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81486 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036

$22,500,000
Property Type: Residential Bedrooms: 7 Baths: 9 Square Footage: 8,878 Lot Size (sq. ft.): 253,520 Status: Active
Current Price: $22,500,000 List Date: 2/07/2026 Last Modified: 4/17/2026

Overview

Description

Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five gener ...

Listing Details MLS# 618525

Location, Tax & Legal

Street #
81486
Street Name
Overseas
Street Suffix
Highway
Key/Island
Upper Matecumbe Key Islamorada
State/Province
FL
Zip Code
33036
County
Monroe
Subdivision
Misc Upper Matacumbe (82.0)
Area
23 - Upper Matecumbe
City
ISLAMORADA
Mile Marker
81.5
Marathon Neighborhood
N/A
Side
Bay/Gulf
Flood Zone
X, AE8, AE9
Alternate Key #
1496847
Handicap Access
Yes
Parcel #
00404590000000
Zoning
NR - Native Residential
Deed Restrictions
Unknown
Legal
32 63 37 Island Of Upper Matecumbe & Subdivision Of Lots 3-4 Pb2-59 Upper Matecumbe Tr 2-3-6 & Adj Bay Btm (2.33Ac) Or3
Taxes
13278.66
Tax Year
2025
Pub Sewer HkUp
No

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
4
Pool
Yes
Year Built
2026
Total Units
Yes
Lot SqFt
253520
Lot Sqft Source
Tax Records
Acres
5.82
Living Apx SqFt
8878
SqFt Source
Builder/Architect
Total Bedrooms
7
Full Baths
7
Half Baths
2
Total Baths
9
Rentals Allowed
With Restrictions
Min Rental Days
28

Association Info

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

Building Style

Above Flood
Yes
Stories
2 Stories

More Information

Vehicle Storage

Car(s)
4+
Carport
Yes
Covered Parking
Yes
Garage
Yes
Guest Parking
Yes
RV Parking Open
Yes
Trailer Storage
Yes

Specialty Rooms

Guest/Servant Qtrs
Legal
Laundry Room
Yes
Media Room
Yes

Pool Info

Dimensions
50' Long
Above Ground
Yes
Lap
Yes
Concrete
Yes
Decked
Yes

Remarks & Misc

Remarks – Consumer
Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five generous en-suite guest bedrooms, a powder room, and a large laundry room. The lower level offers a separate one bed en-suite with its own entrance and patio. A media room with adjoining bathroom is the ideal flex space. A 1,600 square foot three car garage and a carport area completes the lower level. All told, there is nearly 25,000 square feet under roof cover. The estate's tropical grounds are designed to complement the home's architecture. A private floating dock offers unimpeded views of Florida Bay. Located in the heart of Islamorada, this property offers rare walkability to some of the village's most recognizable attractions. This location allows you unparalleled access to the best of Islamorada's dining, entertainment, and waterfront lifestyle. Isla House represents a rare opportunity to own one of Islamorada's most unrivaled, captivating, and serene waterfront estates—a sanctuary of elegance, craftsmanship, and timeless island charm.
Directions
M.M. 81.4 bayside, across from the Green Turtle Restaurant.

Fee Includes

None
Yes

Dockage

None
Yes

Tax Exemptions

None
Yes

Appliances

No Appliances
Yes

Pets

Pets Allowed
Yes

Cooling

Central Air
Yes

Heating

Central
Yes

Waterfront

Bay Front
Yes

Waterview

Bay/Gulf View
Yes

Floor

Tile
Yes

Interior Features

Elevator
Yes
Storage
Yes
Walk-in Closet(s)
Yes

Property Condition

New Construction
Yes

Windows/Doors

Impact Rstnce Doors
Yes
Impact Rstnce Window
Yes
Sliding Glass Doors
Yes

Construction

CBS
Yes
Concrete
Yes

Land Size

5 Less Than 10 Acres
Yes

Furnished

Unfurnished
Yes

Terms

Cash
Yes

Utilities

Buyer to Verify
Yes
Cistern
Yes
Elect Separate Meter
Yes
FKAA
Yes

Title

Title Ins - Buyer
Yes

Exterior Features

Outdoor Kitchen
Yes
Rain Gutters
Yes
Storage
Yes

Roof

Metal Roof
Yes

Accessibility Feat

Accessible Elevator Installed
Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: Bay Front Waterview: Bay/Gulf View Dockage: None Property Condition: New Construction Vehicle Storage: Garage; Carport; Covered Parking; Guest Parking; RV Parking Open; Trailer Storage Furnished: Unfurnished Cooling: Central Air Heating: Central Utilities: Buyer to Verify; Cistern; Elect Separate Meter; FKAA Interior Features: Elevator; Storage; Walk-in Closet(s) Specialty Rooms: Laundry Room; Media Room Appliances: No Appliances Exterior Features: Outdoor Kitchen; Rain Gutters; Storage Accessibility Feat: Accessible Elevator Installed Pool Info: Above Ground; Lap; Concrete; Decked Construction: CBS; Concrete Floor: Tile Roof: Metal Roof Pets: Pets Allowed Land Size: 5 Less Than 10 Acres Terms: Cash Title: Title Ins - Buyer
Listing Office: American Caribbean Real Estate, Christie's International Real Estate
Last Updated: April - 17 - 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.