$2,495,000
33 Pen Key Drive
Upper Matecumbe Key Islamorada, FL 33036
MLS# 616008
3 beds  |  3 baths  |  4537 sqft
33 Pen Key Drive, Upper Matecumbe Key Islamorada, FL 33036
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Property Description
Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where privacy, elegance, and world-class amenities converge. This expansive Key West-style residence is nestled within one of the Florida Keys' most prestigious gated communities, offering full-time property management, a protected marina, and a lifestyle defined by serenity and sophistication. From the moment you pass through the palm-lined entrance, you're surrounded by manicured tropical beauty. The home's vibrant exterior, wraparound porches, and timeless craftsmanship evoke classic island charm, while interiors are bathed in natural light and framed by lush garden views. Designed for effortless indoor-outdoor living, the spacious three-bedroom layout opens to expansive patios ideal for entertaining or quiet reflection. Towering palms, mature trees, and vibrant bougainvillea create a secluded sanctuary, while the scent of salt air and golden sunsets set the tone for unforgettable evenings. Enjoy exclusive access to a resort-style pool, private beach, kayak launch, the sunset point, and a full-service marina with direct access to world-class sport fishing and boating. Full-time on-site property managers ensure peace of mind, whether you're in your residence or away for the season. Located in the heart of Islamorada, this property offers unmatched proximity to fine dining, boutique shopping, and the legendary waters of the sport fishing capital of the world. Whether you're seeking a seasonal escape or a legacy investment, this home offers the perfect blend of luxury, leisure, and long-term value. Schedule your private tour today and experience the rare combination of privacy, prestige, and paradise.

Details
Maps
Contract Information
Current Price: $2,495,000
Listing Date: 2025-08-01
Listing Board: Florida Keys
List Price: $2,495,000
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
Street Suffix: 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: 5
Pool: Yes
Year Built: 1987
Lot Size: 103 x 126 x 103 x 125
Lot SqFt: 12927
Lot Sqft Source: Tax Records
Acres: 0.3
Living Apx SqFt: 4537
SqFt Source: Tax Records
Total Bedrooms: 3
Full Baths: 2
Half Baths: 1
Total Baths: 3
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 $: 745.83
Assoc/Mnt Fee Per: Monthly
Dockage
Dock: Wood
Seawall: Cut/Natural
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: Homestead; Widow/Widower
Waterfront: 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
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
Pool Info: In Ground; Above Ground; Concrete; Decked
Construction: CBS
Floor: 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: December - 24 - 2025

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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