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33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036

$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: 4/21/2026 Last Modified: 8/06/2026

Overview

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 ...

Listing Details MLS# 619577

Location, Tax & Legal

Street #
33
Street Name
Pen Key
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
No
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
Yes
# Stories
2 Stories

Vehicle Storage

Car(s)
3

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: None Waterfront: Bay Front; Gulf Front; Open Water; None Waterview: No Waterview Dockage: Assigned Dock; Basin; Boat Slip; Dock Privileges Property Condition: Updated/Remodeled 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); Window Treatments Pre-Wired: Cable; Satellite Specialty Rooms: Laundry Room; Utility Room Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Microwave; Oven; Range; Refrigerator; Washer; Wine Cooler Exterior Features: Lighting; Rain Gutters; Sprinkler System Accessibility Feat: Accessible Elevator Installed; Parking 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: August - 06 - 2026
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