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33 Pen Key Drive

Upper Matecumbe Key Islamorada, FL 33036
  • $2,495,000
  • STATUS: Active
  • ON SITE: 97 Days
  • MLS #: 616008
UPDATED: 71 min ago
$2,495,000
  • 3
    BEDS
  • 0.3
    ACRES
  • 2
    BATHS
  • 1
    1/2 BATHS
  • 4,537
    SQFT
  • $550
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1987
County:

School Ratings & Info

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.

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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 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/166494638
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33 Pen Key Drive Upper Matecumbe Key Islamorada, FL 33036

  • Price: $2,495,000
  • Status: Active
  • On Site: 97 Days
  • Updated: 71 min ago
  • MLS #: 616008
3
Beds
2
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
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.
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 GarageOff Street ParkingGuest ParkingOpen ParkingAuto Door OpenerAttached Vehicle Storage Cars 3 Waterfront None Waterfront YN Yes 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 InclWindow TreatmentsQuartz CountertopsBuilt-in CabinetsWalk-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 Installed Assoc Approval Req Yes Assoc Fee 695.83 Assoc Hoa YN Yes Assoc Maint Fee Per Monthly 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 2024 Taxes 10525.58 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 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.
 
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Coastal Collection Real Estate Inc.
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Key West FL, 33040