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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
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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