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$27,800,000

  • For Sale
  • Active
  • Single Family
  • 7 Beds
  • 6 Full Baths
  • 4 Partial Baths
  • 8,988 Sq. Ft.
  • Updated 3 hours ago
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Escape to Palm Paradise, a one-of-a-kind oceanfront estate in Islamorada, Florida Keys, where luxury and privacy intertwine on 7.64 secluded acres. This magnificent property boasts 369 feet of pristine ocean frontage, revealing breathtaking panoramic views from nearly every corner. The sprawling 8,988 square foot main residence boasts five spacious bedrooms, five full bathrooms, three half bathrooms, and an array of lavish amenities, including a chef's dream kitchen, a 500-bottle wine cellar, a private gym, an elevator, and a custom pool with a soothing water feature. Expansive outdoor living spaces beckon with a tiki bar, outdoor kitchen, beachside fire pit, lighted tennis court with cabana and half bathroom, and a private beach fringed with swaying palms. A separate two bedroom, one bathroom guest house provides privacy and comfort for visitors, while a whole-house generator ensures uninterrupted tranquility. Indulge in breathtaking sunrises from your private observation pier or perfect your short game on the estate's putting green. Palm Paradise is more than just a home; it's an invitation to embrace a life of unparalleled luxury, seclusion, and the laid-back allure of the Florida Keys.

Full Property Details for 89505 Old Hwy

General

  • Price: $27,800,000
  • Taxes: $56,367 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 616051
  • Updated: 5/13/2026
  • Added to Site: 281 day(s) ago

Interior

  • Interior Features: Utility Room, Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, 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, Patrolled Area

Exterior

  • Exterior Features: Tennis Court(s), Lighting, Bar, Built-in Grill, Chickee Hut, Detached Guest Qtrs, Fencing, 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
  • Parking Features: Covered, Garage Door Opener

Location

  • Area: 25 - Plantation Key
  • County: Monroe
  • Subdivision: Trop Coral Reef (89.0)
  • Driving Directions: MM 89.5 oceanside Old Hwy. No sign on property.

Community

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

Heating & Cooling

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

Structural Information

  • Architectural Style: Above Flood
  • 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

Lot Features

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

Water Features

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

Financial Considerations

  • Tax Amount: $56,367.5
  • Tax Year: 2024

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: 00092570-000100

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
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1283.3 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
12/01/2025
Price Reduced
$27,800,000
-3.47%
MLS
8/05/2025
Listed
$28,800,000
800%
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
—
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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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*These costs are estimates, and the interest rates assume exceptional credit standing.

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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# 616051) is a Single Family property with 7 bedrooms, 6 full bathrooms and 4 partial bathrooms. 89505 Old Highway is currently listed for $27,800,000 and was received on August 05, 2025. 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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