Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036

New Listing

$3,500,000

Property Type: Vacant Land Lot Size (sq. ft.): 229,479 Status: Active

Current Price: $3,500,000 List Date: 9/25/2026 Last Modified: 9/25/2026

Overview

Description

A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of ... (Read more)

Listing Details MLS# 621407

Location, Tax & Legal

Street Name: Overseas
Street Suffix: Highway
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Unplatted Upper Mate (82.0)
Area: 23 - Upper Matecumbe
City: ISLAMORADA
Mile Marker: 82
Marathon Neighborhood: N/A
Side: Bay/Gulf
Alternate Key #: 9105566
Parcel #: 00095920-000200
Zoning: NR - Native Residential
Deed Restrictions: Unknown
Taxes: 0
Tax Year: 2026

Contract Information

Listing Board: Florida Keys
ROGO Exempt: No
Limited Representation: No
Potential Short Sale: No
Bank Owned: No

General Property Description

Realtor.COM Type: Vacant Land
Waterfront: Yes
Lot SqFt: 229478.5
Lot Sqft Source: Property Data Card
Survey Available: Yes
Vegetation Survey: No
Control Depth: 0

Miscellaneous Info

Mobile Home Lot: No

Financial Status

Bank Owned: No
Potential Short Sale: No

More Information

Remarks & Misc

Remarks – Consumer: A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada.

Assoc/Misc Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No

Dockage

None: Yes

Tax Exemptions

None: Yes

Waterfront

Bay Front: Yes

Waterview

Bay View: Yes
Open Water View: Yes

Location/Site

Highway Frontage: Yes
Mangrove: Yes
Water Frontage: Yes
Wooded Lot: Yes

Existing Utilities

None: Yes

BuildingPermit

No Permit: Yes

Land Size

5 Less Than 10 Acres: Yes

Property Features

Tax Exemptions: None Waterfront: Bay Front Dockage: None Waterview: Bay View; Open Water View Existing Utilities: None BuildingPermit: No Permit Land Size: 5 Less Than 10 Acres

Listing Office: Coastal Realty of the Florida Keys

Last Updated: September - 25 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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