7429 N Winchester, Chicago, IL 60626
OFF MARKET

7429 N Winchester
Chicago, IL 60626

Rogers Park
  • 9 Beds
  • 6 Baths
  • 24,000 sqft

$2,977,100

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $20,396/mo*
Refinance Your Home

$2,977,100

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $20,396/mo*
Refinance Your Home
9 Beds
6 Baths
24,000 sqft

Local Information

  • Map ViewExplore the area around 7429 N Winchester.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Living Area
24,000 sqft
Price/Sqft
$124

About this House

This multi-family home is located at 7429 N Winchester, Chicago, IL. 7429 N Winchester is in the Rogers Park neighborhood in Chicago, IL and in ZIP code 60626. This property has 9 bedrooms, 6 bathrooms and approximately 24,000 sqft of floor space.
7429 N Winchester, Chicago, IL 60626 is a 9 bedroom, 6 bathroom, 24,000 sqft multi-family in Rogers Park. It last sold for $2,460,000 on Dec 10, 2019. It is currently off market. The Trulia Estimate is $2,977,100, with a rent estimate of $2,008/month.

Home Details for 7429 N Winchester

Property Information

Property Type / Style
Property Type: Multi Family

Price History for 7429 N Winchester

DatePriceEventSource
12/10/2019$2,460,000Sold
N/A

Market trends in Rogers Park

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$252K
$18KMoM
Sale-to-List Price
100.3%
0.2%MoM
Price per sq ft
$244
Available listings
91
17MoM
Skip to last item
  • Results are loading
Skip to first item

Comparable Sales for 7429 N Winchester

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2032 W Birchwood Ave, Chicago, IL
0.17
Multi-Family Home
$810,000
05/19/26
9
3
-
2036 W Birchwood Ave, Chicago, IL
0.18
Multi-Family Home
$794,000
10/23/25
9
4
-
7708 N Ashland Ave, Chicago, IL
0.48
Multi-Family Home
$1,020,500
11/24/25
8
8
-
2225 W Touhy Ave, Chicago, IL
0.58
Multi-Family Home
$1,000,000
07/10/26
7
5.5
-
1812 W Estes Ave, Chicago, IL
0.41
Multi-Family Home
$650,000
12/11/25
7
5
-
7433 N Damen Ave, Chicago, IL
0.08
Multi-Family Home
$489,000
01/06/26
4
2
-
1104 Austin St, Evanston, IL
0.70
Multi-Family Home
$1,145,000
04/21/26
7
5
-
7223 N Damen Ave, Chicago, IL
0.30
Multi-Family Home
$560,000
05/05/26
5
3
-
1537 W Juneway Ter, Chicago, IL
0.55
Multi-Family Home
$879,900
04/03/26
6
4
-
134 Callan Ave, Evanston, IL
0.22
Multi-Family Home
$640,000
09/15/25
4
3
-

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 7429 N Winchester.

Neighborhood Overview

Rogers Park
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Rogers Park

At least 719 Trulia users voted on each feature.

  • 97 % Say there are sidewalks

  • 94 % Say it's dog friendly

  • 88 % Say it's walkable to restaurants

  • 87 % Say it's walkable to grocery stores

  • 79 % Say streets are well-lit

  • 61 % Say there's holiday spirit

  • 59 % Say kids play outside

  • 58 % Say people would walk alone at night

  • 56 % Say neighbors are friendly

  • 51 % Say they plan to stay for at least 5 years

  • 49 % Say it's quiet

  • 46 % Say there's wildlife

  • 41 % Say car is needed

  • 41 % Say yards are well-kept

  • 38 % Say there are community events

  • 27 % Say parking is easy

Sourced by Trulia users. Learn more about our methodology.
  • Shawn Daniels
    "There are many schools in the neighborhood and has a sense of community and safety. I like it. Very peaceful . Many dogs in community"
    2
    Flag
  • Shawn Daniels
    "Many festivals and community events. Beach is walking distance , peaceful and very safe. Summer time "
    1
    Flag
  • Jill Tarnow Luchtenburg
    "Has unique restaurants and shops people are friendly and there is a feeling of taking care of each other"
    1
    Flag
  • jjohnson
    "Moved here just about a year ago and have loved it ever since. There’s so much to do every night and the food is better than any other city I’ve been to. "
    2
    Flag
  • Christian Lum
    "I work from home and have no commute, but there is plenty of transportation around. The EL, busses are all accessible "
    2
    Flag
  • AB
    "The neighborhood has changed for the worse in the past five years. More crime, acts of violence. I used to be able to safely walk in the alley. People rummaging through alleys at all hours of day and nights. This was not so 5-10 years ago "
    11
    Flag
  • Jon Salzmann
    "We have a block party every summer, usually with music provided by our talented neighbors, a bouncy house, and volleyball in the street. We block off the street for the day’s events."
    3
    Flag
  • Faren D'abell
    "Dog walking in the neighborhood. No dog beach or sanitation stations available. Dog grooming in the neighborhood."
    3
    Flag
  • Trulia User
    "Very easy! I found the directions very easy. I love Chicago transit. I have never had an issue with finding my downtown or uptown "
    3
    Flag
  • Trulia User
    "It is a very nice area, with a lot of thinks to do and close to evanston which has extra activities "
    0
    Flag
  • Trulia User
    "Love living close to the Rogers Park Metro, 5 minutes from the redline and right next to the 22 Clark bus. "
    1
    Flag
  • Trulia User
    "Beautiful community right off the lakefront with beautiful beaches. Lakefront park with tennis courts. BBQ’s on the lakefront. "
    2
    Flag
  • Trulia User
    "The neighborhood is probably the most diverse in the city, with a multitude of races and religions represented."
    14
    Flag
  • Trulia User
    "Neighborly people. It’s one of a kind to live here even though crime rates have been raising. It’s a nice neighborhood regardless "
    0
    Flag
  • Trulia User
    "The people are very friendly and there are a lot of places/stores to go to at your convenience from grocery stores, electronic needs, gyms and clothing nearby."
    0
    Flag
  • Trulia User
    "Very special friendly place. a lot off parade a lot off. Store. bus always. Ready Devon. and Western a lot off Restaurants "
    1
    Flag
  • Trulia User
    "Dog friendly community, my pup loves our neighborhood and the community is welcoming. Love this place! "
    0
    Flag
  • Trulia User
    "Great neighborhood and beautiful beaches close to Loyola university. Tennis courts right by the beach. "
    0
    Flag
  • Trulia User
    "The availability of great education and reasonable safety are the factors I cared about most before choosing Rogers Park. I'm pleased with the results and absolutely love my neighborhood. I have been keeping my eye on the rising crime rate as it's rising across the city. Including our area"
    0
    Flag
  • Trulia User
    "This are is very nice. Nice area to raise children and raise a family. Close to the lake for walks, very beautiful and friendly. "
    0
    Flag
  • Trulia User
    "very peaceful and nice and i would love to live there if the rent is cheap and it is a 3 bedroom and 2 bathroom or 1 bathroom it really does matter if its for a cheap price for rent. And the people are so nice and welcoming and warm and the groccey store and nice and clean and the staff at the store is very nice and repectable."
    0
    Flag
  • Trulia User
    "Rogers Park has gone down. Hard to find a parking spot rats and mice are all over the place. Crime rate has gone up there aren't any good stores around"
    0
    Flag
  • Trulia User
    "Just moved here and it is fabulous so far. I like everything except for the parking. I love waking up to seeing the lake and the sun glistening off it. "
    10
    Flag
  • Trulia User
    "West Rogers Park is a beautiful example for the world in peaceful coexistence. I love the diversity and culture!"
    0
    Flag
  • Trulia User
    "Annual Block Party; street festivals; Loyola basketball games; baseball games at Warren Park; cultural events along Devon. "
    0
    Flag
  • Trulia User
    "It's easy to catch a train to and from downtown. There is plenty of surrounding areas to explore. Many delicious foods and restaurants ."
    0
    Flag
  • Trulia User
    "A lot people don’t clean up after their dogs. A few do and it’s appreciated. Many dogs owners around. Also there are 2 dog parks close by in east Rogers Park ."
    0
    Flag
  • Trulia User
    "Probably the best neighborhood in the city of dog owners. Lots of dog parks open spaces and other dogs."
    0
    Flag
  • Trulia User
    "Good for kids. I have lived here for about three years, and it feels pretty safe. Lots of good grocery stores and restaurants "
    0
    Flag
  • Trulia User
    "I’ve lived here for 2 years now. Great community, lots of entertainment, restaurants, parks, and close to lots of shopping malls."
    3
    Flag
  • Trulia User
    "Neighborhood is very quiet and the people are friendly. Been living in this neighborhood for 2 years have not much to say but I do love Roger's Park."
    13
    Flag
  • Jaime.hovey
    "All kinds of people live here and get to know each other well. There is a good-sized LGBTQ community and there are LGBTQ businesses here that enjoy community support. There is racial and class diversity here. There is a university, a bookstore, good restaurants, artists, people with unusual pets, families. We have great beaches. Rogers Park is the best. "
    17
    Flag
  • Blancareyes8498
    "There are two dog parks in this neighborhood. That’s helpful and convenient. It lets other dog owners get to know each other and socialize their dogs. "
    1
    Flag
  • Mayra V.
    "There are families in the neighborhood. It’s a very diverse neighborhood. It’s a very welcoming neighborhood and you can find markets, stores, public transportation at a walking distance for the most part. "
    2
    Flag
  • Rmiran2
    "I’ve lived in Rogers Park for the last 12 years and I’ve loved every minute of it. It’s a great neighborhood to call home. Reasonable rent, cute local places to eat/drink, and the lake access is absolutely incredible. "
    14
    Flag
  • Dennise O.
    "Majority of residences are multi unit buildings! there are blocks with single family homes but know that it's mostly apartment and condo living and there aren't enough parking spaces for everyone on the street! since we are close to the red line you will see strange characters as you meander closer to the train station. "
    4
    Flag
  • Joel C.
    "Lots of dogs in the neighborhood and people seem friendly and courteous. Wish it was more lit at night."
    3
    Flag
  • Matt A.
    "I feel there are too many dogs per block. This could be bad for some behavioral challenged dogs and your front lawn. "
    2
    Flag
  • Tjruppenthal
    "It is a diverse but not a connected community. The community groups try very hard to connect the community. But, with the diverse cultures it is next to impossible to make that connection."
    0
    Flag
  • Patricia T.
    "There are a lot of dog owners. Is a really pet friendly neighborhood and everybody is respectful of others "
    2
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

4078 pet-friendly rentals in Chicago, IL

Explore by feature - Garage

1594 rentals with a garage in Chicago, IL

Explore by feature - Air Conditioning

4599 rentals with air conditioning in Chicago, IL

Explore by feature - Pool

626 rentals with a pool in Chicago, IL

Explore by feature - Washer/dryer

3927 rentals with a washer/dryer in Chicago, IL

Explore by feature - Outdoor Space

379 rentals with an outdoor space in Chicago, IL

Homes for sale near 7429 N Winchester

Skip to last item
Skip to first item

Off Market Homes Near 7429 N Winchester

Skip to last item
Skip to first item