Date
Details
Price
Change
Source
10/02/2026
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 Just Listed
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Property Description
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, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.
Full Property Details
Full Property Details for 33 Pen Key Club Dr
General
- Price: $2,195,000
- HOA FEE: $646/month
- Taxes: $17,068 (2025)
- Status: Active
- Type: Single Family
- Source: 927
- MLS ID: 621487
- Updated: 10/2/2026
- Added to Site: 4 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, Whirlpool Bath Tub, Window Treatments
- Appliances: Dishwasher, Disposal, Dryer, Freezer, Gas Appliances, Ice Machine, 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: Screened Patio, Open Porch/Balcony, Screened
- Porch/Patio/Deck: Screened Patio, Open Porch/Balcony, Screened
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: GPS
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: CBS
- Roof: Metal
- Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
- Square Feet: 4,537
- Sq. Ft. Source: Tax Records
- Year Built: 1987
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
Financial Considerations
- Association Fee: Yes
- Association Fee: $646
- Assoc Fee Freq.: Monthly
- 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
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 33 Pen Key Club Dr —
Eric M. Rizzo
Ocean Sotheby's International Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 33 Pen Key Club Dr
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 | 6.8 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 Club Dr
Estimate the Cost
Estimate the Cost for 33 Pen Key Club Dr
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![[Address not provided], Islamorada, FL 33036 - Photo 1](https://m.cbhomes.com/p/944/A11932967/58988E0CE0Ed49D/s23cc.webp)
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33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 621487) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 33 Pen Key Club Drive is currently listed for $2,195,000 and was received on October 02, 2026. Want to learn more about 33 Pen Key Club Drive? Do you have questions about finding other Single Family real estate for sale in Upper Matecumbe Key Islamorada? You can browse all Upper Matecumbe Key Islamorada real estate or contact a Coldwell Banker agent to request more information.