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
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
More Information MLS# 621518
Contract Information
Current Price: $1,399,000
Listing Date: 2026-10-06
Listing Board: Key West Association
List Price: $1,399,000
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
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: No
Pool: Yes
Year Built: 1953
Lot Size: 88 X 60
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
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Building Style
Above Flood: Unknown
Stories: 1 Story
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
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