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Ad #6941728
MLS #620986
Listing photo

Experience the ultimate Islamorada waterfront lifestyle in an

144 N Rolling Hill Rd, Plantation Key, FL 33036
$6,195,000
4Beds
5Baths
3,284Sqft
0.19Acres

About this property

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 equipmentbining 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.

Property Features

4 Beds
5 Baths
3,284 Sqft
Built in 2008
0.19 Acres
Siding: CBS, Concrete
Concrete Roof
Central, Electric (Heating), Propane (Heating), Propane Stove
$28,257 / yr property tax
Monroe County
High Point (8) Community

Additional Photos

Additional listing photo 1
Additional listing photo 2
Additional listing photo 3
Additional listing photo 4

Contact Information

Karan Moeller, PA

Ocean Sotheby's International Realty

305-522-2857

Location

Map
Listing Agent: Karan Moeller, PA (License #: 0619230) 305-522-2857
Broker: Ocean Sotheby's International Realty 305-712-8888 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BarrierFreeHome.com
Printed Sep 7, 2026

Photo Gallery

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$6,195,000

4
Beds
5
Baths
3,284
Sqft

144 N Rolling Hill Rd, Plantation Key, FL 33036

By contacting this agent you agree to these Terms and Conditions.
Home Florida Plantation Key
Experience the ultimate Islamorada waterfront lifestyle in an - photo 1
Experience the ultimate Islamorada waterfront lifestyle in an - photo 2
Experience the ultimate Islamorada waterfront lifestyle in an - photo 3
Experience the ultimate Islamorada waterfront lifestyle in an - photo 4
Experience the ultimate Islamorada waterfront lifestyle in an - photo 5
MLS# 620986
Home For Sale
$6,195,000

144 N Rolling Hill Rd, Plantation Key, FL 33036

4
Beds
5
Baths
3,284
Sqft
0.19
Acres
$6,195,000

144 N Rolling Hill Rd, Plantation Key, FL 33036

4 Beds
5 Baths
3,284 Sqft
0.19 Acres
Accessibility Features
Accessible Elevator Installed

Experience the ultimate Islamorada waterfront lifestyle in an

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 equipmentbining 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.
24 days
on BarrierFreeHome.com
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Property Details

HOME DETAILS

4 Beds
5 Baths
3,284 Sqft
Built in 2008
0.19 Acres

EXTERIOR

Siding: CBS, Concrete
Concrete Roof

INTERIOR

Central, Electric (Heating), Propane (Heating), Propane Stove

FINANCIAL & COMMUNITY

$28,257 / yr property tax
Monroe County
High Point (8) Community
See More Details

Location

Map
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Ad Statistics

Ad Number
6941728
Viewed
22 times
Listing Status
Active
Added
Aug 14, 2026
Last Refreshed
Sep 07, 2026 09:42:37 PM

Listing Information

Data Source
Florida Keys Board of REALTORS®
Source Property ID
620986
Listing Agent: Karan Moeller, PA (License #: 0619230) 305-522-2857
Broker: Ocean Sotheby's International Realty 305-712-8888 Listing Site
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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By proceeding, you authorize Dream Home Network Inc., its service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners), its affiliates, and other real estate professionals that may not be associated with Dream Home Network, to contact you using the contact details you provided, via email, phone call, and text (SMS), including using automated dialing technology and prerecorded and artificial voice, for marketing or advertising purposes, including contacting you about your inquiry and other home-related matters. You understand that your consent to the foregoing is not a condition of any purchase. Message and data rates may apply. This consent applies even if you are on a corporate, state or national Do Not Call list. Dream Home Network Inc. may share information about your recent and future site activity with its affiliates and service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners) to help them better understand what you are looking for in a property. To opt-out at any time you can reply "STOP" or contact Dream Home Network Inc. at csv@dreamhomenetwork.com.
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SERVICES
Buy Buy Advertise
COMPANY
Testimonials About Us Office Locations
SUPPORT
Help Contact Us
ADDITIONAL MARKETS
LakeHouse.com MountainHomes.com BeachHouse.com GolfHomes.com
SUBSCRIBE
Receive notifications for new listings
Subscribe
Facebook YouTube

Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 Wheelchair-accessible Housing & Universal Design Homes at Barrier Free Home
Part of Dream Home Network, Inc.
Last updated on 2026.09.07
Terms & Policy