416 Fleming St

Key West, FL 33040

$3,500,000
Price
5
Beds
2,575 Sq. Ft.
$1,359 / Sq. Ft.
2,575
Sq. Ft.
$1,359
per Sq. Ft.
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416 Fleming Street
79 Paces to Duval Street
6+ Parking Spaces
Additional Handicapped Parking
1,000+ SqFt of porched
4 Units Three Full Kitchens
2 Bed 2Bath with Balconies
Upper Room 2/2
Iconic
Expansive Sideyard & Garden
Cottage
Custom cabinets
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Overlooking the garden
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Stunning views
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High 12' ceilings
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Balcony door
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Granite countertops
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DE County Pine
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ADA compliant
ADA compliant Commercial restroom
1938
Commercial office
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Office Store
Mixed Use
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Office or 5th Bedroom
First floor Primary
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Two Primary's with entrance ram
2/1
Vaulted ceiling
Historic Architecture
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Great Room
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Bike rack
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Bonus Space
Vaulted ceiling
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Board Walk
4 Units
Privacy Fence
Garden seating
Side yard
416 Fleming Street

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...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!
  1. Listed by Robin G Nilsson • Keller Williams Key West Compass Realty

Property Details for 416 Fleming Street

Waterfront
None
Waterfront
No
Zoning
HRO - Historic Residential/Office
Subdivision
Old Town - Unlisted (1.0)
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 06/28/2026 11:13 AM

Property Details for 416 Fleming Street

StatusActive
MLS #620434
Days on Market1
Taxes$19,952 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeMulti Family
MLS TypeResidential / Multi-Units
Year Built1938
Lot Size0.15 AC / 6,700 SF
CountyMonroe County
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Location

Listing Courtesy of Keller Williams Key West Compass Realty
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Building Information for 416 Fleming Street

Stories3Residences-Year Built1938Building Size-Lot Size0.15 AC / 6,700 SF

Payment Calculator

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$19,104 per month

30 year fixed, 6.36% Interest

Principal and Interest

$17,441

Property Taxes

$1,663

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 416 Fleming Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.803373
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-S of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Accessibility Feat: Grab Bars, Wheelchair Ramp, Parking
  • Neighborhood Feature: Other Area Features
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: Other
  • Furnished: Unfurnished
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Lot Size: 50 X 134
  • Acres: 0.15
  • Parcel #: 00009900-000000
  • Land Size: Less Than 1/4 Acre
  • License Info: Non Trans Rntl Lic
Property and Assessments
  • 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
  • MLS Approved: Y
  • SqFt Source: Tax Records
  • Flood Zone: X
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 64
  • Document Count: 0
  • Building Style: Above Flood: Yes
  • Property Condition: Updated/Remodeled
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Elect Separate Meter, Cistern, Well
  • Pub Sewer HkUp: Yes
  • Pool: No
  • Porch/Balcony: Open Porch/Balcony, Deck, Patio
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • Floor Number: 3.0
  • Interior Features: Drapes/Blinds Incl, Pull Down Stairs, Built-in Cabinets, Storage, Smoke Alarms, Lobby, Granite Counter Top, Entrance Foyer, Cathedral Ceilings
  • Appliances: Dryer, Microwave, Oven, Refrigerator, Dishwasher
Exterior Features
  • Roof: Metal Roof
  • Shutters: Panel
  • Construction: Frame, Other
  • Dockage: None
  • Exterior Features: Storage

Property History for 416 Fleming Street

DateEvent & SourcePriceAppreciation
Jun 27, 2026

Listed (Active)

FKMLS #620434

$3,500,000—
DateEvent & SourcePrice
06/27/2026

Listed (Active)

FKMLS #620434

$3,500,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 416 Fleming Street

Taxable ValueLand$1,949,700Additions$318,034Total$2,267,734
Tax Record2024$18,402 ($1,533 / month)
Home Facts
Baths2Total Finished SqFt2,575 SqFtAbove Grade Finished SqFt2,575 SqFtStories3Lot Size6,912 SqFtStyleMiscellaneous CommercialYear Built1938Year Renovated1980CountyMONROEAPN00009900-000000

Schools near 416 Fleming Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Gerald Adams Elementary School
Public - PK to 5
Monroe Virtual Franchise
Public - 6 to 12
Key West High School
Public - 9 to 12
Monroe Virtual Instruction Program (District Provided)
Public - K to 5
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Monroe Virtual Franchise
Public6 to 12

Key West High School
Public9 to 12

Monroe Virtual Instruction Program (District Provided)
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 416 Fleming Street, Key West, FL 33040

416 Fleming Street is a multi-family home for sale in Key West, FL 33040. This property was listed for sale on June 27, 2026 by Keller Williams Key West Compass Realty, it's currently listed at $3,500,000. This listing's school district is Monroe. Nearby schools include Gerald Adams Elementary School, Monroe Virtual Franchise and Key West High School. 416 Fleming Street is a 5-bed, 5-bath, 2,575 sqft multi-family home built in 1938.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Keller Williams Key West Compass Realty

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.