908 N Winchester Ave

$1,999,900
Price
5
Beds
4,300 Sq. Ft.
$465 / Sq. Ft.
4,300
Sq. Ft.
$465
per Sq. Ft.

Description

Exceptional Design Meets Modern Luxury in Hot Ukrainian Village / Wicker Park Experience refined living in this one-of-a-kind 5-bedroom, 4.5-bath single-family home showcasing exceptional design and craftsmanship. The open-concept main level features a chef's kitchen with a massive island, high-end appliances, and a pot filler for added convenience. Hardwood floors span every level of the home, enhancing the modern aesthetic and seamless flow of each space. Upstairs, you'll find two private suites,...Exceptional Design Meets Modern Luxury in Hot Ukrainian Village / Wicker Park Experience refined living in this one-of-a-kind 5-bedroom, 4.5-bath single-family home showcasing exceptional design and craftsmanship. The open-concept main level features a chef's kitchen with a massive island, high-end appliances, and a pot filler for added convenience. Hardwood floors span every level of the home, enhancing the modern aesthetic and seamless flow of each space. Upstairs, you'll find two private suites, each with its own full bath. The top floor is a true primary retreat, featuring a bedroom with a cozy fireplace and private balcony, a spa-like bath with elegant French doors, and a custom-built dressing room offering the ultimate boutique-style experience. The finished lower level includes a family room with bar area, full bath, and fourth bedroom-ideal for guests or additional living space. Enjoy outdoor living with a large fenced yard, fiber-composite deck, and spiral staircase connecting every level. A two-car garage completes this remarkable home. Freshly updated and perfectly located near all the restaurants, cafes, and nightlife that make Ukrainian Village and Wicker Park among Chicago's most desirable neighborhoods.
  1. Listed by Konstantin Shelegeda • Inter Properties Inc
    P: (773)-620-0320 k@interproperties.co;k@interproperties.co

Property Details for 908 North Winchester Avenue

Area
CHI - West Town
Township
Jefferson
Ownership
Fee Simple
Num Of Garage Spaces
2.5
Num Of Parking Spaces
2.5
Parking Included in Price
Yes
Air Conditioning Type
Central Air, Zoned
Num of Interior Fireplaces
3
LISTING UPDATED: 11/24/2025 12:07 AM

Property Details for 908 North Winchester Avenue

StatusActive
MLS #12520088
Days on Market59
Taxes$24,693 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeDetached Single / 3 Stories
Year Built2001
Lot Size0.07 AC / 3,125 SF
CountyCook County

Location

Listing Courtesy of Inter Properties Inc
Add your commute

Building Information for 908 North Winchester Avenue

Stories-Year Built2001Building Size-Lot Size0.07 AC / 3,125 SF

Payment Calculator

$11,940 per month

30 year fixed, 6.28% Interest

Principal and Interest

$9,882

Property Taxes

$2,058

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 908 North Winchester Avenue

General Information
School Information
  • Elementary School District: 299
  • High School District: 299
  • Middle Or Junior School District: 299
Addtl Parking Information
  • Parking Details: Other, Garage Door Opener, Yes, Garage Owned, Detached, Garage
Location and General Information
  • Front Exposure: North, South, East, West
Taxes and HOA Information
  • Association Fee Frequency: Not Applicable
  • Association Fee Includes: None
  • Master Association Fee: No
  • Master Association Fee Frequency: Not Required
Property Information
Interior Features
  • Interior Property Features: Cathedral Ceiling(s), Sauna, Wet Bar
  • Num Of Rooms: 10
  • Bedrooms Total: 5
  • Bedrooms (Below Grade): 0
  • Community Features: Curbs, Gated, Sidewalks, Street Lights
  • Bath Amenities: Whirlpool,Separate Shower,Steam Shower,Double Sink
  • Fireplace Features: Wood Burning, Gas Log, Gas Starter
  • Basement Type: Finished, Daylight
  • Bedrooms Possible: 5
  • Air Conditioning: Central Air, Zoned
  • Electric: Circuit Breakers, 200+ Amp Service
  • Flooring: Hardwood
  • Dining Room: Separate
  • Basement Bathrooms: Yes
  • Fireplace Location: Living Room,Basement,Bedroom
  • Room Type: Balcony/Porch/Lanai, Deck, Bedroom 5, Foyer, Utility Room-Lower Level, Walk In Closet, Den
  • Num of Baths: 4.1
Exterior Features
  • Patio And Porch Features: Deck
  • Type: 3 Stories
Utilities / Equipment
  • Sewer: Sewer-Public
  • Water: Lake Michigan
  • Appliances: Range, Microwave, Dishwasher, Refrigerator, High End Refrigerator, Refrigerator-Bar, Washer, Dryer, Disposal, All Stainless Steel Kitchen Appliances
  • Other Equipment: TV-Cable, Security System, Intercom, CO Detectors, Sump Pump
Property/Lot Information
  • Exterior Property Features: Balcony
  • New Construction YN: No
  • Rebuilt: No
  • Rehabilitated: Yes
  • Rehab Year: 2016
  • Built Before 1978: No
  • Age: 21-25 Years
  • Type Detached: 3 Stories
  • Total Sq Ft: 0
  • Aprox Total Finished Sq Ft: 0
  • Total Finished and Unfin Sq Ft: 0
  • Lot Size: Less Than .25 Acre
  • Lot Dimensions: 25X125
  • Waterfront: No
  • Disability Access and/or Equipped: No
  • Construction: Block, Limestone
  • Roof Type: Asphalt
  • Foundation Details: Concrete Perimeter
  • General Information: None
  • North Coordinate: 908
  • South Coordinate: 0
  • East Coordinate: 0
  • West Coordinate: 1950
  • Living Area Source: Estimated
Property and Assessments
  • Public Document Count: 0
  • Photos Count: 50
  • OpenHouse Count: 1
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
Room Information
Master Bedroom Information
  • Master Bedroom Level: Third
  • Room Type: Master Bedroom
  • Master Bedroom Bath: Full
  • Master Bedroom Dimensions: 18X12
Bedroom #2 Information
  • 2nd Bedroom Level: Second
  • Room Type: Bedroom 2
  • Bedroom #2 Room Dimensions: 18X18
Bedroom #3 Information
  • 3rd Bedroom Level: Second
  • Room Type: Bedroom 3
  • Bedroom #3 Room Dimensions: 18X17
Bedroom #4 Information
  • 4th Bedroom Level: Third
  • Room Type: Bedroom 4
  • Bedroom #4 Room Dimensions: 17X15
Bedroom #5 Information
  • 5th Bedroom Level: Lower
  • Room Type: Bedroom 5
  • Bedroom #5 Room Dimensions: 16X16
Dining Room Information
  • Dining Room Level: Main
  • RoomType_DR: Dining Room
  • Dining Room Dimensions: 17X9
Family Room Information
  • Family Room Level: Lower
  • RoomType_FR: Family Room
  • Family Room Dimensions: 29X18
Kitchen Information
  • Kitchen Level: Main
  • RoomType_KT: Kitchen
  • Kitchen Dimensions: 17X9
Laundry Information
  • Laundry Level: Lower
  • Room Type: Laundry
  • Laundry Dimensions: 12X10
Living Room Information
  • Living Room Level: Main
  • Room Type: Living Room
  • Living Room Dimensions: 21X18
Deck Information
  • Room Level: Main
  • Room Type: Deck
  • Dimensions: 18X14
Walk In Closet 1 Information
  • Room Level: Second
  • Room Type: Walk In Closet
  • Dimensions: 8X7
Foyer Information
  • Room Level: Main
  • Room Type: Foyer
  • Dimensions: 11X9
Balcony/Porch/Lanai Information
  • Room Level: Main
  • Room Type: Balcony/Porch/Lanai
  • Dimensions: 9X5
Den Information
  • Room Level: Lower
  • Room Type: Den
  • Dimensions: 9X9
Utility Room Lower Level Information
  • Room Level: Lower
  • Room Type: Utility Room-Lower Level
  • Dimensions: 9X8

Property History for 908 North Winchester Avenue

DateEvent & SourcePriceAppreciation
Nov 18, 2025

Cancelled

MRED #12502672

$1,999,500
Nov 18, 2025

Listed (Active)

MRED #12520088

$1,999,900
Oct 23, 2025

Listed (Active)

MRED #12502672

$1,999,500
Feb 28, 2017

Sold (Public Record)

Public Record #589502716

$1,130,000
Feb 28, 2017

Sold

MRED #09355583

$1,130,000
Jan 10, 2017

Pending

MRED #09355583

Sep 30, 2016

Listed (Active)

MRED #09355583

$1,150,000
Sep 29, 2016

Cancelled

MRED #09325170

$1,199,000
Aug 25, 2016

Cancelled

MRED #09273457

$1,249,000
Aug 25, 2016

Listed (Active)

MRED #09325170

$1,199,000
Jun 30, 2016

Listed (Active)

MRED #09273457

$1,249,000
Jun 29, 2016

Cancelled

MRED #09216173

$1,349,900
May 4, 2016

Listed (Active)

MRED #09216173

$1,399,900
Jun 18, 2015

Sold

MRED #08807018

$690,000
Dec 31, 2014

Pending

MRED #08807018

Dec 29, 2014

Listed (Active)

MRED #08807018

$750,000
Feb 17, 2009

Cancelled

MRED #06910578

$999,000
May 29, 2008

Listed (Active)

MRED #06910578

$1,175,000
Dec 10, 2007

Cancelled

MRED #06726376

$975,000
Nov 8, 2007

Listed (Active)

MRED #06726376

$975,000
DateEvent & SourcePrice
11/18/2025

Cancelled

MRED #12502672

$1,999,500
11/18/2025

Listed (Active)

MRED #12520088

$1,999,900
10/23/2025

Listed (Active)

MRED #12502672

$1,999,500
02/28/2017

Sold (Public Record)

Public Record #589502716

$1,130,000
02/28/2017

Sold

MRED #09355583

$1,130,000
01/10/2017

Pending

MRED #09355583

09/30/2016

Listed (Active)

MRED #09355583

$1,150,000
09/29/2016

Cancelled

MRED #09325170

$1,199,000
08/25/2016

Cancelled

MRED #09273457

$1,249,000
08/25/2016

Listed (Active)

MRED #09325170

$1,199,000
06/30/2016

Listed (Active)

MRED #09273457

$1,249,000
06/29/2016

Cancelled

MRED #09216173

$1,349,900
05/04/2016

Listed (Active)

MRED #09216173

$1,399,900
06/18/2015

Sold

MRED #08807018

$690,000
12/31/2014

Pending

MRED #08807018

12/29/2014

Listed (Active)

MRED #08807018

$750,000
02/17/2009

Cancelled

MRED #06910578

$999,000
05/29/2008

Listed (Active)

MRED #06910578

$1,175,000
12/10/2007

Cancelled

MRED #06726376

$975,000
11/08/2007

Listed (Active)

MRED #06726376

$975,000

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

Public Records for 908 North Winchester Avenue

Taxable ValueLand$22,050Additions$97,950Total$120,000
Tax Record2023$24,693 ($2,058 / month)
Home Facts
Beds4Baths3Total Finished SqFt3,159 SqFtAbove Grade Finished SqFt3,159 SqFtStories3Lot Size3,150 SqFtStyleSingle Family ResidenceYear Built1999CountyCOOKAPN17-06-421-041Fireplace TypeHas Fireplace

Schools near 908 North Winchester Avenue

This home is within Chicago Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Public - PK to 8
Charter - 9 to 12
Rating
School
Distance
Columbus Elementary School
PublicPK to 8

Wells Community Academy High School
Public9 to 12

Golder College Prep
Charter9 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.

Neighborhood Map and Transit

Similar Homes

Similar Sold Homes

908 North Winchester Avenue is a single family home for sale in Chicago, IL 60622. This property was listed for sale on November 18, 2025 by Inter Properties Inc, it's currently listed at $1,999,900. It has been on the market for a total of 59 days and was last sold on February 28, 2017. This listing's school district is Chicago Public Schools. Nearby schools include Columbus Elementary School, Wells Community Academy High School and Lasalle II Language Academy Elementary School. 908 North Winchester Avenue is a 5-bed, 5-bath, 4,300 sqft single family home built in 2001.

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.

Listing Courtesy of Inter Properties Inc

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 11/24/2025 12:07 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.