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81300 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

$6,000,000
Property Type: Residential Bedrooms: 4 Baths: 3 Square Footage: 3,138 Lot Size (sq. ft.): 70,250 Status: Closed
Current Price: $6,000,000 List Date: 3/24/2025 Last Modified: 5/30/2025

Overview

Description

Situated on 1.61 acres of prime oceanfront property in downtown Islamorada, this iconic estate offers unparalleled waterfront living, combining unique charm with exceptional character. This estate blends privacy, tranquility, and breathtaking views of the sparkling waters of the Florida Keys. The main residence, built in 1948, offers four bedrooms and three bathrooms, preserving its timeless elegance while providing modern comforts. Next to the main home is a charming guest/caretaker cottage, complete with three bedrooms and two baths, offering both convenience and comfort. A winding Chicago brick driveway and electric gate provide a sense of exclusivity, while lush landscaping, including tropical plants and fruit trees, create an oasis for relaxation and enjoyment. An incredible sandy beach and dock enhances the property's serene and private retreat-like atmosphere.

Listing Details MLS# 614329

Location, Tax & Legal

Street #
81300
Street Name
Old
Street Suffix
Highway
Key/Island
Upper Matecumbe Key Islamorada
State/Province
FL
Zip Code
33036
County
Monroe
Subdivision
Green Turtle Beach (81.0)
Area
23 - Upper Matecumbe
City
ISLAMORADA
Mile Marker
81
Marathon Neighborhood
N/A
Side
Ocean
Flood Zone
AE,VE,AE,VE,VE,AE
Alternate Key #
1497070
Add'l Parcel #1
00404950-000000
Parcel #
00404780-000000
Bldg Nbr
2
Zoning
RE - Residential Estate
Deed Restrictions
Unknown
Legal
SUBDIVISION OF LOTS 3-4 UPPER MATECUMBE PB2-59 TR 21 (32 63 37) ISLAND OF UPPER MATECUMBE PB1-41 BAY BTM SELY AND ADJ T
Taxes
18080.59
Tax Year
2024
Pub Sewer HkUp
Yes

Contract Information

Listing Board
Florida Keys
As is Rght to Inspct
Yes
Species List
Yes

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
Yes
Control Depth
3
Pool
No
Year Built
1948
Total Units
2
Lot SqFt
70250
Lot Sqft Source
Property Data Card
Acres
1.61
Living Apx SqFt
3138
SqFt Source
Property Data Card
Total Bedrooms
4
Full Baths
3
Total Baths
3
Rentals Allowed
Yes
Min Rental Days
7

Status Change Info

Sold Date
2025-05-29
Sold Comments
Also included in the sale 101 Ocean Terrace.

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No
Association Fee $
0

Dockage

Dock
Wood

More Information

Building Style

Above Flood
Unknown
Stories
2 Stories

Specialty Rooms

Guest/Servant Qtrs
Legal
Sun/Florida Room
Yes

Remarks & Misc

Remarks – Consumer
Situated on 1.61 acres of prime oceanfront property in downtown Islamorada, this iconic estate offers unparalleled waterfront living, combining unique charm with exceptional character. This estate blends privacy, tranquility, and breathtaking views of the sparkling waters of the Florida Keys. The main residence, built in 1948, offers four bedrooms and three bathrooms, preserving its timeless elegance while providing modern comforts. Next to the main home is a charming guest/caretaker cottage, complete with three bedrooms and two baths, offering both convenience and comfort. A winding Chicago brick driveway and electric gate provide a sense of exclusivity, while lush landscaping, including tropical plants and fruit trees, create an oasis for relaxation and enjoyment. An incredible sandy beach and dock enhances the property's serene and private retreat-like atmosphere.
Directions
Ocean front MM81 Old Hwy

Fee Includes

None
Yes

Tax Exemptions

Homestead
Yes

Appliances

More Appliances
Yes
Refrigerator
Yes

Pets

Pets Allowed
Yes

Cooling

Central Air
Yes
Ductless
Yes

Heating

Fireplace(s)
Yes

Waterfront

Oceanfront
Yes

Waterview

Ocean View
Yes
Open Water View
Yes

Floor

Carpet
Yes
Tile
Yes

Interior Features

Dade County Pine
Yes
Entrance Foyer
Yes
Fireplace(s)
Yes

Windows/Doors

Aluminum Windows
Yes

Vehicle Storage

Off Street Parking
Yes

Security

Electric Gate
Yes

Construction

CBS
Yes
Concrete
Yes

Land Size

1 Less Than 2 Acres
Yes

Furnished

Partially
Yes

Utilities

Elect Separate Meter
Yes
FKAA
Yes
Municipal Sewer
Yes

Porch/Balcony

Deck
Yes
Open Porch/Balcony
Yes

Title

Title Ins - Buyer
Yes

Exterior Features

Chickee Hut
Yes
Fencing
Yes
Fruit Tree(s)
Yes
Sandy Beach
Yes
Shed
Yes

Roof

Metal Roof
Yes

Property Features

Fee Includes: None Tax Exemptions: Homestead Waterfront: Oceanfront Waterview: Ocean View; Open Water View Vehicle Storage: Off Street Parking Furnished: Partially Cooling: Central Air; Ductless Heating: Fireplace(s) Utilities: Elect Separate Meter; FKAA; Municipal Sewer Interior Features: Dade County Pine; Entrance Foyer; Fireplace(s) Specialty Rooms: Sun/Florida Room Appliances: More Appliances; Refrigerator Exterior Features: Chickee Hut; Fencing; Fruit Tree(s); Sandy Beach; Shed Construction: CBS; Concrete Floor: Carpet; Tile Roof: Metal Roof Pets: Pets Allowed Security: Electric Gate Land Size: 1 Less Than 2 Acres Title: Title Ins - Buyer
Listing Office: Ocean Sotheby's International Realty
Last Updated: May - 30 - 2025
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.