141 Simonton St, Key West, FL 33040
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FOR SALE
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141 Simonton St
Key West, FL 33040

Historic Seaport
  • 3 Beds
  • 3 Baths
  • 2,691 sqft

$3,500,000

Est. Mortgage $21,870/mo*
Get Pre-Qualified

$3,500,000

Est. Mortgage $21,870/mo*
Get Pre-Qualified
3 Beds
3 Baths
2,691 sqft

Local Information

  • Map ViewExplore the area around 141 Simonton St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

Home Highlights

Parking
Attached Garage
Outdoor
Porch, Deck, Pool
View
Ocean, Harbor/Marina View, Water
HOA
$1,650/Monthly
Price/Sqft
$1,301
Listed
55 days ago

Home Details for 141 Simonton St

Interior Features

Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2691 Square Feet
Appliances & Utilities
Utilities: FKAA, Cable ConnectedAppliances: Washer, Stainless Steel Appliance(s), Microwave, Oven, Range, Refrigerator, Dishwasher, DryerDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Ceiling Fans(s),Heat Pump
Windows, Doors, Floors & Walls
Window: Impact Rstnce WindowDoor: Impact Rstnce DoorsFlooring: Tile
Levels, Entrance, & Accessibility
Stories: 4Levels: 4 StoriesAccessibility: Accessible Elevator InstalledElevatorFloors: Tile
View
Has a ViewView: Ocean, Harbor/Marina View, Water
Security
Security: Fire Sprinkler System, Electric Gate
Room & Shared Space
Shared space is furnished

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, Roof Top DeckHas a Private Pool
Parking & Garage
No CarportHas a GarageHas an Attached GarageNo Open ParkingParking Spaces: 2Parking: Garage,Covered,Off Street,Attached
Pool
Pool: In Ground, ConcretePool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Days on Market

Days on Market: 55

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: ResidentialProperty Subtype: Townhouse, Residential - Condo/TownhouseArchitecture: Townhouse
Building
Construction Materials: CBS, Combo Construction, Stucco, ConcreteNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00000240000141

Price & Status

Price
List Price: $3,500,000Price Per Sqft: $1,301

Active Status

MLS Status: Active

Media

Location

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

Agent Information

Listing Agent
Listing ID: 619959

Community

Community Features: Pool

HOA

HOA Fee Includes: Maintenance Structure, Other, Maintenance Grounds, Building InsuranceAssociation for this Listing: Key West AssociationHas an HOAHOA Fee: $1,650/Monthly

Lot Information

Lot Area: 1306.8 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 619959Water ViewWater View: Ocean, Harbor/Marina View, Water

Additional Information

Pool
Last check for updates: 42 minutes ago
Listing courtesy of Brenda J Donnelly, (305) 304-1116
Brenda Donnelly Real Estate LLC
Originating MLS: Key West Association
Source: FLKMLS, MLS#619959
Also Listed on FLKMLS, Key West AOR, Key West AOR.

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

Price History for 141 Simonton St

DatePriceEventSource
05/19/2026$3,500,000Listed For SaleFLKMLS #619959
06/12/2017$1,668,400Sold
N/A

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Property Tax and Assessment

Year2025
Tax$8,689
Assessment$3,077,293
Home facts updated by county records

Comparable Sales for 141 Simonton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
149 Simonton St, Key West, FL
0.02
Townhouse
$2,900,000
08/01/25
3
3.5
2,697
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
0.46
Townhouse
$2,362,000
04/14/26
3
3
1,608
101 Front St #8, Key West, FL
0.39
Townhouse
$1,345,000
05/20/26
2
2.5
1,216
101 Front St #15, Key West, FL
0.37
Townhouse
$1,220,000
09/30/25
2
2.5
1,216
208 Fleming St, Key West, FL
0.40
Townhouse
$1,070,000
03/02/26
2
2.5
960
528 Porter Ln, Key West, FL
0.46
Townhouse
$1,245,000
04/01/26
2
2.5
960
548 Porter Ln, Key West, FL
0.45
Townhouse
$1,160,000
01/16/26
2
2.5
960
212 Southard St, Key West, FL
0.48
Townhouse
$1,050,000
05/01/26
2
2.5
960

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 141 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

Brenda J Donnelly, Brenda Donnelly Real Estate LLC
Agent Phone: (305) 304-1116
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.
141 Simonton St, Key West, FL 33040 is a 3 bedroom, 3 bathroom, 2,691 sqft townhouse built in 2017. 141 Simonton St is located in Historic Seaport, Key West. This property is currently available for sale and was listed by FLKMLS on May 19, 2026. The MLS # for this home is MLS# 619959.