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144 N Rolling Hill Road ROAD

Islamorada, FL 33036
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$6,195,000 $26,118/Mo
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Bed 4

Bed

Bath 5

Bath

SqFt3,284

Sqft

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 p lus 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.

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Detail Ic Property Details

Property Type : Residential - Single Family

Price : $6,195,000

AD Id : 89551720

MLS Id : 620986

Beds : 4

Living Area Size : 3,284

Year Built : 2008

County : Monroe

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total Bedrooms: 4 Workshop

    Bathroom Information

    Total Baths: 5 Full Baths: 4 Half Baths: 1

  • Interior Features

    Drapes/Blinds Incl,Built-in Cabinets,Window Treatments,Whirlpool Bath Tub,Walk-in Closet(s),Storage,Elevator,Entrance Foyer,Pantry Solar Water Heater Appliances: Washer,Stainless Steel Appliance(s),Wine Cooler,Gas Appliances,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer

  • Roofing Information

    Concrete Roof

    Flooring Information

    Tile,Marble

    Heating & Cooling

    Cooling: Central Air,Ceiling Fans(s) Heating: Central,Propane Stove,Propane,Electric Water Front: Yes Bay Front,Open Water,Gulf Front Bay/Gulf View,Open Water View

    Window Information

    Window Treatments: Sliding Glass Doors,Impact Rstnce Window,Impact Rstnce Doors

  • Building Information

    Year Built: 2008 Floor Location: 8580 Construction: CBS,Concrete Security System: On Premises System Roof: Concrete Roof

  • Exterior Features

    Chickee Hut,Storage,Sprinkler System,Outdoor Shower

  • Lot Information

    Lot Dimensions: Irregular Lot SqFt: 8,580 Lot SqFt Source: Tax Records 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

  • Property Information

    SQ ft (Living Area): 3,284 View: Bay/Gulf View,Open Water View Subdivision: High Point (89.0) Stories: 3 Stories

  • Listing Price Information

    List Price: $6,195,000

  • Listing Information

    No Seller Finance,Conventional,Cash

  • Tax Information

    Taxes: $28,257 Tax Year: 2025 Parcel Number: 00419570000100 Tax Exemptions: None

  • Virtual Tour

    Virtual Tour (External Link)

  • Multi-Unit Information

    Pets Allowed: Pets Allowed

  • Homeowners Association Information

    Mandatory Home Owners Asc: No Voluntary Home Owners Asc: Yes 1st Right of Refusal: No Association Fee: $350.00 Assoc/Mnt Fee Per: Yearly

  • Utility Information

    FKAA,Propane,Cable Available,Elect Separate Meter,Water Separate Meter,Cistern
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
102 Anglers Way, Islamorada, FL, 33036 $1,150,000 2 3 1,376 1,376 SqFt
88351 Old Highway HIGHWAY, Islamorada, FL, 33036 $15,990,000 6 9 7,590 7,590 SqFt
87895 Old Highway HIGHWAY, Islamorada, FL, 33036 $24,995,000 5 8 9,011 9,011 SqFt
88110 Overseas Highway, Islamorada, FL, 33036 $6,999,000 4 5 2,797 2,797 SqFt
87950 Overseas Highway .., Islamorada, FL, 33036 $3,800,000 5 3 2,464 2,464 SqFt
87445 Old Highway HIGHWAY, Islamorada, FL, 33036 $3,995,000 5 4 4,014 4,014 SqFt
87429 Old Highway HIGHWAY, Islamorada, FL, 33036 $18,999,000 6 8 6,692 6,692 SqFt
87429 Old Highway, Islamorada, FL, 33036 $18,999,000 6 6 6,054 6,054 SqFt
316 North Drive DRIVE, Islamorada, FL, 33036 $2,400,000 3 4 2,309 2,309 SqFt
316 N Dr, Islamorada, FL, 33036 $2,400,000 3 4 --

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ByOwner last updated this listing 08/17/2026 @ 22:36

MLS: 620986 LISTED BY: Karan Moeller, PA , Ocean Sotheby's International Realty 305-712-8888 SOURCE: Florida Keys MLS, Inc.

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