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
...
(Read more)
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.
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.
