Address
416 Fleming Street, Key West, FL
Price
$ 3,500,000
Property Attributes
- MLS#620434
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityKey West
- AreaKey West
- NeighborhoodOld Town - Unlisted
- Zip33040
- StyleMulti-Units
- Year Built1938
- Taxes$ 19952
- Price$ 3,500,000
- Bedrooms5
- Full Bathrooms4
- Half Bathrooms1
- Sqr Footage2575
- Lot Size0.15 Acres
Data Source:
Florida Keys MLS (FLKMLS)
Property 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!
| Price History | |
|---|---|
| 6/28/2026 | Listed $3,500,000 |
General Features
| Living Area | 2575.00 |
|---|---|
| Construction | Frame,Other |
| Utilities | FKAA,Elect Separate Meter,Cistern,Well |
| Roof | Metal Roof |
| Appliances | Dryer,Microwave,Oven,Refrigerator,Dishwasher |
| Flood Zone | X |
| Zoning | HRO - Historic Residential/Office |
| HOA Fee | 0.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 4 |
| Half Baths | 1 |
| Year Built | 1938 |
| Subdivision | Old Town - Unlisted (1.0) |
| Style | Multi-Units |
| View | No Waterview |
| Property Type | A |
| Floor Number | 3.00 |
| Neighborhood Feature | Other Area Features |
| Fee Includes | Other |
| Acres | 0.15 |
| Lot Sqft | 6700.00 |
| Rental Allowed | Yes |
| Accessibility Features | Grab Bars,Wheelchair Ramp,Parking |
| Building Style: Above Flood | Yes |
| Building Style: Stories | 3 Stories |
| Dockage | None |
| KW Neighborhood | Old Town-S of Truman |
| Min Rental Days | 28.00 |
| License Info | Non Trans Rntl Lic |
Interior Features
| Interior Amenities | Drapes/Blinds Incl,Pull Down Stairs,Built-in Cabinets,Storage,Smoke Alarms,Lobby,Granite Counter Top,Entrance Foyer,Cathedral Ceilings |
|---|---|
| Total Units | 0.00 |
| Furnished Y/N | Unfurnished |
| Flooring | Tile,Wood |
Exterior Features
| Exterior Amenities | Storage |
|---|---|
| Pool | No |
| Waterfront | None |
| Lot Size | 50 X 134 |
| Land Size | Less Than 1/4 Acre |
| Porch/Balcony | Open Porch/Balcony,Deck,Patio |
| Public Sewer Hookup | Yes |
| Shutters | Panel |
| Side | Median |
| Vehicle Storage | Off Street Parking |
| Vehicle Storage: Car(s) | 4+ |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33040
Price
Taxes
Year Built
Visits
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Updated on September 26, 2026 5:10 AM UTC
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Data Last Updated: September 26, 2026 5:09 AM UTC
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All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
