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$650,000 Just Listed

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,100 Sq. Ft.
  • Updated 1 day ago

Next open house:

Open House: 12:00 PM - 2:00 PM

Saturday 10/17 12:00 PM - 2:00 PM

1252 W Winona Street #1,Chicago, IL 60640

1252 W Winona Street #1ChicagoIL60640

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Meticulously appointed duplex down in an intimate six unit building in a prime Andersonville location. Set on a quiet, tree lined street this two bedroom & 2.5 bath unit features high ceilings, hardwood floors, crown molding throughout. The main level offers a spacious living room anchored by a gas fireplace with built-ins on either side that flows in to the sunroom with windows on two sides that provides the perfect spot to relax. The separate dining room is just off the the fully renovated kitchen (2019), featuring two-tone cabinetry, a stone tile backsplash, and upgraded appliances. An office nook just off the kitchen offers a convenient work from home space and leads directly to a large deck. Both bedrooms are located on the main level, including a primary suite with a private en suite featuring dual sinks and a soaking tub. The spacious second bedroom and full hall bath complete the main floor. The lower level adds more living space with a family room, half bath, and laundry room with utility sink. Originally configured with a third bedroom, the lower level was opened up to create additional common living space, offering flexibility for a future owner to reimagine the layout. One exterior parking space is included in the price. Additional highlights include a newer furnace (2023) and a well run self managed association. Enjoy easy access to the lakefront, beaches, shopping, and dining along Clark & Argyle with buses, the Red Line and Lake Shore Drive blocks away. A wonderful blend of character & convenience in one of Chicago's most sought after neighborhoods!

Full Property Details for 1252 W Winona St #1

General

  • Price: $650,000
  • HOA FEE: $395/month
  • Taxes: $9,427 (2024)
  • Status: Active
  • Type: Condo
  • Source: MRED
  • MLS ID: 12781698
  • Updated: 10/15/2026
  • Added to Site: 2 day(s) ago

Interior

  • Basement: Finished, F
  • Interior Features: Built-in Features, Walk-In Closet(s), Separate Dining Room
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room, Gas Log
  • Appliances: Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Basement Baths: Yes
  • Bathroom Features: Double Sink, Soaking Tub

Bedrooms

  • Total Bedrooms: 2

Additional Information

  • Equipment: Ceiling Fan(s)
  • Other Features: Commuter Bus, Commuter Train

Parking

  • Total Spaces: 1
  • Parking Features: Off-Alley, Assigned, Yes, Other

Location

  • Area: CHI - Uptown
  • County: Cook
  • Township: Lake View
  • Driving Directions: W Winona between N Glenwood and N Broadway

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299
  • Elementary School: Mccutcheon Elementary School
  • Middle School: Mccutcheon Elementary School
  • High School: Senn High School
  • Private School: Senn High School

Community

  • Assoc. Fees Include: Water, Parking, Insurance, Exterior Maintenance, Scavenger, Snow Removal
  • Pets Allowed: Yes
  • Pets: Cats OK, Dogs OK
  • Pet Restrictions: Cats OK, Dogs OK, / 999lbs.
  • Mgmt. Company: Self Managed

Heating & Cooling

  • Cooling Type: Central Air Conditioning
  • Heating Type: Natural Gas, Forced Air, Radiant, Sep Heating Systems - 2+, Radiant Floor

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Structure Type: Condo, Condo/Duplex
  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Finished, Full
  • Foundation: Concrete Perimeter
  • Roof: Asphalt
  • Sub-Flooring: Hardwood
  • Entry Floor Number: 1
  • Stories/Levels: 3
  • Square Feet: 2,100
  • Sq. Ft. Source: Estimated
  • Year Built: 1919
  • Built Before 1978: Yes
  • Remodeled/Updated: 2019

Unit Information

  • Units in Building: 6

Lot Features

  • Lot Dimensions: Common

Animals

  • Animals Allowed: Cats OK, Dogs OK

Financial Considerations

  • Association Fee: $395
  • Assoc Fee Freq.: Monthly
  • Parking Included: Yes
  • Assessment Year: 1919
  • Tax Amount: $9,427.77
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Condo
  • Property ID: 14083020721001

Listed by Redfin Corporation

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— 1252 W Winona St #1 —

  • Redfin Corporation

(312) 836-4263

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NMLS#: 1598647

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Save up to an additional 20% by bundling your home and auto together!

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 1252 W Winona St #1

School District:Chicago Public School District 299
NameGradesDistance
Mccutcheon Elementary School
4865 North Sheridan Road, Chicago, IL 60640
PK-80.5 mi
Senn High School
5900 North Glenwood Avenue, Chicago, IL 60660
9-121 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 1252 W Winona St #1 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/15/2026
Listed
$650,000
47.73%
MLS
4/22/2019
Sold
$440,000
—
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 1252 W Winona St #1

Year
Property Taxes
Change
Tax Assessment
Change
2023
$9,290
—
$52,856
6%
2023
$9,290
3%
$49,999
—
2022
$9,018
2%
$49,999
—
2021
$8,849
19%
$49,999
28%
2020
$7,455
-16%
$39,048
-22%
2019
$8,862
-11%
$50,283
—
2018
$9,933
3%
$50,283
68%
2017
$9,600
60%
$29,964
—
2016
$6,001
9%
$29,964
—
2015
$5,491
-13%
$29,964
-12%
2014
$6,338
2%
$34,162
—
2013
$6,213
1%
$34,162
—
2012
$6,130
—
$34,162
—
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.

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1252 W Winona Street #1, Chicago, IL 60640 (MLS# 12781698) is a Condo property with 2 bedrooms, 2 full bathrooms and 1 partial bathroom. 1252 W Winona Street #1 is currently listed for $650,000 and was received on October 15, 2026. Want to learn more about 1252 W Winona Street #1? 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.

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