16 Azalea Dr, Key West, FL 33040
FOR SALE

16 Azalea Dr
Key West, FL 33040

  • 4 Beds
  • 3 Baths
  • 2,321 sqft

$2,500,000

Original price: $2,600,000
Est. Mortgage $14,110/mo*
Get Pre-Qualified

$2,500,000

Original price: $2,600,000
Est. Mortgage $14,110/mo*
Get Pre-Qualified
4 Beds
3 Baths
2,321 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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 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.

Home Highlights

Parking
No Info
Outdoor
Porch, Deck, Pool
View
Canal
HOA
None
Price/Sqft
$1,077
Listed
180+ days ago

Home Details for 16 Azalea Dr

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2321 Square Feet
Appliances & Utilities
Utilities: FKAAAppliances: Washer, Stainless Steel Appliance(s), Disposal, Microwave, Refrigerator, Dishwasher, DryerDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Central
Windows, Doors, Floors & Walls
Window: Impact Rstnce WindowDoor: Impact Rstnce DoorsFlooring: Tile
Levels, Entrance, & Accessibility
Levels: Multi/SplitFloors: Tile
View
Has a ViewView: Canal

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, DeckHas a Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageNo Open ParkingParking: Off Street
Pool
Pool: In Ground, ConcretePool
Frontage
WaterfrontWaterfront: Canal Front, Waterfront, Dock: ConcreteOn Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Combo ConstructionNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00133950000000

Price & Status

Price
List Price: $2,500,000Price Per Sqft: $1,077

Active Status

MLS Status: Active

Location

Direction & Address
City: Key HavenCommunity: Key Haven 1st Add (5.0)

Agent Information

Listing Agent
Listing ID: 617283

HOA

HOA Fee Includes: NoneAssociation for this Listing: Key West AssociationNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 6098.4 sqft

Miscellaneous

Mls Number: 617283Water ViewWater View: Canal
Last check for updates: about 12 hours ago
Listing courtesy of Tommy Mack, (305) 731-7910
Coastal Collection Real Estate Inc.
Jenny Benson
Coastal Collection Real Estate Inc.
Originating MLS: Key West Association
Source: FLKMLS, MLS#617283
Also Listed on FLKMLS, Key West AOR, Key West AOR.

Market trends in Key West

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.2M
$61.67KMoM
Sale-to-List Price
94.9%
0.4%MoM
Price per sq ft
$940
$14MoM
Available listings
304
28MoM

Price History for 16 Azalea Dr

DatePriceEventSource
04/04/2026$2,500,000PriceChange
Key West AOR #617283
01/27/2026$2,600,000PriceChange
Key West AOR #617283
12/08/2025$2,700,000PriceChange
Key West AOR #617283
11/11/2025$2,849,000Listed For SaleKey West AOR #617283
10/28/2024$1,350,000Sold
FLKMLS #609545
10/25/2024$1,450,000PendingFLKMLS #609545
09/26/2024$1,450,000ContingentFLKMLS #609545
09/05/2024$1,450,000PendingToActiveFLKMLS #609545
06/10/2024$1,450,000ContingentFLKMLS #609545
04/11/2024$1,450,000Listed For SaleFLKMLS #609545
04/11/2024ListingRemovedKey West AOR #604897
05/24/2023$1,589,000PriceChange
FLKMLS #604897
04/11/2023$1,689,000Listed For SaleFLKMLS #604897
07/20/2022ListingRemovedFLKMLS #601827
07/16/2022$1,750,000Listed For SaleFLKMLS #601827
09/28/2011$480,000Sold
FLKMLS #113795
06/19/2007$900,000Sold
N/A
10/11/2001$400,000Sold
N/A
11/01/1994$240,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$12,244
Assessment$1,350,068
Home facts updated by county records

Comparable Sales for 16 Azalea Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Azalea Dr, Key West, FL
0.04
Single-Family Home
$1,800,000
04/17/26
3
2
1,936
30 Key Haven Rd, Key Haven, FL
0.19
Single-Family Home
$1,750,000
12/19/25
3
3
2,715
30 Allamanda Ave, Key West, FL
0.12
Single-Family Home
$2,500,000
06/24/25
4
3
2,102
12 Aster Ter, Key West, FL
0.07
Single-Family Home
$1,100,000
08/01/25
3
2
1,280
26 Bamboo Ter, Key West, FL
0.16
Single-Family Home
$1,925,000
06/19/25
3
3
1,610
24 Aster Ter, Key West, FL
0.08
Single-Family Home
$1,265,000
05/27/26
2
1
1,926
12 Beechwood Dr, Key West, FL
0.22
Single-Family Home
$900,000
10/16/25
3
2
1,232
20 Aster Ter, Key West, FL
0.07
Single-Family Home
$1,300,000
12/02/25
2
1
1,080

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 16 Azalea Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Key West

At least 266 Trulia users voted on each feature.

  • 88 % Say it's dog friendly

  • 83 % Say people would walk alone at night

  • 77 % Say it's walkable to restaurants

  • 74 % Say there are sidewalks

  • 69 % Say streets are well-lit

  • 69 % Say it's walkable to grocery stores

  • 68 % Say yards are well-kept

  • 65 % Say there's holiday spirit

  • 65 % Say it's quiet

  • 54 % Say parking is easy

  • 52 % Say kids play outside

  • 51 % Say they plan to stay for at least 5 years

  • 49 % Say there's wildlife

  • 46 % Say neighbors are friendly

  • 44 % Say car is needed

  • 44 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Gene Graham
    "I’ve lived in this neighborhood for the past seven years. It is close to the airport and Stock Island."
    0
    Flag
  • Ken
    "Walking or bike riding, and extremely bicycle, friendly town! Walking, golf carts, scooters, and bicycles are all very popular here."
    0
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  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
    0
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  • Trulia User
    "Dogs are welcomed at 90% of the restaurants. Everyone will remember your dogs name but not yours! I love living here with my dog Jack."
    0
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  • Angela Garcia
    "It’s a small town with little bar life so it would be relatively safe. There is a high school a block away "
    1
    Flag
  • Trulia User
    "Key West is a huge dog community. They even are allowed in some restaurants . When I walk my dog on the main tourist street (Duval St) I get stopped many times from people wanting to pet my dog. A group of dog owners meet up at the park in the morning every day."
    0
    Flag
  • Bawsnack
    "Themed bike rides, parades, fairs, boat races. There is also a bundle of free activities to do when you are a local on first Sunday of every month downtown"
    0
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  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
    0
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  • Trulia User
    "I ride my bicycle to and from work. It is uneventful but there are natural barriers.t some of the streets are not well lit."
    0
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  • Trulia User
    "It’s a great neighborhood, we absolutely love having the opportunity to be able to live here!! We don’t have young kids so can’t really express things that are impt for them to know!!"
    1
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  • Trulia User
    "Everywhere dogs are welcome here in key west, Florida. Come joining us here in key west. Most food and service places, boats, and entertainment venues are good with dogs."
    0
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  • Trulia User
    "It’s a great community there is tourism so there can be alot of people traffic but for the most part everyone is in good spirits."
    0
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  • Nancy S.
    "So beautiful here everyone calls it paradise! The most relaxing place I have ever been. Welcome to your new Key West Home!(Gieger Key, 10 minutes from Key West downtown) . Make sure you visit all of the wonderful attractions, especially the butterfly garden and don't forget to stop at Gieger Key Marinal for a wonderful meal."
    1
    Flag
  • Trulia User
    "Sunset Carnival and walkability. Beautiful houses and sidewalks. Many houses have gardens and are very well maintained. "
    0
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  • Trulia User
    "too many festivals to name. There's always something going on Old Town and then come on it's Duvall Street crying out loud mark this would not be a family neighborhood. It's definitely an easy rental"
    0
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  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
    0
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  • Trulia User
    "Very beautiful, most people are really nice and cordial. Also very walkable to shops, the marina, and restaurants/bars. But I am just visiting and walking around for a few days."
    0
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  • Trulia User
    "Great people, great neighborhood, great police, family friendly events. Lots of things to do within a decent drive. Very family friendly generally "
    0
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  • Trulia User
    "I love my neighborhood I have lived here since 1976 and my husband since 1951. Love that it’s easy to get around."
    0
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  • Nicholas B.
    "Great place to live; expensive though. Base housing so you give up all your BAH but worth it in this area. "
    0
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  • Key W. B. F.
    "Gatherings on the local Mangia Mangia bench at 900 Southard street, safe & friendly town. Feel connected & welcomed in Key West. Enjoy the peaceful neighborhood & the tropical weather! You can walk or bike to everything you need & want!"
    0
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  • Mari.lindsley
    "I've lived here for 2 years and enjoy the walkability to local theatres and restaurants. There's a strong homeless contingency that detracts from the seaport. But you can't blame them for wanting to be in paradise."
    11
    Flag
  • Rechele M.
    "Easy compared to city life! 25 minutes max to get from one end of the island to the other in 5 o’clock traffic."
    0
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  • Kfowler
    "I am not currently aware of any neighborhood events that would bring the neighbors closer. However, both my husband and I would be open to any such event that would do so and would improve the neighborhood. The area is beautiful and well maintained, with a few exceptions. "
    2
    Flag
  • Tom
    "There are many festivals and events that include the Key West Historic Harbor. Venues include Schooner Wharf, Waterfront Brewery, The Marker, etc.."
    2
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  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
    6
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  • Coltonbutler15
    "I grew up in this neighborhood, There have been many upgrades to the neighborhood that have made it more appealing to families with children. "
    12
    Flag
  • MisterE
    "Bicycles, electric golf carts and scooters are the most popular. Although many people still drive cars the island is small so you never have far to go. "
    0
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  • Caleb G.
    "My neighborhood has the small town vibe mixed with a little party. I love how historic Key West is and how well the history is kept alive. "
    3
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  • MisterE
    "Great place to raise a family, although we sort of live in a bubble. Kids need to understand how things are in the real world and that’s sometimes difficult to teach. "
    0
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  • Romero7648
    "Neighbor is downtown and free transportation in immediate vicinity. Many establishments will provide employee discount if you live in the area. "
    0
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  • Oshry B.
    "open area very friendly neighborhood and neighbors you will love it and your dog would love it even more"
    0
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  • Bwruble
    "Tourist don’t clean up after their dogs, but locals do. This is a wonderful neighborhood. Gecko lane is especially beautiful and very private. "
    1
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  • Ctmortman
    "Perfect place for dogs. There are several dog pearls on the island and some restaurants are pet friendly. I own a dog watching business on Marco Island...a service much needed there"
    2
    Flag
  • Carib28
    "Many places to walk your pet and meet people. It’s also very beautiful with hummingbirds and lovely butterflies."
    0
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LGBTQ Local Legal Protections

Tommy Mack, Coastal Collection Real Estate Inc.
Agent Phone: (305) 731-7910
MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.
16 Azalea Dr, Key West, FL 33040 is a 4 bedroom, 3 bathroom, 2,321 sqft single-family home built in 1965. This property is currently available for sale and was listed by FLKMLS on Nov 11, 2025. The MLS # for this home is MLS# 617283.