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: 6/19/2026

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# 619577

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: 2026-04-21 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 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: 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 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.

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

None: 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 Open Water: 1 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 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: 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: June - 19 - 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.

Search powered by FBS Products