Search


$22,500,000
81486 Overseas Highway
Upper Matecumbe Key Islamorada, FL 33036
MLS# 618525
7 beds  |  9 baths  |  8878 sqft


Bay View
  1 / 32  
Bay View Rear Exterior Front Exterior Front Exterior Pool Pool Pool & Spa Outdoor Kitchen Living Room & Kitchen Living Room Living Room to Pool Deck Foyer Foyer Foyer Bedroom 1 Bedroom 1 Bathroom 1 Office Bedroom 2 Hallway Bathroom Bedroom Bedroom Guest Suite Guest Suite Media/Game Room Garage Aerial View Aerial View Aerial View Isla House (55) Isla House (56)

Property 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 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 bonus 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.

Details
Maps
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Species List: Yes
Current Price: $22,500,000
Listing Date: 2026-02-06
List Price: $22,500,000
Location, Tax & Legal
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
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
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 4
Lot SqFt: 253520
Pool: Yes
Lot Sqft Source: Tax Records
Total Units: 1
Acres: 5.82
SqFt Source: Builder/Architect
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 2026
Living Apx SqFt: 8878
Total Bedrooms: 7
Full Baths: 7
Half Baths: 2
Total Baths: 9
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 bonus 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.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
No Appliances: 1
Pets
Pets Allowed: 1
Cooling
Central Air: 1
Heating
Central: 1
Waterfront
Bay Front: 1
Waterview
Bay/Gulf View: 1
Floor
Tile: 1
Interior Features
Elevator: 1
Storage: 1
Walk-in Closet(s): 1
Property Condition
New Construction: 1
Specialty Rooms
Guest/Servant Qtrs: Legal
Laundry Room: 1
Media Room: 1
Building Style
Above Flood: Yes
Stories: 2 Stories
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Sliding Glass Doors: 1
Vehicle Storage
Car(s): 4+
Carport: 1
Covered Parking: 1
Garage: 1
Guest Parking: 1
RV Parking Open: 1
Trailer Storage: 1
Construction
CBS: 1
Concrete: 1
Land Size
5 Less Than 10 Acres: 1
Furnished
Unfurnished: 1
Terms
Cash: 1
Utilities
Buyer to Verify: 1
Cistern: 1
Elect Separate Meter: 1
FKAA: 1
Title
Title Ins - Buyer: 1
Exterior Features
Outdoor Kitchen: 1
Rain Gutters: 1
Storage: 1
Pool Info
Above Ground: 1
Lap: 1
Concrete: 1
Dimensions: 50' Long
Decked: 1
Roof
Metal Roof: 1
Accessibility Feat
Accessible Elevator Installed: 1
Status Change Info
Status: Active
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: February - 07 - 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.