House for Sale
$18,499,000
6 bd · 8 ba · 6,692 sqft
87429 Old Hwy, Islamorada, FL 33036
PLANTATION BEACH
Islamorada, FL 33036 · MLS# A11962802 · Active · Upper Matecumbe
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.
Estimate only — actual rates, taxes and insurance vary. Not a loan offer or financial advice. Financing through Matthew Gromadzki, NMLS #2560919 · Innovative Mortgage Services, Inc., NMLS #250769.
House for Sale
$18,499,000
6 bd · 8 ba · 6,692 sqft
PLANTATION BEACH
House for Sale
$24,995,000
7 bd · 11 ba · 10,182 sqft
STRATTONS SUBD
House for Sale
$14,990,000
6 bd · 9 ba · 7,590 sqft
PEARL CITY
House for Sale
$29,000,000
4 bd · 6 ba · 8,194 sqft
Matecumbe Ocean Bay (75.0)
House for Sale
$25,000,000
7 bd · 10 ba · 8,288 sqft
Islamorada
House for Sale
$15,950,000
6 bd · 7 ba · 6,680 sqft
ISLAMORADA, TOWNSITE OF
This property is a single family home for sale in Islamorada, FL 33036. This property was listed for sale on February 6, 2026 by American Caribbean Real Estate, it's currently listed at $22,500,000. This listing's school district is Monroe County Public Schools. This property is a 7-bed, 9-bath single family home built in 2026.