Waterfront
Address
144 N Rolling Hill Road, Plantation Key, FL
Price
$ 6,195,000
Property Attributes
- MLS#620986
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityPlantation Key
- AreaPlantation Key
- NeighborhoodHigh Point
- Zip33036
- StyleSingle Family
- Year Built2008
- Taxes$ 28256
- Price$ 6,195,000
- Bedrooms4
- Full Bathrooms4
- Half Bathrooms1
- Sqr Footage3284
- Lot Size0.19 Acres
Data Source:
Florida Keys MLS (FLKMLS)
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.
| Price History | |
|---|---|
| 8/14/2026 | Listed $6,195,000 |
General Features
| Living Area | 3284.00 |
|---|---|
| Construction | CBS,Concrete |
| Utilities | FKAA,Propane,Cable Available,Elect Separate Meter,Water Separate Meter,Cistern |
| Roof | Concrete Roof |
| Appliances | Washer,Stainless Steel Appliance(s),Wine Cooler,Gas Appliances,Disposal,Microwave,Oven,Range,Refrigerator,Dishwasher,Dryer |
| Zoning | R1 - Residential Single Family |
| HOA Fee | 350.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 4 |
| Half Baths | 1 |
| Year Built | 2008 |
| Handicap Access | No |
| Subdivision | High Point (89.0) |
| Style | Single Family |
| View | Bay/Gulf View,Open Water View |
| Property Type | A |
| Neighborhood Feature | Community Boat Ramp |
| Fee Includes | Common Area Mnt,Other |
| Acres | 0.19 |
| Lot Sqft | 8580.00 |
| Rental Allowed | With Restrictions |
| HOA/Maint Fee Per | Yearly |
| Building Style: Above Flood | Yes |
| Building Style: Stories | 3 Stories |
| Control Depth | 5 |
| Dockage | Boat Lift |
| Dockage: Dock | Composite |
| Virtual Tour | https://bcove.video/4rDxxkL |
| Min Rental Days | 28.00 |
Interior Features
| Interior Amenities | Drapes/Blinds Incl,Built-in Cabinets,Window Treatments,Whirlpool Bath Tub,Walk-in Closet(s),Storage,Elevator,Entrance Foyer,Pantry |
|---|---|
| Furnished Y/N | Partially |
| Flooring | Tile,Marble |
| Specialty Rooms | Workshop |
| GF-Interior Features | Solar Water Heater |
| Pre-Wired | Cable |
Exterior Features
| Exterior Amenities | Chickee Hut,Storage,Sprinkler System,Outdoor Shower |
|---|---|
| Pool | No |
| Waterfront | Bay Front,Open Water,Gulf Front |
| Lot Size | Irregular |
| Land Size | Less Than 1/4 Acre |
| Porch/Balcony | Open Porch/Balcony,Roof Top Deck,Patio |
| Public Sewer Hookup | Yes |
| Side | Bay/Gulf |
| Species List | No |
| Vehicle Storage | Carport,Trailer Storage,Covered Parking,Guest Parking |
| Windows/Doors | Sliding Glass Doors,Impact Rstnce Window,Impact Rstnce Doors |
| Off Shore Island | No |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33036
Price
Taxes
Year Built
Visits
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Updated on September 18, 2026 2:38 PM UTC
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Information is deemed to be reliable, but is not guaranteed. © 2026 MLS and FBS. Prepared by Florida Keys MLS, Inc. on September 18, 2026 3:17 PM UTC The information on this sheet has been made available by the MLS and may not be the listing of the provider. 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
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
