33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036
33 Pen Key Club Drive, Upper Matecumbe Key Islamorada, FL 33036
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American Caribbean Real Estate

American Caribbean Real Estate

American Caribbean Real Estate

+1(305) 451-4078
Listed by Eric M. Rizzo Ocean Sotheby's International Realty
$ 2,195,000
Est. payment | /mo

3 Beds

4 Baths

4,537 SqFt


$ 2,195,000
Est. payment | /mo

3 Beds

4 Baths

4,537 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 4,537 sqft

Price per Sqft $483

Subdivision Penn Key Club (83.0)

MLS Listing ID 621487

Style Above Flood,Other Bldg Style

Bedrooms 3

Full Baths 3

Half Baths 1

HOA Fees $645/mo

HOA Y/N Yes

Year Built 1987

Annual Tax Amount $17,068

Tax Year 2025

Lot Size 0.297 Acres

Acres 0.3

Lot Dimensions X

Property Sub-Type Single Family Residence

Land Area 4537

Property 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.

Location

State FL

County Monroe

Community Other Area Features, Manager On Premises, Community Dockage, Beach, Pool

Area 23 - Upper Matecumbe

Zoning R1 - Residential Single Family

Direction GPS

Interior

Interior Features Utility Room, Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Drapes/Blinds Incl, Elevator, Pantry, Quartz Countertops, Smoke Alarms, Split Bedroom, Storage, Whirlpool Bath Tub, Window Treatments

Heating Central, Ductless

Cooling Ductless, Central Air, Ceiling Fans(s)

Flooring Wood, Tile, Carpet

Furnishings Negotiable

Window Features Impact Rstnce Doors,Impact Rstnce Window

Appliance Freezer, Dryer, Washer, Dishwasher, Ice Machine, Disposal, Microwave, Gas Appliances, Oven, Wine Cooler, Range, Refrigerator

Laundry Laundry Room

Exterior

Exterior Feature Lighting, Rain Gutters, Sprinkler System

Parking Features Open, Guest, Off Street, Vehicle Restrictions, Attached, Garage Door Opener

Pool Concrete, In Ground, Above Ground, Decked

Community Features Other Area Features, Manager on Premises, Community Dockage, Beach, Pool

Utilities Available Cable Available, FKAA, Municipal Sewer, Satellite Dish, Buyer To Verify, Propane

Waterfront Description None

Roof Type Metal Roof

Porch Screened Patio, Open Porch/Balcony, Screened

Garage No

Private Pool Yes

Building

Architectural Style Above Flood, Other Bldg Style

Others

HOA Fee Include Other,Common Area Mnt,Security

Senior Community No

Tax ID 00402800-000000

Security Features Electric Gate

Pets Allowed Yes

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33 Pen Key Club Drive