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.
For sale
Price cut: $100K (1/27)
$2,600,000
16 Azalea Dr, Key West, FL 33040
4beds
2,321sqft
Est.:
Single Family Residence
Built in 1965
6,098.4 Square Feet Lot
$2,447,000 Zestimate®
$1,120/sqft
$-- HOA
What's special
Shaker-style cabinetryTropical palmsMaximize lightV-crimp metal roofWood privacy fenceQuartz countertopsDecorative shell features
- 109 days |
- 1,103 |
- 15 |
Zillow last checked: 8 hours ago
Listing updated: February 14, 2026 at 10:55pm
Listed by:
Tommy Mack 305-731-7910,
Coastal Collection Real Estate Inc.,
Jenny Benson 775-835-9668,
Coastal Collection Real Estate Inc.
Source: FLKMLS,MLS#: 617283
Originating MLS: Key West Association
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Central
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Stainless Steel Appliance(s), Disposal, Microwave, Refrigerator, Dishwasher, Dryer
Features
- Cathedral Ceiling(s), Walk-In Closet(s), Utility Room
- Flooring: Tile
- Doors: Impact Rstnce Doors
- Windows: Impact Rstnce Window
Interior area
- Total interior livable area: 2,321 sqft
Property
Parking
- Parking features: Off Street
Features
- Levels: Multi/Split
- Patio & porch: Open Porch/Balcony, Deck
- Has private pool: Yes
- Pool features: In Ground, Concrete
- Has view: Yes
- View description: Canal
- Has water view: Yes
- Water view: Canal
- Waterfront features: Canal Front, Waterfront, Dock: Concrete
Lot
- Size: 6,098.4 Square Feet
- Features: Less Than 1/4 Acre
Details
- Parcel number: 00133950000000
- Zoning: IS
- Zoning description: Improved Subivision District
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Combo Construction
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1965
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA
Community & HOA
Community
- Subdivision: Key Haven 1st Add (5.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Key West
Financial & listing details
- Price per square foot: $1,120/sqft
- Tax assessed value: $1,350,068
- Annual tax amount: $9,387
- Date on market: 11/11/2025
Estimated market value
$2,447,000
$2.32M - $2.57M
$7,402/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/27/2026 | Price change | $2,600,000-3.7%$1,120/sqft |
Source: | ||
| 12/8/2025 | Price change | $2,700,000-5.2%$1,163/sqft |
Source: | ||
| 11/11/2025 | Listed for sale | $2,849,000+111%$1,227/sqft |
Source: | ||
| 10/28/2024 | Sold | $1,350,000-6.9%$582/sqft |
Source: | ||
| 10/25/2024 | Pending sale | $1,450,000$625/sqft |
Source: | ||
| 9/26/2024 | Contingent | $1,450,000$625/sqft |
Source: | ||
| 9/5/2024 | Listed for sale | $1,450,000$625/sqft |
Source: | ||
| 6/10/2024 | Contingent | $1,450,000$625/sqft |
Source: | ||
| 4/11/2024 | Listed for sale | $1,450,000-8.7%$625/sqft |
Source: | ||
| 4/11/2024 | Listing removed | -- |
Source: | ||
| 5/24/2023 | Price change | $1,589,000-5.9%$685/sqft |
Source: | ||
| 4/11/2023 | Listed for sale | $1,689,000-3.5%$728/sqft |
Source: | ||
| 7/20/2022 | Listing removed | -- |
Source: | ||
| 7/16/2022 | Listed for sale | $1,750,000+264.6%$754/sqft |
Source: | ||
| 9/28/2011 | Sold | $480,000-46.7%$207/sqft |
Source: | ||
| 6/19/2007 | Sold | $900,000+125%$388/sqft |
Source: Public Record Report a problem | ||
| 10/11/2001 | Sold | $400,000+66.7%$172/sqft |
Source: Public Record Report a problem | ||
| 11/1/1994 | Sold | $240,000$103/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $12,244 +30.4% | $1,350,068 +44.1% |
| 2024 | $9,387 +20.9% | $937,212 +10% |
| 2023 | $7,767 +5.7% | $852,011 +10% |
| 2022 | $7,351 +7.5% | $774,555 +10% |
| 2021 | $6,835 +3.7% | $704,141 +4.9% |
| 2020 | $6,594 | $671,173 +2.1% |
| 2019 | $6,594 +1.6% | $657,168 +1.2% |
| 2018 | $6,488 -1.5% | $649,311 +2.7% |
| 2017 | $6,588 +3.4% | $632,310 +5.3% |
| 2016 | $6,370 +2% | $600,611 +3.1% |
| 2015 | $6,244 | $582,698 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$14,564/mo
Principal & interest
$12787
Property taxes
$1777
Climate risks
Neighborhood: 33040
Nearby schools
GreatSchools rating
- 4/10Gerald Adams Elementary SchoolGrades: PK-5Distance: 0.9 mi
- NAAdult/Vocational/Community EducationGrades: Distance: 1.1 mi
- 4/10Key West High SchoolGrades: 9-12Distance: 3.4 mi




