Home > 144 N Rolling Hill Road, Plantation Key, FL 33036 (MLS# 620986)
$6,195,000
144 N Rolling Hill Road Plantation Key, FL 33036 MLS# 620986 4 beds | 5 baths | 3284 sqft
|
1 / 65
Property 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
Maps
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Species List: No
Current Price: $6,195,000
Listing Date: 2026-08-14
List Price: $6,195,000
Location, Tax & Legal
City: ISLAMORADA
Off Shore Island: No
Mile Marker: 89
Marathon Neighborhood: N/A
Senior Community YN: No
Side: Bay/Gulf
Alternate Key #: 1517534
Handicap Access: No
Parcel #: 00419570000100
Zoning: R1 - Residential Single Family
Deed Restrictions: No
Legal: Bk 1 Nely 60 Ft Lot 22 High Point Plantation Key Pb4-96 Or467-728 Or860-2239 Or1847-729 Or1956-1067 Or2005-1405 Or2058-3
Taxes: 28256.77
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 144
Direction: N
Street Name: Rolling Hill
Street Suffix: Road
Key/Island: Plantation Key
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: High Point (89.0)
Area: 25 - Plantation Key
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 5
Lot Size: Irregular
Lot SqFt: 8580
Pool: No
Lot Sqft Source: Tax Records
Acres: 0.19
SqFt Source: Tax Records
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 2008
Living Apx SqFt: 3284
Total Bedrooms: 4
Full Baths: 4
Half Baths: 1
Total Baths: 5
Remarks & Misc
Remarks – Consumer: 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.
Directions: Turn bayside onto High Point Rd, Mile Marker 89. Look for sign near end of street.
Listing Office: Ocean Sotheby's International Realty
Last Updated: August - 14 - 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.