144 N Rolling Hill Road, Plantation Key, FL 33036
New Listing
$6,195,000
Property Type:
Residential
Bedrooms:
4
Baths:
5
Square Footage:
3,284
Lot Size (sq. ft.):
8,580
Status:
Active
Current Price:
$6,195,000
List Date:
8/14/2026
Last Modified:
8/14/2026
Overview
Description
...
(Read more)
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.
Listing Details MLS# 620986
Location, Tax & Legal
- Street #
- 144
- Direction
- N
- Street Name
- Rolling Hill
- Street Suffix
- Road
- Key/Island
- Plantation Key
- State/Province
- FL
- Zip Code
- 33036
- County
- Monroe
- Subdivision
- High Point (89.0)
- Area
- 25 - Plantation Key
- City
- ISLAMORADA
- Off Shore Island
- No
- Mile Marker
- 89
- Marathon Neighborhood
- N/A
- Senior Community YN
- No
- Side
- Bay/Gulf
- Alternate Key #
- 1517534
- Handicap Access
- No
- Parcel #
- 00419570000100
- Zoning
- R1 - Residential Single Family
- Deed Restrictions
- No
- Legal
- 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
- Taxes
- 28256.77
- Tax Year
- 2025
- Pub Sewer HkUp
- Yes
Contract Information
- Listing Board
- Florida Keys
- As is Rght to Inspct
- Yes
- Species List
- No
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Single Family
- Waterfront
- Yes
- Control Depth
- 5
- Pool
- No
- Year Built
- 2008
- Lot SqFt
- 8580
- Lot Sqft Source
- Tax Records
- Acres
- 0.19
- Living Apx SqFt
- 3284
- SqFt Source
- Tax Records
- Total Bedrooms
- 4
- Full Baths
- 4
- Half Baths
- Yes
- Total Baths
- 5
- Rentals Allowed
- With Restrictions
- Min Rental Days
- 28
Association Info
- Mandatory Home Owners Asc
- No
- Voluntary Home Owners Asc
- Yes
- 1st Right of Refusal
- No
- Association Fee $
- 350
- Assoc/Mnt Fee Per
- Yearly
Dockage
- Dock
- Composite
- Boat Lift
- Yes
More Information
Building Style
- Above Flood
- Yes
- Stories
- 3 Stories
Financial Status
- Auction
- No
- Standard Sale
- Yes
Remarks & Misc
- Remarks – Consumer
- 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.
- Directions
- Turn bayside onto High Point Rd, Mile Marker 89. Look for sign near end of street.
Fee Includes
- Common Area Mnt
- Yes
- Other
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Disposal
- Yes
- Dryer
- Yes
- Gas Appliances
- Yes
- Microwave
- Yes
- Oven
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Stainless Steel Appliance(s)
- Yes
- Washer
- Yes
- Wine Cooler
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
Heating
- Central
- Yes
- Electric
- Yes
- Propane
- Yes
- Propane Stove
- Yes
Waterfront
- Bay Front
- Yes
- Gulf Front
- Yes
- Open Water
- Yes
Waterview
- Bay/Gulf View
- Yes
- Open Water View
- Yes
Floor
- Marble
- Yes
- Tile
- Yes
Neighborhood Feature
- Community Boat Ramp
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Drapes/Blinds Incl
- Yes
- Elevator
- Yes
- Entrance Foyer
- Yes
- Pantry
- Yes
- Storage
- Yes
- Walk-in Closet(s)
- Yes
- Whirlpool Bath Tub
- Yes
- Window Treatments
- Yes
Property Condition
- Updated/Remodeled
- Yes
Specialty Rooms
- Workshop
- Yes
Windows/Doors
- Impact Rstnce Doors
- Yes
- Impact Rstnce Window
- Yes
- Sliding Glass Doors
- Yes
Vehicle Storage
- Carport
- Yes
- Covered Parking
- Yes
- Guest Parking
- Yes
- Trailer Storage
- Yes
Security
- On Premises System
- Yes
Construction
- CBS
- Yes
- Concrete
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Furnished
- Partially
- Yes
Terms
- Cash
- Yes
- Conventional
- Yes
- No Seller Finance
- Yes
Utilities
- Cable Available
- Yes
- Cistern
- Yes
- Elect Separate Meter
- Yes
- FKAA
- Yes
- Propane
- Yes
- Water Separate Meter
- Yes
Porch/Balcony
- Open Porch/Balcony
- Yes
- Patio
- Yes
- Roof Top Deck
- Yes
Title
- Title Ins - Buyer
- Yes
Exterior Features
- Chickee Hut
- Yes
- Outdoor Shower
- Yes
- Sprinkler System
- Yes
- Storage
- Yes
Pre-Wired
- Cable
- Yes
Roof
- Concrete Roof
- Yes
GF-Interior Features
- Solar Water Heater
- Yes
Property Features
Fee Includes:
Common Area Mnt; Other
Tax Exemptions:
None
Waterfront:
Bay Front; Gulf Front; Open Water
Waterview:
Bay/Gulf View; Open Water View
Dockage:
Boat Lift
Property Condition:
Updated/Remodeled
Vehicle Storage:
Carport; Covered Parking; Guest Parking; Trailer Storage
Furnished:
Partially
Cooling:
Ceiling Fans(s); Central Air
Heating:
Central; Propane; Propane Stove
Utilities:
Cable Available; Cistern; Elect Separate Meter; FKAA; Propane; Water Separate Meter
Interior Features:
Built-in Cabinets; Drapes/Blinds Incl; Elevator; Entrance Foyer; Pantry; Storage; Walk-in Closet(s); Whirlpool Bath Tub; Window Treatments
Pre-Wired:
Cable
Specialty Rooms:
Workshop
Appliances:
Dishwasher; Disposal; Dryer; Gas Appliances; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features:
Chickee Hut; Outdoor Shower; Sprinkler System; Storage
Construction:
CBS; Concrete
Floor:
Marble; Tile
Roof:
Concrete Roof
Pets:
Pets Allowed
Neighborhood Feature:
Community Boat Ramp
Security:
On Premises System
Land Size:
Less Than 1/4 Acre
Terms:
Cash; Conventional; No Seller Finance
Title:
Title Ins - Buyer
GF-Interior Features:
Solar Water Heater
Listing Office:
Ocean Sotheby's International Realty
Last Updated: August - 14 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
