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

$387,600

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,140 sqft

258 Windsor Dr, Bolingbrook, IL 60440

Est. Refi. Payment $2,777/mo*
Refinance Your Home
Currently Off Market - Sold Mar 24, 2023 for $320,000

Home Value

Trulia Estimate
$388K
Since last month
Decreased$2K (-0.5%)
Since last year
Increased$7K (+1.9%)
Since last sale
Increased$68K (+21.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +88% in the last 10 years
MonthEstimated value
2026
August 2026$388K
August 2026$388K
July 2026$390K
June 2026$394K
May 2026$394K
April 2026$389K
March 2026$387K
February 2026$380K
January 2026$376K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
261 Bryant Way, Bolingbrook, IL
0.04
Single-Family Home
$365,000
05/12/26
3
2.5
1,948
257 Bryant Way, Bolingbrook, IL
0.03
Single-Family Home
$336,900
12/30/25
3
2
1,671
252 Yellow Pine Dr, Bolingbrook, IL
0.12
Single-Family Home
$300,000
07/20/26
3
1.5
1,441
213 Windsor Dr, Bolingbrook, IL
0.15
Single-Family Home
$320,000
05/01/26
4
2.5
2,220
266 Seneca Way, Bolingbrook, IL
0.05
Single-Family Home
$346,000
06/12/26
4
1.5
1,768
233 Seneca Ct, Bolingbrook, IL
0.10
Single-Family Home
$410,000
04/30/26
4
2.5
2,610
557 Cottonwood Cir, Bolingbrook, IL
0.41
Single-Family Home
$317,000
12/16/25
3
2
2,021
518 Emerson Cir, Bolingbrook, IL
0.32
Single-Family Home
$265,000
09/17/25
3
2
1,720
565 Cottonwood Cir, Bolingbrook, IL
0.40
Single-Family Home
$340,000
12/05/25
3
2
1,671
534 Cottonwood Cir, Bolingbrook, IL
0.37
Single-Family Home
$345,000
02/06/26
3
2
1,671

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
257 Bryant Way, Bolingbrook, IL 60440
0.03
$336,900
3
2
1,671
Recently Sold
261 Bryant Way, Bolingbrook, IL 60440
0.04
$365,000
3
2.5
1,948
Recently Sold
238 Windsor Dr, Bolingbrook, IL 60440
0.06
$373,700
3
2
1,729
Off Market
239 Seneca Way, Bolingbrook, IL 60440
0.06
$330,400
3
1.5
1,441
Off Market
234 Windsor Dr, Bolingbrook, IL 60440
0.08
$336,200
4
3
2,220
Off Market
300 Redwing Dr, Bolingbrook, IL 60440
0.05
$276,400
3
1.5
2,013
Off Market
266 Seneca Way, Bolingbrook, IL 60440
0.05
$346,000
4
1.5
1,768
Recently Sold
308 Redwing Dr #308, Bolingbrook, IL 60440
0.06
$294,400
3
1.5
1,536
Off Market
232 Seneca Way, Bolingbrook, IL 60440
0.09
$379,500
3
1.5
1,441
Off Market
649 Sundance Dr, Bolingbrook, IL 60440
0.06
$260,700
3
1.5
1,536
Off Market
312 Redwing Dr, Bolingbrook, IL 60440
0.07
$283,500
4
1.5
-
Off Market
641 Sundance Dr, Bolingbrook, IL 60440
0.06
$305,000
3
2.5
1,536
Recently Sold

Local Information

  • Map ViewExplore the area around 258 Windsor Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1976
Living Area
2,140 sqft
Price/Sqft
$181
Parking
Garage

About this House

GOURGEOUS SPLIT LEVEL WITH OVER 2500 FINISHED SQUARE FEET OF LIVING SPACE! FEATURES LARGE LIVING AND DINNING ROOM. GREAT SIZE KITCHEN. NEW LAMINATE FLOORING THROUGHOUT MAIN FLOOR. SECOND LEVEL OFFERS THREE BEDROOMS AND TWO FULL BATHS (MASTER WITH PRIVATE BATH AND WALK IN CLOSET). FINISHED BASEHMENT WITH FAMILY ROOM, BONUS ROOM, LAUNDRY AND 1/2 BATH (WITH NEW VANITY AND CERAMIC FLOOR. OFFERS NEWER ROOF. ATTACHED TWO CAR GARAGE WITH AMPLE SPACE IN DRIVEWAY. YOUR SEARCH IS OVER!
258 Windsor Dr, Bolingbrook, IL 60440 is a 3 bedroom, 3 bathroom, 2,140 sqft single-family home built in 1976. It last sold for $320,000 on Mar 24, 2023. More recently, it was listed as a rental in June 2017 with an asking price of $1,850 per month. That rental listing was removed on September 25, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $387,600, with a rent estimate of $2,969/month.

Home Details for 258 Windsor Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Carpet, Laminate
Interior Details
Number of Rooms: 8Types of Rooms: Dining Room
Appliances & Utilities
Refrigerator

Exterior Features

Exterior Home Features
Roof: CompositionExterior: VinylFoundation Type: Slab
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1976
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 7840 sqft

Price and Tax history

DateEventPrice
Mar 24, 2023
Source: MRED as distributed by MLS GRID #11678360
Sold
$320,000
Feb 1, 2023
Source: RE/MAX International #11678360
Pending
$320,000
Jan 31, 2023
Source: MRED as distributed by MLS GRID #11678360
Contingent
$320,000
Dec 21, 2022
Source: MRED as distributed by MLS GRID #11678360
PriceChange
$320,000
Price decreased by 2%
Dec 9, 2022
Source: MRED as distributed by MLS GRID #11678360
PriceChange
$325,000
Price decreased by 2%

Market trends in Bolingbrook

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$398K
$14.5KMoM
Sale-to-List Price
100.9%
0.3%MoM
Price per sq ft
$216
$2MoM
Available listings
154
23MoM

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
    Flag
  • 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
    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
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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
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  • Sebastianjacob
    "I have living in this neighborhood for five year and its great.cool place for families. a well planned city "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 258 Windsor Dr

  • What is 258 Windsor Dr estimated to be worth?
    Trulia's estimated value for 258 Windsor Dr in Bolingbrook, IL is $387,600.
  • What is the price history for 258 Windsor Dr?
    258 Windsor Dr in Bolingbrook, IL last sold for $320,000 in March 2023.
  • 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 258 Windsor Dr have air conditioning?
    Yes, 258 Windsor Dr in Bolingbrook, IL has air conditioning.
  • How big is the lot at 258 Windsor Dr?
    The lot at 258 Windsor Dr in Bolingbrook, IL is about 0.18 acres (7,841 sq ft).

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Off Market Homes Near 258 Windsor Dr

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