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$2,495,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,537 Sq. Ft.
  • Updated 4 days ago
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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.

Full Property Details for 33 Pen Key Dr

General

  • Price: $2,495,000
  • HOA FEE: $745/month
  • Taxes: $10,525 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 616008
  • Updated: 1/12/2026
  • Added to Site: 168 day(s) ago

Interior

  • Rooms/Areas: Laundry Room, Utility Room
  • 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
  • Appliances: Washer, Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • Furnishings: Negotiable
  • Flooring: Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Shared Amenities: Community Pool, Other Area Features, Beach, Manager on Premises, Community Dockage
  • Pool: Yes
  • Pool Description: In Ground, Decked, Concrete, Above Ground
  • Security/Safety: Electric Gate

Exterior

  • Exterior Features: Rain Gutters, Sprinkler System, Lighting
  • Deck/Patio: Open Porch/Balcony, Screened Patio, Windowed P/B, Screened P/B

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 3
  • Parking: Garage, Off Street Parking, Guest Parking, Open Parking, Auto Door Opener, Attached

Location

  • Area: 23 - Upper Matecumbe
  • County: Monroe
  • Subdivision: Penn Key Club (83.0)
  • Driving Directions: GPS

Community

  • Assoc. Fees Include: Common Area Mnt, Other, Security
  • Pets Allowed: Yes

Heating & Cooling

  • Cooling Type: Central Air, Ductless, Ceiling Fans(s)
  • Heating Type: Central, Ductless

Utilities

  • Water: No Waterview
  • Utility Description: FKAA, Propane, Satellite Dish, Cable Available, Buyer to Verify, Municipal Sewer

Structural Information

  • Architectural Style: Single Family
  • Construction Status: Updated/Remodeled
  • Construction: CBS
  • Roof: Metal Roof
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
  • Sprinklers: Yes
  • Wiring: Cable, Satellite
  • Disability Access: Yes
  • Stories/Levels: 2 Stories
  • Square Feet: 4,537
  • Sq. Ft. Source: Tax Records
  • Year Built: 1987
  • Property Condition: Updated/Remodeled

Lot Features

  • Lot Size (Sq. Ft.): 12,927
  • Lot Dimensions: 103 x 126 x 103 x 125
  • Zoning: R1 - Residential Single Family

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Type: None
  • Boat Dock Slip: Yes
  • Dock Description: Dock Privileges, Basin, Boat Slip, Assigned Dock

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $745
  • Assoc Fee Freq.: Monthly
  • Tax Amount: $10,525
  • Tax Year: 2024
  • Terms: No Seller Finance, Conventional, Cash

Disclosures and Reports

  • Legal Description: 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
  • Restrictions: Yes
  • Flood Zone: AE, AE
  • APN: 00402800-000000

Listed by Ocean Sotheby's International Realty, Eric M. Rizzo (305) 394-3062 and Ocean Sotheby's International Realty, Taylor Globus (305) 401-7675

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Listing agents

— 33 Pen Key Dr —

  • Eric M. Rizzo

    Ocean Sotheby's International Realty

  • Taylor Globus

    Ocean Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Price & Sales History for 33 Pen Key Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/01/2025
Listed
$2,495,000
206.13%
MLS
8/08/2012
Sold
$815,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 33 Pen Key Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$10,526
—
$1,795,418
61%
2024
$10,526
1%
$1,116,839
3%
2023
$10,451
—
$1,084,310
6%
2021
$10,429
1%
$1,022,067
-3%
2022
$10,299
-1%
$1,052,729
4%
2021
$10,429
1%
$1,007,956
2%
2019
$10,302
2%
$985,295
2%
2018
$10,060
4%
$966,924
2%
2017
$9,667
-3%
$947,037
2%
2016
$10,010
-4%
$927,559
-6%
2015
$10,454
—
$989,488
1%
2014
$10,466
-10%
$981,635
-6%
2013
$11,590
—
$1,040,313
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 33 Pen Key Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Ocean Sotheby's International Realty, Eric M. Rizzo (305) 394-3062 and Ocean Sotheby's International Realty, Taylor Globus (305) 401-7675

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33 Pen Key Drive, Islamorada, FL 33036 (MLS# 616008) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 33 Pen Key Drive is currently listed for $2,495,000 and was received on August 01, 2025. Want to learn more about 33 Pen Key Drive? Do you have questions about finding other Single Family real estate for sale in Islamorada? You can browse all Islamorada real estate or contact a Coldwell Banker agent to request more information.

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