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1221 Ashby Street, 
Key West, FL 33040

$1,399,000

3

Beds

3

Baths

1,374

Sq Ft

Single Family

Active

Listed by

Justyn Ewald

, 

Mason C Kelly

Expert Realty LLC. (Hq)

Last updated:

October 6, 2026, 10:42 PM

MLS#

621518

Source:

FL FKBOR

About This Home

1221 Ashby Street

Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

Home Facts

Single Family

3 Baths

3 Bedrooms

Built in 1953

Subdivision & Development:

Macros Subd (2.0)

Price Summary

1,399,000

$1,018 per Sq. Ft.

MLS #:

621518

Last Updated:

October 6, 2026, 10:42 PM

Added:

a day ago

Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Structure

Structure

Building Area:

1,374 Sq. Ft.

Year Built:

1953

Lot

Lot Size (Sq. Ft):

5,280

Finances & Disclosures

Finances

Price:

$1,399,000

Price per Sq. Ft:

$1,018 per Sq. Ft.

Source:FL FKBOR
The information being provided by Florida Keys Board Of REALTORS®, Inc. is for the 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 information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Florida Keys Board Of REALTORS®, Inc. All rights reserved. FL FKBOR Member Broker: Brian Schmitt

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.