Skip To Content

33 Pen Key Drive

Upper Matecumbe Key Islamorada, FL 33036
  • $2,495,000
  • STATUS: Active
  • ON SITE: 13 Days
  • MLS #: 618190
UPDATED: 52 min ago
$2,495,000
  • 3
    BEDS
  • 0.3
    ACRES
  • 3
    BATHS
  • 1
    1/2 BATHS
  • 4,537
    SQFT
  • $550
    $/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 Bascom Grooms Real Estate are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
www.realtorkeywestfl.com/homes/172408358
Print Image

33 Pen Key Drive Upper Matecumbe Key Islamorada, FL 33036

  • Price: $2,495,000
  • Status: Active
  • On Site: 13 Days
  • Updated: 52 min ago
  • MLS #: 618190
3
Beds
3
Baths
1
½ Baths
0.3
Acres
4,537
SQFT
$550
$/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

Above Flood Yes Building Style Other Bldg Style Construction CBS Dockage Dock PrivilegesBasinBoat SlipAssigned Dock Dockage Dock Wood Dockage Seawall Cut/Natural Exterior Features Rain GuttersSprinkler SystemLighting Land Size 1/4 - 1/2 Acre Lot Size 103 x 126 x 103 x 125 Pool Info In GroundDeckedConcreteAbove Ground Pool YN Yes Porch Balcony Open Porch/BalconyScreened PatioWindowed P/BScreened P/B Roof Metal Roof Side Bay/Gulf Stories 2 Stories Style Single Family Vehicle Storage GarageVehicle RestrictionsOff Street ParkingGuest ParkingOpen ParkingAuto Door OpenerAttached Vehicle Storage Cars 3 Waterfront Bay FrontGulf Front Waterfront YN No Waterview No Waterview

Interior Features

Appliances WasherWine CoolerGas AppliancesFreezerDisposalMicrowaveOvenRangeRefrigeratorDishwasherDryer Cooling Heating Central AirDuctlessCeiling Fans(s) Floor TileWood Furnished Negotiable Green Interior Features Dual Flush Guest Servant Quarters Legal Interior Features Drapes/Blinds InclBuilt-in CabinetsQuartz CountertopsWindow TreatmentsWalk-in Closet(s)StorageSmoke AlarmsElevatorPantrySplit BedroomCathedral Ceilings Pre Wired CableSatellite Specialty Rooms Laundry RoomUtility Room Windows Doors Impact Rstnce WindowImpact Rstnce Doors

Property Features

Accessibility Features Accessible Elevator InstalledParking Assoc Approval Req Yes Assoc Fee 50000.00 Assoc Hoa YN Yes Assoc Maint Fee Per Monthly Assoc Maintenance Fee 695.83 Assoc Right Of Refusal Yes Auction No Bank Owned No Bank Owned Financial Status No City ISLAMORADA Condition Updated/Remodeled Control Depth 5 Deed Restrictions Yes Fee Includes Common Area MntOtherSecurity Flood Zone AEAE Handicap Access Yes Listing Board Florida Keys Mile Marker 83.00 Neighborhood Features Community PoolOther Area FeaturesBeachManager on PremisesCommunity Dockage Off Shore Island No Pets Pets Allowed Potential Short Sale No Potential Short Sale Financial Status No Public Sewer Hookup Yes Rentals Allowed No Security Electric Gate Species List No Sq Ft Source Tax Records Tax Exemptions HomesteadWidow/Widower Tax Year 2025 Taxes 17068.90 Terms No Seller FinanceConventionalCash Title Title Ins - Buyer Utilities FKAAPropaneSatellite DishCable AvailableBuyer to VerifyMunicipal Sewer 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 Bascom Grooms Real Estate 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_618190-2.jpg https://bt-photos.global.ssl.fastly.net/flkeys/1280_boomver_1_618190-2.jpg https://bt-photos.global.ssl.fastly.net/flkeys/1280_boomver_1_618190-2.jpg
Logo
Bascom Grooms Real Estate
1110 Truman Ave
Key West FL, 33040