Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$625,000 Just Listed

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1,500 Sq. Ft.
  • Updated 1 hour ago

Next open house:

Open House: 10:00 AM - 12:00 PM

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

5055 N Winchester Avenue #3,Chicago, IL 60640

5055 N Winchester Avenue #3ChicagoIL60640

Get directions
See This Home
Save This Home
See This Home
Save This Home
If you've been waiting for an extra-wide, sun-drenched condo with exposed brick, a fireplace framed by original built-ins, and true Lincoln Square charm, your search ends here. Tucked away on a quiet, tree-lined street, this beautifully renovated third story unit blends boutique hotel style with warm, inviting living spaces. Oversized bay windows flood the open-concept living and dining area with natural light, flowing seamlessly into a stunning designer kitchen featuring Quartz countertops and backsplash, custom white oak cabinetry, open shelving, upgraded KitchenAid stainless steel appliances, pantry storage, and an added window for even more sunshine. The spacious primary suite feels like a private retreat with a walk-in closet, French doors to the deck, and a spa-inspired bath with soaking tub, steam shower, marble sink, and custom oak/walnut vanity. A large second bedroom and beautifully updated guest bath complete the home. Additional highlights include refinished hardwood floors, cozy gas fireplace, designer lighting from Rejuvenation and RH, newer in-unit laundry, and curated designer paint colors throughout. The oversized deck, accessible from both the hallway and primary suite, is perfect for morning coffee, summer dinners, or unwinding beneath a gorgeous mature tree. One parking space and additional basement storage included. Incredible location just steps from Winnemac Park, the Ravenswood Metra, Damen Brown Line, Mariano's, Malt Row, and the restaurants, cafes, breweries, and neighborhood charm that make Lincoln Square, Ravenswood, and Andersonville some of Chicagos most sought-after neighborhoods.

Full Property Details for 5055 N Winchester Ave #3

General

  • Price: $625,000
  • HOA FEE: $330/month
  • Taxes: $8,650 (2024)
  • Status: Active
  • Type: Condo
  • Source: MRED
  • MLS ID: 12659919
  • Updated: Today (10/15/2026)
  • Added to Site: Today

Interior

  • Basement: Partially
  • Interior Features: Bookcases, Historic/Period Mlwk, Dining Combo
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room, Gas Log
  • Appliances: Range, Dishwasher, Refrigerator, High-End Refrigerator, Washer, Dryer, Disposal, Stainless Steel Appliance(s), Gas Cooktop
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Additional Information

  • Shared Amenities: Storage, Security Door Lock(s)

Parking

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

Location

  • Area: CHI - Lincoln Square
  • County: Cook
  • Township: Lake View
  • Driving Directions: Damen, East on Winnemac, North on Winchester

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299

Community

  • Assoc. Fees Include: Water, Insurance, Scavenger
  • 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

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Structure Type: Condo, Low-Rise (1 to 3 Stories)
  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Partially Finished, Storage Space, Walk-Out Access
  • Windows: Window Treatments
  • Sub-Flooring: Hardwood
  • Entry Floor Number: 3
  • Stories/Levels: 3
  • Square Feet: 1,500
  • Sq. Ft. Source: Estimated
  • Built Before 1978: Yes

Unit Information

  • Units in Building: 6

Lot Features

  • Lot Dimensions: COMMON

Animals

  • Animals Allowed: Cats OK, Dogs OK

Financial Considerations

  • Association Fee: $330
  • Assoc Fee Freq.: Monthly
  • Parking Included: Yes
  • Tax Amount: $8,650.32
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Condo
  • Special Conditions: List Broker Must Accompany
  • Property ID: 14074060201006
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agent

Meet the listing agent
— 5055 N Winchester Ave #3 —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Get a Great Insurance Rate

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!

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 5055 N Winchester Ave #3

School District:Chicago Public School District 299
NameGradesDistance
McPherson Elementary School
4728 North Wolcott Avenue, Chicago, IL 60640
K-80.4 mi
Amundsen High School
5110 North Damen Avenue, Chicago, IL 60625
9-120.2 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 5055 N Winchester Ave #3 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/15/2026
Listed
$625,000
-13.19%
MLS
8/28/2020
Sold
$720,000
—
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 5055 N Winchester Ave #3

Year
Property Taxes
Change
Tax Assessment
Change
2023
$8,650
—
$51,401
25%
2023
$8,650
3%
$40,999
—
2022
$8,433
2%
$40,999
—
2021
$8,245
10%
$40,999
11%
2020
$7,520
1%
$36,858
-9%
2019
$7,482
2%
$40,671
—
2018
$7,355
-10%
$40,671
7%
2017
$8,157
15%
$37,893
—
2016
$7,089
10%
$37,893
—
2015
$6,463
26%
$37,893
26%
2014
$5,113
2%
$30,126
—
2013
$5,001
1%
$30,126
—
2012
$4,958
—
$30,126
—
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.

Estimate the Cost for 5055 N Winchester Ave #3

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Similar Properties near 5055 N Winchester Ave #3

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2448 N Southport Ave, Chicago, IL 60614 - Photo 1
$625,000
Open House

2448 N Southport Ave  #3  Chicago, IL 60614

  • Condo
  • Active
  • Updated 9 days ago
  • 2
    Beds
  • 2
    Total Baths
Listed by Stephanie Cutter Group (312) 266-7000
330 W Diversey Pkwy, Chicago, IL 60657 - Photo 1
$625,000

330 W Diversey Pkwy  #2007-09  Chicago, IL 60657

  • Condo
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,750
    Sq. Ft.
4939 N Damen Ave, Chicago, IL 60625 - Photo 1
$639,000

4939 N Damen Ave  #304  Chicago, IL 60625

  • Condo
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,200
    Sq. Ft.
3325 N Lincoln Ave, Chicago, IL 60657 - Photo 1
$645,000

3325 N Lincoln Ave  #302  Chicago, IL 60657

  • Condo
  • Active
  • 2
    Beds
  • 2
    Total Baths

Just Listed near 5055 N Winchester Ave #3

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1804 S 49th Ct, Cicero, IL 60804 - Photo 1 Just Listed
$339,500

1804 S 49th Ct  Cicero, IL 60804

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,070
    Sq. Ft.
5101 W 31st Pl, Cicero, IL 60804 - Photo 1 Just Listed
$400,000

5101 W 31st Pl  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 1 day ago
  • 6
    Total Beds
5701 W Cermak Rd, Cicero, IL 60804 - Photo 1 Just Listed
$17

5701 W Cermak Rd  #5701  Cicero, IL 60804

  • Commercial Lease
  • Active
  • Updated 18 hours ago
1601 S 51st Ct, Cicero, IL 60804 - Photo 1 Just Listed
$380,000

1601 S 51st Ct  Cicero, IL 60804

  • Single Family
  • Active
  • Updated 3 days ago
  • 6
    Beds
  • 2
    Total Baths
  • 3,703
    Sq. Ft.

Price Reduced near 5055 N Winchester Ave #3

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1519 S 61st Ave, Cicero, IL 60804 - Photo 1 Price Reduced
-$20,999 (-6%)
$329,000

1519 S 61st Ave  Cicero, IL 60804

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 2
    Total Baths
  • 1,988
    Sq. Ft.
Listed by Ericka Taylor (708) 822-7426
5640 W Cermak Rd, Cicero, IL 60804 - Photo 1 Price Reduced
-$50,000 (-7.69%)
$599,900

5640 W Cermak Rd  Cicero, IL 60804

  • Commercial
  • Active
  • Updated 2 days ago
  • 7,000
    Sq. Ft.
1801 S Lombard Ave, Cicero, IL 60804 - Photo 1 Price Reduced
-$20,000 (-4.94%)
$385,000

1801 S Lombard Ave  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 1 day ago
  • 6
    Total Beds
4816 W 24th St, Cicero, IL 60804 - Photo 1 Price Reduced
-$20,000 (-6.78%)
$275,000

4816 W 24th St  Cicero, IL 60804

  • Multi-Family
  • Active
  • Updated 1 day ago
  • 5
    Total Beds

Recent Sales near 5055 N Winchester Ave #3

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1801 W Winnemac Ave, Chicago, IL 60640 - Photo 1 Sold
$680,000

1801 W Winnemac Ave  #F  Chicago, IL 60640

  • Townhouse
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,900
    Sq. Ft.
4939 N Damen Ave, Chicago, IL 60625 - Photo 1 Sold
$645,000

4939 N Damen Ave  #404  Chicago, IL 60625

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
1965 W Berwyn Ave, Chicago, IL 60640 - Photo 1 Sold
$545,000

1965 W Berwyn Ave  Chicago, IL 60640

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 1,262
    Sq. Ft.
1730 W Winona St, Chicago, IL 60640 - Photo 1 Sold
$665,000

1730 W Winona St  Chicago, IL 60640

  • Single Family
  • Closed
  • Updated 7 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,885
    Sq. Ft.

5055 N Winchester Avenue #3, Chicago, IL 60640 (MLS# 12659919) is a Condo property with 2 bedrooms and 2 full bathrooms. 5055 N Winchester Avenue #3 is currently listed for $625,000 and was received on October 15, 2026. This property is listed by Crystal Riley from our Lincoln Park Office.Want to learn more about 5055 N Winchester Avenue #3? Do you have questions about finding other Condo real estate for sale in Lincoln Square? You can browse all Lincoln Square real estate or contact a Coldwell Banker agent to request more information.

Tour this property