Residential

18 Pen Key Club, Upper Matecumbe Key Islamorada

$3,900,000.00

Bedroom 3 bedrooms
Bathroom 3 baths

  • MLS #: 621575
  • Address: 18 Pen Key Club, Upper Matecumbe Key Islamorada, FL 33036
  • Date Listed: 10/10/2026
  • Days on Market: 0
  • SQFT: 2600
  • Acres: 0.24
  • Restrictions: Unknown
  • Subdivision: Penn Key Club (83.0)

Location Location

Agent Comments Agent Comments
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.

Amenities Amenities
  • Stainless Steel Appliance(s)
  • Dishwasher
  • Dryer
  • Gas Appliances
  • Oven
  • Washer

Interior Features Interior Features
  • Cool System: Central Air
  • Heat System: Central
  • Floors: Marble
  • Rooms: Laundry Room, SunFlorida Room
  • Interior: Cathedral Ceilings, Granite Counter Top, Pantry, Split Bedroom, Sun/Florida Room

Exterior Features Exterior Features
  • Parking: Off Street
  • Roof: Metal
  • Pool: Yes

Additional Features Additional Features
  • County: Monroe
  • Property Type: Single Family Residence
  • Tax Number: 2147483647
  • Waterfront Features: Bay Front
  • Water/Sewer: FKAA, Municipal Sewer
  • Year Built: 1962