253 Windsor Dr, Bolingbrook, IL 60440
Property image
Property image
OFF MARKET

253 Windsor Dr
Bolingbrook, IL 60440

  • 5 Beds
  • 3 Baths
  • 2,400 sqft

$371,800

Trulia Estimate
as of Aug 24, 2026

$371,800

Trulia Estimate
as of Aug 24, 2026
  • 5 Beds
  • 3 Baths
  • 2,400 sqft

Home Highlights

Property Type
Single-Family Home
Year Built
1970
Living Area
2,400 sqft
Price/Sqft
$155
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 253 Windsor Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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
253 Windsor Dr, Bolingbrook, IL 60440 is a 5 bedroom, 3 bathroom, 2,400 sqft single-family home built in 1970. It last sold for $820,000 on Nov 14, 2003 (27,697% above the $2,950 asking price). More recently, it was listed as a rental in October 2025 with an asking price of $2,950 per month. That rental listing was removed on December 1, 2025. It is currently off market. The Trulia Estimate is $371,800, with a rent estimate of $3,347/month.

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

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 sqft
261 Bryant Way, Bolingbrook, IL
0.02
Single-Family Home
$365,000
05/12/26
3
2.5
1,948 sqft
213 Windsor Dr, Bolingbrook, IL
0.13
Single-Family Home
$320,000
05/01/26
4
2.5
2,220 sqft
298 Clarendon Ln, Bolingbrook, IL
0.22
Single-Family Home
$435,000
06/23/26
4
2.5
1,719 sqft
565 Emerson Cir, Bolingbrook, IL
0.30
Single-Family Home
$361,900
02/06/26
4
3
2,355 sqft
353 Foster Way, Bolingbrook, IL
0.30
Single-Family Home
$420,000
01/27/26
4
2.5
2,009 sqft
266 Seneca Way, Bolingbrook, IL
0.09
Single-Family Home
$346,000
06/12/26
4
1.5
1,768 sqft
208 Flagstaff Dr, Bolingbrook, IL
0.34
Single-Family Home
$378,000
11/19/25
4
3
2,355 sqft
530 Cottonwood Cir, Bolingbrook, IL
0.38
Single-Family Home
$350,000
10/10/25
5
3
2,220 sqft
526 Cottonwood Cir, Bolingbrook, IL
0.38
Single-Family Home
$330,000
07/23/26
5
3
2,355 sqft

Nearby homes

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Around this home

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.
  • Trulia User
    "I’ve lived in this neighborhood for 34 yrs. It is quiet, friendly, well kept, and has many nearby amenities. "
    0
    Flag
  • 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
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  • Carlette King
    "There are many great schools, parks, shopping & restaurants. Great community for families. Peoplear friendly, grocery stores are are plentiful."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Sandro C.
    "the variety of cultures. people from all over the world live in Bolingbrook and are very kind to each other."
    0
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  • 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
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LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Dec 1, 2025
Source: Zillow Rentals
ListingRemoved
$2,950
Oct 10, 2025
Source: Zillow Rentals
Listed For Rent
$2,950
Oct 10, 2025
Source: MRED as distributed by MLS GRID #12490576
ListingRemoved
$2,950
Oct 7, 2025
Source: MRED as distributed by MLS GRID #12490576
Listed For Rent
$2,950
Nov 7, 2023
Source: Zillow Rentals
ListingRemoved

Frequently asked questions about 253 Windsor Dr

  • What is 253 Windsor Dr estimated to be worth?
    Trulia's estimated value for 253 Windsor Dr in Bolingbrook, IL is $371,800.
  • What is the price history for 253 Windsor Dr?
    253 Windsor Dr in Bolingbrook, IL last sold for $820,000 in November 2003.
  • Is Bolingbrook a buyer's or seller's market?
    Bolingbrook is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Bolingbrook?
    The median sale price in Bolingbrook is $398K. That is up $14.5K from the prior month.
  • Does 253 Windsor Dr have air conditioning?
    Yes, 253 Windsor Dr in Bolingbrook, IL has air conditioning.
  • Does 253 Windsor Dr have laundry facilities?
    Yes, 253 Windsor Dr in Bolingbrook, IL has in-unit laundry.

Homes for rent near 253 Windsor Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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