416 Fleming Street, Key West, FL 33040
Local realty services provided by:CENTURY 21 Circle
416 Fleming Street,Key West, FL 33040
$3,500,000
- 5 Beds
- 5 Baths
- 2,575 sq. ft.
- Multi-family
- Active
Listed by: robin g nilsson
Office: keller williams key west compass realty
MLS#:620434
Source:FL_FKBOR
Price summary
- Price:$3,500,000
- Price per sq. ft.:$1,359.22
About this home
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!...
Contact an agent
Home facts
- Year built:1938
- Subdivision & Development:Old Town - Unlisted (1.0)
- Listing ID #:620434
- Added:102 day(s) ago
- Updated:October 08, 2026 at 03:28 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Kitchen Description:Built-in Cabinets, Granite Counter Top
- Living area:2,575 sq. ft.
Heating and cooling
- Cooling:Central Air, Wall/Window Unit(s)
- Heating:Electric
Structure and exterior
- Year built:1938
- Building area:2,575 sq. ft.
- Lot area:0.15 Acres
- Construction Materials:Frame
- Exterior Features:Storage
Finances and disclosures
- Price:$3,500,000
- Price per sq. ft.:$1,359.22
- Tax amount:$19,952
Features and amenities
- Amenities:Built-in Cabinets, Cathedral Ceilings, Drapes Included, Lobby, Pull Down Stairs, Smoke Alarms, Storage
Parking
- Parking description:Off Street
New listings near 416 Fleming Street
- New
$1,795,000Active4 beds 3 baths1,773 sq. ft.809 Fleming Street, Key West, FL 33040
MLS# 621528Listed by: CENTURY 21 CIRCLE- ISLAMORADA - New
$3,700,000Active5 beds 5 baths3,091 sq. ft.3728 Flagler Avenue, Key West, FL 33040
MLS# 621515Listed by: MEADOWS REALTY GROUP - Open Sun, 12 to 2pmNew
$1,350,000Active2 beds 3 baths1,387 sq. ft.5 Mccoy Circle # 5, Key West, FL 33040
MLS# 621523Listed by: BERKSHIRE HATHAWAY HOMESERVICES KNIGHT & GARDNER REALTY - New
$5,200,000Active4 beds 3 baths2,058 sq. ft.1100 Johnson Street, Key West, FL 33040
MLS# 621521Listed by: TRUMAN & CO. (KW) - Open Sat, 11am to 1pmNew
$1,399,000Active3 beds 3 baths1,374 sq. ft.1221 Ashby Street, Key West, FL 33040
MLS# 621518Listed by: EXPERT REALTY LLC (HQ) - New
$1,895,000Active4 beds 4 baths2,282 sq. ft.1423 Rose Street, Key West, FL 33040
MLS# 621516Listed by: ISLAND HOME REALTY INC. - Open Fri, 11am to 1pmNew
$1,699,000Active2 beds 3 baths1,463 sq. ft.615 Amelia Street, Key West, FL 33040
MLS# 621509Listed by: BERKSHIRE HATHAWAY HOMESERVICES KNIGHT & GARDNER REALTY - New
$3,850,000Active5 beds 4 baths2,280 sq. ft.415 & 417 Truman Avenue, Key West, FL 33040
MLS# 621501Listed by: BASCOM GROOMS REAL ESTATE (KW) - New
$1,999,999Active4 beds 4 baths2,342 sq. ft.220 Angela Street #A&B, Key West, FL 33040
MLS# 621502Listed by: USA TRUST REALTY, INC. - New
$3,750,000Active3 beds 4 baths2,421 sq. ft.1010 Olivia Street, Key West, FL 33040
MLS# 621485Listed by: SUZANNE MOORE REAL ESTATE