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33 Pen Key Club Drive

Upper Matecumbe Key Islamorada, FL 33036
  • $2,195,000
  • STATUS: Active
  • ON SITE: 6 Days
  • MLS #: 621487
New On Site 6 Days Ago
UPDATED: 63 min ago
$2,195,000
  • 3
    BEDS
  • 0.3
    ACRES
  • 3
    BATHS
  • 1
    1/2 BATHS
  • 4,537
    SQFT
  • $484
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1987
County:

School Ratings & Info

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.

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The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Florida Keys MLS, Inc. Real estate listings held by brokerage firms other than Key West Luxury Real Estate Inc are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
www.keywestluxuryrealestateinc.com/homes/181769118
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33 Pen Key Club Drive Upper Matecumbe Key Islamorada, FL 33036

  • Price: $2,195,000
  • Status: Active
  • On Site: 6 Days
  • Updated: 63 min ago
  • MLS #: 621487
3
Beds
3
Baths
1
½ Baths
0.3
Acres
4,537
SQFT
$484
$/SQFT
1987
Built
Neighborhood:
Penn Key Club (83.0)
County:
Monroe
Area:
23 - Upper Matecumbe
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.
Exterior Features

Architectural Style Other Bldg Style Attached Garage YN Yes Construction Materials CBS Dock Wood Dockage Dock PrivilegesAssigned DockBoat SlipBasin Exterior Features Rain GuttersLightingSprinkler System Garage YN Yes Parking Features AttachedGarage Door OpenerOpen Patio And Porch Features Open Porch/BalconyScreened Patio Pool Features In GroundAbove GroundConcreteDecked Pool Private YN Yes Roof Metal Roof Vehicle Storage GarageAttachedAuto Door OpenerOpen ParkingGuest ParkingOff Street ParkingVehicle Restrictions Vehicle Storage Cars 4+ View [] Waterview No Waterview Window Features [] Windows Doors Impact Rstnce WindowImpact Rstnce Doors

Interior Features

Accessibility Features Accessible Elevator Installed Appliances WasherDryerDishwasherRefrigeratorRangeOvenMicrowaveDisposalFreezerGas AppliancesIce MachineWine Cooler Cooling Central AirCeiling Fans(s)Ductless Cooling YN Yes Flooring TileWoodCarpet Furnished Unfurnished Guest Servant Qtrs Legal Heating CentralDuctless Heating YN True Interior Drapes/Blinds InclCathedral CeilingsSplit BedroomPantryBuilt-in CabinetsElevatorSmoke AlarmsStorageWalk-in Closet(s)Whirlpool Bath TubWindow TreatmentsQuartz Countertops Interior Features Built-in CabinetsElevatorStorageWalk-in Closet(s)Quartz Countertops Laundry Features Laundry Room Levels [] Rooms Total 0 Specialty Rooms Laundry RoomUtility Room

Property Features

Association Approval Req Yes Association Fee 645.83 Association Fee Frequency Monthly Association Fee Includes Common Area MntSecurityOther Association YN Yes Association1st Right Of Refusal Yes Bank Owned No Building Features [] Community Features Community DockageManager on PremisesBeachOther Area Features Control Depth 4 Deed Restricts Yes Electric [] Flood Zone AEAE Frontage Type [] Green Energy Generation [] Green Water Conservation [] Handicap Access Yes Land Size 1/4 - 1/2 Acre Listing Terms No Seller FinanceCashConventional Marathon Nbhd N/A Mile Marker 83 Off Shore Island YN No Other Equipment [] Other Structures [] Pets Allowed Yes Potential Short Sale No Pre Wired CableSatellite Property Condition [] Property Sub Type Single Family Residence Public Sewer Hookup Yes Rental Allowed No Seawall Cut/Natural Security Features Electric Gate Special Licenses [] Tax Annual Amount 17068.95 Tax Legal Description LOT 33 AND SE 1/2 LOT 32 PEN KEY CLUB SEC 2 PB4-54 UPPER MATECUMBE KEY OR917-2027/28 OR1399-307/08 OR1456-1149/51 OR1456 Tax Year 2025 Title Title Ins - Buyer Utilities Cable AvailableSatellite Dish Utilities Info FKAAMunicipal SewerBuyer to VerifyPropaneCable AvailableSatellite Dish Voluntary Home Owners Asosc No Water Source [] Waterfront None Waterfront Features [] Waterfront YN No Zoning R1 - Residential Single Family

Listing courtesy of Eric Rizzo of Ocean Sotheby's International Realty: 305-712-8888.


The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Florida Keys MLS, Inc. Real estate listings held by brokerage firms other than Key West Luxury Real Estate Inc are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
 
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Key West Luxury Real Estate Inc
619 Eaton Street, #2
Key West FL, 33040