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$6,195,000
59 Days On Site

144 N Rolling Hill Road
Plantation Key, FL 33036

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
3,284
SqFt
$1,886
/SqFt
2008
Built
Subdivision:
High Point (89.0)
County:
Monroe
Listing courtesy of Karan Moeller, PA of Ocean Sotheby's International Realty
Call Now: 305-395-3300
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305-395-3300
144 N Rolling Hill Road144 N Rolling Hill Road144 N Rolling Hill Road144 N Rolling Hill Road
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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.

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Listing Snapshot
Price 
$6,195,000
Days On Site 
59 Days
Bedrooms 
4
Inside Area (SqFt) 
3,284 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
0.19 Acres
Year Built 
2008
MLS® Number 
620986
Status 
Active
Property Tax 
$28,256.77
HOA/Condo/Coop Fees 
$29.17 monthly
Sq Ft Source 
N/A
Friends & Family
Recent Activity
2 months agoListing first seen on site
2 months agoListing updated with changes from the MLS®
General Features
Acres 
0.19
Parking 
StorageCarportCoveredGuest
Pets 
Yes
Property Condition 
Updated/Remodeled
Property Sub Type 
Single Family Residence
Security 
Security System
SqFt Total 
3284
Utilities 
Cable AvailablePropane
Zoning 
R1 - Residential Single F
Interior Features
Appliances 
WasherDryerDishwasherRefrigeratorRangeOvenMicrowaveDisposalWine CoolerStainless Steel Appliance(s)
Cooling 
Central AirCeiling Fan(s)
Flooring 
TileMarble
Furnished 
Partially
Heating 
CentralElectricPropanePropane Stove
Interior 
ElevatorStorageWalk-In Closet(s)Built-in FeaturesPantryEntrance Foyer
Window Features 
BlindsDrapesWindow Treatments
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Exterior Features
Construction Details 
Concrete
Exterior 
Outdoor ShowerStorageRain Barrel/Cistern(s)
Patio And Porch 
PatioPorchDeck
View 
Bay
Waterfront 
Yes
Waterview 
Bay
Windows/Doors 
BlindsDrapesWindow Treatments
Community Features
Accessibility Features 
Therapeutic Whirlpool
Association Fee 
$350.0
Association Fee Frequency 
Annually
MLS Area 
25 - Plantation Key
Financing Terms Available 
CashConventional
Listing courtesy of Karan Moeller, PA of Ocean Sotheby's International Realty



Listing information is provided by Participants of the Florida Keys Board of REALTORS MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2026, Florida Keys Board of REALTORS MLS.
Data last updated at: 2026-10-13 03:50 PM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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