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
...
(Read more)
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.
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.
