144 N Rolling Hill Road, Plantation Key, FL

$6,195,000

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4

Beds

5

Baths

3,284

Square feet

8,276

Land Size

About 144 N Rolling Hill Road

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.

Features of 144 N Rolling Hill Road

MLS® # 620986
Price $6,195,000
Bedrooms 4
Bathrooms 5.00
Full Baths 4
Half Baths 1
Square Footage 3,284
Land Size 8,276
Year Built 2008
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 144 N Rolling Hill Road
Area 25 - Plantation Key
Subdivision High Point (89.0)
City Plantation Key
County Monroe
State FL
Zip Code 33036

Amenities

Amenities Community Boat Ramp
Utilities FKAA, Cistern, Propane, Water Separate Meter, Elect Separate Meter, Cable Available
Parking Carport, Guest Parking, Trailer Storage, Covered Parking
View Bay/Gulf View, Open Water View
Is Waterfront Yes
Waterfront Bay Front, Gulf Front, Open Water
Has Pool No

Interior

Interior Features Drapes/Blinds Incl, Pantry, Entrance Foyer, Built-in Cabinets, Elevator, Storage, Walk-in Closet(s), Whirlpool Bath Tub, Window Treatments
Appliances Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s)
Heating Central, Electric, Propane, Propane Stove
Cooling Central Air, Ceiling Fans(s)
Fireplace No
Has Basement No

Exterior

Exterior Features Chickee Hut, Outdoor Shower, Sprinkler System, Storage
Lot Description Less Than 1/4 Acre
Windows Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors
Roof Concrete Roof
Construction CBS, Concrete

Additional Information

Date Listed August 14th, 2026
Zoning R1 - Residential Single Family
Short Sale No
RE / Bank Owned No
HOA Fees 350
HOA Fees Freq. Yearly

Listing Details

AgentKaran Moeller, Pa
OfficeOcean Sotheby's International Realty

Listing Map

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