About 33 Pen Key
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.
Features of 33 Pen Key
| MLS® # | 619577 |
|---|---|
| Price | $2,195,000 |
| Bedrooms | 3 |
| Bathrooms | 4.00 |
| Full Baths | 3 |
| Half Baths | 1 |
| Square Footage | 4,537 |
| Acres | 0.30 |
| Year Built | 1987 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Other Bldg Style |
| Status | Active |
Community Information
| Address | 33 Pen Key |
|---|---|
| Area | 23 - Upper Matecumbe |
| Subdivision | Penn Key Club (83.0) |
| City | Upper Matecumbe Key Islamorada |
| County | Monroe |
| State | FL |
| Zip Code | 33036 |
Amenities
| Amenities | Community Dockage, Manager on Premises, Beach, Other Area Features |
|---|---|
| Utilities | FKAA, Municipal Sewer, Buyer to Verify, Propane, Cable Available, Satellite Dish |
| Parking Spaces | 3 |
| Parking | Garage, Attached, Auto Door Opener, Open Parking, Guest Parking, Off Street Parking, Vehicle Restrictions |
| View | No Waterview |
| Is Waterfront | No |
| Waterfront | Bay Front, Gulf Front, Open Water, None |
| Has Pool | Yes |
| Pool | In Ground, Above Ground, Concrete, Decked |
Interior
| Interior Features | Drapes/Blinds Incl, Cathedral Ceilings, Split Bedroom, Pantry, Built-in Cabinets, Elevator, Smoke Alarms, Storage, Walk-in Closet(s), Window Treatments, Quartz Countertops |
|---|---|
| Appliances | Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler |
| Heating | Central, Ductless |
| Cooling | Central Air, Ceiling Fans(s), Ductless |
| Fireplace | No |
| Stories | 2 Stories |
| Has Basement | No |
Exterior
| Exterior Features | Rain Gutters, Lighting, Sprinkler System |
|---|---|
| Lot Description | 1/4 - 1/2 Acre |
| Windows | Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | CBS |
Additional Information
| Date Listed | April 21st, 2026 |
|---|---|
| Zoning | R1 - Residential Single Family |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 50000 |
| HOA Fees Freq. | Monthly |
Listing Details
| Agent | Eric M. Rizzo |
|---|---|
| Office | Ocean Sotheby's International Realty |