33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 621487)

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

Overview

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 mari ...

Listing Details MLS# 621487

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

Contract Information

Listing Board
Florida Keys
As is Rght to Inspct
Yes
Potential Short Sale
No
Bank Owned
No
Species List
No

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
Yes
Control Depth
4
Pool
Yes
Year Built
1987
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
Yes
Total Baths
4
Rentals Allowed
No

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

More Information

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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