1221 Ashby Street, Key West, FL 33040

$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: 10/10/2026

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.

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
KW Neighborhood: Midtown West
City: KEY WEST
Off Shore Island: No
Mile Marker: 2
Marathon Neighborhood: N/A
Side: Median
Flood Zone: AE
Alternate Key #: 1045179
Parcel #: 00044560-000000
Zoning: SF - Single Family
Deed Restrictions: Unknown
Legal: LOT 12 SQR 17 RESUB OF SQRS -17-18-19-20 AND PT OF 21 AND 23 TRACT 20 PB3-10 OF MONROE INV CO PLAT PB1-41 G68-524 OR752-
Taxes: 9484.05
Tax Year: 2025
Pub Sewer HkUp: Yes

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
Control Depth: 0
Total Units: 0

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Building Style

Above Flood: Unknown
Stories: 1 Story
Ground Level: Yes

More Information

Remarks & Misc

Remarks – Consumer: 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.

License Info

Non Trans Rntl Lic: Yes

Fee Includes

None: Yes

Dockage

None: Yes

Tax Exemptions

None: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Freezer: Yes
Microwave: Yes
Oven: Yes
Refrigerator: Yes
Washer: Yes

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Central Air: Yes
Wall/Window Unit(s): Yes

Waterfront

None: Yes

Waterview

No Waterview: Yes

Floor

Tile: Yes

Windows/Doors

French Doors: Yes
Sliding Glass Doors: Yes

Vehicle Storage

Carport: Yes
Covered Parking: Yes
Off Street Parking: Yes

Construction

CBS: Yes

Land Size

Less Than 1/4 Acre: Yes

Furnished

Negotiable: Yes

Terms

Cash: Yes
Conventional: Yes
FHA: Yes
VA: Yes

Utilities

Buyer to Verify: Yes

Porch/Balcony

Deck: Yes
Patio: Yes

Title

Negotiable: Yes

Exterior Features

Detached Guest Qtrs: Yes
Outdoor Shower: Yes
Privacy Wall/Fence: Yes

Pool Info

In Ground: Yes
Concrete: Yes

Roof

Metal Roof: Yes

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 - 10 - 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.

Search powered by FBS Products