87445 Old Highway, Upper Sugarloaf Key, FL 33036 - Photo 1

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$3,995,000

For Sale
Active
Single Family
5 Beds
4 Full Baths
4,014 Sq. Ft.
Updated 2 hours ago

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Property Description

This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior. With five spacious bedrooms and four well-appointed bathrooms, this residence offers ample space for family and guests. Enjoy stunning ocean views from various vantage points within the home, enhancing the comfort and breathtaking natural beauty. The observation dock provides a perfect spot for relaxation, while the saltwater pool equipped with heater/chiller, ensures year-round enjoyment. Added features are quartz countertops, top-of-the-line appliances , impact resistant windows ,and the Residential Estate zoning allows weekly vacation rentals with a high-income stream. This combination of amenities creates an inviting atmosphere that reflects the privacy and charm of the Florida Keys lifestyle.

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Full Property Details

Full Property Details for 87445 Old Hwy

General

Price: $3,995,000
Taxes: $22,084 (2024)
Status: Active
Type: Single Family
Source: 927
MLS ID: 616426
Updated: 5/13/2026
Added to Site: 246 day(s) ago

Interior

Interior Features: Entrance Foyer, Drapes/Blinds Incl, Quartz Countertops, Split Bedroom, Window Treatments
Appliances: Stainless Steel Appliance(s), Dishwasher, Dryer, Microwave, More Appliances, Oven, Refrigerator, Washer
Flooring: Tile

Rooms

Bathrooms

Total Bathrooms: 4
Full Bathrooms: 4

Bedrooms

Total Bedrooms: 5

Additional Information

Pool: Yes
Pool Description: Heated, Salt Water, In Ground
Security/Safety: Electric Gate, Patrolled Area

Exterior

Exterior Features: Privacy Wall/Fence
Deck/Patio: Open Porch/Balcony, Patio
Porch/Patio/Deck: Open Porch/Balcony, Patio

Parking

Garage: Yes
Parking Features: Off Street, Covered, Carport

Location

Area: 25 - Plantation Key
County: Monroe
Subdivision: Plant Beach (87.5)

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, Electric

Structural Information

Architectural Style: Above Flood
Construction: CBS, Concrete
Roof: Metal
Windows/Doors: Impact Rstnce Window, Sliding Glass Doors, Shutters
Square Feet: 4,014
Sq. Ft. Source: LA Measured
Year Built: 1999

Lot Features

Property View: Open Water View, Ocean
Lot Size (Acres): 1.82
Lot Size (Sq. Ft.): 79,399
Lot Size Source: Property Data Card
Zoning: RE - Residential Estate

Water Features

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

Financial Considerations

Tax Amount: $22,084.73
Tax Year: 2024

Disclosures and Reports

Legal Description: TR M PLANTATION BEACH PB2-76 PLANTATION KEY OR559-723 OR781-687 OR1143-2292 OR1368-1602 OR1479-1205 OR1718-1824 OR2122-
Flood Zone: AE, AE, AE, VE
APN: 00415170-000000

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

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Listing agents

— 87445 Old Hwy —

Cheri Tindall

Ocean Sotheby's International Realty
Leslie Leopold

Ocean Sotheby's International Realty

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Schools

Schools serving 87445 Old Hwy

School District:Monroe County School District, Middle Torch Key, FL

Name	Grades	Distance
Plantation Key School 100 Lake Road, Tavernier, FL 33070	PK-8	2.1 mi
Key West High School 2100 Flagler Avenue, Key West, FL 33040	9-12	81.5 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 87445 Old Hwy Get Price Alerts and Save Property

Date

Details

Price

Change

Source

1/23/2026

Price Reduced

$3,995,000

-11.12%

MLS

9/09/2025

Listed

$4,495,000

136.58%

MLS

3/30/2017

Sold

$1,900,000

—

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.

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87445 Old Highway, Upper Sugarloaf Key, FL 33036 (MLS# 616426) is a Single Family property with 5 bedrooms and 4 full bathrooms. 87445 Old Highway is currently listed for $3,995,000 and was received on September 09, 2025. Want to learn more about 87445 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.

87445 Old Hwy Upper Sugarloaf Key, FL 33036