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

149 Simonton St
Key West, FL 33040

Historic Seaport
  • 3 Beds
  • 3.5 Baths
  • 2,697 sqft

$2,925,300

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $16,866/mo*
Refinance Your Home

$2,925,300

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $16,866/mo*
Refinance Your Home
3 Beds
3.5 Baths
2,697 sqft

Local Information

  • Map ViewExplore the area around 149 Simonton St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
2017
Living Area
2,697 sqft
Price/Sqft
$1,085
Parking
Garage
HOA
$1,650/Monthly

About this House

Old Town Villas at Key West is a luxurious gated development just 1 block off of Duval Street. This townhome has 3 bedrooms, 3.5 baths on 4 floors. A private elevator in each unit takes you from the 2 car garage to the rooftop terrace. Just under 2,700 SF of solid concrete construction accompanied with high end appliances, a large community pool & cabana area.
149 Simonton St, Key West, FL 33040 is a 3 bedroom, 4 bathroom, 2,697 sqft townhouse in Historic Seaport, built in 2017. It last sold for $2,900,000 on Aug 1, 2025 (8% below the $3,150,000 asking price). It is currently off market. The Trulia Estimate is $2,925,300, with a rent estimate of $7,909/month.

Home Details for 149 Simonton St

Interior Features

Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2697 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Wine Cooler, Stainless Steel Appliance(s)DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile
Levels, Entrance, & Accessibility
Accessibility: Accessible Elevator Installed, ParkingElevatorFloors: Tile
View
No View
Security
Security: Security Gate, Fire Sprinkler System

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, Roof Top DeckHas a Private Pool
Parking & Garage
Has a GarageNo Attached GarageParking: Garage Door Opener
Pool
Pool: In GroundPool
Frontage
Not on Waterfront

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: ResidentialProperty Subtype: Townhouse
Building
Construction Materials: CBS, Concrete, Stucco, Combo Construction
Property Information
Parcel Number: 00000240000149

Price & Status

Price
List Price: $3,150,000

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 2697 Square Feet

HOA

HOA Fee Includes: Maintenance Structure, Insurance, Common Area Mnt, Security, OtherHas an HOAHOA Fee: $1,650/Monthly

Lot Information

Lot Area: 1306.8 sqft

Miscellaneous

Mls Number: 613629
Last check for updates: about 6 hours ago
Listed by Team Gardner/Langley, (305) 902-2447
Berkshire Hathaway HomeServices Knight & Gardner Realty
Bought with: Coastal Collection Real Estate Inc.
Source: FLKMLS, MLS#613629

Price History for 149 Simonton St

DatePriceEventSource
08/01/2025$2,900,000Sold
FLKMLS #613629
06/16/2025$3,150,000ContingentFLKMLS #613629
05/25/2025$3,150,000PriceChange
Key West AOR #613629
04/26/2025$3,299,000PriceChange
Key West AOR #613629
04/04/2025$3,395,000PriceChange
FLKMLS #613629
03/11/2025$3,499,000PriceChange
FLKMLS #613629
02/10/2025$3,650,000Listed For SaleKey West AOR #613629
02/01/2025$3,750,000ListingRemovedFLKMLS #612200
01/22/2025$3,750,000PriceChange
Key West AOR #612200
01/04/2025$3,850,000PriceChange
FLKMLS #612200
11/10/2024$3,999,000Listed For SaleKey West AOR #612200
03/18/2022$2,900,000Sold
FLKMLS #599161
02/27/2022$3,499,995Listed For SaleFLKMLS #599161
02/20/2022ListingRemovedFLKMLS #599161
02/13/2022$3,499,995ContingentFLKMLS #599161
01/12/2022$3,499,995Listed For SaleFLKMLS #599161
05/07/2021$2,225,000Sold
N/A
04/13/2021$2,250,000Listed For SaleKey West AOR #595609
07/31/2017$1,839,200Sold
N/A

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$25,779
Assessment$3,065,615
Home facts updated by county records

Comparable Sales for 149 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
129 Simonton St, Key West, FL
0.03
Townhouse
$3,300,000
08/28/25
4
4
2,697
506 Emma St, Key West, FL
0.47
Townhouse
$2,362,000
04/14/26
3
3
1,608
101 Front St #8, Key West, FL
0.38
Townhouse
$1,345,000
05/20/26
2
2.5
1,216
101 Front St #15, Key West, FL
0.38
Townhouse
$1,220,000
09/30/25
2
2.5
1,216
208 Fleming St, Key West, FL
0.42
Townhouse
$1,070,000
03/02/26
2
2.5
960
528 Porter Ln, Key West, FL
0.47
Townhouse
$1,245,000
04/01/26
2
2.5
960
548 Porter Ln, Key West, FL
0.46
Townhouse
$1,160,000
01/16/26
2
2.5
960
212 Southard St, Key West, FL
0.50
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 149 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

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Homes for sale near 149 Simonton St

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Off Market Homes Near 149 Simonton St

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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.