18 Pen Key Club, Upper Matecumbe Key Islamorada, FL 33036
New Listing
$3,900,000
Property Type:
Residential
Bedrooms:
3
Baths:
3
Square Footage:
2,600
Lot Size (sq. ft.):
10,480
Status:
Active
Current Price:
$3,900,000
List Date:
10/10/2026
Last Modified:
10/10/2026
Description
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.
More Information MLS# 621575
Contract Information
Current Price: $3,900,000
Listing Date: 2026-10-10
Listing Board: Florida Keys
List Price: $3,900,000
As is Rght to Inspct: Yes
Location Tax Legal
Street #: 18
Street Name: Pen Key Club
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Penn Key Club (83.0)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: Yes
Year Built: 1962
Total Units: 1
Lot Size: 119 x 90+/-
Lot SqFt: 10480
Lot Sqft Source: Tax Records
Acres: 0.24
Living Apx SqFt: 2600
SqFt Source: Tax Records
Total Bedrooms: 3
Full Baths: 3
Total Baths: 3
Rentals Allowed: No
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: Yes
1st Right of Refusal: Yes
Assoc Approval Req: Yes
Association Fee $: 646
Assoc/Mnt Fee Per: Monthly
Dockage
Dock Length: 32
Building Style
Above Flood: Yes
Pool Info
Other: shared pool
Property Features
Fee Includes: Common Area Mnt; Other
Tax Exemptions: Homestead
Waterfront: Bay Front
Waterview: Bay/Gulf View; Harbor/Marina View
Dockage: Assigned Dock; Basin; Dock Privileges
Property Condition: Updated/Remodeled
Building Style: Ground Level
Vehicle Storage: Garage; Off Street Parking
Furnished: Negotiable
Cooling: Central Air
Heating: Central
Utilities: FKAA; Municipal Sewer
Interior Features: Cathedral Ceilings; Granite Counter Top; Pantry; Split Bedroom
Specialty Rooms: Laundry Room; Sun/Florida Room
Appliances: Dishwasher; Dryer; Gas Appliances; Oven; Stainless Steel Appliance(s); Washer
Pool Info: In Ground
Construction: Concrete
Floor: Marble
Roof: Metal Roof
Pets: Pets Allowed
Neighborhood Feature: Community Dockage; Community Pool; Manager on Premises
Security: Electric Gate
Land Size: Less Than 1/4 Acre
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: October - 10 - 2026
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