1221 Ashby Street, Key West, FL 33040 (MLS# 621518)

1221 Ashby Street, Key West, FL 33040

New Listing
$1,399,000
Property Type: Residential Bedrooms: 3 Baths: 3 Square Footage: 1,374 Lot Size (sq. ft.): 5,280 Status: Active
Current Price: $1,399,000 List Date: 10/06/2026 Last Modified: 10/07/2026

Overview

Description

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.

Open Houses

  • Saturday, October 10, 11:00 am - 1:00 pm
  • Sunday, October 11, 11:00 am - 1:00 pm

Listing Details MLS# 621518

Location, Tax & Legal

Street #
1221
Street Name
Ashby
Street Suffix
Street
Key/Island
Key West
State/Province
FL
Zip Code
33040
County
Monroe
Subdivision
Macros Subd (2.0)
Area
03 - Key West

Contract Information

Listing Board
Key West Association

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
No
Pool
Yes
Year Built
1953
Lot SqFt
5280
Acres
0.12
Living Apx SqFt
1374
SqFt Source
Property Data Card
Total Bedrooms
3
Full Baths
3
Total Baths
3
Rentals Allowed
With Restrictions
Min Rental Days
30

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No

Building Style

Above Flood
Unknown
# Stories
1 Story

More Information

Property Features

Fee Includes: None Tax Exemptions: None License Info: Non Trans Rntl Lic Waterfront: None Waterview: No Waterview Dockage: None Building Style: Ground Level Vehicle Storage: Carport; Covered Parking; Off Street Parking Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air; Wall/Window Unit(s) Utilities: Buyer to Verify Appliances: Dishwasher; Dryer; Freezer; Microwave; Oven; Refrigerator; Washer Exterior Features: Detached Guest Qtrs; Outdoor Shower; Privacy Wall/Fence Pool Info: In Ground; Concrete Construction: CBS Floor: Tile Roof: Metal Roof Pets: Pets Allowed Land Size: Less Than 1/4 Acre Terms: Cash; Conventional; FHA; VA Title: Negotiable
Listing Office: Expert Realty LLC (HQ)
Last Updated: October - 07 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
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