416 Fleming Street, Key West, FL 33040
$3,500,000
Property Type:
Residential
Bedrooms:
5
Baths:
5
Square Footage:
2,575
Lot Size (sq. ft.):
6,700
Status:
Active
Current Price:
$3,500,000
List Date:
6/28/2026
Last Modified:
7/13/2026
Listing Details MLS# 620434
Location, Tax & Legal
- Street #
- 416
- Street Name
- Fleming
- Street Suffix
- Street
- Key/Island
- Key West
- State/Province
- FL
- Zip Code
- 33040
- County
- Monroe
- Subdivision
- Old Town - Unlisted (1.0)
- Area
- 02 - Key West
- KW Neighborhood
- Old Town-S of Truman
- City
- KEY WEST
- Mile Marker
- 1
- Marathon Neighborhood
- N/A
- Side
- Median
- Flood Zone
- X
- Alternate Key #
- 1010171
- Parcel #
- 00009900-000000
- Zoning
- HRO - Historic Residential/Office
- Deed Restrictions
- Unknown
- Legal
- KW PT LOT 3 SQR 51 OR298-36/37 OR321-306/08 OR398-938/39 OR972-2202/03 OR1078-824 OR1093-2402 OR1078-824 OR1093-2402 OR1
- Taxes
- 19952.19
- Tax Year
- 2025
- Pub Sewer HkUp
- Yes
Contract Information
- Listing Board
- Key West Association
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Multi-Units
- Waterfront
- No
- Pool
- No
- Year Built
- 1938
- Lot SqFt
- 6700
- Lot Sqft Source
- Tax Records
- Acres
- 0.15
- Living Apx SqFt
- 2575
- SqFt Source
- Tax Records
- Total Bedrooms
- 5
- Full Baths
- 4
- Half Baths
- Yes
- Total Baths
- 5
- Floor Number
- 3
- Rentals Allowed
- Yes
- Min Rental Days
- 28
- Control Depth
- 0
- Total Units
- 0
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
Building Style
- Above Flood
- Yes
- Stories
- 3 Stories
More Information
Vehicle Storage
- Car(s)
- 4+
- Off Street Parking
- Yes
Remarks & Misc
- Remarks – Consumer
- 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!
License Info
- Non Trans Rntl Lic
- Yes
Fee Includes
- Other
- Yes
Dockage
- None
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Dryer
- Yes
- Microwave
- Yes
- Oven
- Yes
- Refrigerator
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Central Air
- Yes
- Wall/Window Unit(s)
- Yes
Heating
- Electric
- Yes
Waterfront
- None
- Yes
Waterview
- No Waterview
- Yes
Floor
- Tile
- Yes
- Wood
- Yes
Neighborhood Feature
- Other Area Features
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Cathedral Ceilings
- Yes
- Drapes/Blinds Incl
- Yes
- Entrance Foyer
- Yes
- Granite Counter Top
- Yes
- Lobby
- Yes
- Pull Down Stairs
- Yes
- Smoke Alarms
- Yes
- Storage
- Yes
Property Condition
- Updated/Remodeled
- Yes
Construction
- Frame
- Yes
- Other
- Yes
Land Size
- Less Than 1/4 Acre
- Yes
Furnished
- Unfurnished
- Yes
Utilities
- Cistern
- Yes
- Elect Separate Meter
- Yes
- FKAA
- Yes
- Well
- Yes
Porch/Balcony
- Deck
- Yes
- Open Porch/Balcony
- Yes
- Patio
- Yes
Title
- Negotiable
- Yes
Exterior Features
- Storage
- Yes
Roof
- Metal Roof
- Yes
Accessibility Feat
- Grab Bars
- Yes
- Parking
- Yes
- Wheelchair Ramp
- Yes
Shutters
- Panel
- Yes
Property Features
Fee Includes:
Other
Tax Exemptions:
None
License Info:
Non Trans Rntl Lic
Waterfront:
None
Waterview:
No Waterview
Dockage:
None
Property Condition:
Updated/Remodeled
Vehicle Storage:
Off Street Parking
Furnished:
Unfurnished
Cooling:
Central Air; Wall/Window Unit(s)
Heating:
Electric
Utilities:
Cistern; Elect Separate Meter; FKAA; Well
Interior Features:
Built-in Cabinets; Cathedral Ceilings; Drapes/Blinds Incl; Entrance Foyer; Granite Counter Top; Lobby; Pull Down Stairs; Smoke Alarms; Storage
Appliances:
Dishwasher; Dryer; Microwave; Oven; Refrigerator
Exterior Features:
Storage
Accessibility Feat:
Grab Bars; Parking; Wheelchair Ramp
Construction:
Frame; Other
Shutters:
Panel
Floor:
Tile; Wood
Roof:
Metal Roof
Pets:
Pets Allowed
Neighborhood Feature:
Other Area Features
Land Size:
Less Than 1/4 Acre
Title:
Negotiable
Listing Office:
Keller Williams Key West Compass Realty
Last Updated: July - 13 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.