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144 N Rolling Hill Road, 
Plantation Key, FL 33036

$6,195,000


4

Beds


5

Baths


3,284

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Karan Moeller, Pa

Ocean Sotheby'S International Realty

Last updated:

September 12, 2026, 03:08 PM

MLS#

620986

Source:

FL FKBOR

About This Home

144 N Rolling Hill Road

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.

Home Facts

Single Family

5 Baths

4 Bedrooms

Built in 2008

Subdivision & Development:

High Point (89.0)

Price Summary

6,195,000

$1,886 per Sq. Ft.

MLS #:

620986

Last Updated:

September 12, 2026, 03:08 PM

Added:

a month ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

5


Structure

Structure

Building Area:

3,284 Sq. Ft.

Year Built:

2008


Lot

Lot Size (Sq. Ft):

8,580


Finances & Disclosures

Finances

Price:

$6,195,000

Price per Sq. Ft:

$1,886 per Sq. Ft.

Source:FL FKBOR
The information being provided by Florida Keys Board Of REALTORS®, Inc. is for the 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 information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Florida Keys Board Of REALTORS®, Inc. All rights reserved. FL FKBOR Member Broker: Brian Schmitt
See this home in person
144 N Rolling Hill Road
Attend an upcoming open house
Thu, Sep 17
10:00 AM01:00 PM

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.