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$1,399,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1,374 Sq. Ft.
  • Updated 6 days ago
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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.

Full Property Details for 1221 Ashby St

General

  • Price: $1,399,000
  • Taxes: $9,484 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 621518
  • Updated: 10/6/2026
  • Added to Site: 6 day(s) ago

Interior

  • Appliances: Dishwasher, Dryer, Freezer, Microwave, Oven, Refrigerator, Washer
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Pool: Yes
  • Pool Description: Concrete, In Ground

Exterior

  • Exterior Features: Detached Guest Qtrs, Outdoor Shower, Privacy Wall/Fence
  • Deck/Patio: Deck, Patio
  • Porch/Patio/Deck: Deck, Patio

Parking

  • Parking Features: Off Street, Covered, Carport

Location

  • Area: 03 - Key West
  • County: Monroe
  • Subdivision: Macros Subd (2.0)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Wall/Window Unit(s), Central Air, Ceiling Fans(s)

Structural Information

  • Architectural Style: Above Flood
  • Construction: CBS
  • Roof: Metal
  • Windows/Doors: French Doors, Sliding Glass Doors
  • Square Feet: 1,374
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1953

Lot Features

  • Property View: No Waterview
  • Lot Size (Acres): 0.12
  • Lot Size (Sq. Ft.): 5,280
  • Lot Dimensions: 88 x 60
  • Zoning: SF - Single Family

Water Features

  • Water View: Yes

Financial Considerations

  • Tax Amount: $9,484.05
  • Tax Year: 2025
  • Terms: Cash, Conventional, VA Loan, FHA

Disclosures and Reports

  • Legal Description: 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-
  • Flood Zone: AE
  • APN: 00044560-000000

Listed by Expert Realty LLC (HQ), Justyn Ewald (305) 587-7330 and Expert Realty LLC (HQ), Mason C Kelly (305) 587-4051

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Listing agents

— 1221 Ashby St —

  • Justyn Ewald

    Expert Realty LLC (HQ)

  • Mason C Kelly

    Expert Realty LLC (HQ)

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1221 Ashby St

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Horace O'bryant School
1105 Leon Street, Key West, FL 33040
6-80.1 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-120.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1221 Ashby St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/06/2026
Listed
$1,399,000
50.43%
MLS
3/31/2021
Sold
$930,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1221 Ashby St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,484
13%
$1,135,991
18%
2024
$8,382
-5%
$959,713
-9%
2023
$8,787
59%
$1,060,415
71%
2021
$5,538
-28%
$618,842
-29%
2022
$7,653
38%
$873,135
71%
2021
$5,538
11%
$511,330
-1%
2019
$4,992
-8%
$518,863
-6%
2018
$5,401
—
$553,896
1%
2017
$5,425
4%
$546,689
10%
2016
$5,240
9%
$497,321
13%
2015
$4,795
-6%
$438,644
2%
2014
$5,100
-21%
$431,772
-4%
2013
$6,480
—
$450,928
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1221 Ashby St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Expert Realty LLC (HQ), Justyn Ewald (305) 587-7330 and Expert Realty LLC (HQ), Mason C Kelly (305) 587-4051

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1221 Ashby Street, Key West, FL 33040 (MLS# 621518) is a Single Family property with 3 bedrooms and 3 full bathrooms. 1221 Ashby Street is currently listed for $1,399,000 and was received on October 06, 2026. Want to learn more about 1221 Ashby Street? Do you have questions about finding other Single Family real estate for sale in Key West? You can browse all Key West real estate or contact a Coldwell Banker agent to request more information.

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