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$225,000
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Property Description
BEST AND FINAL DUE MONDAY AT 3PM. - Recently rehabbed Andersonville 1 Bedroom Penthouse on a tree-lined one-way street. East-facing light-filled home with modern open floor plan with generous room dimensions and vintage charm. Open kitchen with beautiful cherry cabinets, granite countertops, and stainless steel appliances. Marble bathroom, private deck off living room, common deck off kitchen, in-unit washer and dryer, and large extra storage room. 7 min walk to public transit and blocks away from everything Andersonville has to offer. Street parking and off-site rental options are available. Roof recoated in 2025, new butterfly entrance system, furnace and AC from 2024, laundry 2021. HOA 287. Tax 4036.30. Built in 1927 and fully gutted in 2004. Rentals allowed-rental cap of 4 units-currently 3 rented. Must live in the unit for 1 year before renting. 40k in reserves - no specials planned
Full Property Details
Full Property Details for 1258 W Winona St #4B
General
- Price: $225,000
- HOA FEE: $287/month
- Taxes: $4,036 (2025)
- Status: Active
- Type: Condo
- Source: MRED
- MLS ID: 12763794
Interior
- Basement: None
- Interior Features: Storage
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Living Room, Gas Log, Gas Starter
- Appliances: Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 1
- Full Bathrooms: 1
Bedrooms
- Total Bedrooms: 1
Additional Information
- Shared Amenities: Storage
Exterior
- Exterior Features: Balcony
Location
- Area: CHI - Uptown
- County: Cook
- Township: North Chicago
- Driving Directions: CLARK TO WINONA, EAST TO PROPERTY
School Information
- School District: 299
- Elem School District: 299
- Midd School District: 299
- High School District: 299
Community
- Assoc. Fees Include: Water, Insurance, Exterior Maintenance, Scavenger
- Pets Allowed: Yes
- Pets: Cats OK, Dogs OK
- Pet Restrictions: Cats OK, Dogs OK, / 999lbs.
- Mgmt. Company: Winona Terrace Condominum assoc
Heating & Cooling
- Cooling Type: Central Air Conditioning
- Heating Type: Natural Gas, Forced Air
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan
Structural Information
- Structure Type: Condo
- Construction: Brick
- Exterior Const.: Brick
- Basement Desc.: None
- Roof: Asphalt
- Windows: Screens
- Sub-Flooring: Hardwood
- Entry Floor Number: 4
- Stories/Levels: 3
- Sq. Ft. Source: Not Reported
- Year Built: 1927
- Built Before 1978: Yes
- Remodeled/Updated: 2004
Unit Information
- Units in Building: 17
Lot Features
- Lot Dimensions: COMMON
Animals
- Animals Allowed: Cats OK, Dogs OK
Financial Considerations
- Association Fee: $287
- Assoc Fee Freq.: Monthly
- Assessment Year: 1927
- Tax Amount: $4,036.3
- Tax Year: 2025
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Condo
- Property ID: 14083020741007
Listed by Jameson Sotheby's Int'l Realty
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Schools
Schools serving 1258 W Winona St #4B
School District:Chicago Public School District 299
| Name | Grades | Distance |
|---|---|---|
Mccutcheon Elementary School 4865 North Sheridan Road, Chicago, IL 60640 | PK-8 | 0.5 mi |
Senn High School 5900 North Glenwood Avenue, Chicago, IL 60660 | 9-12 | 0.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Tax History
Tax History for 1258 W Winona St #4B
Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,587
—
$19,438
14%
2023
$3,587
3%
$16,999
—
2022
$3,496
2%
$16,999
—
2021
$3,418
2%
$16,999
13%
2020
$3,345
1%
$15,016
-9%
2019
$3,328
28%
$16,565
—
2018
$2,594
25%
$16,565
27%
2017
$2,077
-1%
$13,023
—
2016
$2,108
11%
$13,023
—
2015
$1,906
6%
$13,023
6%
2014
$1,794
3%
$12,240
—
2013
$1,748
—
$12,240
—
2012
$1,749
—
$12,240
—
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
Estimate the Cost for 1258 W Winona St #4B
1258 W Winona Street #4B, Chicago, IL 60640 (MLS# 12763794) is a Condo property with 1 bedroom and 1 full bathroom. 1258 W Winona Street #4B is currently listed for $225,000 and was received on September 21, 2026. Want to learn more about 1258 W Winona Street #4B? Do you have questions about finding other Condo real estate for sale in Uptown? You can browse all Uptown real estate or contact a Coldwell Banker agent to request more information.

