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33 Pen Key

Islamorada, FL 33036

$2,195,000 $9,254/Mo

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Overview

Bed

Bath

4,537

Sqft

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 palm s, 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.

Property Details

Property Type : Residential - Single Family

Price : $2,195,000

AD Id : 77638460

MLS Id : 619577

Beds : 3

Living Area Size : 4,537

Year Built : 1987

County : Monroe

Map

What's Nearby

Nearby Areas

Features

Bedroom Information

Total Bedrooms: 3 Laundry Room,Utility Room

Bathroom Information

Total Baths: 4 Full Baths: 3 Half Baths: 1
Interior Features

Drapes/Blinds Incl,Window Treatments,Quartz Countertops,Built-in Cabinets,Walk-in Closet(s),Storage,Smoke Alarms,Elevator,Pantry,Split Bedroom,Cathedral Ceilings Dual Flush Appliances: Washer,Wine Cooler,Gas Appliances,Freezer,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer
Roofing Information

Metal Roof

Flooring Information

Tile,Carpet,Wood

Heating & Cooling

Cooling: Central Air,Ductless,Ceiling Fans(s) Heating: Central,Ductless Water Front: No Bay Front,None,Open Water,Gulf Front No Waterview

Window Information

Window Treatments: Impact Rstnce Window,Impact Rstnce Doors

Building Information

Year Built: 1987 Total Units: 0.00 Floor Location: 12927 Construction: CBS Security System: Electric Gate Roof: Metal Roof
Exterior Features

Rain Gutters,Sprinkler System,Lighting

Pool Information

In Ground,Decked,Concrete,Above Ground
Guest House Information

Legal

Lot Information

Lot Dimensions: X Lot SqFt: 12,927 Lot SqFt Source: Tax Records 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
Property Information

SQ ft (Living Area): 4,537 View: No Waterview Subdivision: Penn Key Club (83.0) Stories: 2 Stories

Listing Price Information

List Price: $2,195,000
Listing Information

No Seller Finance,Conventional,Cash

Tax Information

Taxes: $17,069 Tax Year: 2025 Parcel Number: 00402800-000000 Tax Exemptions: None

Multi-Unit Information

Pets Allowed: Pets Allowed
Homeowners Association Information

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: $50000.00 Maintenance Fee: $695.83 Assoc/Mnt Fee Per: Monthly

Utility Information

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

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Nearby Home Value

Address	Estimate	Bed	Bath	Sq. Ft	Lot Size
109 Columbus Dr, Islamorada, FL, 33036	$6,700,000	4	5	--
82719 Old Hwy, Islamorada, FL, 33036	$24,995,000	7	11	10,182	10,182 SqFt
75761 Overseas Hwy, Islamorada, FL, 33036	$4,999,900	4	4	3,001	3,001 SqFt
122 Court Contessa, Islamorada, FL, 33036	$2,795,000	3	3	2,374	2,374 SqFt
Residential, Islamorada, FL, 33036	$2,649,000	3	4	1,768	1,768 SqFt
82768 Overseas Highway, Islamorada, FL, 33036	$25,000,000	7	10	8,288	8,288 SqFt
111 Anglers Way, Islamorada, FL, 33036	$1,199,990	2	3	1,376	1,376 SqFt
20 Avacado St, Islamorada, FL, 33036	$15,950,000	6	7	6,680	6,680 SqFt
75840 Overseas Highway, Islamorada, FL, 33036	$13,950,000	7	7	--
74049 Overseas, Islamorada, FL, 33036	$3,999,999	4	4	--