# 144 N Rolling Hill Road, Plantation Key, FL 33036 > **TL;DR:** 4bd/5ba single family, $6,195,000 ($1886/sqft), built 2008, 3,284 sqft. > Waterfront, View, A/C. Est. $33,482/mo. Listed 80 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $6,195,000 | | Price/sqft | $1886 | | Bedrooms | 4 | | Bathrooms | 4 full, 1 half | | Square Feet | 3,284 | | Year Built | 2008 | | Lot Size | 8,276 sqft (0.19 acres) | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 80 | ## Why This Home Stands Out - **Waterfront** - Waterfront location listed - **Views** - Water ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $31,325 | | Estimated Insurance | $1,807 | | HOA | $350 | | **Total** | **$33,482** | ## Key Amenities - Waterfront - View - A/C ## Property Highlights - Built in 2008 - 0.19 acre lot - Waterfront ## Description ### Agent 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. ## Location - **Address:** 144 N Rolling Hill Road, Plantation Key, FL 33036 - **County:** Monroe - **Neighborhood:** High Point (89.0) - **Coordinates:** 24.980171, -80.554574 - **Google Maps:** https://www.google.com/maps?q=24.980171,-80.554574 ## Virtual Tour & Media - **Video Tour:** https://bcove.video/4rDxxkL ## Listing Agent - **Name:** Karan Moeller, PA · **License:** 0619230 - **Brokerage:** Ocean Sotheby's International Realty - **Broker Phone:** 3057128888 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/144-N-Rolling-Hill-Rd_Plantation-Key_FL_33036_M92248-56666?f=listhub&s=FLKEYSMLSFL&m=620986&c=propsimple) ## Photos ![144 N Rolling Hill Road - Photo 1](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f2591727078r.jpg) ![144 N Rolling Hill Road - Photo 2](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f1964933763r.jpg) ![144 N Rolling Hill Road - Photo 3](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f897813221r.jpg) ![144 N Rolling Hill Road - Photo 4](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f49350926r.jpg) ![144 N Rolling Hill Road - Photo 5](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f1197202230r.jpg) ![144 N Rolling Hill Road - Photo 6](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f3084340730r.jpg) ![144 N Rolling Hill Road - Photo 7](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f3748966065r.jpg) ![144 N Rolling Hill Road - Photo 8](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f327561909r.jpg) ![144 N Rolling Hill Road - Photo 9](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f1788598273r.jpg) ![144 N Rolling Hill Road - Photo 10](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f3929657476r.jpg) ![144 N Rolling Hill Road - 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Photo 51](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f3714078780r.jpg) ![144 N Rolling Hill Road - Photo 52](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f2144155939r.jpg) ![144 N Rolling Hill Road - Photo 53](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f1446304507r.jpg) ![144 N Rolling Hill Road - Photo 54](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f2687334450r.jpg) ![144 N Rolling Hill Road - Photo 55](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f1607799007r.jpg) ![144 N Rolling Hill Road - Photo 56](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f860223448r.jpg) ![144 N Rolling Hill Road - Photo 57](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f2873619627r.jpg) ![144 N Rolling Hill Road - Photo 58](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f1414087404r.jpg) ![144 N Rolling Hill Road - Photo 59](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f920000378r.jpg) ![144 N Rolling Hill Road - Photo 60](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f1116789344r.jpg) ![144 N Rolling Hill Road - Photo 61](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f670363836r.jpg) ![144 N Rolling Hill Road - Photo 62](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f4292584770r.jpg) ![144 N Rolling Hill Road - Photo 63](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f3824608139r.jpg) ![144 N Rolling Hill Road - Photo 64](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f2195136857r.jpg) ![144 N Rolling Hill Road - Photo 65](http://lh.rdcpix.com/2fbdb38e316fe52b7d8c7e7708ccca89l-f2439251074r.jpg) --- **MLS#:** 620986 | **Updated:** 2026-10-24 **Source:** listhub *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.* [View on PropertySimple](https://www.propertysimple.ai/listing/144-n-rolling-hill-road-plantation-key-fl-33036-ce7053e6c3094a1987cd5f276adfcd60) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/144-n-rolling-hill-road-plantation-key-fl-33036-ce7053e6c3094a1987cd5f276adfcd60#listing", "url": "https://www.propertysimple.ai/listing/144-n-rolling-hill-road-plantation-key-fl-33036-ce7053e6c3094a1987cd5f276adfcd60", "name": "144 N Rolling Hill Road, Plantation Key, FL 33036", "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. 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