Date
Details
Price
Change
Source
8/14/2026
Listed
$6,195,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/65
$6,195,000
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Property 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.
Full Property Details
Full Property Details for 144 N Rolling Hill Rd
General
- Price: $6,195,000
- HOA FEE: $29/month
- HOA FEE FREQ.: Yearly
- Taxes: $28,256 (2025)
- Status: Active
- Type: Single Family
- Source: 927
- MLS ID: 620986
- Updated: 8/14/2026
- Added to Site: 14 day(s) ago
Interior
- Interior Features: Workshop, Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Drapes/Blinds Incl, Elevator, Pantry, Storage, Whirlpool Bath Tub, Window Treatments
- Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Gas Appliances, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
- Flooring: Tile, Marble
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Additional Information
- Shared Amenities: Community Boat Ramp
- Security/Safety: On Premises System
Exterior
- Exterior Features: Chickee Hut, Outdoor Shower, Sprinkler System, Storage
- Deck/Patio: Roof Top Deck, Open Porch/Balcony, Patio
- Porch/Patio/Deck: Roof Top Deck, Open Porch/Balcony, Patio
Parking
- Parking Features: Guest, Covered, Carport
Location
- Area: 25 - Plantation Key
- County: Monroe
- Subdivision: High Point (89.0)
- Driving Directions: Turn bayside onto High Point Rd, Mile Marker 89. Look for sign near end of street.
Community
- Assoc. Fees Include: Other, Common Area Mnt
- Pets Allowed: Yes
Heating & Cooling
- Central air: Yes
- Air Conditioning: Yes
- Cooling Type: Central Air, Ceiling Fans(s)
- Heating Type: Central, Electric, Propane, Propane Stove
Structural Information
- Architectural Style: Above Flood
- Construction Status: Updated/Remodeled
- Construction: CBS, Concrete
- Roof: Concrete
- Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window, Sliding Glass Doors
- Square Feet: 3,284
- Sq. Ft. Source: Tax Records
- Year Built: 2008
- Property Condition: Updated/Remodeled
Lot Features
- Property View: Open Water View, Bay
- Lot Size (Acres): 0.19
- Lot Size (Sq. Ft.): 8,580
- Lot Size Source: Tax Records
- Lot Dimensions: Irregular
- Zoning: R1 - Residential Single Family
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: Bay Front, Gulf Front, Open Water
Financial Considerations
- Association Fee: Yes
- Association Fee: $350
- Assoc Fee Freq.: Yearly
- Tax Amount: $28,256.77
- Tax Year: 2025
Disclosures and Reports
- Legal Description: Bk 1 Nely 60 Ft Lot 22 High Point Plantation Key Pb4-96 Or467-728 Or860-2239 Or1847-729 Or1956-1067 Or2005-1405 Or2058-3
- APN: 419570000100
Listed by Ocean Sotheby's International Realty, Karan Moeller, PA (305) 522-2857
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Listing agent
— 144 N Rolling Hill Rd —
Karan Moeller, PA
Ocean Sotheby's International Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 144 N Rolling Hill Rd
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Plantation Key School 100 Lake Road, Tavernier, FL 33070 | PK-8 | 1.1 mi |
Coral Shores High School 89901 Old Highway, Tavernier, FL 33070 | 9-12 | 1.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 144 N Rolling Hill Rd
Tax History
Tax History for 144 N Rolling Hill Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$28,257
33%
$3,049,673
31%
2024
$21,242
1%
$2,319,838
3%
2023
$21,100
23%
$2,252,270
34%
2021
$17,187
-17%
$1,682,556
-23%
2022
$20,702
20%
$2,186,670
29%
2021
$17,187
-3%
$1,695,360
—
2019
$17,799
4%
$1,703,561
4%
2018
$17,123
58%
$1,635,101
53%
2017
$10,836
-3%
$1,067,978
2%
2016
$11,226
2%
$1,046,012
1%
2015
$10,953
—
$1,038,741
1%
2014
$10,967
1%
$1,030,497
1%
2013
$10,911
—
$1,015,268
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 144 N Rolling Hill Rd
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- Single Family
- Active
- Updated 5 days ago
- 5Beds
- 4Total Baths
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- Single Family
- Closed
- 5Beds
- 6Total Baths
- 4,951Sq. Ft.
144 N Rolling Hill Road, Plantation Key, FL 33036 (MLS# 620986) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 144 N Rolling Hill Road is currently listed for $6,195,000 and was received on August 14, 2026. Want to learn more about 144 N Rolling Hill Road? Do you have questions about finding other Single Family real estate for sale in Plantation Key? You can browse all Plantation Key real estate or contact a Coldwell Banker agent to request more information.