• Home
  • Property Search
    • Key West Real Estate
      • Key West Homes
      • Key West Condos
      • Key West Townhomes
      • Key West Commercial
      • Key West Land
    • Florida Keys Real Estate
      • Florida Keys Homes
      • Florida Keys Condos
      • Florida Keys Townhomes
      • Florida Keys Commercial
      • Florida Keys Land
    • MLS Search
  • Property Estimate
  • Neighborhoods
    • Casa Marina
    • Golf Club
    • Key Haven
    • Meadows
    • Midtown
    • New Town
    • Old Town
    • Sunset Key
    • Truman Annex
  • Islands
    • Big Coppitt Key
    • Big Pine Key
    • Cudjoe Key
    • Duck Key
    • Islamorada
    • Key Colony Beach
    • Key Largo
    • Lower Matecumbe Key
    • Marathon Key
    • Plantation Key
    • Sugarloaf Key
    • Summerland Key
  • Contact Us

Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

With a portal you are able to:
  1. Save your searches
  2. Get updates on listings
  3. Track listings
  4. Add notes and messages
  5. Personalize your dashboard

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


Front Exterior Twilight
  1 / 26  
Front Exterior Twilight Pool at Twilight Living Room & Kitchen Virtually Staged Living Room Virtually Staged Front Exterior Front Exterior Pool Pool Pool & Spa Outdoor Kitchen Living Room & Kitchen Living Room Living Room to Pool Deck Foyer Bedroom 1 Bedroom 1 Virtually Staged Bedroom 1 Office Bedroom 2 Hallway Bathroom Bedroom Bedroom Guest Suite Guest Suite Garage

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 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.

Details
Maps
Contract Information
Current Price: $22,500,000
Listing Date: 2026-02-06
Listing Board: Florida Keys
Monthly Rent: $22,500,000
As is Rght to Inspct: Yes
Species List: Yes
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
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: Yes
Year Built: 2026
Total Units: 1
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
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Yes
# Stories: 2 Stories
Vehicle Storage
Car(s): 4+
Pool Info
Dimensions: 50' Long
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: April - 23 - 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.


Search powered by FBS Products
Create A Real Estate Portal
With a portal you are able to:
  1. Save your searches
  2. Get updates on listings
  3. Track listings
  4. Add notes and messages
  5. Personalize your dashboard

Anchor Line Realty on Social Media:

Facebook
Facebook
fb-share-icon
Twitter
Visit Us
Follow Me

E-mail Us Directly

Please provide details below:

  • Home
  • Property Search
  • Property Estimate
  • Neighborhoods
  • Islands
  • Contact Us

Copyright © 2026 · AgentPress Pro on Genesis Framework · WordPress · Log in

David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)