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For Sale

144 N Rolling Hill Road

144 N Rolling Hill Road, Plantation Key, FL 33036

$6,195,000
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.

9/17/2026 10:00AM - 1:00PM EDT

4
beds

5
baths

3,284 Sq.Ft. LIVING AREA

8,580 Sq.Ft. lot

Karan Moeller

Karan Moeller

Features & Amenities

Interior

  • total bedrooms4
  • Total bathrooms5
  • full bathrooms4
  • half bathroom1
  • Flooring Tile, Marble
  • APPLIANCES Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Gas Appliances, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
  • other interior Features Workshop, Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Drapes/Blinds Incl, Elevator, Pantry, Storage, Whirlpool Bath Tub, Window Treatments

Area & Lot

  • Status For Sale
  • OPEN HOUSE

    9/17/2026 10:00AM - 1:00PM EDT

  • Living Area3,284 Sq.Ft.
  • Total Area3,284 Sq.Ft.
  • Lot Area8,580 Sq.Ft.
  • MLS® ID620986
  • TypeResidential
  • YEAR BUILT2008
  • NeighborhoodIslamorada
  • Architecture StylesAbove Flood
  • View DescriptionOpen Water View, Bay

Exterior

  • roofConcrete
  • parkingGuest, Covered, Carport
  • HEAT TYPECentral, Electric, Propane, Propane Stove
  • AIR CONDITIONINGCentral Air, Ceiling Fans(s)
  • security FeaturesOn Premises System
  • other exterior FeaturesChickee Hut, Outdoor Shower, Sprinkler System, Storage

Financial

  • Sales Price$6,195,000
  • Real Estate Tax $28,257/yr
  • HOA $350/yr
  • Zoning R1 - Residential Single Family
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Schedule a Showing

We would love to show you this beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Thank you for your interest in 144 N Rolling Hill Road, Plantation Key, FL 33036. We are reviewing your request and will be in touch shortly!
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OCEAN SIR

License # : CQ1039964

Phone

305.712.8888

Email

marketing@oceansir.com

Address

81888 Overseas Highway Islamorada FL 33036 12420 Overseas Highway Marathon FL 33050 1075 Duval Street Suite 15C Key West FL 33040

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