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144 N Rolling Hill Road
144 N Rolling Hill Road
144 N Rolling Hill Road
144 N Rolling Hill Road
144 N Rolling Hill Road
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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 PA

Karan Moeller PA

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
  • NeighborhoodPlantation Key
  • 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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I’d be happy to show you this beautiful property. Select your preferred date and time below, and I’ll personally 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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Plantation Key

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With nearly three decades in the Florida Keys and firsthand experience building homes, Karan offers insight you won’t find anywhere else—guiding you with clarity, care, and a deep understanding of coastal living.
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Contact Details

Karan Moeller PA

Phone

305.522.2857

Email

[email protected]

Address

81888 Overseas Hwy Islamorada, FL 33036

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