5258 Windsor, Chicago, IL 60630
OFF MARKET

5258 Windsor
Chicago, IL 60630

Jefferson Park
  • 7 Beds
  • 4 Baths

$893,100

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $6,044/mo*
Refinance Your Home

$893,100

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $6,044/mo*
Refinance Your Home
7 Beds
4 Baths

Local Information

  • Map ViewExplore the area around 5258 Windsor.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This multi-family home is located at 5258 Windsor, Chicago, IL. 5258 Windsor is in the Jefferson Park neighborhood in Chicago, IL and in ZIP code 60630. This property has 7 bedrooms and 4 bathrooms.
5258 Windsor, Chicago, IL 60630 is a 7 bedroom, 4 bathroom multi-family in Jefferson Park. It last sold for $662,000 on Aug 12, 2020. It is currently off market. The Trulia Estimate is $893,100, with a rent estimate of $2,386/month.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 5258 Windsor

Property Information

Property Type / Style
Property Type: Multi Family

Price History for 5258 Windsor

DatePriceEventSource
08/12/2020$662,000Sold
N/A
06/10/2016$425,000Sold
N/A

Market trends in Jefferson Park

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$428K
$37.5KMoM
Sale-to-List Price
100.8%
Price per sq ft
$270
$12MoM
Available listings
60
13MoM
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Comparable Sales for 5258 Windsor

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5352 W Sunnyside Ave, Chicago, IL
0.16
Multi-Family Home
$875,000
12/02/25
10
4
-
5338 W Montrose Ave, Chicago, IL
0.22
Multi-Family Home
$625,000
12/04/25
9
3
-
4241 N Laramie Ave, Chicago, IL
0.38
Multi-Family Home
$800,000
12/23/25
8
4
-
5043 W Sunnyside Ave, Chicago, IL
0.26
Multi-Family Home
$775,000
01/30/26
5
3.5
-
5428 W Sunnyside Ave, Chicago, IL
0.24
Multi-Family Home
$650,000
05/14/26
5
2
-
5030 W Hutchinson St, Chicago, IL
0.47
Multi-Family Home
$725,000
07/16/25
8
5
2,724
5221 W Montrose Ave, Chicago, IL
0.22
Multi-Family Home
$512,500
03/19/26
5
3
-
5015 W Montrose Ave, Chicago, IL
0.37
Multi-Family Home
$635,000
10/18/25
6
3
-
5354 W Montrose Ave, Chicago, IL
0.24
Multi-Family Home
$717,000
06/26/26
4
3
-
5205 W Montrose Ave, Chicago, IL
0.22
Multi-Family Home
$300,000
12/30/25
5
3
3,332

Nearby homes

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Assigned Schools

These are the assigned schools for 5258 Windsor.

Neighborhood Overview

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

What Locals Say about Jefferson Park

At least 310 Trulia users voted on each feature.

  • 97 % Say there are sidewalks

  • 95 % Say it's dog friendly

  • 84 % Say streets are well-lit

  • 80 % Say parking is easy

  • 78 % Say it's walkable to grocery stores

  • 77 % Say it's walkable to restaurants

  • 77 % Say yards are well-kept

  • 76 % Say people would walk alone at night

  • 73 % Say kids play outside

  • 72 % Say there's holiday spirit

  • 62 % Say car is needed

  • 60 % Say neighbors are friendly

  • 60 % Say they plan to stay for at least 5 years

  • 52 % Say it's quiet

  • 50 % Say there's wildlife

  • 49 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • David O
    "I lived in this neighborhood for 30 years. Some are still here and new neighbors are friendly and trying to feel part of the community "
    2
    Flag
  • AE
    "I’ve been around for sometime and have not encountered any issues with anyone. I have managed to live here at peace with everyone. "
    5
    Flag
  • Cheapkiks000
    "Great neighborhood. Family friendly. Close to everything. Close to the highways and the city. Lots to do."
    4
    Flag
  • Trulia User
    "The neighbors are friendly and the streets are always taken care of. The proximity to the expressway makes the neighborhood very easily accessible "
    0
    Flag
  • Trulia User
    "The hotdog event and walking to the park with my grandkids and feeling great from a hard day work and can come home feeling great "
    0
    Flag
  • Trulia User
    "My commute to downtown is good, I work closer to Lakeview and is very convenient for me live here. This is a good and reliable neighborhood."
    0
    Flag
  • Trulia User
    "I lived in the area for 4 years and I love the great atmosphere and lovely people and animals lovers and I love that "
    0
    Flag
  • Trulia User
    "I have lived in this area for the 3and a half years that I have lived in Chicago, and I wouldn't want it any other way. I have every advantages of the big city, without the worries of a big city"
    4
    Flag
  • Trulia User
    "The community and the parks or school are really good. Also the stores and just the neighborhood is really great place to live."
    0
    Flag
  • Trulia User
    "It’s peaceful, safe. Plenty of parking in the residential area. A few bars with good parking as well. It’s a very nice place to live at. "
    0
    Flag
  • Trulia User
    "Quiet neighborhood, dog friendly, all races and nationalities live in the area. I am a long time resident"
    0
    Flag
  • Trulia User
    "I love this neighborhood and wish to stay close or nearby it. We wish to find a nice home on a decent neighborhood."
    1
    Flag
  • Trulia User
    "Been here 3 years and people are very kind. My neighbors have been the sweetest people. I Can take walks and feel safe. It’s a really quiet, clean and safe neighborhood. "
    1
    Flag
  • Trulia User
    "I live near Jefferson park bus stand.. I love to live Here because it’s very near to the park for kids, stores for groceries and medicine.. very near to downtown.. and most importantly it’s very safe here.. school is near police station is near.. for me it’s the perfect place to live.. there is a lot activity happening here in summer, schools can do sports in park it’s always entertaining.. we bring our kids and participate every activity.. we can do all functions here.. neighborhood is also very quiet.. "
    2
    Flag
  • Trulia User
    "I’ve lived here for over 16 years and the neighborhood has restaurants and shops as well as metro and blue line and bus service. The neighborhood is quiet. "
    1
    Flag
  • Trulia User
    "Decent place to live at. Most people are friendly. Area is clean for the most part as well. Schools are decent and strive to help the students. "
    2
    Flag
  • Trulia User
    "Theres a train and bus station around the area. Easy rides for the communters. Theres a bus stop at every street in Jefferson Park. The local stores are easy for the commuters because the bus stop are right outside the stores. "
    0
    Flag
  • Trulia User
    "Tons of dog owners live here. Going to walk the dogs is a good opportunity to meet your neighbors, even if you end up referring to them as "Barkley's mom"."
    0
    Flag
  • Trulia User
    "Easy to commute to work. Easy to get to the trains and bus stop and expressways. My commute is straight up montrose to get to 90/94."
    0
    Flag
  • Trulia User
    "it's a great neighborhood for dogs. my pup makes a new friend every day and people ask each other if they can approach before letting their dog beat yours."
    0
    Flag
  • Trulia User
    "Jefferson Park is an extremely nice area, dogs of all sizes from Yorkies to huskies all on leashes and nice. have not seen any aggressive ones."
    0
    Flag
  • Trulia User
    "it's very nice and quiet and nice neighbors very convenient for shopping hhhhjjjjkkkk................"
    0
    Flag
  • Trulia User
    "its quite, nice neighborhood. easy access to bus and train station. I work from home but I sometimes go out . I mostly drive so I dont use public transportation. Jefferson park is great neighborhood when it comes to commuting. "
    0
    Flag
  • Trulia User
    "how safe the neighborhood is. where are the parks located. how gar the grocery store is. is there a neighborhood watch. how fast it is to get to places from where we live. "
    0
    Flag
  • Trulia User
    "There is a park and lots of areas to sniff for the dog. There are lots of dog owners in the area who like their pets."
    0
    Flag
  • Trulia User
    "We have block parties in our park, and work together to improve our neighborhood.by improving landscaping. "
    0
    Flag
  • Trulia User
    "So many families walking their dogs! Great sidewalks. Tree lined streets. Feels safe, plenty of parks. "
    0
    Flag
  • Trulia User
    "easy to walk to blue line cta. I take it to go to o'hare airport and rosemont mall. otherwise I work from home and don't need to commute with public transportation. there are many bus stops as well"
    0
    Flag
  • Anthony
    "There are plenty of parks for the kids and first preserves for the dogs to run in. great families and neighbors "
    1
    Flag
  • Courtney C.
    "Lots of people walking dogs. Dog park nearby by Taft high school. Dog friendly but too much barking and your neighbors might not like."
    0
    Flag
  • Gfayta
    "Nice area to walk pets. They would like it. Please always remember to pick up after your pet........"
    2
    Flag
  • Gfayta
    "An abundance of areas to walk them. A friendly neighborhood fir them. Please pick up after your pet!"
    0
    Flag
  • Askar B.
    "Good area fo living. nice transportation. Police department me by. postal office. School. Any kind of departments. "
    0
    Flag
  • Sara M.
    "Great family neighborhood with lots of Parking and close to public transportation. Good schools. Plenty of restaurants in neighborhood "
    0
    Flag
  • Glenn S.
    "Polish and Columbian Festivals. Strong Chicago political events. Farmer’s Market. Copernicus Center."
    0
    Flag
  • Paul.d.lim88
    "Safe area. Quiet and not to much going on. Minutes from anything you want to do. Very close to transportation. A lot of parks around for walk dogs or kids to play in. Public pools around the area perfect for the summertime. Streets are regularly cleaned and alleys are not dirty like city alleys. The community really seems to work together to make it a nice clean safe area for anyone to live. There is a lot to do for adults as well. Downtown Jefferson park is alive with restaurants, bars and stores to visit. "
    0
    Flag
  • Tim A.
    "Summer Festivals, Movies in the Park, Greal Local Restaurants. Dog friendly / great neighbors! Easy access to PT"
    0
    Flag
  • Angela.burke265
    "Jeff Fest; concerts and community meetings at the Copernicus Center; neighborhood block parties, community police meetings, and other neighbor gatherings at local churches and community groups. "
    2
    Flag
  • Gabriella C.
    "I’ve lived here for 2 years. Great place to live. Peaceful, quiet, and clean. Great neighborhood. Never once did I or my spouse have to worry about anything."
    0
    Flag
  • Koertgenjacob
    "The open space of the community that is a mix between Chicago and suburban has best of both worlds, there’s privacy, but also stores, schools, church’s, and other city cites all within walking distance. Everyone is pretty friendly, too "
    0
    Flag

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Homes for sale near 5258 Windsor

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Off Market Homes Near 5258 Windsor

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