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
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.
More Information MLS# 620986
Contract Information
Current Price: $6,195,000
Listing Date: 2026-08-14
Listing Board: Florida Keys
List Price: $6,195,000
As is Rght to Inspct: Yes
Species List: No
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
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 5
Pool: No
Year Built: 2008
Lot Size: Irregular
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: 1
Total Baths: 5
Rentals Allowed: With Restrictions
Min Rental Days: 28
Status Change Info
Status: Active
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
Building Style
Above Flood: Yes
Stories: 3 Stories
Financial Status
Auction: No
Standard Sale: 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.