Save
Ask
Tour
Hide
Share
$6,195,000
60 Days On Site

144 N Rolling Hill Road
ISLAMORADA, FL 33036

For Sale|Single Family Residence|Active
4
Beds
4.5
Total Baths
4
Full Baths
1
Partial Bath
3,284
SqFt
$1,886
/SqFt
2008
Built
Subdivision:
High Point (89.0)
County:
Monroe
Call Now: 305-395-3300
Is this the listing for you? We can help make it yours.
305-395-3300
144 N Rolling Hill Road144 N Rolling Hill Road144 N Rolling Hill Road144 N Rolling Hill Road
Save
Ask
Tour
Hide
Share

Mortgage Calculator

Monthly Payment (Est.)

Enter an interest rate to see your estimated monthly payment.
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$6,195,000
Days On Site 
60 Days
Bedrooms 
4
Inside Area (SqFt) 
3,284 sqft
Total Baths 
4.5
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 weeks agoListing updated with changes from the MLS®
2 months agoListing first seen on site
General Features
Acres 
0.19
Parking 
CarportCoveredGuest
Pets 
Yes
Property Sub Type 
Single Family Residence
Security 
Security System
Sewer 
Public Sewer
SqFt Total 
3284
Style 
Single Family
Utilities 
Cable AvailablePropane
Zoning 
R1 - Residential Single Family
Interior Features
Appliances 
WasherStainless Steel Appliance(s)Wine CoolerDisposalMicrowaveOvenRangeRefrigeratorDishwasherDryerSolar Hot Water
Cooling 
Central AirCeiling Fan(s)
Flooring 
TileMarble
Furnished 
Partially
Heating 
CentralPropane StovePropaneElectric
Interior 
ElevatorEntrance FoyerPantryWalk-In Closet(s)Storage
Save
Ask
Tour
Hide
Share
Exterior Features
Exterior 
StorageOutdoor ShowerRain Barrel/Cistern(s)
Lot Features 
Waterfront
Other Structures 
StorageWorkshop
Patio And Porch 
PatioDeck
Roof 
Concrete
View 
Bay
Waterfront 
Yes
Waterview 
Bay
Windows/Doors 
Sliding Doors
Community Features
Association Fee 
$350.0
Association Fee Frequency 
Annually
MLS Area 
25 - Plantation Key
Financing Terms Available 
ConventionalCash
Listing courtesy of Ocean Sotheby's International Realty


Copyright © 2026 Key West Multiple Listing Service. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) of the Key West Multiple Listing Service. Real estate listings held by brokerage firms other than Ocean Sotheby's International Realtyare marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' 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 has not been verified, is not guaranteed, and is subject to change.

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