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$2,195,000
Upper Matecumbe Key Islamorada, FL 33036
MLS# 621487
3 beds | 4 baths | 4537 sqft
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Property Description
Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.
Details
Maps
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No
Species List: No
Current Price: $2,195,000
Listing Date: 2026-10-02
List Price: $2,195,000
Location, Tax & Legal
City: ISLAMORADA
Off Shore Island: No
Mile Marker: 83
Marathon Neighborhood: N/A
Senior Community YN: No
Side: Bay/Gulf
Flood Zone: AE,AE
Alternate Key #: 1495140
Handicap Access: Yes
Parcel #: 00402800-000000
Zoning: R1 - Residential Single Family
Deed Restrictions: Yes
Legal: LOT 33 AND SE 1/2 LOT 32 PEN KEY CLUB SEC 2 PB4-54 UPPER MATECUMBE KEY OR917-2027/28 OR1399-307/08 OR1456-1149/51 OR1456
Taxes: 17068.95
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 33
Street Name: Pen Key Club Drive
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: X
Lot SqFt: 12927
Pool: Yes
Lot Sqft Source: Tax Records
Total Units: 0
Acres: 0.3
SqFt Source: Tax Records
Rentals Allowed: No
Style: Single Family
Year Built: 1987
Living Apx SqFt: 4537
Total Bedrooms: 3
Full Baths: 3
Half Baths: 1
Total Baths: 4
Remarks & Misc
Remarks – Consumer: Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys.
Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment.
Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away.
Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities.
Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.
Directions: GPS
Association Info
Mandatory Home Owners Asc: Yes
Voluntary Home Owners Asc: No
1st Right of Refusal: Yes
Condo Doc's: Yes
Assoc Approval Req: Yes
Association Fee $: 645.83
Assoc/Mnt Fee Per: Monthly
Fee Includes
Common Area Mnt: 1
Security: 1
Other: 1
Dockage
Dock: Wood
Assigned Dock: 1
Basin: 1
Boat Slip: 1
Dock Privileges: 1
Seawall: Cut/Natural
Tax Exemptions
Homestead: 1
Widow/Widower: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Freezer: 1
Gas Appliances: 1
Ice Machine: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Washer: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Ductless: 1
Heating
Central: 1
Ductless: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Carpet: 1
Tile: 1
Wood: 1
Neighborhood Feature
Beach: 1
Community Dockage: 1
Community Pool: 1
Manager on Premises: 1
Other Area Features: 1
Interior Features
Built-in Cabinets: 1
Cathedral Ceilings: 1
Drapes/Blinds Incl: 1
Elevator: 1
Pantry: 1
Quartz Countertops: 1
Smoke Alarms: 1
Split Bedroom: 1
Storage: 1
Walk-in Closet(s): 1
Whirlpool Bath Tub: 1
Window Treatments: 1
Specialty Rooms
Guest/Servant Qtrs: Legal
Laundry Room: 1
Utility Room: 1
Building Style
Above Flood: Unknown
Stories: 2 Stories
Other Bldg Style: 1
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Car(s): 4+
Garage: 1
Guest Parking: 1
Open Parking: 1
Vehicle Restrictions: 1
Attached: 1
Auto Door Opener: 1
Off Street Parking: 1
Security
Electric Gate: 1
Construction
CBS: 1
Land Size
1/4 - 1/2 Acre: 1
Furnished
Negotiable: 1
Terms
Cash: 1
Conventional: 1
No Seller Finance: 1
Utilities
Buyer to Verify: 1
Cable Available: 1
FKAA: 1
Municipal Sewer: 1
Propane: 1
Satellite Dish: 1
Porch/Balcony
Open Porch/Balcony: 1
Screened P/B: 1
Screened Patio: 1
Title
Title Ins - Buyer: 1
Exterior Features
Lighting: 1
Rain Gutters: 1
Sprinkler System: 1
Pool Info
In Ground: 1
Above Ground: 1
Concrete: 1
Decked: 1
Pre-Wired
Cable: 1
Satellite: 1
Roof
Metal Roof: 1
Financial Status
Auction: No
Bank Owned: No
Potential Short Sale: No
Standard Sale: Yes
Accessibility Feat
Accessible Elevator Installed: 1
GF-Interior Features
Dual Flush: 1
Status Change Info
Status: Active
Property Features
Fee Includes: Common Area Mnt; Security; Other
Tax Exemptions: Homestead; Widow/Widower
Waterfront: None
Waterview: No Waterview
Dockage: Assigned Dock; Basin; Boat Slip; Dock Privileges
Building Style: Other Bldg Style
Vehicle Storage: Garage; Attached; Auto Door Opener; Guest Parking; Off Street Parking; Open Parking; Vehicle Restrictions
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air; Ductless
Heating: Central; Ductless
Utilities: Buyer to Verify; Cable Available; FKAA; Municipal Sewer; Propane; Satellite Dish
Interior Features: Built-in Cabinets; Cathedral Ceilings; Drapes/Blinds Incl; Elevator; Pantry; Quartz Countertops; Smoke Alarms; Split Bedroom; Storage; Walk-in Closet(s); Whirlpool Bath Tub; Window Treatments
Pre-Wired: Cable; Satellite
Specialty Rooms: Laundry Room; Utility Room
Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Ice Machine; Microwave; Oven; Range; Refrigerator; Washer; Wine Cooler
Exterior Features: Lighting; Rain Gutters; Sprinkler System
Accessibility Feat: Accessible Elevator Installed
Pool Info: In Ground; Above Ground; Concrete; Decked
Construction: CBS
Floor: Carpet; Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Neighborhood Feature: Beach; Community Dockage; Community Pool; Manager on Premises; Other Area Features
Security: Electric Gate
Land Size: 1/4 - 1/2 Acre
Terms: Cash; Conventional; No Seller Finance
Title: Title Ins - Buyer
GF-Interior Features: Dual Flush
Listing Office: Ocean Sotheby's International Realty
Last Updated: October - 02 - 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.