Address
33 Pen Key, Upper Matecumbe Key Islamorada, FL
Price
$ 2,195,000
Property Attributes
- MLS#619577
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityUpper Matecumbe Key Islamorada
- AreaUpper Matecumbe
- NeighborhoodPenn Key Club
- Zip33036
- StyleBldg Style
- Year Built1987
- Taxes$ 17068
- Price$ 2,195,000
- Bedrooms3
- Full Bathrooms3
- Half Bathrooms1
- Sqr Footage4537
- Lot Size0.3 Acres
Data Source:
Florida Keys MLS (FLKMLS)
Property 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.
| Price History | |
|---|---|
| 4/21/2026 | Listed $2,195,000 |
General Features
| Living Area | 4537.00 |
|---|---|
| Construction | CBS |
| Utilities | FKAA,Propane,Satellite Dish,Cable Available,Buyer to Verify,Municipal Sewer |
| Roof | Metal Roof |
| Appliances | Washer,Wine Cooler,Gas Appliances,Freezer,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer |
| Flood Zone | AE,AE |
| Zoning | R1 - Residential Single Family |
| HOA Fee | 645.83 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 3 |
| Half Baths | 1 |
| Year Built | 1987 |
| Handicap Access | Yes |
| Subdivision | Penn Key Club (83.0) |
| Style | Single Family |
| View | No Waterview |
| Property Type | A |
| Neighborhood Feature | Community Pool,Other Area Features,Beach,Manager on Premises,Community Dockage |
| Fee Includes | Common Area Mnt,Other,Security |
| Acres | 0.30 |
| Lot Sqft | 12927.00 |
| Bank Owned | No |
| Rental Allowed | No |
| Accessibility Features | Accessible Elevator Installed,Parking |
| HOA Approval Required | Yes |
| HOA/Maint Fee Per | Monthly |
| Building Style: Above Flood | Yes |
| Building Style: Stories | 2 Stories |
| Control Depth | 4 |
| Dockage | Dock Privileges,Basin,Boat Slip,Assigned Dock |
| Dockage: Dock | Wood |
| Dockage: Seawall | Cut/Natural |
Interior Features
| Interior Amenities | Drapes/Blinds Incl,Window Treatments,Quartz Countertops,Built-in Cabinets,Walk-in Closet(s),Storage,Smoke Alarms,Elevator,Pantry,Split Bedroom,Cathedral Ceilings |
|---|---|
| Total Units | 0.00 |
| Furnished Y/N | Negotiable |
| Flooring | Tile,Carpet,Wood |
| Specialty Rooms | Laundry Room,Utility Room |
| GF-Interior Features | Dual Flush |
| Pre-Wired | Cable,Satellite |
| Specialty Rooms: Guest/Servant Qtrs | Legal |
Exterior Features
| Exterior Amenities | Rain Gutters,Sprinkler System,Lighting |
|---|---|
| Pool | Yes |
| Waterfront | Bay Front,None,Open Water,Gulf Front |
| Building Style | Other Bldg Style |
| Lot Size | X |
| Land Size | 1/4 - 1/2 Acre |
| Pool Info | In Ground,Decked,Concrete,Above Ground |
| Porch/Balcony | Open Porch/Balcony,Screened Patio,Windowed P/B,Screened P/B |
| Public Sewer Hookup | Yes |
| Side | Bay/Gulf |
| Species List | No |
| Vehicle Storage | Garage,Vehicle Restrictions,Off Street Parking,Guest Parking,Open Parking,Auto Door Opener,Attached |
| Vehicle Storage: Car(s) | 3 |
| Windows/Doors | Impact Rstnce Window,Impact Rstnce Doors |
| Off Shore Island | No |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33036
Price
Taxes
Year Built
Visits
Information is deemed to be reliable, but is not guaranteed. © 2026 MLS and FBS. Prepared by Florida Keys MLS, Inc. on September 22, 2026 5:44 PM UTC The information on this sheet has been made available by the MLS and may not be the listing of the provider. The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information
