$2,195,000
3 Beds
3.5 Baths
4,537 sqft (on 0.30 acres)
33 Pen Key Clb, Islamorada, FL 33036
Est. Mortgage $13,892/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 1987
0.3 acre lot
$484/sqft
Attached Garage
HOA $646/mo
Local Information
- Map ViewExplore the area around 33 Pen Key Clb.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
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.
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.
Last check for updates: about 7 hours ago
Listing courtesy of Eric M. Rizzo, (305) 394-3062
Ocean Sotheby's International Realty
Source: FLKMLS, MLS#619577
Also Listed on FLKMLS.
Home Details for 33 Pen Key Clb
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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 |
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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 |
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Days on Market: 153 |
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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 |
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Price List Price: $2,195,000Price Per Sqft: $484 |
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MLS Status: Active |
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Direction & Address City: Upper Matecumbe Key IslamoradaCommunity: Penn Key Club (83.0) |
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Listing Agent Listing ID: 619577 |
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Building Area Building Area: 4537 Square Feet |
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Community Features: Community Dockage, Manager on Premises, Beach, OtherNot Senior Community |
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HOA Fee Includes: Common Area Mnt, Security, OtherHas an HOAHOA Fee: $646/Monthly |
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Lot Area: 0.30 acres |
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Listing Terms: No Seller Finance, Cash, Conventional |
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Mls Number: 619577 |
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Community DockageManager on PremisesBeachOther |
Around this home
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
55 % 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.
Market trends in Islamorada
Last updated August 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
149
11MoM
Home Value
Trulia Estimate
$2.05MSince last month
Increased$1K (+0.1%)Since last year
Decreased$264K (-11.6%)Since last sale
Increased$1M (+147.9%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +26% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $2.02M |
| August 2026 | $2.02M |
| July 2026 | $2.02M |
| June 2026 | $2.03M |
| May 2026 | $2.05M |
| April 2026 | $2.09M |
| March 2026 | $2.29M |
| February 2026 | $2.3M |
| January 2026 | $2.36M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.49 | Single-Family Home | $880,000 | 04/15/26 | 3 | 3 | 2,314 | |
0.40 | Single-Family Home | $1,700,000 | 03/30/26 | 4 | 4 | 2,728 | |
0.41 | Single-Family Home | $600,000 | 06/26/26 | 3 | 2 | 1,376 | |
0.47 | Single-Family Home | $775,000 | 05/01/26 | 2 | 2 | 1,120 | |
0.74 | Single-Family Home | $5,400,000 | 05/08/26 | 3 | 2.5 | 3,019 | |
0.14 | Single-Family Home | $12,000,000 | 02/13/26 | 5 | 6 | 5,489 | |
0.79 | Single-Family Home | $775,000 | 06/18/26 | 2 | 2 | 1,224 | |
0.26 | Single-Family Home | $3,800,000 | 07/07/26 | 4 | 4.5 | 2,574 | |
0.39 | Single-Family Home | $650,000 | 12/30/25 | 2 | 1 | 882 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.09 | $4,236,400 | 4 | 4 | 3,044 | Off Market | |
0.07 | $1,412,100 | 3 | 2 | 1,552 | Off Market | |
0.12 | $15,950,000 | 6 | 7.5 | 6,680 | For Sale | |
0.14 | $13,750,000 | 5 | 6 | 5,489 | For Sale | |
0.17 | $6,750,000 | - | - | - | For Sale | |
0.16 | $3,139,400 | 5 | 4 | 2,845 | Off Market | |
0.18 | $2,100,000 | 3 | 3.5 | 2,036 | For Sale | |
0.18 | $825,000 | 2 | 2 | 1,275 | Recently Sold | |
0.18 | $1,050,000 | 2 | 2 | 1,275 | Recently Sold | |
0.18 | $905,000 | 2 | 2 | 1,275 | Recently Sold | |
0.18 | $859,300 | 2 | 2 | 1,275 | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Apr 21, 2026 Source: Key West AOR #619577 | Listed For Sale | $2,195,000 |
Apr 20, 2026 Source: FLKMLS #618190 | ListingRemoved | $2,495,000 |
Jan 23, 2026 Source: FLKMLS #618190 | Listed For Sale | $2,495,000 |
Jan 19, 2026 Source: Key West AOR #616008 | ListingRemoved | $2,495,000 |
Aug 1, 2025 Source: Key West AOR #616008 | Listed For Sale | $2,495,000 |
Aug 1, 2025 Source: Key West AOR #613198 | ListingRemoved | $2,800,000 |
Jan 18, 2025 Source: Key West AOR #613198 | Listed For Sale | $2,800,000 |
Aug 8, 2012 Source: FLKMLS #558712 | Sold | $815,000 |
Mar 22, 2012 Source: Agent Provided | ListingRemoved | $925,000 |
Dec 2, 2011 Source: Agent Provided | Listed For Sale | $925,000 |
Aug 4, 2011 Source: Agent Provided | ListingRemoved | $925,000 |
Mar 12, 2010 Source: Agent Provided | PriceChange | $925,000 Price decreased by 20% |
Jan 10, 2009 Source: Agent Provided | Listed For Sale | $1,150,000 |
Apr 17, 1996 Source: N/A | Sold | $335,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $17,069 | $1,795,418 |
Home facts updated by county records
LGBTQ Local Legal Protections
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.
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Frequently asked questions about 33 Pen Key Clb
- What is the estimated monthly payment for 33 Pen Key Clb?Based on a $2,195,000 list price with 20% down at today's rates, the estimated monthly payment for 33 Pen Key Clb in Islamorada, FL is approximately $13,471 (about $11,896 principal & interest, $1,500 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Islamorada?Residents describe Islamorada, FL as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Islamorada, FL.
- What are the closest schools to 33 Pen Key Clb?The closest schools to 33 Pen Key Clb in Islamorada, FL are Coral Shores High School (rated 5/10), Plantation Key School (Pre-K/Elementary/Middle, rated 10/10).
- What is 33 Pen Key Clb estimated to be worth?Trulia's estimated value for 33 Pen Key Clb in Islamorada, FL is $2,045,900.
- Does 33 Pen Key Clb have air conditioning?Yes, 33 Pen Key Clb in Islamorada, FL has air conditioning.
- Does 33 Pen Key Clb have a pool?Yes, 33 Pen Key Clb in Islamorada, FL has a pool.
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.