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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$3,900,000
18 Pen Key Club
Upper Matecumbe Key Islamorada, FL 33036
MLS# 621575
3 beds  |  3 baths  |  2600 sqft

 | 

refined island living in Pen Key Club
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refined island living in Pen Key Club Perfect place to watch the sunset incredible access to the Keys' best fishing waterside view at sunset Perfect place to watch the sunset refined island living in Pen Key Club incredible access to the Keys' best fishing incredible access to the Keys' best fishing incredible access to the Keys' best fishing incredible access to the Keys' best fishing Gated Pen Key Club - complete privacy, onsite property manager 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 dockage available for boats to 32' not including engines Sunset Point Sunset Point Pool for Pen Key Club members only Pen Key Club takes care of all the landscaping concrete, impact windows/doors, metal roof bay views from the 'upper' living room bay views from the 'upper' living room high ceilings and a spacious feel bay views from the 'upper' living room bay views from the 'upper' living room More bay views from the Florida room More bay views from the Florida room Enjoy bay views while you have your breakfast! 18 Pen Key Club 18 Pen Key Club 18 Pen Key Club 18 Pen Key Club 18 Pen Key Club Grill space, just outside the kitchen 18 Pen Key Club 18 Pen Key Club Guest bedrooms and office flank the entry way water side water side 18 Pen Key Club Patio off primary suite Primary suite with bay and sunset views Primary suite with bay and sunset views Primary suite with bay and sunset views Primary suite with bay and sunset views entrances to the dual walk in closets flank the sinks entrances to the dual walk in closets flank the sinks shower in primary suite bedroom 2 of 3 bedroom two of three Guest bath for bedroom two bedroom suite three of three bedroom suite three of three bedroom suite three of three office - an additional room in bedroom suite three office - an additional room in bedroom suite three Pen Key Club maintains the landscaping keep your car cool and protected magnificent sunsets 18 Pen Key Club Dockage for boats to 32' Slips are assigned by the Pen Key Club harbor master based on boat size. Dockage for boats to 32' Slips are assigned by the Pen Key Club harbor master based on boat size. Dockage for boats to 32' Slips are assigned by the Pen Key Club harbor master based on boat size. 18 Pen Key Club

Property 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.

Details
Maps
Contract Information
Current Price: $3,900,000
Listing Date: 2026-10-10
Listing Board: Florida Keys
Monthly Rent: $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
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
Status Change Info
Status: Active
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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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)