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

123 Simonton St
Key West, FL 33040

Historic Seaport
  • 3 Beds
  • 4 Baths
  • 2,541 sqft

$3,280,200

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $18,902/mo*
Refinance Your Home

$3,280,200

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $18,902/mo*
Refinance Your Home
3 Beds
4 Baths
2,541 sqft

Local Information

  • Map ViewExplore the area around 123 Simonton St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2019
Living Area
2,541 sqft
Price/Sqft
$1,291
Parking
Garage

About this House

Address- 123 Simonton St.
$9-10K in the fall season: high seasons winter spring $12K
Portside Villa, a multi-million dollar old town treasure
Vacation Townhouse for rent by the month

Welcome to the most significant gated landmark community in Key West history.
Portside Villa (123) is a beautifully appointed Townhouse with a traditional
Key West flair for color and comfort.

Located in the heart of Old Town Key West are 20 new Townhomes with a resort feel, one large
shared pool, 2 electronic security gates, tasteful landscaping, and a large shared pool.
All of Duval, Seaport and Conch Harbour are easily within walking distance to Sloppy Joe's,
Captain Tony's, Irish Kevins, The Sandbar Sports Grill, and towards Caroline Street, Only Wood,
Pepe's and the Cuban Queen for a true Cuban breakfast with coffee.
A natural island beach at Ft. Zachary Taylor and the Splash Pad
in the new Truman Waterfront Park are less than a half-mile away for the kids, old and young.

Portside Villa has four private elevator access floors with three large bedrooms each with
its own en-suite spacious bath (ADA compliant).
The main floor, as you enter either from the front or rear door or 2 car garage you may choose
the wide staircase or the comfortable private elevator to take you up one flight to a lovely
open floor plan.
A spacious living room/dining with a large well-appointed top line, state of the art,
a gourmet kitchen is just the beginning of a relaxing no pressure visit. This kitchen is fully equipped
with stainless steel appliances and trendy sleek white marble countertops.
The living room has a large flat-screen TV, comfortable seating and french doors
to a balcony.
The first guest bedroom is located on this floor with a comfortable King bed (also
configurable as 2 twins), an Armoire for two, flat-screen TV and en-suite bath.

The third floor is home to a Master Suite with a balcony, laundry center, and a VIP suite.
The Master has island classic Tommy Bahama furnishings complete with a King size bed,
an en-suite bath with double sinks, Jacuzzi and a separate shower. A very large walk-in closet
completes the suite.
The VIP has a King bed (also configurable as 2 twins), a flat-screen TV, a large closet and an
en-suite bath with ample glass shower.

The fourth floor opens dramatically onto a high octagonal ceiling with french doors to
the upscale outdoor patio lounge and entertainment center. Here is a near theater-like
environment to hang out with a pizza or a feast, football or a romantic movie.
For "occasional guests overnight there are two convertible couches.

Additional features:

A powder room and wet bar on the 4th floor
Central AC & ceiling fans throughout including roof deck fan
Starter supply paper products
Starter set cleaning products
Linens, bath and pool towels
Kitchen cookware, dishes, flatware, glassware
Wireless high-speed internet
AT&T Uverse cable, smart TV capable thru-out
Fully fenced private landscaped community
Housekeeping services available
Chihuly green glass chandelier
Original Art
123 Simonton St, Key West, FL 33040 is a 3 bedroom, 4 bathroom, 2,541 sqft single-family home in Historic Seaport, built in 2019. It last sold for $3,395,000 on Feb 24, 2023. More recently, it was listed as a rental in May 2020 with an asking price of $12,000 per month. That rental listing was removed on February 23, 2022. It is currently off market. The Trulia Estimate is $3,280,200, with a rent estimate of $7,581/month.

Home Details for 123 Simonton St

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: OtherHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
DryerWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: MetalExterior: OtherFoundation Type: Slab
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 2019
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Furnished

Building

Levels, Entrance, & Accessibility
Disabled Access

Community

Units in Building: 1

Lot Information

Lot Area: 1398 sqft

Price History for 123 Simonton St

DatePriceEventSource
02/24/2023$3,395,000Sold
FLKMLS #604027
02/11/2023$3,450,000ContingentFLKMLS #604027
01/31/2023$3,450,000Listed For SaleFLKMLS #604027
02/23/2022ListingRemovedZillow Rental Manager
05/18/2020$12,000Listed For RentAgent Provided
04/08/2020$12,000ListingRemovedAgent Provided
11/05/2019$12,000PriceChange
Agent Provided
10/31/2019$10,000Listed For RentAgent Provided
02/26/2019$1,825,000Sold
FLKMLS #584265
02/12/2019$1,950,000Listed 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$23,214
Assessment$2,753,725
Home facts updated by county records

Comparable Sales for 123 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
312 Margaret St, Key West, FL
0.28
Single-Family Home
$2,295,000
04/15/26
3
3
1,916
312 William St, Key West, FL
0.22
Single-Family Home
$1,650,000
10/30/25
3
2
1,376
510 Margaret St, Key West, FL
0.41
Single-Family Home
$2,850,000
04/17/26
4
4
1,968
728 Love Ln, Key West, FL
0.38
Single-Family Home
$3,150,000
09/19/25
3
3
2,100
517 Elizabeth St, Key West, FL
0.37
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
316 Southard St, Key West, FL
0.51
Single-Family Home
$3,500,000
10/20/25
3
3.5
2,532
215 Whitehead St, Key West, FL
0.23
Single-Family Home
$2,300,000
02/25/26
3
3
1,514
418 William St, Key West, FL
0.32
Single-Family Home
$3,285,000
03/18/26
4
3
1,852
1020 Southard St, Key West, FL
0.56
Single-Family Home
$3,350,000
12/03/25
3
3.5
2,438
906 Southard St, Key West, FL
0.49
Single-Family Home
$3,250,000
05/27/26
3
3
2,188

Nearby homes

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Assigned Schools

These are the assigned schools for 123 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

Historic Seaport
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Historic Seaport

At least 38 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 90 % Say people would walk alone at night

  • 88 % Say it's walkable to restaurants

  • 84 % Say it's walkable to grocery stores

  • 83 % Say there are sidewalks

  • 79 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 59 % Say there are community events

  • 57 % Say it's quiet

  • 43 % Say parking is easy

  • 42 % Say neighbors are friendly

  • 35 % Say kids play outside

  • 30 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • 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
  • 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
  • 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
  • Sue S.
    "We vacationed here for the month of February 2014. We did not rent a car but had bikes for a week. We are walkers and walked an average of 1-2 miles for dinner and many miles during the day touring, hiking, etc. This area is accessible to most anything."
    1
    Flag

LGBTQ Local Legal Protections

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 123 Simonton St

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Off Market Homes Near 123 Simonton St

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Frequently asked questions about 123 Simonton St

  • What is 123 Simonton St estimated to be worth?
    Trulia's estimated value for 123 Simonton St in Key West, FL is $3,280,200.
  • What is the price history for 123 Simonton St?
    123 Simonton St in Key West, FL last sold for $3,395,000 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 123 Simonton St have air conditioning?
    Yes, 123 Simonton St in Key West, FL has air conditioning.
  • Does 123 Simonton St have laundry facilities?
    Yes, 123 Simonton St in Key West, FL has in-unit laundry.