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.
For sale
$2,495,000
33 Pen Key Clb, Islamorada, FL 33036
3beds
4,537sqft
Est.:
Single Family Residence
Built in 1987
0.3 Acres Lot
$2,335,600 Zestimate®
$550/sqft
$50,696/mo HOA
What's special
Private beachKey west-inspired residenceTimeless architectural charmKayak launch
- 13 days |
- 881 |
- 13 |
Zillow last checked: 8 hours ago
Listing updated: January 26, 2026 at 12:11am
Listed by:
Eric M. Rizzo 305-394-3062,
Ocean Sotheby's International Realty,
Taylor Globus 305-401-7675,
Ocean Sotheby's International Realty
Source: FLKMLS,MLS#: 618190
Originating MLS: Florida Keys
Originating MLS: Florida KeysTour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Heating
- Central, Ductless
Cooling
- Central Air, Ductless, Ceiling Fans(s)
Appliances
- Included: Washer, Wine Cooler, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
- Laundry: Laundry Room
Features
- Built-in Cabinets, Quartz Countertops, Walk-In Closet(s), Storage, Elevator, Pantry, Split Bedroom, Cathedral Ceiling(s), Utility Room
- Flooring: Tile, Wood
- Doors: Impact Rstnce Doors
- Windows: Drapes/Blinds Incl, Window Treatments, Impact Rstnce Window
Interior area
- Total interior livable area: 4,537 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Garage, Vehicle Restrictions, Off Street, Guest, Open, Garage Door Opener, Attached
- Has attached garage: Yes
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Yes, Accessible Elevator Installed, Parking
Features
- Levels: Two
- Stories: 2
- Patio & porch: Open Porch/Balcony, Screened Patio, Windowed P/B, Screened P/B
- Exterior features: Rain Gutters, Sprinkler System, Lighting, Boat Slip
- Has private pool: Yes
- Pool features: In Ground, Decked, Concrete, Above Ground
- Water view: None
- Waterfront features: Bay Front, Gulf Front, Seawall: Cut/Natural, Dock: Wood, Dockage: Dock Privileges, Basin, Boat Slip, Assigned Dock
Lot
- Size: 0.3 Acres
- Dimensions: 103 x 126 x 103 x 125
- Features: 1/4 - 1/2 Acre
Details
- Additional structures: Guest House
- Parcel number: 00402800000000
- Zoning: R1
- Zoning description: Residential Single Family
- Special conditions: Standard
- Other equipment: Satellite Dish, Satellite
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other Bldg Style
- Property subtype: Single Family Residence
Materials
- CBS
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1987
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA, Propane, Cable Available, Buyer to Verify, Cable Connected
Green energy
- Water conservation: Dual Flush
Community & HOA
Community
- Features: Pool, Other, Beach, Manager on Premises, Community Dockage
- Security: Smoke Detector(s), Electric Gate
- Subdivision: Penn Key Club (83.0)
HOA
- Has HOA: Yes
- Services included: Maintenance Grounds, Other, Security
- HOA fee: $50,000 monthly
- Second HOA fee: $696 monthly
Location
- Region: Islamorada
Financial & listing details
- Price per square foot: $550/sqft
- Tax assessed value: $1,795,418
- Annual tax amount: $17,068
- Date on market: 1/23/2026
- Listing terms: No Seller Finance,Conventional,Cash
Estimated market value
$2,335,600
$2.22M - $2.45M
$6,599/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/23/2026 | Listed for sale | $2,495,000$550/sqft |
Source:  FLKMLS #618190 Report a problem | ||
| 1/19/2026 | Listing removed | $2,495,000$550/sqft |
Source:  Key West AOR #616008 Report a problem | ||
| 8/1/2025 | Listed for sale | $2,495,000-10.9%$550/sqft |
Source: Key West AOR #616008 Report a problem | ||
| 8/1/2025 | Listing removed | $2,800,000$617/sqft |
Source: Key West AOR #613198 Report a problem | ||
| 1/18/2025 | Listed for sale | $2,800,000+243.6%$617/sqft |
Source: Key West AOR #613198 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $17,069 +62.2% | $1,795,418 +60.8% |
| 2024 | $10,526 +0.7% | $1,116,839 +3% |
| 2023 | $10,451 +1.5% | $1,084,310 +3% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$65,691/mo
Principal & interest
$12417
HOA Fees
$50696
Other costs
$2578
Climate risks
Neighborhood: 33036
Nearby schools
GreatSchools rating
- 10/10Plantation Key SchoolGrades: PK-8Distance: 6.5 mi
- 4/10Coral Shores High SchoolGrades: 9-12Distance: 6.8 mi
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