About This Home

This 4-bedroom, 5-bathroom single family at 144 N Rolling Hill Road in Plantation Key, FL is listed for $6,195,000 ($1,886 per sqft). Built in 2008, the home offers 3,284 sqft of living space on a 0.19 acres lot.

Key Features

  • Built in 2008
  • 0.19 acre lot
  • Waterfront

Property Details

4 full, 1 half
2008

Amenities

WaterfrontViewA/C
Listing 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.

Monthly Cost Estimate

$33,482/mo

20% down · 6.5% · 30 years

Principal$4,480
Interest$26,845
Insurance$1,807
HOA$350

Estimates only. Actual payments may vary.

Location

144 N Rolling Hill Road

Plantation Key, FL 33036

High Point (89.0)

Features & Amenities

Interior Features

Built-in CabinetsElevatorStorageWalk-in Closet(s)

Exterior Features

Chickee HutOutdoor ShowerSprinkler SystemStorage

Property Details

Flooring

TileMarble

Construction

CBS Concrete

Views

Water

Outdoor Features

DeckPatioPorch

Heating

CentralPropane (Heating)Propane StoveElectric (Heating)

Cooling

Central Air

Appliances

WasherDryerDishwasherRefrigeratorRangeOvenMicrowaveDisposalGas AppliancesWine CoolerStainless Steel Appliance(s)

Questions & Answers

This 4-bedroom, 5-bathroom single family at 144 N Rolling Hill Road is listed at $6,195,000 ($1,886/sqft). The estimated monthly payment is $33,482 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance, HOA fees.

HOA fees are $350/month.

Key features include: Built in 2008, 0.19 acre lot, Waterfront. Interior Features: Built-in Cabinets, Elevator, Storage. Exterior Features: Chickee Hut, Outdoor Shower, Sprinkler System.

This property is listed by Karan Moeller, PA.

KP

Karan Moeller, PA

License 0619230

Agent at Ocean Sotheby's International Realty

Listed by Ocean Sotheby's International Realty · Broker phone: 3057128888 · View on Broker Site · Broker website

MLS# 620986· Source: Florida Keys Board of REALTORS®· 75 days on PropertySimple

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.

144 N Rolling Hill Road, Plantation Key, FL 33036

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