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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.

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