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81486 Overseas Hwy, Upper Matecumbe Key Islamorada, FL - photo 1
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81486 Overseas Hwy, Upper Matecumbe Key Islamorada, FL - photo 2
81486 Overseas Hwy, Upper Matecumbe Key Islamorada, FL - photo 3
81486 Overseas Hwy, Upper Matecumbe Key Islamorada, FL - photo 4
81486 Overseas Hwy, Upper Matecumbe Key Islamorada, FL - photo 5
+21

$22,500,000

7 beds9 baths8,878 sqft|618525 MLS#

81486 Overseas Hwy, Upper Matecumbe Key Islamorada, FL 33036

Est.$135,000/moGet pre-qualified

Single Family Residence

Residential

Built in

2026

Lot size

253,519 sqft

Price/sqft

$2534

HOA

None

Listed by: KELLY K SHAW PA 305-664-7303, American Caribbean Real Estate, Christie's International Real Estate 305-664-4966

Source:Florida Keys MLS (FLKMLS)|MLS #618525

Get price drop alert on this property the moment it happen

Preferred Brokerage Partner

Kinsfolk Realty

Kinsfolk Signature Realty

What's special

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.

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Facts & features

Bedrooms & bathrooms

  • Bedrooms:7
  • Bathrooms:9
  • Full bathrooms:0

Heating

  • Has Heating:Yes

Interior area

  • Total structure area:8,878 sqft
  • Total interior livable area:8,878 sqft

Parking

  • Parking features:N/A
  • Garage spaces:0
  • Has attached garage:No

Lot

  • Size:253,519 sqft

Details

  • Parcel number:N/A

Type & style

  • Home type:Single Family Residence
  • Property subtype:Residential

Materials

  • • N/A

Condition

  • Year built:2026

Contact agent

Price history

DateEventPrice
9/15/2026Listed for sale$22,500,000$2534/sqft

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