About This Home

This 7-bedroom, 11-bathroom single family at 82719 Old Highway in Upper Matecumbe Key Islamorada, FL is listed for $24,995,000 ($2,455 per sqft). Built in 1995, the home offers 10,182 sqft of living space on a 1.83 acres lot.

Key Features

  • Built in 1995
  • 1.83 acre lot
  • 2 stories
  • Private pool
  • Fireplace
  • Waterfront

Property Details

2 stories
10 full, 1 half
1995

Amenities

PoolFireplaceWaterfrontViewA/C
Listing Description

Experience unparalleled oceanfront living at the Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami.

From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship.

Set on just under an acre of pristine coastline, the property offers 19,784 SF of total living and entertaining space, including 10,182 SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors with natural light and highlighting refined, couture-level finishes.

Amenities include a fitness center, indoor basketball and pickleball court, a Baccarat-inspired grand ballroom, and a custom Glamour Suite. Outdoors, a mosaic pool and spa overlook the Atlantic Ocean, complemented by alfresco dining, a firepit lounge, putting green and multiple terraces with sweeping coastal views.

A 300 inch outdoor LED theater and rooftop terrace elevate the experience. A 100ft private dock provides direct ocean access. Approved plans include 6 additional suites, including 2 oceanfront residences, allowing expansion into a multi-structure compound. A rare legacy estate defined by privacy, scale, and presence

Monthly Cost Estimate

$133,679/mo

20% down · 6.5% · 30 years

Principal$18,077
Interest$108,312
Insurance$7,290

Estimates only. Actual payments may vary.

Location

82719 Old Highway

Upper Matecumbe Key Islamorada, FL 33036

Strattons (82.5)

Features & Amenities

Interior Features

Smart ThermostatBuilt-in CabinetsGranite Counter TopElevatorFire SprinklerSecurity SystemStorageWalk-in Closet(s)BarWired for SoundGym

Exterior Features

BarBuilt-in GrillRain GuttersHot TubLightingOutdoor KitchenOutdoor ShowerPrivacy Wall/FenceSandy BeachShedStorageWater Display

Property Details

Flooring

WoodMarbleConcreteCombo

Construction

CBS Concrete Combo Construction

Views

WaterOcean

Pool Features

Pool

Outdoor Features

DeckPorchPatio

Heating

CentralFireplace(s)Hot Water(Heating)

Cooling

Central Air

Appliances

WasherDryerDishwasherRefrigeratorRangeOvenMicrowaveDisposalFreezerIce MachineWine CoolerStainless Steel Appliance(s)

Questions & Answers

This 7-bedroom, 11-bathroom single family at 82719 Old Highway is listed at $24,995,000 ($2,455/sqft). The estimated monthly payment is $133,678 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1995, 1.83 acre lot, 2 stories, Private pool, Fireplace, Waterfront. Interior Features: Smart Thermostat, Built-in Cabinets, Granite Counter Top. Exterior Features: Bar, Built-in Grill, Rain Gutters.

This property is listed by Pamela DiMartino.

PD

Pamela DiMartino

License 3123363

Agent at Coldwell Banker Realty - Adventura

Listed by Coldwell Banker Realty - Adventura · Broker phone: (305) 931-8266 · View on Broker Site

MLS# 621626· Source: Florida Keys Board of REALTORS®· 16 days on PropertySimple

Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

82719 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

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