$6,195,000
 $33,256 est/mo Sourced by Back At You

144 N Rolling Hill Road,ISLAMORADA, FL 33036

ISLAMORADA, FL 33036

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Description

Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

Details

MLS #620986
Listing TypeFor Sale
StyleHouse
HOA Dues$350
Sub-TypeResale
StatusActive
Year2008
Days On Site15
Listing Provided ByOcean Sotheby's International Realty | Karan Moeller, PA

Features

Bed(s)4
Bath(s) 5 Total
SQ Feet3,284
ZoningR1 - Residential Single Family
Acreage0.19
Water FrontYes
Property ViewOpen Water View, Bay

Taxes

Property28256

Area Information

StateFL
CountyMonroe
CityISLAMORADA
Zip Code33036
Area25 Plantation Key
Community NameHigh Point (89.0)
Listing VS Median (in High Point (89.0))
Price:
$6,195,000
low | high
Med:
$6,195,000
50% of Average
sqft:
3,284
low | high
Med:
3,284
50% of Average
$ / sqft:
$1,886
low | high
Med:
$1,886
50% of Average
On site:
15
low | high
Med:
15
100% of Average
Sourced by Back At You

Market Activity 33036

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Learn More About This Property

StateFL
CountyMonroe
CityISLAMORADA
Zip Code33036
Area25 Plantation Key
Community NameHigh Point (89.0)
Listing VS Median (in High Point (89.0))
Price:
$6,195,000
low | high
Med:
$6,195,000
50% of Average
sqft:
3,284
low | high
Med:
3,284
50% of Average
$ / sqft:
$1,886
low | high
Med:
$1,886
50% of Average
On site:
15
low | high
Med:
15
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/4 mile)
Price: $4.646M - $7.743M
sqft: 2,000 - 4,000
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Listing Updated: August 14, 2026 at 1:42:55 PM PDT