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415 & 417 Truman Avenue, Key West, FL - photo 1

$3,850,000

415 & 417 Truman Avenue

Key West, FL 33040

Estimated payment $23,100/month

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5Beds
4Baths
2,280Sq Ft
$1689Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

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Highlights

No HOA
Built in 1909
1,306 sqft Lot

About This Home

JUST LISTED! Two transiently licensed properties just off Duval Street with pool and parking! Amazing opportunity to own two historic homes in the heart of Old Town Key West. Ideal compound with options for renting each home individually or together for large groups. Two Key West furnished cottages with a total of five bedrooms, three and a half baths, private parking, a hot tub, and a pool! Together, both can comfortably accommodate up to 16 guests.417 TRUMAN AVENUE CORNER LOT WITH POOL This spacious home boasts three bedrooms, two and a half bathrooms, a pool, a fully equipped kitchen, a cozy outdoor dining area, a living room with plenty of seating, a private sundeck, private laundry, and a front porch perfect for people-watching. The recently updated kitchen is fully stocked with everything you need to cook up a storm, and the bar that seats eight makes it easy to entertain your crew. An outdoor table is perfect for sharing meals while enjoying the sunshine. The living room offers ample seating for your entire party, and a queen sleeper sofa is available for extra guests. The downstairs bedroom is complete with a king-size bed and an en-suite bathroom, while the upstairs bedrooms include a queen bed and two queen beds with access to the sundeck. 415 TRUMAN AVENUE This cozy Key West cottage is equipped with two bedrooms, one bathroom, a fully outfitted kitchen, a cozy outdoor dining area, a living room with tons of seating, another private sundeck, a second laundry location, and a front porch perfect for people-watching. The living room offers plenty of space for your entire group to relax, and a queen sleeper sofa is available for extra guests. The downstairs bedroom has a comfortable queen-size bed and an adjacent bathroom, while the upstairs bedroom features a king-size bed, plenty of storage, and access to the sundeck.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:5
  • •Bathrooms:4
  • •Full bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:2,280 sqft
  • •Total interior livable area:2,280 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:1,306 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1909

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Price history

DateEventPrice
10/8/2026Listed for sale$3,850,000$1689/sqft

Listing Agent

Bascom L Grooms

Bascom Grooms Real Estate (KW)

Brokerage Phone: 305-295-7511

Source: Florida Keys MLS · MLS #621501

Data Powered by Home Junction, Inc.

Nearby

Schools

KEY WEST MONTESSORI CHARTER SCHOOL, INC

Elementary · 0.7 mi

MONROE VIRTUAL INSTRUCTION PROGRAM

Elementary · 0.9 mi

MONROE VIRTUAL FRANCHISE

High · 0.9 mi

Supermarkets

K

0.1 mi

Johnson's Grocery

0.2 mi

Island Grocery

0.3 mi

Dining

Grand Havana

0.1 mi

Italian Sea Food

0.1 mi

Origami Sushi Bar

0.1 mi

Parks

Nelson English City Park

0.2 mi

Bill Butler Park

0.3 mi

Gato Village Pocket Park

0.3 mi

Beaches

South Beach

0.4 mi

Dog Beach

0.5 mi

Truman Beach

0.7 mi

Nearby amenity locations include data © OpenStreetMap contributors.