18 Pen Key Club, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 621575)

18 Pen Key Club, Upper Matecumbe Key Islamorada, FL 33036

$3,900,000

Virtual Tour

https://my.matterport.com/show/?m=GVwpZNV9GvE

incredible access to the Keys' best fishing

Gated Pen Key Club - complete privacy, onsite property manager

fewer than three dozen homes share this lovely community

dockage available for boats to 32' not including engines

Pen Key Club takes care of all the landscaping

concrete, impact windows/doors, metal roof

Enjoy bay views while you have your breakfast!

Guest bedrooms and office flank the entry way

entrances to the dual walk in closets flank the sinks

office - an additional room in bedroom suite three

Dockage for boats to 32' Slips are assigned by the Pen Key Club harbor master based on boat size.

Property Type: Residential Bedrooms: 3 Baths: 3 Square Footage: 2,600 Lot Size (sq. ft.): 10,480 Status: Contingent

Current Price: $3,900,000 List Date: 10/10/2026 Last Modified: 10/18/2026

Overview

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 pro ... (Read more)

Listing Details MLS# 621575

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

Contract Information

Listing Board: Florida Keys
As is Rght to Inspct: Yes

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: Yes
Year Built: 1962
Total Units: Yes
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

Contingent: Contingent
Contingent Remarks: inspections

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

More Information

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 - 18 - 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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