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  • 144 N Rolling Hill Road, Plantation Key, FL 33036 (MLS# 620986)

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

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, unforge ...

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.

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