 616008 |
|---|---|
| Price | $2,495,000 |
| Bedrooms | 3 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 4,537 |
| Land Size | 13,068 |
| Year Built | 1987 |
| Type | Residential |
| Sub-Type | Single Family |
| Style | Other Bldg Style |
| Status | Active |
Community Information
| Address | 33 Pen Key Drive |
|---|---|
| Area | 23 - Upper Matecumbe |
| Subdivision | Penn Key Club (83.0) |
| City | ISLAMORADA |
| County | Monroe |
| State | FL |
| Zip Code | 33036 |
Amenities
| Amenities | Community Pool, Other Area Features, Beach, Manager on Premises, Community Dockage |
|---|---|
| Utilities | FKAA, Propane, Satellite Dish, Cable Available, Buyer to Verify, Municipal Sewer |
| Parking Spaces | 3 |
| Parking | Garage, Off Street Parking, Guest Parking, Open Parking, Auto Door Opener, Attached |
| View | No Waterview |
| Is Waterfront | Yes |
| Waterfront | None |
| Has Pool | Yes |
| Pool | In Ground, Decked, Concrete, Above Ground |
Interior
| 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 |
|---|---|
| Appliances | Washer, Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer |
| Heating | Central, Ductless |
| Cooling | Central Air, Ductless, Ceiling Fans(s) |
| Fireplace | No |
| Stories | 2 Stories |
Exterior
| Exterior Features | Rain Gutters, Sprinkler System, Lighting |
|---|---|
| Lot Description | 1/4 - 1/2 Acre |
| Windows | Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | CBS |
| Neighborhood Features | Community Pool, Other Area Features, Beach, Manager on Premises, Community Dockage |
Additional Information
| Date Listed | August 1st, 2025 |
|---|---|
| Days on Market | 74 |
| Zoning | R1 - Residential Single Family |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 695.83 |
| HOA Fees Freq. | Monthly |
Listing Details
| Agent | Eric M. Rizzo |
|---|---|
| Office | Ocean Sotheby's International Realty |