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$6,195,000
144 N Rolling Hill Road
Plantation Key, FL 33036
MLS# 620986
4 beds  |  5 baths  |  3284 sqft

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Primary Bayside Elevation Rooftop Deck View Front Elevation Deep Water Dockage Front Elevation Waterside View Front Elevation Front Elevation Living Area Overlooking Bay Living Area Overlooking Bay Living Area Overlooking Bay Living Area Overlooking Bay Patio off Main Level Patio off Main Level View off Main Level Patio Gourmet Kitchen Gourmet Kitchen Gourmet Kitchen Dining Area + Counter Seating Bayside Dining Patio Bayside Dining Patio Bayside Dining Patio Half Bath Off Main Level Primary Suite Primary Suite Primary Suite Primary Suite Paitio off Primary Suite Paitio off Primary Suite Guest Bedroom 1 Guest Bathroom 1 Guest Bedroom 2 Guest Bathroom 2 Guest Bedroom 3 Guest Bathroom 3 Stairway to Rooftop Deck Rooftop Deck Rooftop Deck Rooftop Deck Rooftop Deck Rooftop Deck Rooftop Deck Entry Foyer Elevator to All Living Levels Carport Side Yard Side Yard Side Yard Backyard Chickee Hut Deep Water Dock Deep Water Dock Deep Water Dock Aerial View Aerial View Aerial View Aerial View Aerial View Aerial View Aerial View Front Elevation Front Elevation Future Pool Rendering Year Round Sunsets

Property Description
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.

Details
Maps
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Species List: No
Current Price: $6,195,000
Listing Date: 2026-08-14
List Price: $6,195,000
Location, Tax & Legal
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
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
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 5
Lot Size: Irregular
Lot SqFt: 8580
Pool: No
Lot Sqft Source: Tax Records
Acres: 0.19
SqFt Source: Tax Records
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 2008
Living Apx SqFt: 3284
Total Bedrooms: 4
Full Baths: 4
Half Baths: 1
Total Baths: 5
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.
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
Fee Includes
Common Area Mnt: 1
Other: 1
Dockage
Dock: Composite
Boat Lift: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Gas Appliances: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Heating
Central: 1
Electric: 1
Propane: 1
Propane Stove: 1
Waterfront
Bay Front: 1
Gulf Front: 1
Open Water: 1
Waterview
Bay/Gulf View: 1
Open Water View: 1
Floor
Marble: 1
Tile: 1
Neighborhood Feature
Community Boat Ramp: 1
Interior Features
Built-in Cabinets: 1
Drapes/Blinds Incl: 1
Elevator: 1
Entrance Foyer: 1
Pantry: 1
Storage: 1
Walk-in Closet(s): 1
Whirlpool Bath Tub: 1
Window Treatments: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Workshop: 1
Building Style
Above Flood: Yes
Stories: 3 Stories
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Sliding Glass Doors: 1
Vehicle Storage
Carport: 1
Covered Parking: 1
Guest Parking: 1
Trailer Storage: 1
Security
On Premises System: 1
Construction
CBS: 1
Concrete: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Partially: 1
Terms
Cash: 1
Conventional: 1
No Seller Finance: 1
Utilities
Cable Available: 1
Cistern: 1
Elect Separate Meter: 1
FKAA: 1
Propane: 1
Water Separate Meter: 1
Porch/Balcony
Open Porch/Balcony: 1
Patio: 1
Roof Top Deck: 1
Title
Title Ins - Buyer: 1
Exterior Features
Chickee Hut: 1
Outdoor Shower: 1
Sprinkler System: 1
Storage: 1
Pre-Wired
Cable: 1
Roof
Concrete Roof: 1
Financial Status
Auction: No
Standard Sale: Yes
GF-Interior Features
Solar Water Heater: 1
Status Change Info
Status: Active
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

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