1933 N Winchester Ave

Chicago, IL 60622

$1,499,900
Price
6
Beds
—Sq. Ft.
— / Sq. Ft.
—
Sq. Ft.
—
per Sq. Ft.
Listed By @properties
Listed By @properties

Description

Perfectly positioned in the heart of Bucktown, this five-unit, all-brick vintage gem combines unbeatable location, standout curb appeal, and a proven rental track record. Featuring front and rear 1-bedroom/1-bath units on the first two floors, plus a spacious 2-bedroom/1-bath penthouse. Every unit has been fully rehabbed with today's most sought-after finishes-sleek white high-gloss kitchen cabinetry, quartz countertops, stainless steel appliances, and hardwood flooring throughout. In-unit washers...Perfectly positioned in the heart of Bucktown, this five-unit, all-brick vintage gem combines unbeatable location, standout curb appeal, and a proven rental track record. Featuring front and rear 1-bedroom/1-bath units on the first two floors, plus a spacious 2-bedroom/1-bath penthouse. Every unit has been fully rehabbed with today's most sought-after finishes-sleek white high-gloss kitchen cabinetry, quartz countertops, stainless steel appliances, and hardwood flooring throughout. In-unit washers and dryers add everyday convenience, while separately metered gas and electric, individual HVAC systems, and dedicated hot water heaters keep expenses streamlined. Some oversized laundry rooms offer exceptional bonus space-perfect for a home office, additional storage, or a dream walk-in closet. A generous common rear deck provides inviting outdoor space for tenants and two garage parking spots create additional income. With strong rental history and modern upgrades, this is a true turn-key investment - ready to generate reliable cash flow for its next long-term owner. Broker owned
  1. Listed by D Waveland Kendt • @properties Christie’s International Real Estate
    P: (312)-330-3321 C: (312)-330-3321 dwk@atproperties.com

Property Details for 1933 North Winchester Avenue

Area
CHI - Logan Square
Township
West Chicago
Air Conditioning Type
Central Air
Num of Interior Fireplaces
0
Zoning
MULTI
LISTING UPDATED: 02/22/2026 02:05 AM

Property Details for 1933 North Winchester Avenue

StatusNew
MLS #12567816
Days on Market4
Taxes$18,426 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeMulti Family 5+ / Flats
Year Built1920
Lot Size0.07 AC / 3,125 SF
CountyCook County

Location

Add your commute

Building Information for 1933 North Winchester Avenue

Stories3Residences5Year Built1920Building Size-Lot Size0.07 AC / 3,125 SF

Payment Calculator

$8,846 per month

30 year fixed, 6.15% Interest

Principal and Interest

$7,310

Property Taxes

$1,536

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 1933 North Winchester Avenue

General Information
Addtl Parking Information
  • Indoor Parking: 1-5 Spaces
Location and General Information
  • Information: 24-Hr Notice Required
Taxes and HOA Information
  • Additional Parcels: No
Property Information
Interior Features
  • Air Conditioning: Central Air
  • Electric: Circuit Breakers, Separate Meters, Service - 0 to 100 Amps
  • # Of Washers: 5
  • Heat/Ventilation: Central Heat/Indiv Controls,Forced Air,Gas,Separate Per Unit
  • # Of Window/Ac: 0
  • # Of Refrigerators: 5
  • Washer/Dryer Lsd: No
  • # Of Dryers: 5
  • # Of Disposals: 5
  • # Of Dishwashers: 5
  • Num of Baths: 5.0
Property/Lot Information
  • Owners Association: No
  • Tenant Pays: Air Conditioning, Electricity, Heat, Hot Water
  • Built Before 1978: Yes
  • Approximate Age: Older
  • Multi-Family Type: Flats
  • Lot Dimensions: 25X125
  • Stories: 3
  • Construction: Brick
  • Roof Type: Composition
  • Roof Structure: Pitched
  • # Of Ranges: 5
  • MRD_UNC: No
Property and Assessments
  • Public Document Count: 6
  • Document Date: 2026-02-18T17:46:31
  • Photos Count: 33
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
Multi Family
Multi-Family Information
  • Number Of Units Total: 5
Income & Expenses
  • Electric Expense: $998.00
  • Fuel Expense: $285.00
  • Gross Income: $125,940.00
  • Insurance Expense: $4,488.00
  • Maintenance Expense: $.00
  • Electric Expense Source: Actual
  • Total Annual Expense Source: Actual
  • Fuel Expense Source: Actual
  • Insurance Expense Source: Actual
  • Janitor Expense: 0
  • Repairs-Decor Expense Source: Actual
  • Trash Expense Source: Actual
  • Total Monthly Income: 10495
  • Water Expense Source: Actual
  • Net Operating Income: $99,554.00
  • Operating Expense: $26,396.00
  • Other Expense: $.00
  • Trash Expense: $.00
  • Water Sewer Expense: $2,189.00
Unit 1
  • Unit Type Baths Total: 1
  • Unit Type Beds Total: 1
  • Unit Type Type: Unit 1
  • Unit Type Units Total: 2
Unit 2
  • Unit Type Baths Total: 1
  • Unit Type Beds Total: 1
  • Unit Type Type: Unit 2
  • Unit Type Units Total: 2
Unit 3
  • Unit Type Baths Total: 1
  • Unit Type Beds Total: 2
  • Unit Type Type: Unit 3
  • Unit Type Units Total: 1
Unit 4
  • Unit Type Beds Total: 0
  • Unit Type Type: Unit 4
  • Unit Type Units Total: 0
Unit 5
  • Unit Type Beds Total: 0
  • Unit Type Type: Unit 5
  • Unit Type Units Total: 0
Unit 6
  • Unit Type Beds Total: 0
  • Unit Type Type: Unit 6
  • Unit Type Units Total: 0
Unit 7
  • Unit Type Beds Total: 0
  • Unit Type Type: Unit 7
  • Unit Type Units Total: 0

Property History for 1933 North Winchester Avenue

DateEvent & SourcePriceAppreciation
Feb 20, 2026

Listed (Active)

MRED #12567816

$1,499,900—
Jul 4, 2008

Cancelled

MRED #06836156

$899,900—
Mar 20, 2008

Listed (Active)

MRED #06836156

$899,900—
Sep 10, 2001

Sold (Public Record)

Public Record #79007768

$640,000—
DateEvent & SourcePrice
02/20/2026

Listed (Active)

MRED #12567816

$1,499,900
07/04/2008

Cancelled

MRED #06836156

$899,900
03/20/2008

Listed (Active)

MRED #06836156

$899,900
09/10/2001

Sold (Public Record)

Public Record #79007768

$640,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1933 North Winchester Avenue

Taxable ValueLand$21,000Additions$66,352Total$87,352
Tax Record2023$18,496 ($1,541 / month)
Home Facts
Baths4Total Finished SqFt3,190 SqFtAbove Grade Finished SqFt3,190 SqFtStories2Lot Size3,000 SqFtStyleMulti-Family Res (5+ Units)Year Built1890CountyCOOKAPN14-31-401-017

Schools near 1933 North Winchester Avenue

This home is within Chicago Public Schools.
Rating
School
Type
Grades
Distance
Pulaski International School of Chicago
Public - PK to 8
Wells Community Academy High School
Public - 9 to 12
Art in Motion Charter School
Charter - 7 to 11
York Alternative High School
Public - 9 to 12
Rating
School
Distance
Pulaski International School of Chicago
PublicPK to 8

Wells Community Academy High School
Public9 to 12

Art in Motion Charter School
Charter7 to 11

York Alternative High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1933 North Winchester Avenue, Chicago, IL 60622

1933 North Winchester Avenue is a multi-family home for sale in Chicago, IL 60622. This property was listed for sale on February 20, 2026 by Compass, it's currently listed at $1,499,900. It has been on the market for a total of 4 days and was last sold on September 10, 2001. This listing's school district is Chicago Public Schools. Nearby schools include Pulaski International School of Chicago, Wells Community Academy High School and Art in Motion Charter School. 1933 North Winchester Avenue is a 6-bed, 5-bath, multi-family home built in 1920.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Based on information from one of the following Multiple Listing Services: Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 02/22/2026 02:05 AM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.