Skip To Content

33 Pen Key

Upper Matecumbe Key Islamorada, FL 33036
  • $2,195,000
  • STATUS: Active
  • ON SITE: 23 Days
  • MLS #: 619577
UPDATED: 79 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 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 owners. A protected marina provides direct access to world‑class sport fishing and boating, while full‑time on‑site property management ensures peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. Whether you're seeking a seasonal escape or a long‑term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.

Monthly Payment Calculator



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 Coastal Collection Real Estate Inc. are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
www.buythekeys.com/homes/175603814
Print Image

33 Pen Key Upper Matecumbe Key Islamorada, FL 33036

  • Price: $2,195,000
  • Status: Active
  • On Site: 23 Days
  • Updated: 79 min ago
  • MLS #: 619577
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 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 owners. A protected marina provides direct access to world‑class sport fishing and boating, while full‑time on‑site property management ensures peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. Whether you're seeking a seasonal escape or a long‑term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.
Exterior Features

Architectural Style Other Bldg Style Attached Garage YN Yes Building Stories 2 Stories 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/BalconyWindowed P/BScreened 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 3 View [] Waterview No Waterview Window Features [] Windows Doors Impact Rstnce WindowImpact Rstnce Doors

Interior Features

Accessibility Features Accessible Elevator InstalledParking Appliances WasherDryerDishwasherRefrigeratorRangeOvenMicrowaveDisposalFreezerGas AppliancesWine 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)Window 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

Above Flood Yes Association Approval Req Yes Association Fee 50000 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 New Construction YN No Off Shore Island YN No Other Equipment [] Other Structures [] Pets Allowed Yes Potential Short Sale No Pre Wired CableSatellite Property Condition Updated/Remodeled 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 [] Waterfrnt No Waterfront Bay FrontGulf FrontOpen WaterNone 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 Coastal Collection Real Estate Inc. are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
 
https://bt-photos.global.ssl.fastly.net/flkeys/1280_boomver_1_619577-2.jpg https://bt-photos.global.ssl.fastly.net/flkeys/1280_boomver_1_619577-2.jpg https://bt-photos.global.ssl.fastly.net/flkeys/1280_boomver_1_619577-2.jpg
Logo
Coastal Collection Real Estate Inc.
422 Fleming St Suite 7
Key West FL, 33040