$3,500,000
5 Beds
4.5 Baths
2,575 sqft
416 Fleming St, Key West, FL 33040
Est. Mortgage $20,165/mo*
Get Pre-QualifiedHome Highlights
Outdoor
Porch, Patio, Deck
HOA
None
Price/Sqft
$1,359
Listed
62 days ago
Climate Control
Heating & Central Air, Wall Units
Local Information
- Map ViewExplore the area around 416 Fleming St.
- Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
- Shop & Eat
-- mins to
About this House
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!
Last check for updates: about 4 hours ago
Listing courtesy of Robin G Nilsson, (239) 221-4230
Keller Williams Key West Compass Realty
Source: FLKMLS, MLS#620434
Also Listed on FLKMLS.
Home Details for 416 Fleming St
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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: Elect Separate MeterAppliances: Dryer, Dishwasher, Refrigerator, Oven, MicrowaveDishwasherDryerMicrowaveRefrigerator |
Heating & Cooling Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Wall/Window Unit(s)Has HeatingHeating Fuel: Has Heating Unspecified Type |
Windows, Doors, Floors & Walls Flooring: Tile, Wood |
Levels, Entrance, & Accessibility Accessibility: Grip-Accessible Features, Parking, Accessible Approach with RampFloors: Tile, Wood |
View No View |
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Exterior Home Features Patio / Porch: Open Porch/Balcony, Deck, PatioExterior: StorageNo Private Pool |
Parking & Garage No Attached Garage |
Frontage Not on Waterfront |
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Days on Market: 62 |
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Year Built Year Built: 1938 |
Property Type / Style Property Type: ResidentialProperty Subtype: Multi Family |
Building Construction Materials: Frame, OtherNot a New Construction |
Property Information Condition: Updated/RemodeledParcel Number: 00009900000000 |
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Price List Price: $3,500,000Price Per Sqft: $1,359 |
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MLS Status: Active |
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Direction & Address City: Key WestCommunity: Old Town - Unlisted (1.0) |
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Listing Agent Listing ID: 620434 |
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Building Area Building Area: 2575 Square Feet |
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Community Features: Other |
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HOA Fee Includes: OtherNo HOAHOA Fee: No HOA Fee |
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Lot Area: 6534 sqft |
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Mls Number: 620434Attic: Pull Down Stairs |
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Other |
Around this home
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Duvall Street
Market trends in Key West
Last updated July 2026
Avg. sale price
$1.28M
$50KMoM
Sale-to-List Price
95.1%
0.5%MoM
Price per sq ft
$933
$26MoM
Available listings
271
17MoM
Home Value
Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.39 | Multi-Family Home | $1,400,000 | 01/14/26 | 5 | 3.5 | 2,068 | |
0.37 | Multi-Family Home | $1,752,000 | 11/17/25 | 4 | 3.5 | 1,967 | |
0.30 | Multi-Family Home | $2,000,000 | 02/27/26 | 8 | 8 | 3,532 | |
0.30 | Multi-Family Home | $1,275,000 | 05/12/26 | 8 | 10 | 2,432 | |
0.20 | Multi-Family Home | $4,500,000 | 07/06/26 | 8 | 9 | 8,472 | |
0.39 | Multi-Family Home | $1,350,000 | 10/20/25 | 3 | 4 | 1,989 | |
0.62 | Multi-Family Home | $1,500,000 | 12/23/25 | 8 | 5 | 1,830 | |
0.28 | Multi-Family Home | $1,625,000 | 04/20/26 | 3 | 2 | 1,594 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.06 | $1,095,000 | - | - | - | For Sale | |
0.07 | - | Studio | - | - | Off Market | |
0.12 | $1,275,000 | 3 | 3 | 1,748 | Recently Sold | |
0.11 | $1,695,000 | 3 | 3 | 1,553 | Recently Sold | |
0.13 | $2,033,000 | 2 | 1 | 888 | For Sale | |
0.12 | $3,542,100 | 3 | 3.5 | 2,532 | Off Market | |
0.14 | $3,300,000 | 5 | 6 | 3,667 | Recently Sold | |
0.13 | $900,000 | 3 | 2 | 1,451 | Recently Sold | |
0.14 | $979,000 | 2 | 1.5 | 823 | Recently Sold | |
0.15 | $3,100,000 | 3 | 3 | 2,262 | For Sale | |
0.14 | $5,736,500 | 5 | 5.5 | 3,342 | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jun 28, 2026 Source: FLKMLS #620434 | Listed For Sale | $3,500,000 |
LGBTQ Local Legal Protections
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 MLS.
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Frequently asked questions about 416 Fleming St
- What is the estimated monthly payment for 416 Fleming St?Based on a $3,500,000 list price with 20% down at today's rates, the estimated monthly payment for 416 Fleming St in Key West, FL is approximately $20,745 (about $18,278 principal & interest, $2,392 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- How does the list price for 416 Fleming St compare to homes in Key West?416 Fleming St in Key West, FL is listed at $3,500,000, about 174% above the $1.28M median sale price in Key West.
- What are the closest schools to 416 Fleming St?The closest schools to 416 Fleming St in Key West, FL are Gerald Adams Elementary School (Pre-K, rated 4/10), Key West High School (rated 4/10), Monroe Virtual Instruction Program (Elementary/Middle/High).
- Does 416 Fleming St have air conditioning?Yes, 416 Fleming St in Key West, FL has air conditioning.
- Does 416 Fleming St have laundry facilities?Yes, 416 Fleming St in Key West, FL has laundry facilities.
- Does 416 Fleming St have parking?Yes, 416 Fleming St in Key West, FL has on-site parking.
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.