Date
Details
Price
Change
Source
4/21/2026
Listed
$2,195,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$2,195,000
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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.
Full Property Details
Full Property Details for 33 Pen Key
General
- Price: $2,195,000
- HOA FEE: $50,000/month
- Taxes: $17,068 (2025)
- Status: Active
- Type: Single Family
- Source: 927
- MLS ID: 619577
- Updated: 5/13/2026
- Added to Site: 22 day(s) ago
Interior
- Interior Features: Utility Room, Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Drapes/Blinds Incl, Elevator, Pantry, Quartz Countertops, Smoke Alarms, Split Bedroom, Storage, Window Treatments
- Appliances: Dishwasher, Disposal, Dryer, Freezer, Gas Appliances, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
- Flooring: Wood, Tile, Carpet
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Other Area Features, Manager on Premises, Community Dockage, Beach, Pool
- Pool: Yes
- Pool Description: Concrete, In Ground, Above Ground, Decked
- Security/Safety: Electric Gate
Exterior
- Exterior Features: Rain Gutters, Lighting, Sprinkler System, Boat Slip
- Deck/Patio: Windowed P/B, Screened Patio, Open Porch/Balcony, Screened
- Porch/Patio/Deck: Windowed P/B, Screened Patio, Open Porch/Balcony, Scr
Parking
- Garage: Yes
- Attached garage: Yes
- Parking Features: Open, Guest, Off Street, Vehicle Restrictions, Attached, Garage Door Opener
Location
- Area: 23 - Upper Matecumbe
- County: Monroe
- Subdivision: Penn Key Club (83.0)
- Driving Directions: Call listing agents to arrange access through the gate.
Community
- Association: Yes
- Assoc. Fees Include: Other, Common Area Mnt, Security
- Pets Allowed: Yes
Heating & Cooling
- Central air: Yes
- Air Conditioning: Yes
- Cooling Type: Ductless, Central Air, Ceiling Fans(s)
- Heating Type: Central, Ductless
Structural Information
- Architectural Style: Above Flood, Other Bldg Style
- Construction Status: Updated/Remodeled
- Construction: CBS
- Roof: Metal
- Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
- Square Feet: 4,537
- Sq. Ft. Source: Tax Records
- Year Built: 1987
- Property Condition: Updated/Remodeled
Lot Features
- Property View: No Waterview
- Lot Size (Acres): 0.3
- Lot Size (Sq. Ft.): 12,927
- Lot Size Source: Tax Records
- Lot Dimensions: x
- Zoning: R1 - Residential Single Family
Water Features
- Water View: Yes
- Water Front Desc.: Bay Front, Gulf Front, Open Water
Financial Considerations
- Association Fee: Yes
- Association Fee: $50,000
- Assoc Fee Freq.: Monthly
- Maint. Fee: $696
- Maint. Fee/Month: $696
- Tax Amount: $17,068.95
- Tax Year: 2025
Disclosures and Reports
- Legal Description: 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
- Flood Zone: AE, AE
- APN: 00402800-000000
Listed by Ocean Sotheby's International Realty, Eric M. Rizzo (305) 394-3062 and Ocean Sotheby's International Realty, Taylor Globus (305) 401-7675
We Value Your Privacy
We Value Your Privacy
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Listing agents
— 33 Pen Key —
Eric M. Rizzo
Ocean Sotheby's International Realty
Taylor Globus
Ocean Sotheby's International Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 33 Pen Key
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Plantation Key School 100 Lake Road, Tavernier, FL 33070 | PK-8 | 6.4 mi |
Coral Shores High School 89901 Old Highway, Tavernier, FL 33070 | 9-12 | 6.7 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 33 Pen Key
Estimate the Cost
Estimate the Cost for 33 Pen Key
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33 Pen Key, Upper Sugarloaf Key, FL 33036 (MLS# 619577) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 33 Pen Key is currently listed for $2,195,000 and was received on April 21, 2026. Want to learn more about 33 Pen Key? Do you have questions about finding other Single Family real estate for sale in Upper Sugarloaf Key? You can browse all Upper Sugarloaf Key real estate or contact a Coldwell Banker agent to request more information.