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33 Pen Key Drive, Upper Matecumbe Key Islamorada, FL 33036

$2,495,000
Property Type: Residential Bedrooms: 3 Baths: 3 Square Footage: 4,537 Lot Size (sq. ft.): 12,927 Status: Active
Current Price: $2,495,000 List Date: 8/01/2025 Last Modified: 9/03/2025

Description

Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where privacy, elegance, and world-class amenities converge. This expansive Key West-style residence is nestled within one of the Florida Keys' most prestigious gated communities, offering full-time property management, a protected marina, and a lifestyle defined by serenity and sophistication. From the moment you pass through the palm-lined entrance, you're surrounded by manicured tropical beauty. The home's vibrant exterior, wraparound porches, and timeless craftsmanship evoke classic island charm, while interiors are bathed in natural light and framed by lush garden views. Designed for effortless indoor-outdoor living, the spacious three-bedroom layout opens to expansive patios ideal for entertaining or quiet reflection. Towering palms, mature trees, and vibrant bougainvillea create a secluded sanctuary, while the scent of salt air and golden sunsets set the tone for unforgettable evenings. Enjoy exclusive access to a resort-style pool, private beach, kayak launch, the sunset point, and a full-service marina with direct access to world-class sport fishing and boating. Full-time on-site property managers ensure peace of mind, whether you're in your residence or away for the season. Located in the heart of Islamorada, this property offers unmatched proximity to fine dining, boutique shopping, and the legendary waters of the sport fishing capital of the world. Whether you're seeking a seasonal escape or a legacy investment, this home offers the perfect blend of luxury, leisure, and long-term value. Schedule your private tour today and experience the rare combination of privacy, prestige, and paradise.

More Information MLS# 616008

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: 2025-08-01 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 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 OR145 Taxes: 10525.58 Tax Year: 2024 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: Yes 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: 2 Half Baths: 1 Total Baths: 3

Remarks & Misc

Remarks – Consumer: Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where privacy, elegance, and world-class amenities converge. This expansive Key West-style residence is nestled within one of the Florida Keys' most prestigious gated communities, offering full-time property management, a protected marina, and a lifestyle defined by serenity and sophistication. From the moment you pass through the palm-lined entrance, you're surrounded by manicured tropical beauty. The home's vibrant exterior, wraparound porches, and timeless craftsmanship evoke classic island charm, while interiors are bathed in natural light and framed by lush garden views. Designed for effortless indoor-outdoor living, the spacious three-bedroom layout opens to expansive patios ideal for entertaining or quiet reflection. Towering palms, mature trees, and vibrant bougainvillea create a secluded sanctuary, while the scent of salt air and golden sunsets set the tone for unforgettable evenings. Enjoy exclusive access to a resort-style pool, private beach, kayak launch, the sunset point, and a full-service marina with direct access to world-class sport fishing and boating. Full-time on-site property managers ensure peace of mind, whether you're in your residence or away for the season. Located in the heart of Islamorada, this property offers unmatched proximity to fine dining, boutique shopping, and the legendary waters of the sport fishing capital of the world. Whether you're seeking a seasonal escape or a legacy investment, this home offers the perfect blend of luxury, leisure, and long-term value. Schedule your private tour today and experience the rare combination of privacy, prestige, and paradise. 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 $: 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

None: 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 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

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 Property Condition: Updated/Remodeled Building Style: Other Bldg Style Vehicle Storage: Garage; Attached; Auto Door Opener; Guest Parking; Off Street Parking; Open Parking 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 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: September - 03 - 2025
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