16 Azalea Dr

$2,700,000
Price
4
Beds
2,321 Sq. Ft.
$1,163 / Sq. Ft.
2,321
Sq. Ft.
$1,163
per Sq. Ft.

Description

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...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.
  1. Listed by Tommy Mack • Coastal Collection Real Estate Inc.
  2. Listed by Jenny Benson • Coastal Collection Real Estate Inc.

Property Details for 16 Azalea Drive

Waterfront
Canal Front
Waterfront
Yes
Zoning
IS - Improved Subivision District
Subdivision
Key Haven 1st Add (5.0)
Building Style
Split Level
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 12/08/2025 09:28 AM

Property Details for 16 Azalea Drive

StatusActive
MLS #617283
Days on Market47
Taxes$9,387 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1965
Lot Size0.14 AC / 6,000 SF
CountyMonroe County

Location

Listing Courtesy of Coastal Collection Real Estate Inc.
Add your commute

Building Information for 16 Azalea Drive

Stories-Year Built1965Building Size-Lot Size0.14 AC / 6,000 SF

Payment Calculator

$14,124 per month

30 year fixed, 6.28% Interest

Principal and Interest

$13,342

Property Taxes

$782

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 16 Azalea Drive

Summary
Location and General Information
  • Waterview: Canal View
  • Area: 05 - Stock Island to Shark Key
  • Absolute Longitude: 81.731658
  • Control Depth: 3
  • Listing Board: Key West Association
  • Side: Bay/Gulf
  • Mile Marker: 5.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key Haven
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.14
  • Parcel #: 00133950-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: LT 8 KEY HAVEN PB4-46 RACCOON KEY OR483-211 OR1137-727 OR1148-1520/21 OR1328-1997/98 OR1731-50 OR2302-1542/43 OR2536-977
  • MLS Approved: Y
  • SqFt Source: Seller
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 79
  • Document Count: 0
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: In Ground, Concrete
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile
  • Interior Features: Cathedral Ceilings, Walk-in Closet(s)
  • Appliances: Washer, Stainless Steel Appliance(s), Disposal, Microwave, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Dockage: Dock: Concrete
  • Construction: Combo Construction
  • Windows/Doors: Impact Rstnce Window, Impact Rstnce Doors
Room Information
  • Specialty Rooms: Utility Room

Property History for 16 Azalea Drive

DateEvent & SourcePriceAppreciation
Nov 11, 2025

Price Change

FKMLS #617283

$2,849,000
Nov 11, 2025

Listed (Active)

FKMLS #617283

$2,700,000
Oct 28, 2024

Sold (Public Record)

Public Record #1544302559

$1,350,000

+8.2% / yr

Oct 28, 2024

Sold

FKMLS #609545

$1,350,000
Oct 25, 2024

Pending

FKMLS #609545

Sep 26, 2024

Backup Contract

FKMLS #609545

Sep 23, 2024

Pending

FKMLS #609545

Sep 4, 2024

Listed (Active)

FKMLS #609545

Jun 10, 2024

Backup Contract

FKMLS #609545

Apr 11, 2024

Listed (Active)

FKMLS #609545

$1,450,000
Apr 10, 2024

Expired

MiamiRE #A11397641

Apr 10, 2024

Expired

FKMLS #604897

Jun 20, 2023

Listed (Active)

MiamiRE #A11397641

$1,589,000
Apr 10, 2023

Price Change

FKMLS #604897

$1,689,000
Apr 10, 2023

Listed (Active)

FKMLS #604897

$1,589,000
Jan 15, 2023

Expired

FKMLS #601827

Jul 20, 2022

Temp Off Market

FKMLS #601827

Jul 15, 2022

Listed (Active)

FKMLS #601827

$1,750,000
Sep 28, 2011

Sold (Public Record)

Public Record #318105514

$480,000

-13.5% / yr

Sep 28, 2011

Sold

FKMLS #113795

$480,000
Sep 27, 2011

Pending

FKMLS #113795

Oct 30, 2010

Listed (Active)

FKMLS #113795

$530,000
Oct 25, 2010

Expired

FKMLS #109364

Oct 1, 2008

Listed (Active)

FKMLS #109364

$555,000
Sep 28, 2008

Expired

FKMLS #108841

Jun 27, 2008

Listed (Active)

FKMLS #108841

$895,000
Jun 1, 2007

Sold (Public Record)

Public Record #222907447

$900,000
Jun 1, 2007

Sold

FKMLS #105281

$900,000
Jun 1, 2007

Pending

FKMLS #105281

Mar 15, 2007

Listed (Active)

FKMLS #105281

$925,000
Oct 3, 2001

Sold

FKMLS #506678

$400,000
Aug 23, 2001

Pending

FKMLS #506678

Apr 16, 2001

Listed (Active)

FKMLS #506678

$418,000
DateEvent & SourcePrice
11/11/2025

Price Change

FKMLS #617283

$2,849,000
11/11/2025

Listed (Active)

FKMLS #617283

$2,700,000
10/28/2024

Sold (Public Record)

Public Record #1544302559

$1,350,000

+8.2% / yr

10/28/2024

Sold

FKMLS #609545

$1,350,000
10/25/2024

Pending

FKMLS #609545

09/26/2024

Backup Contract

FKMLS #609545

09/23/2024

Pending

FKMLS #609545

09/04/2024

Listed (Active)

FKMLS #609545

06/10/2024

Backup Contract

FKMLS #609545

04/11/2024

Listed (Active)

FKMLS #609545

$1,450,000
04/10/2024

Expired

MiamiRE #A11397641

04/10/2024

Expired

FKMLS #604897

06/20/2023

Listed (Active)

MiamiRE #A11397641

$1,589,000
04/10/2023

Price Change

FKMLS #604897

$1,689,000
04/10/2023

Listed (Active)

FKMLS #604897

$1,589,000
01/15/2023

Expired

FKMLS #601827

07/20/2022

Temp Off Market

FKMLS #601827

07/15/2022

Listed (Active)

FKMLS #601827

$1,750,000
09/28/2011

Sold (Public Record)

Public Record #318105514

$480,000

-13.5% / yr

09/28/2011

Sold

FKMLS #113795

$480,000
09/27/2011

Pending

FKMLS #113795

10/30/2010

Listed (Active)

FKMLS #113795

$530,000
10/25/2010

Expired

FKMLS #109364

10/01/2008

Listed (Active)

FKMLS #109364

$555,000
09/28/2008

Expired

FKMLS #108841

06/27/2008

Listed (Active)

FKMLS #108841

$895,000
06/01/2007

Sold (Public Record)

Public Record #222907447

$900,000
06/01/2007

Sold

FKMLS #105281

$900,000
06/01/2007

Pending

FKMLS #105281

03/15/2007

Listed (Active)

FKMLS #105281

$925,000
10/03/2001

Sold

FKMLS #506678

$400,000
08/23/2001

Pending

FKMLS #506678

04/16/2001

Listed (Active)

FKMLS #506678

$418,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 16 Azalea Drive

Taxable ValueLand$966,570Additions$383,498Total$1,350,068
Tax Record2024$9,387 ($782 / month)
Home Facts
Beds4Baths3Total Finished SqFt1,997 SqFtAbove Grade Finished SqFt1,997 SqFtStories2Lot Size6,000 SqFtStyleSingle Family ResidenceYear Built1965Year Renovated2005CountyMONROEAPN00133950-000000

Schools near 16 Azalea Drive

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Charter - K to 8
Public - 9 to 12
Charter - 9 to 12
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Sigsbee Charter School
CharterK to 8

Key West High School
Public9 to 12

The College Of The Florida Keys Academy
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

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16 Azalea Drive is a single family home for sale in Key West, FL 33040. This property was listed for sale on November 11, 2025 by Coastal Collection Real Estate Inc., it's currently listed at $2,700,000. It has been on the market for a total of 47 days and was last sold on October 28, 2024. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Sigsbee Charter School and Key West High School. 16 Azalea Drive is a 4-bed, 3-bath, 2,321 sqft single family home built in 1965.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coastal Collection Real Estate Inc.

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.