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18 Pen Key Club, Upper Matecumbe Key Islamorada, FL - photo 1

$3,900,000

18 Pen Key Club

Upper Matecumbe Key Islamorada, FL 33036

Estimated payment $23,400/month

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3Beds
3Baths
2,600Sq Ft
$1500Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

No HOA
Built in 1962
10,454 sqft Lot

About This Home

Sunset views in Islamorada's most coveted location: PEN KEY CLUB. From the front doorstep, you can see straight through the house to the sparkling waters of Florida Bay, so the view will take your breath away before you put a foot inside the house! Established in the 1950s, Pen Key Club is a small, private, gated bayfront community on Upper Matecumbe Key, Islamorada's ''downtown'' island. The location is excellent by land and sea. Boating access is exceptional. In fact, it's why the club was founded here. Immediate access to Florida Bay and quick, easy access to the ocean through Whale Harbor Channel. Dockage for boats to 32 feet (plus engines) is available for club members only. Quiet and tucked away, it's close to many of Islamorada's favorite restaurants, including Chef Michael's, Kaiyo and Pierre's, as well as shops and local gathering places like the Cheeca Lodge. Owners share a pool, marina and sunset viewing areas, while the association cares for the landscaping. An onsite property manager receives packages and helps owners with day-to-day needs, making it easy to live here full time or to come and go. Overlooking the marina and bay, this one-level home has high ceilings and two large living areas lined with wide banks of impact glass doors. Expansive bay views extend throughout the main living areas and primary bedroom suite. The large covered patio offers plenty of space for morning coffee, dinner with friends and a front-row seat for the sunset. The comfortable layout puts everything on one floor, with three bedrooms, each with an en suite bath, plus a separate office, laundry room and garage. Concrete construction, impact windows and doors and a metal roof add strength and peace of mind. You really can have it all: big bay views, dockage, excellent boating access and favorite restaurants and shops nearby, with the ease of a single-level home in a peaceful community where living is easy.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:3
  • •Bathrooms:3
  • •Full bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:2,600 sqft
  • •Total interior livable area:2,600 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:10,454 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1962

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Price history

DateEventPrice
10/13/2026Listed for sale$3,900,000$1500/sqft

Listing Agent

Christy Hughes

Coldwell Banker Schmitt Islamorada

Brokerage Phone: 305-664-4470

Source: Florida Keys MLS · MLS #621575

Data Powered by Home Junction, Inc.

Nearby

Supermarkets

Publix

0.2 mi

Dining

Hog Heaven Sports Bar & Grill

0.1 mi

Bently's

0.2 mi

The Whistle Stop Bar & Grill And Wood Oven Pizza

0.3 mi

Beaches

Anne's Beach

9.6 mi

North Beach

17.6 mi

South Beach

17.9 mi

Nearby amenity locations include data © OpenStreetMap contributors.