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33 Pen Key, Upper Matecumbe Key Islamorada, FL 33036

$2,195,000
Property Type: Residential Bedrooms: 3 Baths: 4 Square Footage: 4,537 Lot Size (sq. ft.): 12,927 Status: Active
Current Price: $2,195,000 List Date: 4/21/2026 Last Modified: 4/21/2026

Overview

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 bre ...

Listing Details MLS# 619577

Location, Tax & Legal

Street #
33
Street Name
Pen Key
Key/Island
Upper Matecumbe Key Islamorada
State/Province
FL
Zip Code
33036
County
Monroe
Subdivision
Penn Key Club (83.0)
Area
23 - Upper Matecumbe
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

Contract Information

Listing Board
Florida Keys
As is Rght to Inspct
Yes
Potential Short Sale
No
Bank Owned
No
Species List
No

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
No
Control Depth
4
Pool
Yes
Year Built
1987
Lot SqFt
12927
Lot Sqft Source
Tax Records
Acres
0.3
Living Apx SqFt
4537
SqFt Source
Tax Records
Total Bedrooms
3
Full Baths
3
Half Baths
Yes
Total Baths
4
Rentals Allowed
No
Total Units
0

Association Info

Mandatory Home Owners Asc
Yes
Condo Doc's
Yes
Voluntary Home Owners Asc
No
1st Right of Refusal
Yes
Assoc Approval Req
Yes
Association Fee $
50000
Maintenance Fee $
695.83
Assoc/Mnt Fee Per
Monthly

Dockage

Dock
Wood
Seawall
Cut/Natural
Assigned Dock
Yes
Basin
Yes
Boat Slip
Yes
Dock Privileges
Yes

More Information

Building Style

Above Flood
Yes
Stories
2 Stories
Other Bldg Style
Yes

Vehicle Storage

Car(s)
3
Garage
Yes
Guest Parking
Yes
Open Parking
Yes
Vehicle Restrictions
Yes
Attached
Yes
Auto Door Opener
Yes
Off Street Parking
Yes

Specialty Rooms

Guest/Servant Qtrs
Legal
Laundry Room
Yes
Utility Room
Yes

Financial Status

Auction
No
Bank Owned
No
Potential Short Sale
No
Standard Sale
Yes

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 arrange access through the gate.

Fee Includes

Common Area Mnt
Yes
Security
Yes
Other
Yes

Tax Exemptions

None
Yes

Appliances

Dishwasher
Yes
Disposal
Yes
Dryer
Yes
Freezer
Yes
Gas Appliances
Yes
Microwave
Yes
Oven
Yes
Range
Yes
Refrigerator
Yes
Washer
Yes
Wine Cooler
Yes

Pets

Pets Allowed
Yes

Cooling

Ceiling Fans(s)
Yes
Central Air
Yes
Ductless
Yes

Heating

Central
Yes
Ductless
Yes

Waterfront

Bay Front
Yes
Gulf Front
Yes
Open Water
Yes
None
Yes

Waterview

No Waterview
Yes

Floor

Carpet
Yes
Tile
Yes
Wood
Yes

Neighborhood Feature

Beach
Yes
Community Dockage
Yes
Community Pool
Yes
Manager on Premises
Yes
Other Area Features
Yes

Interior Features

Built-in Cabinets
Yes
Cathedral Ceilings
Yes
Drapes/Blinds Incl
Yes
Elevator
Yes
Pantry
Yes
Quartz Countertops
Yes
Smoke Alarms
Yes
Split Bedroom
Yes
Storage
Yes
Walk-in Closet(s)
Yes
Window Treatments
Yes

Property Condition

Updated/Remodeled
Yes

Windows/Doors

Impact Rstnce Doors
Yes
Impact Rstnce Window
Yes

Security

Electric Gate
Yes

Construction

CBS
Yes

Land Size

1/4 - 1/2 Acre
Yes

Furnished

Negotiable
Yes

Terms

Cash
Yes
Conventional
Yes
No Seller Finance
Yes

Utilities

Buyer to Verify
Yes
Cable Available
Yes
FKAA
Yes
Municipal Sewer
Yes
Propane
Yes
Satellite Dish
Yes

Porch/Balcony

Open Porch/Balcony
Yes
Screened P/B
Yes
Screened Patio
Yes
Windowed P/B
Yes

Title

Title Ins - Buyer
Yes

Exterior Features

Lighting
Yes
Rain Gutters
Yes
Sprinkler System
Yes

Pool Info

In Ground
Yes
Above Ground
Yes
Concrete
Yes
Decked
Yes

Pre-Wired

Cable
Yes
Satellite
Yes

Roof

Metal Roof
Yes

Accessibility Feat

Accessible Elevator Installed
Yes
Parking
Yes

GF-Interior Features

Dual Flush
Yes

Property Features

Fee Includes: Common Area Mnt; Security; Other Tax Exemptions: None Waterfront: Bay Front; Gulf Front; Open Water; None 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: 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: April - 21 - 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.