Zumper
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Updated 21 Hours Ago

Highlights

  • Ceiling fans
  • Hardwood flooring
  • Laundry on-site
  • Heat & water included
  • Good closet space
  • Street parking

Location

4344 N Winchester Ave, Chicago, IL 60613, USA|North Center
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Contact

Management

BERTSCH PROPERTIES, LLC

Leasing office

(773) 267-1115

Property Overview

Winchester has a strong overall renter appeal, with a 7.6 expert rating, especially high marks for amenities and location. It features hardwood flooring, ceiling fans, heat and water included, on-site laundry, good closet space, and street parking, while nearby pet services and outdoor spaces add to its appeal.

This summary uses Zumper’s proprietary data. “Zumper Expert Ratings,” “Things you’ll love,” and “Great for” are based on our internal analyses of market trends and renter insights.

Zumper Expert Rating

8.3
Very Good
With a solid 8.3 out of 10 overall, Winchester is a great option for renters. While some aspects, like Quality, might not be as distinguished as other properties nearby, Winchester has a number of attractive features—namely its Amenities— so you can be assured your rent will come with a high standard of living.

Things you’ll love

  • Middle school nearby
  • Less expensive

Great for

  • Pet owners

Floor plans

2BR/1.0BA2 bed1 bath600 sqft$1,750 /mo1 unit availableNeighborhood: Ravenswood 2 Bedroom @ Winchester & Montrose Features: Heat & Water Included Kitchen w/ Dishwasher, Gas Stove, Microwave, & Pantry Hardwood Flooring Ceiling Fans Spacious Bedrooms Great Closet Space Shared Deck Space Laundry On-Site Nearby: Koval Distillery / Tasting Room, Welles Park, Montrose Shops & Restaurants Transportation: Montrose Brown line, Damen Bus , Montrose Bus, Irving Park Bus, Ravenswood Metra, Street Parking Pet Policy: One-Time, Non-Refundable, Pet Fee: $250 for 1st Cat, $100 for 2nd Cat at signing (2 Cats Max) Monthly Cat Rent: $20/Cat Sorry No Dogs $75 Application Fee $550 Move in Fee (Due at Time of Application) - Security Deposit Waived

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Amenities for Winchester

Apartment Amenities

Central HeatHeat Included
HeatingWater

Appliances

DishwasherGas Range
MicrowaveRange
Refrigerator

Building

Cats OKOnsite Laundry
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.

Policies and fees

Applicants

Applicants

One-time.

Contact Property

REQUIRED FEES

Security Deposit

One-time. Refundable.

Contact Property

Dog Policy

Not allowed

Cat Policy

Allowed
Limit1

Questions about this property’s policies and fees?

Building details

Property details

Units32
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About Winchester

HomeApartments in ChicagoNorth Center Winchester

Neighborhood: Ravenswood South wing was redone floor-to-ceiling North wing is preserved vintage with modern upgrades Apartment Features: Heat & Water Included Hardwood Flooring Ceiling Fans Built-in Pantry Kitchens w/ Microwave, Gas Stove, & Refrigerator - some w/ Dishwashers Laundry On-Site Large Deck Nearby: Koval Distillery / Tasting Room, Welles Park, Montrose Shops & Restaurants Transportation: Montrose Brown line, Damen Bus , Montrose Bus, Irving Park Bus, Ravenswood Metra, Street Parking Pet Policy: One-Time, Non-Refundable, Pet Fee: $250 for 1st Cat, $100 for 2nd Cat at signing (2 Cats Max) Monthly Cat Rent: $20/Cat Sorry No Dogs $75 Application Fee $550 Move in Fee (Due at Time of Application) - Security Deposit Waived


Zumper Expert Rating

Our expert rating is based on a weighted average score of property attributes that renters care about most: price, amenities, location, quality, and trust.
8.3
/10
Very Good
With a solid 8.3 out of 10 overall, Winchester is a great option for renters. While some aspects, like Quality, might not be as distinguished as other properties nearby, Winchester has a number of attractive features—namely its Amenities— so you can be assured your rent will come with a high standard of living.
How we rated Winchester
Price·8A score that weighs the cost and location of the property, which we calculate by comparing rent prices of recent units to the median price of nearby rentals, adjusting for overall quality and features.
Scoring a 8/10, Winchester is a great option for renters looking for apartments in North Center. The rent is significantly lower than the median rent for the area, therefore this property is competitively priced for its location and its features. Residents here will find a home that meets their needs with few trade-offs.
Amenities·9A score based on the amenities offered at this property compared to other rentals in the area. We consider the quantity, quality, and popularity of features both on site and within the units.
Winchester goes above and beyond to provide sought-after conveniences and desirable perks, including cats allowed. Renters looking for popular or luxurious features will find them here—and for that reason, Winchester receives one of the highest amenities scores.
Location·9A score based on proximity and ease of access to shops, restaurants, schools, and public transportation while considering the desirability of the area.
Winchester is exceptional when it comes to location and conveniences. Communication with management or leasing staff is usually quick and easy and they often use advanced scheduling and communication tools to streamline the process. The location of this property offers easy access to popular points of interest in the area and options for getting around.
Quality·7A score based on what makes the property stand out, such as luxury features, unique offerings, age of the building, and our ability to verify the accuracy of these details.
While it may not have as many distinctive features as similar properties in the surrounding area, renters can trust Winchester to provide reasonable accomodations and accurate details about its community.
Trustworthiness·8A score based on the accuracy, completeness, recency, and usefulness of the information provided by this property, so you can trust that what you see is what you get.
The level of transparency this property provides distinguishes it as a great rental. With a high attention to detail and desirable features, renters can be sure they will get an accurate picture of their potential new home.

Winchester is great for:

Pet owners

  • Outdoor spaces are available at this property
  • 14 pet grooming services nearby
  • Pet deposit required
  • 12 pet hospitals in the area

Property highlights

We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.

How Winchester compares to other nearby properties.

Positives

Middle school nearby
There is a middle school 2 miles away
Less expensive
The 2-bedrooms are cheaper than other similar listings nearby

Considerations

Greater distance from grade schools
The nearest elementary school is farther than 0.3 mile away
Lacks images
Fewer than 10 photos available for this location

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Rent trends in North Center

2-bedroom apartments at Winchester cost about 39% less than the average rent price for 2-bedroom apartments in North Center.

Median rents as of Jul 4 2026.
North Center
Chicago
A table of studio rental data trends in Chicago
MonthMedian Rent
July 2024$1,922
August 2024$1,691
September 2024$1,682
October 2024$1,630
November 2024$1,568
December 2024$1,501
January 2025$1,483
February 2025$1,495
March 2025$1,520
April 2025$1,512
May 2025$1,502
June 2025$1,531
July 2025$1,580
August 2025$1,516
September 2025$1,473
October 2025$1,495
November 2025$1,520
December 2025$1,495
January 2026$1,496
February 2026$1,516
March 2026$1,657
April 2026$1,637
May 2026$1,684
June 2026$1,691
July 2026$1,695
A table of studio rental data trends in North Center
MonthMedian Rent
July 2024$1,845
January 2025$1,684
February 2025$1,579
March 2025$1,588
April 2025$1,405
May 2025$1,499
June 2025$1,457
July 2025$1,305
August 2025$1,025
September 2025$1,133
October 2025$1,300
November 2025$1,297
December 2025$1,300
January 2026$1,300
February 2026$1,395
March 2026$1,411
April 2026$1,478
June 2026$1,631
July 2026$1,723

Affordability calculator

Can I afford to live at 4344 N Winchester Ave?

Bedrooms

2 bedrooms

Rent-to-income ratio

30%

Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income

$70,000/yr

With your selected rent-to-income ratio, you'd ideally want to make $70,000 annually to afford this 2-bedrooms monthly rent price of $1,750.
For more information on rent affordability, visit our rent calculator.

Schools near Winchester

Ravenswood Elementary School

4332 n paulina st

chicago, IL, 60613

PK, K-8Public
A-

North River Elementary School

4416 n troy st

chicago, IL, 60625

PK, K-8Public
C+

Albany Park Community Center

5101 n kimball ave 1

chicago, IL, 60625

PKPublic

Chicago Commons Taylor Center for New Experiences

1633 north hamlin ave

chicago, IL, 60647

PKPublic

Skinner North Elementary School

640 w scott st

chicago, IL, 60610

K-8Public
A-
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Neighborhood

North Center | Chicago, IL

NEIGHBORHOOD VIBE
Lively and energetic
You’ll be in the heart of the action in this bustling and vibrant area with plenty of shopping, nightlife, and culture.

Getting around Chicago near 4344 N Winchester Ave

Walking

10/10
No car? No problem. Everything you need is within a few blocks.

Driving

4/10
This area is accessible to thoroughfares and has ample parking options.

Cycling

7/10
Peddling isn’t a problem with cyclist-friendly streets and bikeable destinations.

Transit

8/10
Getting around is a breeze; rapid transit and bus lines are a few blocks away.

Points of interest for 4344 N Winchester Ave, Chicago

Groceries

9/10
Exceptional variety of groceries within a few minutes' walk

Shopping

9/10
Wide variety of shops within a few minutes' walk

Cafes

10/10
Exceptional variety of cafés within a few minutes’ walk

Restaurants

9/10
Exceptional variety of restaurants within a few minutes’ walk

Primary schools

10/10
At least one elementary school within a 5-minute walk

High schools

9/10
At least one high school within a 5-minute walk

Parks

7/10
Large amount of park space nearby

Nightlife

9/10
Exceptional variety of bars right within a few minutes’ walk

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