1023 Simonton St, Key West, FL 33040
Property image
Property image
OFF MARKET

1023 Simonton St
Key West, FL 33040

Upper Duvall
  • 2 Beds
  • 3 Baths
  • 1,425 sqft

$1,160,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $6,738/mo*
Refinance Your Home

$1,160,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $6,738/mo*
Refinance Your Home
2 Beds
3 Baths
1,425 sqft

Local Information

  • Map ViewExplore the area around 1023 Simonton St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
2015
Living Area
1,425 sqft
Price/Sqft
$815
HOA
$285/Monthly

About this House

With the charm of Old Town Key West and the peace of mind of modern hurricane rated living, this townhome is a rare find. While conveniently located just one block from Duval Street, it is tucked back in the quiet, cozy 21 home enclave of Southernmost Cabanas. A few steps out your back door and you'll find yourself at your highly coveted private parking space in the covered garage. A few more steps and you're at the heated pool with gorgeous waterfall. Built in 2015, this home was made to be low maintenance. With impact doors and windows, you'll enjoy low insurances, utilities, and HOA fees. Monthly rentals are allowed at this property and its close proximity to Duval Street and Key West's most popular spots make for a desirable location.
Walking up to the property you are greeted with a charming white picket fence and tropical front yard. As soon as you step inside the townhome you'll notice the high ceilings and modern feeling. Just a bit further, entering into the kitchen and living areas, you'll discover stainless steel appliances, an abundance of counter space, washer & dryer, wood-look tile floors, and plenty of natural light. Modern furnishings are throughout. Upstairs are two large bedrooms, primary and guest, both featuring king sized beds and their own en suite bathrooms. The guest bedroom, which is on the front of the home, has a private outdoor balcony overlooking Old Town. Stepping out to your spacious private back deck, you'll find space for your grill and comfortable outdoor furniture set. Enjoy listening to the wind through the palms and tropical birds singing as the island awakens each morning and winds down each evening. Just off your deck is a beautiful stone pathway weaving throughout the cabanas. Throughout the property you'll notice beautiful mature trees and landscaping which make the entire property feel like a tropical paradise. Being sold turnkey, this home is entirely furnished including dishes and housewares. Come live your island life.
1023 Simonton St, Key West, FL 33040 is a 2 bedroom, 3 bathroom, 1,425 sqft townhouse in Upper Duvall, built in 2015. It last sold for $1,150,000 on Sep 24, 2025 (11% below the $1,299,000 asking price). It is currently off market. The Trulia Estimate is $1,160,800, with a rent estimate of $5,469/month.

Home Details for 1023 Simonton St

Interior Features

Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 1425 Square Feet
Appliances & Utilities
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Stainless Steel Appliance(s)DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Ceiling Fans(s)
Windows, Doors, Floors & Walls
Flooring: Tile
Levels, Entrance, & Accessibility
Floors: Tile
View
No View
Room & Shared Space
Shared space is furnished

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, DeckHas a Private Pool
Parking & Garage
No Attached Garage
Pool
Pool: In GroundPool
Frontage
Not on Waterfront

Property Information

Year Built
Year Built: 2015
Property Type / Style
Property Type: ResidentialProperty Subtype: TownhouseArchitecture: Townhouse
Building
Construction Materials: Frame, Hardi Board Siding
Property Information
Parcel Number: 00027070001200

Price & Status

Price
List Price: $1,299,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Key WestCommunity: Old Town - Unrecord (1.0)

Building

Building Area
Building Area: 1425 Square Feet

HOA

HOA Fee Includes: Common Area MntHas an HOAHOA Fee: $285/Monthly

Offer

Listing Terms: Cash, Conventional

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 607016
Last check for updates: about 10 hours ago
Listed by The Little Island Group, (305) 767-3222
Island Home Realty Inc.
Bought with: J. Michael Caron, (508) 269-8565, Keller Williams Key West Compass Realty
Source: FLKMLS, MLS#607016

Price History for 1023 Simonton St

DatePriceEventSource
09/24/2025$1,150,000Sold
N/A
11/21/2023$1,275,000Sold
FLKMLS #607016
11/02/2023$1,299,000PendingFLKMLS #607016
10/18/2023$1,299,000ContingentKey West AOR #607016
10/13/2023$1,299,000Listed For SaleKey West AOR #607016
10/13/2023ListingRemovedFLKMLS #605457
09/23/2023$1,350,000PendingToActiveFLKMLS #605457
09/18/2023$1,350,000ContingentFLKMLS #605457
09/08/2023$1,350,000Listed For SaleFLKMLS #605457
07/28/2023ListingRemovedKey West AOR #605457
07/15/2023$1,375,000PriceChange
FLKMLS #605457
05/26/2023$1,395,000Listed For SaleKey West AOR #605457
04/20/2017$675,000Sold
FLKMLS #120159

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$9,294
Assessment$1,061,398
Home facts updated by county records

Comparable Sales for 1023 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1019 Simonton St #102, Key West, FL
0.03
Townhouse
$1,325,000
11/21/25
2
3
1,440
1017 Simonton St #103, Key West, FL
0.02
Townhouse
$1,160,000
09/23/25
2
2
1,242
613 Virginia St, Key West, FL
0.03
Townhouse
$1,400,000
10/10/25
3
3
1,425
606 Truman Ave #7, Key West, FL
0.06
Townhouse
$1,799,000
11/21/25
2
2
1,120
1209 Grinnell St #G, Key West, FL
0.37
Townhouse
$1,500,000
09/05/25
2
2.5
1,360
907 United St, Key West, FL
0.32
Townhouse
$1,254,750
08/04/26
3
3
1,513
808 Virginia St #4, Key West, FL
0.22
Townhouse
$905,000
04/10/26
2
1.5
896
212 Southard St, Key West, FL
0.46
Townhouse
$1,050,000
05/01/26
2
2.5
960

Nearby homes

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Assigned Schools

These are the assigned schools for 1023 Simonton St.
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.

Neighborhood Overview

Upper Duvall
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Upper Duvall

At least 25 Trulia users voted on each feature.

  • 90 % Say it's walkable to restaurants

  • 87 % Say it's dog friendly

  • 77 % Say there are sidewalks

  • 74 % Say it's walkable to grocery stores

  • 74 % Say people would walk alone at night

  • 72 % Say streets are well-lit

  • 60 % Say there's holiday spirit

  • 59 % Say yards are well-kept

  • 58 % Say it's quiet

  • 52 % Say there's wildlife

  • 44 % Say they plan to stay for at least 5 years

  • 43 % Say there are community events

  • 41 % Say kids play outside

  • 38 % Say neighbors are friendly

  • 22 % Say parking is easy

  • 10 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Sunset Carnival and walkability. Beautiful houses and sidewalks. Many houses have gardens and are very well maintained. "
    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
  • Marjoe55
    "We live on Shanty Creek, wish flows into Maumee bay. We face East on a tiny peninsula of forty houses."
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

22 pet-friendly rentals in Key West, FL

Explore by feature - Garage

9 rentals with a garage in Key West, FL

Explore by feature - Air Conditioning

100 rentals with air conditioning in Key West, FL

Explore by feature - Pool

72 rentals with a pool in Key West, FL

Explore by feature - Washer/dryer

71 rentals with a washer/dryer in Key West, FL

Explore by feature - Outdoor Space

10 rentals with an outdoor space in Key West, FL

Homes for sale near 1023 Simonton St

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Off Market Homes Near 1023 Simonton St

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Frequently asked questions about 1023 Simonton St

  • What is 1023 Simonton St estimated to be worth?
    Trulia's estimated value for 1023 Simonton St in Key West, FL is $1,160,800.
  • What is the price history for 1023 Simonton St?
    1023 Simonton St in Key West, FL last sold for $1,150,000 in September 2025.
  • 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 1023 Simonton St have air conditioning?
    Yes, 1023 Simonton St in Key West, FL has air conditioning.
  • Does 1023 Simonton St have a pool?
    Yes, 1023 Simonton St in Key West, FL has a pool.
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 MLS.