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 (4/4)
$2,500,000
16 Azalea Dr, Key West, FL 33040
4beds
2,321sqft
Single Family Residence
Built in 1965
6,098 Square Feet Lot
$2,381,500 Zestimate®
$1,077/sqft
$-- HOA
What's special
Shaker-style cabinetryTropical palmsMaximize lightV-crimp metal roofWood privacy fenceQuartz countertopsDecorative shell features
- 226 days |
- 454 |
- 22 |
Zillow last checked:
Listing updated:
Listed by:
Tommy Mack 305-731-7910,
Coastal Collection Real Estate Inc.,
Jenny Benson,
Coastal Collection Real Estate Inc.
Source: FLKMLS,MLS#: 617283
Originating MLS: Key West Association
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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 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: $1,077/sqft
- Tax assessed value: $1,350,068
- Annual tax amount: $9,387
- Date on market: 11/11/2025
Estimated market value
$2,381,500
$2.26M - $2.50M
$6,869/mo
Price history
| Date | Event | Price |
|---|---|---|
| 4/4/2026 | Price change | $2,500,000-3.8%$1,077/sqft |
Source: | ||
| 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
| 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 | $582,698 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
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
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Monroe County
- Key West
- 33040
- 16 Azalea Dr



