416 Fleming St, Key West, FL 33040
FOR SALE
NEW - 1 DAY AGO

416 Fleming St
Key West, FL 33040

Duvall Street
  • 5 Beds
  • 4.5 Baths
  • 2,575 sqft

$3,500,000

Est. Mortgage $19,489/mo*
Get Pre-Qualified

$3,500,000

Est. Mortgage $19,489/mo*
Get Pre-Qualified
5 Beds
4.5 Baths
2,575 sqft

Local Information

  • Map ViewExplore the area around 416 Fleming St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

Home Highlights

Parking
4 Parking Spaces
Outdoor
Porch, Patio, Deck
View
No Info
HOA
None
Price/Sqft
$1,359
Listed
1 day ago

Home Details for 416 Fleming St

Interior Features

Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2575 Square Feet
Appliances & Utilities
Utilities: FKAAAppliances: Dryer, Microwave, Oven, Refrigerator, DishwasherDishwasherDryerMicrowaveRefrigerator
Heating & Cooling
Heating: ElectricHas CoolingAir Conditioning: Central Air,Wall/Window Unit(s)Has HeatingHeating Fuel: Electric
Gas & Electric
Electric: Elect Separate Meter
Windows, Doors, Floors & Walls
Window: Drapes/Blinds Incl, PanelFlooring: Tile, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: 3 StoriesAccessibility: Grip-Accessible Features, Accessible Approach with Ramp, ParkingFloors: Tile, Wood
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, Deck, PatioExterior: StorageNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageNo Open ParkingParking Spaces: 4Parking: Off Street
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Days on Market: 1

Property Information

Year Built
Year Built: 1938
Property Type / Style
Property Type: ResidentialProperty Subtype: Multi Family, Single Family Residence
Building
Building: LobbyConstruction Materials: Frame, OtherNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00009900000000

Price & Status

Price
List Price: $3,500,000Price Per Sqft: $1,359

Active Status

MLS Status: Active

Location

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

Agent Information

Listing Agent
Listing ID: 620434

Community

Community Features: Other

HOA

HOA Fee Includes: OtherAssociation for this Listing: Key West AssociationNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 6534 sqft

Miscellaneous

Mls Number: 620434Attic: Pull Down StairsWater View: None

Additional Information

Other
Last check for updates: about 16 hours ago
Listing courtesy of Robin G Nilsson, (239) 221-4230
Keller Williams Key West Compass Realty
Originating MLS: Key West Association
Source: FLKMLS, MLS#620434
Also Listed on FLKMLS, Key West AOR, Key West AOR.

Market trends in Key West

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.2M
$61.67KMoM
Sale-to-List Price
94.9%
0.4%MoM
Price per sq ft
$940
$14MoM
Available listings
304
28MoM

Price History for 416 Fleming St

DatePriceEventSource
06/28/2026$3,500,000Listed For SaleFLKMLS #620434

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$1,275,000
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Nearby homes

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Assigned Schools

These are the assigned schools for 416 Fleming 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

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

What Locals Say about Duvall Street

  • 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
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  • 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
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  • Romero7648
    "Neighbor is downtown and free transportation in immediate vicinity. Many establishments will provide employee discount if you live in the area. "
    0
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  • Anne H.
    "none where I live. More events near where I work, which is an upscale store on Duval st. such as live music, art vendors, good restaurants."
    3
    Flag

LGBTQ Local Legal Protections

Robin G Nilsson, Keller Williams Key West Compass Realty
Agent Phone: (239) 221-4230
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.
416 Fleming St, Key West, FL 33040 is a 5 bedroom, 5 bathroom, 2,575 sqft multi-family built in 1938. 416 Fleming St is located in Duvall Street, Key West. This property is currently available for sale and was listed by FLKMLS on Jun 28, 2026. The MLS # for this home is MLS# 620434.