33 Pen Key Drive, Upper Matecumbe Key Islamorada, FL 33036
$2,495,000
Property Type:
Residential
Bedrooms:
3
Baths:
4
Square Footage:
4,537
Lot Size (sq. ft.):
12,927
Status:
Active
Current Price:
$2,495,000
List Date:
1/23/2026
Last Modified:
1/26/2026
Description
Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort‑style living awaits in this Key West-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined by serenity and sophistication.
A palm‑lined entrance leads to a vibrant exterior with wraparound porches and sun‑filled interiors framed by lush garden views. The spacious three‑bedroom layout is designed for effortless indoor‑outdoor living, with multiple gathering spaces opening to expansive patios ideal for entertaining, unwinding, or savoring golden sunsets. Mature palms, bougainvillea, and the scent of salt air create a secluded sanctuary that feels worlds away.
Residents enjoy exclusive access to a resort‑style pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to world‑class sport fishing and boating, while full‑time on‑site property management ensures peace of mind whether you're home or away.
Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world.
Whether you're seeking a seasonal escape or a long‑term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.
More Information MLS# 618190
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No
Species List: No
Current Price: $2,495,000
Listing Date: 2026-01-23
List Price: $2,495,000
Location, Tax & Legal
City: ISLAMORADA
Off Shore Island: No
Mile Marker: 83
Marathon Neighborhood: N/A
Side: Bay/Gulf
Flood Zone: AE,AE
Alternate Key #: 1495140
Handicap Access: Yes
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 OR145
Taxes: 17068.9
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 33
Street Name: Pen Key
Street Suffix: 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: No
Control Depth: 5
Lot Size: 103 x 126 x 103 x 125
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 your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort‑style living awaits in this Key West-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined by serenity and sophistication.
A palm‑lined entrance leads to a vibrant exterior with wraparound porches and sun‑filled interiors framed by lush garden views. The spacious three‑bedroom layout is designed for effortless indoor‑outdoor living, with multiple gathering spaces opening to expansive patios ideal for entertaining, unwinding, or savoring golden sunsets. Mature palms, bougainvillea, and the scent of salt air create a secluded sanctuary that feels worlds away.
Residents enjoy exclusive access to a resort‑style pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to world‑class sport fishing and boating, while full‑time on‑site property management ensures peace of mind whether you're home or away.
Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world.
Whether you're seeking a seasonal escape or a long‑term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.
Directions: Call listing agents to provide access to the gate and directions to the house.
Thank you.
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 $: 50000
Maintenance Fee $: 695.83
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
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
Bay Front: 1
Gulf Front: 1
Waterview
No Waterview: 1
Floor
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
Window Treatments: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Guest/Servant Qtrs: Legal
Laundry Room: 1
Utility Room: 1
Building Style
Above Flood: Yes
Stories: 2 Stories
Other Bldg Style: 1
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Car(s): 3
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
Windowed P/B: 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
Parking: 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: Bay Front; Gulf Front
Waterview: No Waterview
Dockage: Assigned Dock; Basin; Boat Slip; Dock Privileges
Property Condition: Updated/Remodeled
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); Window Treatments
Pre-Wired: Cable; Satellite
Specialty Rooms: Laundry Room; Utility Room
Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Microwave; Oven; Range; Refrigerator; Washer; Wine Cooler
Exterior Features: Lighting; Rain Gutters; Sprinkler System
Accessibility Feat: Accessible Elevator Installed; Parking
Pool Info: In Ground; Above Ground; Concrete; Decked
Construction: CBS
Floor: 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: January - 26 - 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.