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

144 N Rolling Hill Road, Plantation Key, FL 33036

$6,195,000

Virtual Tour

https://bcove.video/4rDxxkL

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 ... (Read more)

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

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

More Information

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.