For sale

$1,399,000

1221 Ashby St, Key West, FL 33040

3beds

1,374sqft

$8,826/mo

Get pre-qualified

Single Family Residence

Built in 1953

5,227 Square Feet Lot

$1,316,500 Zestimate^®

$1,018/sqft

$-- HOA

What's special

Large swimming poolRecently updatedLounge chairsCovered off-street parkingInviting living spacesSpacious corner lotSpacious decking

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.

17 hours
313
36

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 3
Full bathrooms: 3

Cooling

Central Air, Wall/Window Unit(s), Ceiling Fans(s)

Appliances

Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Freezer

Features

Flooring: Tile

Interior area

Total structure area: 1,374
Total interior livable area: 1,374 sqft

Property

Features

Levels: Ground Level
Patio & porch: Deck, Patio
Exterior features: Outdoor Shower
Has private pool: Yes
Pool features: In Ground, Concrete
Fencing: Privacy

Lot

Size: 5,227 Square Feet
Dimensions: 88 X 60

Details

Additional structures: Guest House
Parcel number: 00044560000000
Zoning: SF - Single Family

Construction

Type & style

Home type: SingleFamily
Property subtype: Single Family Residence

Materials

Condition

Year built: 1953

Community & HOA

Community

Subdivision: Macros Subd (2.0)

HOA

Has HOA: No
Services included: None

Location

Region: Key West

Financial & listing details

Price per square foot: $1,018/sqft
Tax assessed value: $1,135,991
Annual tax amount: $9,484
Date on market: 10/6/2026
Listing terms: Cash,Conventional,FHA

Estimated market value

$1,316,500

$1.25M - $1.38M

$6,243/mo

Price history

Date	Event	Price
10/6/2026	Listed for sale	$1,399,000+50.4%$1,018/sqft
Source: FLKMLS #621518 Report a problem
3/31/2021	Sold	$930,000+0.5%$677/sqft
Source: FLKMLS #594405 Report a problem
3/6/2021	Contingent	$925,000$673/sqft
Source: FLKMLS #594405 Report a problem
3/2/2021	Listed for sale	$925,000$673/sqft
Source: FLKMLS #594405 Report a problem
2/17/2021	Listing removed	--
Source: Key West AOR Report a problem
2/13/2021	Contingent	$925,000$673/sqft
Source: FLKMLS #594405 Report a problem
2/9/2021	Listed for sale	$925,000$673/sqft
Source: FLKMLS #594405 Report a problem
2/1/2021	Contingent	$925,000$673/sqft
Source: FLKMLS #594405 Report a problem
1/29/2021	Listed for sale	$925,000+85%$673/sqft
Source: FLKMLS #594405 Report a problem
2/16/2016	Sold	$500,000-28.1%$364/sqft
Source: FLKMLS #122586 Report a problem
6/2/2003	Sold	$695,000+297.1%$506/sqft
Source: Public Record Report a problem
11/15/2001	Sold	$175,000-34.2%$127/sqft
Source: Public Record Report a problem
9/14/1999	Sold	$265,800$193/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$9,484 +13.1%	$1,055,684 +10%
2024	$8,382 -4.6%	$959,713 -0.1%
2023	$8,787 +14.8%	$960,449 +10%
2022	$7,653 +38.2%	$873,135 +55.2%
2021	$5,538 +13.3%	$562,463 +10%
2020	$4,888	$511,330 -1.5%
2019	$4,888 -2.1%	$518,863 -6.3%
2018	$4,992 -7.6%	$553,896 +1.3%
2017	$5,401 -0.4%	$546,689 +9.9%
2016	$5,425 +3.5%	$497,321 +13.4%
2015	$5,240	$438,644