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$3,900,000
Upper Matecumbe Key Islamorada, FL 33036
MLS# 621575
3 beds | 3 baths | 2600 sqft
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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
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Current Price: $3,900,000
Listing Date: 2026-10-10
List Price: $3,900,000
Location, Tax & Legal
City: ISLAMORADA
Mile Marker: 83
Marathon Neighborhood: N/A
Senior Community YN: No
Side: Bay/Gulf
Alternate Key #: 1494941
Parcel #: 00402600000000
Zoning: R1 - Residential Single Family
Deed Restrictions: Unknown
Legal: Lot 18 Pen Key Club Subd Pb3-170 Upper Matecumbe Key
Taxes: 9351.96
Tax Year: 2025
Pub Sewer HkUp: Yes
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
Waterfront: Yes
Control Depth: 4
Lot Size: 119 x 90+/-
Lot SqFt: 10480
Pool: Yes
Lot Sqft Source: Tax Records
Total Units: 1
Acres: 0.24
SqFt Source: Tax Records
Rentals Allowed: No
Min Rental Days: 0
Style: Single Family
Year Built: 1962
Living Apx SqFt: 2600
Total Bedrooms: 3
Full Baths: 3
Total Baths: 3
Remarks & Misc
Remarks – Consumer: 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.
Directions: Discreet private drive to gate is between Ziggie's and History of Diving Museum.
Association Info
Mandatory Home Owners Asc: Yes
1st Right of Refusal: Yes
Assoc Approval Req: Yes
Association Fee $: 646
Assoc/Mnt Fee Per: Monthly
Fee Includes
Common Area Mnt: 1
Other: 1
Dockage
Dock Length: 32
Assigned Dock: 1
Basin: 1
Dock Privileges: 1
Tax Exemptions
Homestead: 1
Appliances
Dishwasher: 1
Dryer: 1
Gas Appliances: 1
Oven: 1
Stainless Steel Appliance(s): 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Central Air: 1
Heating
Central: 1
Waterfront
Bay Front: 1
Waterview
Bay/Gulf View: 1
Harbor/Marina View: 1
Floor
Marble: 1
Neighborhood Feature
Community Dockage: 1
Community Pool: 1
Manager on Premises: 1
Interior Features
Cathedral Ceilings: 1
Granite Counter Top: 1
Pantry: 1
Split Bedroom: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Laundry Room: 1
Sun/Florida Room: 1
Building Style
Above Flood: Yes
Ground Level: 1
Windows/Doors
Impact Rstnce Window: 1
Other Windows/Doors: 1
Vehicle Storage
Garage: 1
Off Street Parking: 1
Security
Electric Gate: 1
Construction
Concrete: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Negotiable: 1
Utilities
FKAA: 1
Municipal Sewer: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Patio: 1
Pool Info
In Ground: 1
Other: shared pool
Roof
Metal Roof: 1
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
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