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$12,500,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1,243 Sq. Ft.
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Pure magic. Every step on this property is like a step back in time. Once you pass through the gated coral rock entrance you are instantly transported back to the Old Keys as you wind down the driveway through the shady tropical hammock and meander your way to the settler's beach home circa 1934. The charming 3/3 fishing cabin was meticulously updated to add modern comforts but still maintain its relaxing Old Florida appeal. The kitchen, living room and primary bedroom all enjoy open ocean views and all three bedrooms are ensuite. Just sitting on the shady back porch, enjoying the hush of the palms, you could mistake this breathtaking oceanfront for a postcard of yesterday's Florida Keys a century ago. This one-of-a-kind oceanfront estate property includes 4.3 acres of upland plus another 2.65 acres of baybottom and approximately 400 feet along the water! There is also a deep water dock (going into permitting for repair) and a unique collection of rare mature palms. The Native Residential (NR) Zoning allows for many different options for future development and also allows for weekly rentals. This is one of the rare, truly private large parcels on Plantation Key in Islamorada. Don't miss the opportunity to make this unspoiled piece of the past part of your future in the Keys! Call today for more details and to request a private showing.

Full Property Details for 89251 Old Hwy

General

  • Price: $12,500,000
  • Taxes: $45,353 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 615248
  • Updated: 5/30/2025
  • Added to Site: 271 day(s) ago

Interior

  • Appliances: Refrigerator, Oven, Range
  • Furnishings: Negotiable
  • Flooring: Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3

Exterior

  • Exterior Features: Fruit Tree(s), Storage, Sandy Beach, Outdoor Shower
  • Deck/Patio: Open Porch/Balcony, Deck

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Parking: Garage, RV Parking Open, Trailer Storage, Off Street Parking, Guest Parking, Open Parking, Attached

Location

  • Area: 25 - Plantation Key
  • County: Monroe
  • Subdivision: Trop Coral Reef (89.0)
  • Driving Directions: Mile marker 89 Old Highway oceanside. Privately gated. No entry without an appointment and listing agent present.

Community

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

Heating & Cooling

  • Cooling Type: Central Air, Ceiling Fans(s)

Utilities

  • Water: Ocean View, Open Water View
  • Utility Description: FKAA, Elect Separate Meter, Water Separate Meter, Buyer to Verify, Municipal Sewer

Structural Information

  • Architectural Style: Single Family
  • Construction: Concrete, Other
  • Roof: Metal Roof
  • Windows/Doors: Other Windows/Doors
  • Dock Size: 200
  • Square Feet: 1,243
  • Sq. Ft. Source: Tax Records
  • Year Built: 1934

Lot Features

  • Lot Size (Sq. Ft.): 302,742
  • Lot Dimensions: 4.3 acres upland + 2.65 acres bay bottom
  • Zoning: NR - Native Residential

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Type: Oceanfront, Open Water

Financial Considerations

  • Tax Amount: $45,353
  • Tax Year: 2024

Disclosures and Reports

  • Legal Description: 8 63 38 PLANTATION KEY OR LONG ISLAND PT GOVT LOT 1 AND ADJ BB LYING SE'LY GOVT LOT 1 (see deed)
  • Flood Zone: VE, AE
  • Rentals Allowed: Yes
  • APN: 00092870-000100

Listed by Coldwell Banker Schmitt Islamorada, Brett Newman (305) 393-1770

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Listing agent

— 89251 Old Hwy —

  • Brett Newman

    Coldwell Banker Schmitt Islamorada

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 89251 Old Hwy

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-80.5 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1283.1 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 89251 Old Hwy Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/30/2025
Listed
$12,500,000
114.41%
MLS
10/03/2018
Sold
$5,830,000
—
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 89251 Old Hwy

Year
Property Taxes
Change
Tax Assessment
Change
2024
$45,354
—
$5,213,544
3%
2024
$45,354
1%
$5,066,613
3%
2023
$45,055
—
$4,919,042
6%
2021
$44,954
2%
$4,636,669
-3%
2022
$44,189
-2%
$4,775,769
3%
2021
$44,954
21%
$4,642,743
26%
2019
$37,210
8%
$3,697,939
12%
2018
$34,400
8%
$3,298,302
-11%
2017
$31,961
-2%
$3,713,768
-4%
2016
$32,545
1%
$3,865,325
56%
2015
$32,310
37%
$2,478,063
10%
2014
$23,538
-18%
$2,252,785
-18%
2013
$28,810
—
$2,742,018
—
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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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Coldwell Banker Schmitt Islamorada, Brett Newman (305) 393-1770

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89251 Old Highway, Islamorada, FL 33070 (MLS# 615248) is a Single Family property with 3 bedrooms and 3 full bathrooms. 89251 Old Highway is currently listed for $12,500,000 and was received on May 30, 2025. Want to learn more about 89251 Old Highway? Do you have questions about finding other Single Family real estate for sale in Islamorada? You can browse all Islamorada real estate or contact a Coldwell Banker agent to request more information.

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