33 Pen Key Dr

Islamorada, FL 33036

$2,495,000
Price
3
Beds
4,537 Sq. Ft.
$550 / Sq. Ft.
4,537
Sq. Ft.
$550
per Sq. Ft.
Pen Key Sunsets
a view of a porch with wooden floor and furniture
a view of a house with a porch
a view of front door of house
a front view of a house with a yard
33 PKC
a view of a house with large trees
a view of a field with trees in the background
a view of a house with backyard and trees
a view of a house with a tree and a yard
a balcony with chairs and a table
a very nice looking room with a large window
a living room with furniture and wooden floor
a living room with furniture and a book shelf
a living room with furniture and a book shelf
Living Room
a large kitchen with a table and chairs
a living room filled with furniture and a wooden floor
Kitchen From Hallway
a kitchen with stainless steel appliances kitchen island granite countertop a stove and a refrigerator
a living room with stainless steel appliances kitchen island a table and chairs in it
a kitchen with a stove a sink and a refrigerator
a view of a walk in closet
Elevator
a bathroom with a toilet a sink and mirror
a bed sitting in a bedroom next to a window
a bedroom with a bed and a window
a bathroom with a granite countertop sink a toilet and shower
a view of a living room with windows
a bathroom with a sink a toilet and a mirror
a bedroom with a bed and a couch
a spacious bedroom with a bed a couch and dresser with wooden floor
a large bedroom with a bed and wooden floor
a bathroom with a sink and a mirror
a bathroom with a sink a toilet and shower
Closet In Primary Bedroom
Second Closet In Primary Bedroom
a view of entryway and hall with wooden floor
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a living room with furniture
a bedroom with a bed and wooden floor
a bedroom with a bed and a chandelier
a view of small space
a bathroom with a sink a toilet and shower
a living room with furniture and a couch
Attic Storage
a storage room
a view of a room with lots of white furniture
a view of a balcony
a view of a house with a yard
a view of a backyard with plants
view of a yard
Aerial Community View
a view of an ocean
a view of a door with a tree
Pen Key Club Aerial
a view of a lake with an outdoor space
a view of a lake with a city
a ocean view with beach

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...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.
  1. Listed by Eric M. Rizzo • Ocean Sotheby's International Realty
  2. Listed by Taylor Globus • Ocean Sotheby's International Realty

Property Details for 33 Pen Key Drive

Waterfront
Bay Front, Gulf Front
Waterfront
No
Zoning
R1 - Residential Single Family
Subdivision
Penn Key Club (83.0)
Directions
Call listing agents to provide access to the gate and directions to the house. Thank you.
Building Style
Other Bldg Style
Vehicle Storage
Garage, Vehicle Restrictions, Off Street Parking, Guest Parking, Open Parking, Auto Door Opener, Attached
Pets
Pets Allowed
LISTING UPDATED: 01/26/2026 08:11 AM

Property Details for 33 Pen Key Drive

StatusActive
MLS #618190
Days on Market16
Taxes$17,069 / year
HOA Fees$50,000 / month
Condo/Co-op Fees$696 / month
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1987
Lot Size0.30 AC / 12,927 SF
CountyMonroe County

Location

Listing Courtesy of Ocean Sotheby's International Realty
Add your commute

Building Information for 33 Pen Key Drive

Stories2Year Built1987Building Size-Lot Size0.30 AC / 12,927 SF

Payment Calculator

$64,279 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,160

Property Taxes

$1,422

HOA Dues

$50,696

The Payment Calculator is for illustrative purposes only.

Property Information for 33 Pen Key Drive

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 23 - Upper Matecumbe
  • Absolute Longitude: 80.620996
  • Control Depth: 5
  • Off Shore Island: No
  • Listing Board: Florida Keys
  • Side: Bay/Gulf
  • Mile Marker: 83.0
  • Marathon Neighborhood: N/A
  • Accessibility Feat: Accessible Elevator Installed, Parking
  • Neighborhood Feature: Community Pool, Other Area Features, Beach, Manager on Premises, Community Dockage
  • Key/Island: Upper Matecumbe Key Islamorada
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: Condo Doc's: Yes
  • Association Info: Voluntary Home Owners Asc: No
  • Association Info: 1st Right of Refusal: Yes
  • Association Info: Assoc Approval Req: Yes
  • Fee Includes: Common Area Mnt, Other, Security
  • Furnished: Negotiable
  • Tax Year: 2025
  • Tax Exemptions: Homestead, Widow/Widower
Virtual Tour
Property
Lot Information
  • Lot Size: 103 x 126 x 103 x 125
  • Acres: 0.3
  • Land Size: 1/4 - 1/2 Acre
Property and Assessments
  • 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
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Tax Records
  • Flood Zone: AE,AE
  • Rentals Allowed: No
  • Deed Restrictions: Yes
  • Picture Count: 60
  • Document Count: 5
  • Building Style: Above Flood: Yes
  • Property Condition: Updated/Remodeled
  • Security: Electric Gate
  • Title: Title Ins - Buyer
Utilities
  • Utilities: FKAA, Propane, Satellite Dish, Cable Available, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: No
  • Pool: Yes
  • Handicap Access: Yes
  • Pool Info: In Ground, Decked, Concrete, Above Ground
  • Porch/Balcony: Open Porch/Balcony, Screened Patio, Windowed P/B, Screened P/B
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • GF-Interior Features: Dual Flush
  • Interior Features: Drapes/Blinds Incl, Built-in Cabinets, Quartz Countertops, Window Treatments, Walk-in Closet(s), Storage, Smoke Alarms, Elevator, Pantry, Split Bedroom, Cathedral Ceilings
  • Pre-Wired: Cable, Satellite
  • Appliances: Washer, Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Dockage: Dock: Wood
  • Dockage: Seawall: Cut/Natural
  • Construction: CBS
  • Dockage: Dock Privileges, Basin, Boat Slip, Assigned Dock
  • Exterior Features: Rain Gutters, Sprinkler System, Lighting
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
Room Information
  • Specialty Rooms: Laundry Room, Utility Room
  • Specialty Rooms: Guest/Servant Qtrs: Legal

Property History for 33 Pen Key Drive

DateEvent & SourcePriceAppreciation
Jan 23, 2026

Listed (Active)

FKMLS #618190

$2,495,000—
Jan 19, 2026

Temp Off Market

FKMLS #616008

$2,495,000—
Jan 17, 2026

Expired

FKMLS #613198

$2,800,000—
Aug 1, 2025

Temp Off Market

FKMLS #613198

—
Aug 1, 2025

Listed (Active)

FKMLS #616008

$2,495,000—
Jan 17, 2025

Listed (Active)

FKMLS #613198

$2,800,000—
DateEvent & SourcePrice
01/23/2026

Listed (Active)

FKMLS #618190

$2,495,000
01/19/2026

Temp Off Market

FKMLS #616008

$2,495,000
01/17/2026

Expired

FKMLS #613198

$2,800,000
08/01/2025

Temp Off Market

FKMLS #613198

—
08/01/2025

Listed (Active)

FKMLS #616008

$2,495,000
01/17/2025

Listed (Active)

FKMLS #613198

$2,800,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 33 Pen Key Drive

This home is within Monroe.
Rating
School
Type
Grades
Distance
Plantation Key School
Public - PK to 8
Coral Shores High School
Public - 9 to 12
Treasure Village Montessori Charter School
Charter - PK to 8
Upper Keys Academic Connections for Excellence
Public - 6 to 12
Rating
School
Distance
Plantation Key School
PublicPK to 8

Coral Shores High School
Public9 to 12

Treasure Village Montessori Charter School
CharterPK to 8

Upper Keys Academic Connections for Excellence
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 33 Pen Key Drive, Islamorada, FL 33036

33 Pen Key Drive is a single family home for sale in Islamorada, FL 33036. This property was listed for sale on January 23, 2026 by Ocean Sotheby's International Realty, it's currently listed at $2,495,000. This listing's school district is Monroe. Nearby schools include Plantation Key School, Coral Shores High School and Treasure Village Montessori Charter School. 33 Pen Key Drive is a 3-bed, 4-bath, 4,537 sqft single family home built in 1987.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Ocean Sotheby's International Realty

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.