253 Windsor Dr, Bolingbrook, IL 60440
OFF MARKET

253 Windsor Dr
Bolingbrook, IL 60440

  • 5 Beds
  • 3 Baths
  • 2,400 sqft

$380,700

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $2,678/mo*
Refinance Your Home

$380,700

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $2,678/mo*
Refinance Your Home
5 Beds
3 Baths
2,400 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Very well maintained rare to find 5BR, 3 bath Raised Ranch. Spacious kitchen opens to a large deck overlooking a fenced yard. Large family and living room. Large laundry room with washer and dryer. Two car attached garage. $35 (nonrefundable) for credit check. No pets. Smoking not allowed in the home. Credit score over 650. $4000 for security deposit. Tenant responsible for all utilities and yard maintenance. Agent owned.

Tenant responsible for all utilities, yard maintenance, snow removal and general maintenance of the property. No pets allowed. No smoking allowed in the house.

Must have good credit score and verifiable employment information. No pets No smokers
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from October 10, 2025

Home Highlights

Parking
Attached Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 253 Windsor Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Attached, On Site

Price History for 253 Windsor Dr

DatePriceEventSource
12/01/2025$2,950ListingRemovedZillow Rentals
10/10/2025$2,950Listed For RentZillow Rentals
10/10/2025$2,950ListingRemovedMRED as distributed by MLS GRID #12490576
10/07/2025$2,950Listed For RentMRED as distributed by MLS GRID #12490576
11/07/2023ListingRemovedZillow Rentals
10/30/2023$2,650Listed For RentZillow Rentals
08/14/2022ListingRemovedRE/MAX International
08/02/2022$2,475PriceChange
RE/MAX International #11474825
07/09/2022$2,500Listed For RentZillow Rental Manager
09/28/2015$1,875ListingRemovedAgent Provided
08/29/2015$1,875Listed For RentAgent Provided
08/15/2013$1,850ListingRemovedAgent Provided
07/25/2013$1,850Listed For RentAgent Provided
11/14/2003$820,000Sold
N/A
08/29/2003$136,603Sold
N/A
12/19/1994$125,000Sold
N/A
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$9,746
Assessment$316,578
Home facts updated by county records

Comparable Sales for 253 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
233 Seneca Ct, Bolingbrook, IL
0.12
Single-Family Home
$410,000
04/30/26
4
2.5
2,610
261 Bryant Way, Bolingbrook, IL
0.02
Single-Family Home
$365,000
05/12/26
3
2.5
1,948
146 Cheyenne Ct, Bolingbrook, IL
0.26
Single-Family Home
$425,000
07/28/25
5
3
2,130
213 Windsor Dr, Bolingbrook, IL
0.13
Single-Family Home
$320,000
05/01/26
4
2.5
2,220
565 Emerson Cir, Bolingbrook, IL
0.30
Single-Family Home
$361,900
02/06/26
4
3
2,355
353 Foster Way, Bolingbrook, IL
0.30
Single-Family Home
$420,000
01/27/26
4
2.5
2,009
208 Flagstaff Dr, Bolingbrook, IL
0.34
Single-Family Home
$378,000
11/19/25
4
3
2,355
530 Cottonwood Cir, Bolingbrook, IL
0.38
Single-Family Home
$350,000
10/10/25
5
3
2,220
257 Bryant Way, Bolingbrook, IL
0.02
Single-Family Home
$336,900
12/30/25
3
2
1,671
390 Foster Way, Bolingbrook, IL
0.37
Single-Family Home
$415,000
06/05/25
4
2.5
2,258

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 253 Windsor Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Bolingbrook

At least 571 Trulia users voted on each feature.

  • 89 % Say there are sidewalks

  • 88 % Say it's dog friendly

  • 84 % Say car is needed

  • 81 % Say yards are well-kept

  • 80 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 71 % Say it's quiet

  • 67 % Say people would walk alone at night

  • 65 % Say there's wildlife

  • 62 % Say streets are well-lit

  • 55 % Say it's walkable to restaurants

  • 54 % Say it's walkable to grocery stores

  • 54 % Say they plan to stay for at least 5 years

  • 48 % Say neighbors are friendly

  • 38 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • A.C.
    "Hard working and respectful people. Great restaurants and schools, ample medical facilities, close to the city of Chicago and local attractions."
    0
    Flag
  • A.C.
    "Safe, family oriented, spacious, great schools and parks. Close to all kinds of shopping and great food."
    0
    Flag
  • Carlette King
    "There are many great schools, parks, shopping & restaurants. Great community for families. Peoplear friendly, grocery stores are are plentiful."
    0
    Flag
  • Zagaceta2010
    "Everything is very nice, tidy and quiet, we have all the supermarkets, churches and malls nearby, the people are very friendly with everyone, We would always like to live in this part of Illinois"
    0
    Flag
  • Trulia User
    "The library is amazing, the best thing the village has to offer. Plenty of activities and things to do at the library. Village has many parks for outdoor recreation for all ages. "
    0
    Flag
  • Michael Feder
    "Lots of dog owners around. Most part friendly and leashed. I feel safe walking with my dogs…………………….."
    0
    Flag
  • V64shdbysf
    "Safe neighborhood to walk your dog. Great parks to take your pets as well. And their is doggie parks too. Most neighborhoods have dogs. And most homes are fenced in for your pets. "
    1
    Flag
  • Laconia.unseld
    "Everything is close by and not a dare commute. Bolingbrook is known as a big circle but convenient so you can’t get lost "
    0
    Flag
  • Danielle Brody
    "There’s a nice forest preserve and the neighborhood we’re in is quiet and friendly. Kid-friendly as well. "
    1
    Flag
  • Avis Calhoun
    "I work in Chicago, so living neat I-55 gets me there in less than 30 minutes. I’m close enough to the expressway, but also close major roads like boughton road."
    0
    Flag
  • Unknown N.
    "Park district here is wonderful , pelican harbor does air of great events. The promenade has a lot of great events for the family. We have a lot of parks and places to visit a great place to grow. "
    2
    Flag
  • LaShay R.
    "People walk their dogs all the time. Dogs are welcome in this area. People also pick up behind their dogs in this area. "
    0
    Flag
  • Ferili89
    "It needs improvements for safety. We have been having some robberies lately, but for the most part, it is a safe place to live. "
    8
    Flag
  • Brandi H.
    "You often see people walking their dogs. Although there are quite a few fogs, there isn't a lot of barking."
    2
    Flag
  • Trulia User
    "its a great place too live with your family i lived here for a very long time its amazing................"
    1
    Flag
  • D.miller8991630
    "Fairly decent depending on traffic times but it’s fairly quick and there’s a lot of convenient places to shop right on the strip"
    0
    Flag
  • Carol J.
    "I have lived in this neighborhood for three years. But I’m getting ready to move. It is a nice really neighborhood."
    0
    Flag
  • Andrew S.
    "Halloween The Fourth of July ,Christmas, New Year’s Eve , Labor Day, memorial day, spring break and all of summer"
    5
    Flag
  • Noor A.
    "very diverse neighborhood, convienent living, humble residents and good schools, lots of parks and family friendly "
    0
    Flag
  • Jose V.
    "This is a good town to grow your family and to stay away from the big city with all accommodations of it. Also it’s close to major highways to get any big town around with 30 mins. The schools are good. The village hall have many activities over the summer. Park district have so many programs for kids young adults and adults. Ty j hi is is a great town to live in. I love Bolingbrook "
    0
    Flag
  • Caroljeansutton
    "Area is safe to walk dogs as long as on a leash. Homeowners would line the walkers to pick up after their dogs "
    0
    Flag
  • Adrian N.
    "Nice place to live. Safe quiet yet populated. Best of both worlds. Plenty of shopping and dinning. Love it. "
    0
    Flag
  • Alyssah S.
    "It’s a friendly area and nice places to walk and take your dogs. There is a nice field that the dogs can run "
    0
    Flag
  • Sandra L.
    "I just recently moved in. It seems like a nice neighborhood with lots of stores to shop around and eat in restaurants. "
    0
    Flag
  • Sharif F.
    "I don’t know any special events but I believe the mall in Bolingbrook have a special events going on with they serve food in summer time and there is this little program they give away free food and school supplies for kids in need"
    0
    Flag
  • Sebastianjacob
    "I have living in this neighborhood for five year and its great.cool place for families. a well planned city "
    0
    Flag
  • Xxstar L.
    "Its a great place for small families, if your have a 45k or 50k yearly income you can live comfortably. "
    0
    Flag
  • Patrick O.
    "I work locally. Commute to Naperville. Only takes 15 minutes. Similar commute time in the evening. I355 and I55 are close for traveling longer distances"
    0
    Flag
  • Sheree K. W.
    "Great neighborhood very family friendly great schools overall just a great community to live in abs raise a family "
    0
    Flag
  • Jennifer M. K.
    "Short and congested most days. Boughton rd is usually a heavy traffic area. Over by the Promande also is fairly congested. "
    0
    Flag
  • Kim.robinson1105
    "Every Halloween all the neighbors hand out candy on the driveway some burning fire pits. With everyone outside it feels safe for the kids. "
    2
    Flag
  • Unspecified
    "Dog owners will like the neighborhood. There as at least 1 dog in every other house on each block. As long as you don’t mind all the barking they will fit right in."
    3
    Flag
  • Sara.armeanu
    "The community is great! The park district is very involving if you take advantage of it. Parking is very much available and there are plenty of shopping places in the area."
    1
    Flag
  • Aide2618
    "It’s affordable beautiful clean Everyone is friendly great restaurants and shops great high school "
    0
    Flag
  • Aeogirls
    "i live there 20yrs. looking for a nice town home or ranch to purchase in 6 months. i really miss it. i highly recommend living in this affordable and safe neighborhood..love it!!"
    0
    Flag
  • Brianramos1bmf
    "Shopping and dining at the Promenade. Summer music events and Bolingbrook golf courses. Dog park and fishing at Whalen Park"
    0
    Flag
  • Deandria H.
    "I love it here great place to live. Great schools, lots of jobs, shopping fun and entertainment. fun in the sun and twenty five min from down town Chicago! good times."
    0
    Flag
  • Sandro C.
    "the variety of cultures. people from all over the world live in Bolingbrook and are very kind to each other."
    0
    Flag
  • Chowardstubbs
    "I’ve lived in the neighborhood when it was nothing but cornfields and watch it grew tremendously. It’s very diverse & creative in its own unique way. There is always room for improvement but it’s a community that definitely wants to grow together."
    0
    Flag
  • Dcar12
    "Been here almost 20 years. I very much enjoy the green spaces and outdoor activities. Neighbors are always friendly and helpful when needed."
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature

Homes for sale near 253 Windsor Dr

Skip to last item
Skip to first item

Off Market Homes Near 253 Windsor Dr

Skip to last item
Skip to first item

Homes for rent near 253 Windsor Dr

Skip to last item
Skip to first item
253 Windsor Dr, Bolingbrook, IL 60440 is a 5 bedroom, 3 bathroom, 2,400 sqft single-family home built in 1970. This property is not currently available for sale. 253 Windsor Dr was last sold on Nov 14, 2003 for $820,000 (27,697% higher than the asking price of $2,950). The current Trulia Estimate for 253 Windsor Dr is $380,700.