16 Azalea Dr Key West, FL 33040
Estimated payment $13,945/month
Total Views
103,377
4
Beds
3
Baths
2,321
Sq Ft
$1,077
Price per Sq Ft
About This Home
Welcome to 16 Azalea Drive, a completely reimagined home that embodies sophisticated coastal living, blending modern elegance with meticulous attention to detail at every turn. Thoughtfully redesigned from the ground up, this 4-bedroom, 3-bath property spans nearly 2,400 sq ft of refined living space. The open layout creates a seamless flow between the living, dining & kitchen areas, each curated to maximize light, function & aesthetic appeal. Impact-rated windows & sliding glass doors frame lush tropical views & invite in the natural beauty of the Florida Keys, while the soft coastal palette & high-end finishes create a serene, contemporary atmosphere. The custom kitchen is both striking & functional, featuring quartz countertops, shaker-style cabinetry, a farmhouse sink & top-of-the-line stainless steel appliances. Bathrooms are masterfully finished with designer vanities, custom glass shower enclosures & LED-lit mirrors, creating a spa-like retreat. Throughout the interior, new tile flooring laid in a herringbone pattern adds visual interest & luxury underfoot, complemented by modern black fixtures & ceiling fans that bring a clean architectural touch. This property underwent a comprehensive renovation, including full replacement of plumbing & electrical components, a seamless V-Crimp metal roof, exterior stucco, & interior/exterior painting. The landscape was redesigned with artificial turf, tropical palms & decorative shell features, creating a refined, low-maintenance aesthetic. Expansive deck & patio areas are ideal for outdoor living, with paver walkways leading to a pool & hot tub beside a private canal-front setting. Situated on a wide canal with excellent boating access, this residence offers the ultimate Keys lifestyle for those who appreciate fine craftsmanship, privacy & quick access to open water. A new wood privacy fence, polished detailing & smart LED lighting complete this exceptional home where craftsmanship, comfort & design excellence converge.
Co-Listing Agent
Jenny Benson
Coastal Collection Real Estate Inc. License #3567724
Home Details
Home Type
- Single Family
Year Built
- 1965
Kitchen
- Farmhouse Sink
Map
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Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $9,387 | $1,350,068 | $966,570 | $383,498 |
| 2024 | $7,767 | $1,265,646 | $869,610 | $396,036 |
| 2023 | $7,767 | $887,014 | $502,980 | $384,034 |
| 2022 | $7,351 | $886,608 | $502,980 | $383,628 |
| 2021 | $6,835 | $704,141 | $371,175 | $332,966 |
| 2020 | $6,594 | $671,173 | $363,600 | $307,573 |
| 2019 | $6,488 | $657,168 | $348,450 | $308,718 |
| 2018 | $6,588 | $649,311 | $339,360 | $309,951 |
| 2017 | $6,370 | $632,310 | $0 | $0 |
| 2016 | $6,244 | $600,611 | $0 | $0 |
| 2015 | $6,292 | $582,698 | $0 | $0 |
| 2014 | $6,088 | $537,926 | $0 | $0 |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 04/04/2026 04/04/26 | Price Changed | $2,500,000 | -3.8% | $1,077 / Sq Ft | |
| 01/27/2026 01/27/26 | Price Changed | $2,600,000 | -3.7% | $1,120 / Sq Ft | |
| 12/08/2025 12/08/25 | Price Changed | $2,700,000 | -5.2% | $1,163 / Sq Ft | |
| 11/11/2025 11/11/25 | For Sale | $2,849,000 | +111.0% | $1,227 / Sq Ft | |
| 10/28/2024 10/28/24 | Sold | $1,350,000 | -6.9% | $676 / Sq Ft | View Prior Sale |
| 09/23/2024 09/23/24 | Pending | -- | -- | -- | |
| 04/11/2024 04/11/24 | For Sale | $1,450,000 | -- | $726 / Sq Ft |
Source: Key West Association of REALTORS®
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $1,350,000 | None Listed On Document | |
| Warranty Deed | $11,528 | None Listed On Document | |
| Warranty Deed | -- | None Available | |
| Warranty Deed | $480,000 | First American Title Ins Co | |
| Warranty Deed | $900,000 | First American Title Ins Co | |
| Warranty Deed | $400,000 | -- | |
| Warranty Deed | $240,000 | -- | |
| Warranty Deed | $210,300 | -- | |
| Warranty Deed | $204,700 | -- | |
| Warranty Deed | $139,900 | -- | |
| Deed | $33,500 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $900,000 | New Conventional | |
| Previous Owner | $150,000 | New Conventional | |
| Previous Owner | $630,000 | Purchase Money Mortgage | |
| Previous Owner | $75,000 | Credit Line Revolving | |
| Previous Owner | $230,000 | New Conventional | |
| Previous Owner | $250,000 | No Value Available |
Source: Public Records
About the Listing Agent
After countless family vacations to Key West during his childhood, it was only natural that Tommy would eventually make the island his home. He finally made the move in his early 20's and hasn't looked back since. After years of enjoying the laid back Keys lifestyle, Tommy decided to pursue a career in real estate and found that he was a natural. His easy manner and friendly disposition combined with his perseverance create the perfect combination to provide his clients the real estate
Tommy's Other Listings
Source: Key West Association of REALTORS®
MLS Number: 617283
APN: 00133950-000000
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