33 Pen Key Clb, Islamorada, FL 33036
Property image
Property image
FOR SALE
0.3 ACRES

33 Pen Key Clb
Islamorada, FL 33036

  • 3 Beds
  • 3.5 Baths
  • 4,537 sqft (on 0.30 acres)

$2,195,000

Est. Mortgage $62,871/mo*
Get Pre-Qualified

$2,195,000

Est. Mortgage $62,871/mo*
Get Pre-Qualified
3 Beds
3.5 Baths
4,537 sqft
(on 0.30 acres)

Home Highlights

Parking
Attached Garage
Outdoor
Porch, Patio, Pool
Climate Control
Heating & Cooling
HOA
$50,000/Monthly
Price/Sqft
$484
Listed
106 days ago

Local Information

  • Map ViewExplore the area around 33 Pen Key Clb.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.

Home Details for 33 Pen Key Clb

Interior Features

Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4537 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine CoolerDishwasherDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s),DuctlessHas HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile, Wood, Carpet
Levels, Entrance, & Accessibility
Accessibility: Accessible Elevator Installed, ParkingElevatorFloors: Tile, Wood, Carpet
View
No View
Security
Security: Security Gate

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, Windowed P/B, Screened PatioExterior: Rain Gutters, LightingHas a Private Pool
Parking & Garage
Has a GarageHas an Attached GarageHas Open ParkingParking: Attached,Garage Door Opener,Open
Pool
Pool: In Ground, Above Ground, Concrete, DeckedPool
Frontage
Not on Waterfront

Days on Market

Days on Market: 106

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Other
Building
Construction Materials: CBSNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00402800000000

Price & Status

Price
List Price: $2,195,000Price Per Sqft: $484

Active Status

MLS Status: Active

Location

Direction & Address
City: Upper Matecumbe Key IslamoradaCommunity: Penn Key Club (83.0)

Agent Information

Listing Agent
Listing ID: 619577

Building

Building Area
Building Area: 4537 Square Feet

Community

Community Features: Community Dockage, Manager on Premises, Beach, OtherNot Senior Community

HOA

HOA Fee Includes: Common Area Mnt, Security, OtherHas an HOAHOA Fee: $50,000/Monthly

Lot Information

Lot Area: 0.30 acres

Offer

Listing Terms: No Seller Finance, Cash, Conventional

Miscellaneous

Mls Number: 619577

Additional Information

Community DockageManager on PremisesBeachOther
Last check for updates: about 8 hours ago
Listing courtesy of Eric M. Rizzo, (305) 394-3062
Ocean Sotheby's International Realty
Jamie Daniels, (305) 522-6872
Ocean Sotheby's International Realty
Source: FLKMLS, MLS#619577
Also Listed on FLKMLS, Key West AOR, Key West AOR.

Market trends in Islamorada

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.08M
$16.67KMoM
Sale-to-List Price
—
Price per sq ft
$710
$35MoM
Available listings
161
14MoM

Price History for 33 Pen Key Clb

DatePriceEventSource
04/21/2026$2,195,000Listed For SaleKey West AOR #619577
04/20/2026$2,495,000ListingRemovedFLKMLS #618190
01/23/2026$2,495,000Listed For SaleFLKMLS #618190
01/19/2026$2,495,000ListingRemovedKey West AOR #616008
08/01/2025$2,495,000Listed For SaleKey West AOR #616008
08/01/2025$2,800,000ListingRemovedKey West AOR #613198
01/18/2025$2,800,000Listed For SaleKey West AOR #613198
08/08/2012$815,000Sold
FLKMLS #558712
03/22/2012$925,000ListingRemovedAgent Provided
12/02/2011$925,000Listed For SaleAgent Provided
08/04/2011$925,000ListingRemovedAgent Provided
03/12/2010$925,000PriceChange
Agent Provided
01/10/2009$1,150,000Listed For SaleAgent Provided
04/17/1996$335,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$17,069
Assessment$1,795,418
Home facts updated by county records

Comparable Sales for 33 Pen Key Clb

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
82260 Overseas Hwy, Upper Matecumbe Key, FL
0.49
Single-Family Home
$880,000
04/15/26
3
3
2,314
82762 Overseas Hwy #3, Upper Matecumbe Key, FL
0.40
Single-Family Home
$1,700,000
03/30/26
4
4
2,728
130 N Hammock Rd, Islamorada, FL
0.41
Single-Family Home
$600,000
06/26/26
3
2
1,376
20 Park Rd, Islamorada, FL
0.48
Single-Family Home
$775,000
05/01/26
2
2
1,120
100 List St, Islamorada, FL
0.74
Single-Family Home
$5,400,000
05/08/26
3
2.5
3,019
19 Avacado St, Upper Matecumbe Key, FL
0.14
Single-Family Home
$12,000,000
02/13/26
5
6
5,489
19 Avacado Street Upper Matecumbe Ky, Islamorada, FL
0.14
Single-Family Home
$12,000,000
02/13/26
5
6
5,489
82779 Old Hwy #16, Islamorada, FL
0.26
Single-Family Home
$3,800,000
07/07/26
4
4.5
2,574
82207 Old Hwy, Islamorada, FL
0.79
Single-Family Home
$775,000
06/18/26
2
2
1,224

Nearby homes

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Assigned Schools

These are the assigned schools for 33 Pen Key Clb.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Islamorada

At least 24 Trulia users voted on each feature.

  • 88 % Say people would walk alone at night

  • 88 % Say parking is easy

  • 84 % Say it's dog friendly

  • 83 % Say yards are well-kept

  • 79 % Say car is needed

  • 72 % Say kids play outside

  • 70 % Say it's quiet

  • 67 % Say it's walkable to restaurants

  • 58 % Say they plan to stay for at least 5 years

  • 56 % Say there's holiday spirit

  • 54 % Say neighbors are friendly

  • 53 % Say there's wildlife

  • 44 % Say there are community events

  • 41 % Say it's walkable to grocery stores

  • 39 % Say streets are well-lit

  • 23 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • John Hermansen
    "Fishing tournaments and HOA lunches are nice. The marina is a great community and everyone on the airstrip are very kind. Great place for kids and dogs. "
    1
    Flag
  • Jnmarcil
    "The area is awesome. Safe, clean , everyone knows everyone and keep an eye out for our neighbors best place to live. "
    0
    Flag
  • Trulia User
    "Neighborhood feels safe and secure. I love the area. Live right near the Montessori school. Beware because there are sometimes fast drivers. "
    0
    Flag
  • Trulia User
    "Lots of grass to play in. Easy living in the Keys. Lots of places to run you dogs. Pebbles & Bambam enjoy it. "
    0
    Flag
  • Fabelomaribel
    "I've lived in this neighborhood for a while and the people are very nice I love my neighbor's the schools are closed by"
    1
    Flag
  • Cinnapep
    "Beautiful area with friendly people. Clean neighborhood and low crime rate. Very walkable with great galleries and restaurants. "
    0
    Flag
  • Jessica G.
    "I’ve lived here for almost 2 years now and i live net the boat ramp and everyone is very nice and the schools are close as they can be"
    0
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  • Jessica
    "It is near the high school and close to Winn Dixie along with close by gas stations .................."
    0
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  • Amie B.
    "we've lived her for 1 year and lovve it, beautiful ocean views and multi million dollar homes atl around. "
    0
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  • Lynne G.
    "Love it here in Safety Harbor. Everything about this home and neighborhood is wonderful. Kind neigbors, lovely views, best of Islamorada communities. Plenty to do if you are looking for it and plenty of peace & privacy at the same time. "
    0
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  • Lucytwo259
    "This is one of the best areas in Islamorada, It is a beautiful ocean-side location with easy ocean access. It is far enough away from the hustle and noise of the commercial area but not so far that it is inconvenient."
    0
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  • Kathy D.
    "Coral Harbour Club is located in the heart of Islamorada near shopping and dining."
    0
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  • Interested I. A.
    "Islamorada is a wonderful community with lots of things to do for all ages and lifestyles. Fishing, bird watching, hiking, swimming, snorkeling, kayaking, biking, running, great nightlife and restaurants. All around fun and relaxation!"
    0
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LGBTQ Local Legal Protections

Eric M. Rizzo, Ocean Sotheby's International Realty
Agent Phone: (305) 394-3062
MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.
33 Pen Key Clb, Islamorada, FL 33036 is a 3 bedroom, 4 bathroom, 4,537 sqft single-family home built in 1987. This property is currently available for sale and was listed by FLKMLS on Apr 21, 2026. The MLS # for this home is MLS# 619577.