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33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036

New Listing
$2,195,000
Property Type: Residential Bedrooms: 3 Baths: 4 Square Footage: 4,537 Lot Size (sq. ft.): 12,927 Status: Active
Current Price: $2,195,000 List Date: 10/02/2026 Last Modified: 10/02/2026

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.

More Information MLS# 621487

Contract Information

Current Price: $2,195,000 Listing Date: 2026-10-02 Listing Board: Florida Keys List Price: $2,195,000 As is Rght to Inspct: Yes Potential Short Sale: No Bank Owned: No Species List: No

Location Tax Legal

Street #: 33 Street Name: Pen Key Club Drive Key/Island: Upper Matecumbe Key Islamorada State/Province: FL Zip Code: 33036 County: Monroe Subdivision: Penn Key Club (83.0) Area: 23 - Upper Matecumbe

General Property Description

Realtor.COM Type: Residential - Single Family Style: Single Family Waterfront: Yes Control Depth: 4 Pool: Yes Year Built: 1987 Lot Size: X Lot SqFt: 12927 Lot Sqft Source: Tax Records Acres: 0.3 Living Apx SqFt: 4537 SqFt Source: Tax Records Total Bedrooms: 3 Full Baths: 3 Half Baths: 1 Total Baths: 4 Rentals Allowed: No

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: Yes Condo Doc's: Yes Voluntary Home Owners Asc: No 1st Right of Refusal: Yes Assoc Approval Req: Yes Association Fee $: 645.83 Assoc/Mnt Fee Per: Monthly

Dockage

Dock: Wood Seawall: Cut/Natural

Building Style

Above Flood: Unknown Stories: 2 Stories

Vehicle Storage

Car(s): 4+

Specialty Rooms

Guest/Servant Qtrs: Legal

Financial Status

Auction: No Bank Owned: No Potential Short Sale: No Standard Sale: Yes

Property Features

Fee Includes: Common Area Mnt; Security; Other Tax Exemptions: Homestead; Widow/Widower Waterfront: None Waterview: No Waterview Dockage: Assigned Dock; Basin; Boat Slip; Dock Privileges Building Style: Other Bldg Style Vehicle Storage: Garage; Attached; Auto Door Opener; Guest Parking; Off Street Parking; Open Parking; Vehicle Restrictions Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air; Ductless Heating: Central; Ductless Utilities: Buyer to Verify; Cable Available; FKAA; Municipal Sewer; Propane; Satellite Dish Interior Features: Built-in Cabinets; Cathedral Ceilings; Drapes/Blinds Incl; Elevator; Pantry; Quartz Countertops; Smoke Alarms; Split Bedroom; Storage; Walk-in Closet(s); Whirlpool Bath Tub; Window Treatments Pre-Wired: Cable; Satellite Specialty Rooms: Laundry Room; Utility Room Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Ice Machine; Microwave; Oven; Range; Refrigerator; Washer; Wine Cooler Exterior Features: Lighting; Rain Gutters; Sprinkler System Accessibility Feat: Accessible Elevator Installed Pool Info: In Ground; Above Ground; Concrete; Decked Construction: CBS Floor: Carpet; Tile; Wood Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Beach; Community Dockage; Community Pool; Manager on Premises; Other Area Features Security: Electric Gate Land Size: 1/4 - 1/2 Acre Terms: Cash; Conventional; No Seller Finance Title: Title Ins - Buyer GF-Interior Features: Dual Flush
Listing Office: Ocean Sotheby's International Realty
Last Updated: October - 02 - 2026
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 being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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