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
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