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$26,400,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 7 Beds
  • 6 Full Baths
  • 4 Partial Baths
  • 8,988 Sq. Ft.
  • Updated 32 minutes ago
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Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8,988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

Full Property Details for 89505 Old Hwy

General

  • Price: $26,400,000
  • Taxes: $58,331 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 620022
  • Updated: Today (5/24/2026)
  • Added to Site: Today

Interior

  • Interior Features: Utility Room, Entrance Foyer, Walk-in Closet(s), Bar, Built-in Cabinets, Cathedral Ceilings, Drapes/Blinds Incl, Elevator, Fireplace(s), Granite Counter Top, Security System, Smoke Alarms, Split Bedroom, Storage, Wet Bar, Gym, Loft, Sauna, Sun/Florida Room
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Gas Appliances, Ice Machine, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
  • Flooring: Wood, Tile, Marble

Rooms

Bathrooms

  • Total Bathrooms: 10
  • Full Bathrooms: 6
  • Half Bathrooms: 4

Bedrooms

  • Total Bedrooms: 7

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Community Boat Ramp, Bike Paths, Beach, Tennis Court(s), Pool
  • Pool: Yes
  • Pool Description: Concrete, Heated, Salt Water, In Ground, Decked
  • Security/Safety: Electric Gate, On Premises System, Patrolled Area

Exterior

  • Exterior Features: Tennis Court(s), Lighting, Bar, Built-in Grill, Chickee Hut, Detached Guest Qtrs, Fencing, Gazebo, Hot Tub, Lanai, Outdoor Kitchen, Outdoor Shower, Privacy Wall/Fence, Sandy Beach, Sprinkler System, Storage, Water Display
  • Deck/Patio: Screened Patio, Open Porch/Balcony, Deck, Patio
  • Porch/Patio/Deck: Screened Patio, Open Porch/Balcony, Deck, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Parking Features: Covered, Attached, Garage Door Opener

Location

  • Area: 25 - Plantation Key
  • County: Monroe
  • Subdivision: Trop Coral Reef (89.0)
  • Driving Directions: MM 89.5, Old Hwy, Gated.

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

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

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: Updated/Remodeled
  • Construction: CBS, Concrete
  • Roof: Metal
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
  • Square Feet: 8,988
  • Sq. Ft. Source: Property Data Card
  • Year Built: 2008
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Open Water View, Ocean
  • Lot Size (Acres): 7.64
  • Lot Size (Sq. Ft.): 207,346
  • Lot Size Source: Property Data Card
  • Lot Dimensions: x
  • Zoning: NR - Native Residential

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Oceanfront, Open Water

Financial Considerations

  • Tax Amount: $58,331.33
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: 5 63 38 Plantation Key Or Long Island Pt Govt Lot 6 & Adj Bay Btm Se'ly G37-221 Or186-271(Ii Deed 22485) Or556-986/89 Or
  • Flood Zone: VE, AE, AE, AE, VE, VE
  • APN: 92570000100

Listed by Ocean Sotheby's International Realty, Leslie Leopold (305) 942-0215 and Ocean Sotheby's International Realty, Cheri Tindall (305) 664-7661

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Listing agents

— 89505 Old Hwy —

  • Leslie Leopold

    Ocean Sotheby's International Realty

  • Cheri Tindall

    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

Schools serving 89505 Old Hwy

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-80.2 mi
Coral Shores High School
89901 Old Highway, Tavernier, FL 33070
9-120.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 89505 Old Hwy Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/24/2026
Listed
$26,400,000
725%
MLS
8/12/2004
Sold
$3,200,000
—
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 89505 Old Hwy

Year
Property Taxes
Change
Tax Assessment
Change
2024
$56,368
—
$6,460,158
3%
2024
$56,368
1%
$6,278,094
3%
2023
$56,000
—
$6,095,237
6%
2021
$55,852
2%
$5,745,346
-3%
2022
$54,927
-2%
$5,917,706
2%
2021
$55,852
1%
$5,788,167
5%
2019
$55,301
-4%
$5,508,906
-4%
2018
$57,534
-4%
$5,761,209
-9%
2017
$59,843
1%
$6,336,755
3%
2016
$59,158
3%
$6,148,676
24%
2015
$57,596
23%
$4,968,436
10%
2014
$46,678
-12%
$4,516,760
-11%
2013
$52,884
—
$5,072,845
—
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.

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NMLS#: 1598647

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Listed by Ocean Sotheby's International Realty, Leslie Leopold (305) 942-0215 and Ocean Sotheby's International Realty, Cheri Tindall (305) 664-7661

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89505 Old Highway, Upper Sugarloaf Key, FL 33070 (MLS# 620022) is a Single Family property with 7 bedrooms, 6 full bathrooms and 4 partial bathrooms. 89505 Old Highway is currently listed for $26,400,000 and was received on May 24, 2026. Want to learn more about 89505 Old Highway? Do you have questions about finding other Single Family real estate for sale in Upper Sugarloaf Key? You can browse all Upper Sugarloaf Key real estate or contact a Coldwell Banker agent to request more information.

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