153 Key Haven Rd, Key West, FL 33040
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Property image
OFF MARKET

153 Key Haven Rd
Key West, FL 33040

  • 4 Beds
  • 3 Baths
  • 4,825 sqft (on 0.32 acres)

$5,598,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $32,212/mo*
Refinance Your Home

$5,598,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $32,212/mo*
Refinance Your Home
4 Beds
3 Baths
4,825 sqft
(on 0.32 acres)

Local Information

  • Map ViewExplore the area around 153 Key Haven Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1986
Lot Size
0.32 acres
Living Area
4,825 sqft
Price/Sqft
$1,160
Parking
Garage

About this House

This single-family home is located at 153 Key Haven Rd, Key West, FL. 153 Key Haven Rd is in Key West, FL and in ZIP code 33040. This property has 4 bedrooms, 3 bathrooms and approximately 4,825 sqft of floor space. This property has a lot size of 0.32 acres and was built in 1986.
153 Key Haven Rd, Key West, FL 33040 is a 4 bedroom, 3 bathroom, 4,825 sqft single-family home built in 1986. It last sold for $5,700,000 on Feb 1, 2023. It is currently off market. The Trulia Estimate is $5,598,800, with a rent estimate of $7,848/month.

Home Details for 153 Key Haven Rd

Interior Features

Heating & Cooling
Heating: Other, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Other, Hardwood
Interior Details
AtticIn-law unitNumber of Rooms: 12Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, PantryWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: Stucco, Cement ConcreteFoundation Type: PilingGardenLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached, Off Street, On Street

Property Information

Year Built
Year Built: 1986Year Updated: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Spanish

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Mobile R/V

RV Parking
Rv Parking

Price History for 153 Key Haven Rd

DatePriceEventSource
02/01/2023$5,700,000Sold
FLKMLS #603594
01/31/2023$5,700,000PendingFLKMLS #603594
01/27/2023$5,700,000ContingentKey West AOR #603594
01/13/2023$5,700,000PendingToActiveKey West AOR #603594
01/09/2023$5,700,000ContingentKey West AOR #603594
01/01/2023$5,700,000Listed For SaleKey West AOR #603594
04/29/2014$874,500Sold
FLKMLS #119597
04/24/2014$897,600PendingAgent Provided
03/29/2014$897,600Listed For SaleAgent Provided
11/18/2013$440,100Sold
N/A
04/10/2011$1,195,000ListingRemovedAgent Provided
01/23/2011$1,195,000PriceChange
Agent Provided
06/12/2010$1,249,000PriceChange
Agent Provided
04/30/2010$1,295,000PriceChange
Agent Provided
04/02/2010$1,395,000Listed For SaleAgent Provided

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
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Property Tax and Assessment

Year2025
Tax$41,601
Assessment$4,747,008
Home facts updated by county records

Comparable Sales for 153 Key Haven Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Cypress Ter, Key West, FL
0.25
Single-Family Home
$3,000,000
01/14/26
3
3
3,024
33 Cypress Ave, Key West, FL
0.21
Single-Family Home
$3,250,000
02/12/26
4
4.5
4,102
37 Evergreen Ave, Key West, FL
0.29
Single-Family Home
$2,425,000
09/30/25
3
3
2,685
8 Floral Ave, Key West, FL
0.20
Single-Family Home
$2,522,000
10/30/25
3
3
2,521
39 Evergreen Ave, Key West, FL
0.31
Single-Family Home
$5,400,000
01/28/26
8
9.5
6,611
412 Cactus Dr, Key West, FL
0.23
Single-Family Home
$2,350,000
03/31/26
3
2
2,308
117 Key Haven Rd, Key West, FL
0.25
Single-Family Home
$1,850,000
03/10/26
3
2
2,090
13 Arbutus Dr, Key West, FL
0.58
Single-Family Home
$2,150,000
07/06/26
4
3
1,957
30 Key Haven Rd, Key Haven, FL
0.56
Single-Family Home
$1,750,000
12/19/25
3
3
2,715
20 Bamboo Ter, Key West, FL
0.44
Single-Family Home
$1,650,000
10/03/25
3
2
1,428

Nearby homes

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Assigned Schools

These are the assigned schools for 153 Key Haven Rd.
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 267 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

  • 64 % 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
    Flag
  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Nicholas B.
    "Great place to live; expensive though. Base housing so you give up all your BAH but worth it in this area. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
    6
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Romero7648
    "Neighbor is downtown and free transportation in immediate vicinity. Many establishments will provide employee discount if you live in the area. "
    0
    Flag
  • Oshry B.
    "open area very friendly neighborhood and neighbors you will love it and your dog would love it even more"
    0
    Flag
  • 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
    Flag
  • 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
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

23 pet-friendly rentals in Key West, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Outdoor Space

9 rentals with an outdoor space in Key West, FL

Homes for sale near 153 Key Haven Rd

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Off Market Homes Near 153 Key Haven Rd

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Frequently asked questions about 153 Key Haven Rd

  • What is 153 Key Haven Rd estimated to be worth?
    Trulia's estimated value for 153 Key Haven Rd in Key West, FL is $5,598,800.
  • What is the price history for 153 Key Haven Rd?
    153 Key Haven Rd in Key West, FL last sold for $5,700,000 in February 2023.
  • Is Key West a buyer's or seller's market?
    Key West is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Key West?
    The median sale price in Key West is $1.23M. That is up $20.83K from the prior month.
  • Does 153 Key Haven Rd have air conditioning?
    Yes, 153 Key Haven Rd in Key West, FL has air conditioning.
  • Does 153 Key Haven Rd have a pool?
    Yes, 153 Key Haven Rd in Key West, FL has a pool.