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144 N Rolling Hill Road, Plantation Key, FL - photo 1
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144 N Rolling Hill Road, Plantation Key, FL - photo 2
144 N Rolling Hill Road, Plantation Key, FL - photo 3
144 N Rolling Hill Road, Plantation Key, FL - photo 4
144 N Rolling Hill Road, Plantation Key, FL - photo 5
+64

$6,195,000

4 beds5 baths3,284 sqft|620986 MLS#

144 N Rolling Hill Road, Plantation Key, FL 33036

Est.$37,170/moGet pre-qualified

Single Family Residence

Residential

Built in

2008

Lot size

8,276 sqft

Price/sqft

$1886

HOA

None

Listed by: Karan Moeller, PA 305-522-2857, Ocean Sotheby's International Realty 305-712-8888

Source:Florida Keys MLS (FLKMLS)|MLS #620986

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Preferred Brokerage Partner

Kinsfolk Realty

Kinsfolk Signature Realty

What's special

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.

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Facts & features

Bedrooms & bathrooms

  • Bedrooms:4
  • Bathrooms:5
  • Full bathrooms:0

Heating

  • Has Heating:Yes

Interior area

  • Total structure area:3,284 sqft
  • Total interior livable area:3,284 sqft

Parking

  • Parking features:N/A
  • Garage spaces:0
  • Has attached garage:No

Lot

  • Size:8,276 sqft

Details

  • Parcel number:N/A

Type & style

  • Home type:Single Family Residence
  • Property subtype:Residential

Materials

  • • N/A

Condition

  • Year built:2008

Contact agent

Price history

DateEventPrice
9/14/2026Listed for sale$6,195,000$1886/sqft

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