258 E Bailey Rd, Naperville, IL 60565
Property image
Property image
OFF MARKET

258 E Bailey Rd
Naperville, IL 60565

  • 2 Beds
  • 1.5 Baths
  • 980 sqft

$203,600

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $1,108/mo*
Refinance Your Home

$203,600

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $1,108/mo*
Refinance Your Home
2 Beds
1.5 Baths
980 sqft

Local Information

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

Home Highlights

Property Type
Apartment
Living Area
980 sqft
Price/Sqft
$208

About this House

Beautiful and spacious newly painted 2-bedroom condo in the highly desirable
Olive Trees community. This top-floor unit features an open layout, large living
room, private balcony, and an updated kitchen with plenty of storage. Heat, water,
and cooking gas are included in the rent. Enjoy access to the community pool,
clubhouse, and on-site laundry. Minutes from I-88, downtown
Naperville, and the Riverwalk. Available immediately.

Owner pays for water, cooking gas, heat, snow removal, and trash
Renter pays for electricity
258 E Bailey Rd, Naperville, IL 60565 is a 2 bedroom, 2 bathroom, 980 sqft apartment. It last sold for $60,000 on Jun 29, 1993 (2,902% above the $1,999 asking price). More recently, it was listed as a rental in February 2026 with an asking price of $2,195 per month. That rental listing was removed on April 18, 2026. It is currently off market. The Trulia Estimate is $203,600, with a rent estimate of $1,937/month.

Home Details for 258 E Bailey Rd

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Wall UnitHeating Fuel: Baseboard
Appliances & Utilities
Dishwasher

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Pool
Pool

Additional Information

Pool

Price History for 258 E Bailey Rd

DatePriceEventSource
04/18/2026$1,999ListingRemovedZillow Rentals
02/04/2026$1,999PriceChange
Zillow Rentals
02/02/2026$2,195Listed For RentZillow Rentals
01/24/2026$2,197ListingRemovedZillow Rentals
01/15/2026$2,197PriceChange
Zillow Rentals
01/14/2026$1,665PriceChange
Zillow Rentals
12/18/2025$2,195Listed For RentZillow Rentals
12/05/2025$2,195ListingRemovedZillow Rentals
10/25/2025$2,195PriceChange
Zillow Rentals
10/02/2025$2,240PriceChange
Zillow Rentals
09/21/2025$2,195Listed For RentZillow Rentals
11/15/2023ListingRemovedZillow Rentals
10/25/2023$2,110PriceChange
Zillow Rentals
10/16/2023$1,985Listed For RentZillow Rentals
06/29/1993$60,000Sold
N/A

Market trends in Naperville

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$575K
$11.67KMoM
Sale-to-List Price
99.9%
0.1%MoM
Price per sq ft
$260
$6MoM
Available listings
484
34MoM
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Property Tax and Assessment

Year2024
Tax$2,730
Assessment$52,560
Home facts updated by county records

Comparable Sales for 258 E Bailey Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5950 Oakwood Dr #4A, Lisle, IL
3.39
Apartment
$241,000
07/14/26
2
1.5
1,020
446 Valley Dr #201, Naperville, IL
3.85
Apartment
$240,000
08/05/26
2
1
1,000
5600 Hillcrest Ln #2C, Lisle, IL
3.72
Apartment
$155,000
07/22/26
1
1
760
5700 Hillcrest Ln #3L, Lisle, IL
4.00
Apartment
$215,000
07/30/26
2
1.5
990
2809 Kentshire Ct, Naperville, IL
4.19
Apartment
$275,000
05/22/26
2
2
1,414
2300 Old Tavern Rd #205, Lisle, IL
4.72
Apartment
$170,000
05/20/26
2
2
1,086
4418 Beau Monde Dr #201, Lisle, IL
4.72
Apartment
$180,000
07/09/26
2
2
1,084
141 Gregory St #8, Aurora, IL
5.18
Apartment
$190,000
08/25/25
2
2
890
1813 Ogden Ave #1B, Lisle, IL
4.66
Apartment
$1,800,000
04/20/26
3
1
1,205
121 Gregory St #2, Aurora, IL
5.18
Apartment
$186,000
10/27/25
2
2
890
Home facts updated by county records

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 258 E Bailey Rd.
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 Naperville

At least 1032 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 90 % Say there are sidewalks

  • 89 % Say car is needed

  • 82 % Say parking is easy

  • 79 % Say there's holiday spirit

  • 78 % Say people would walk alone at night

  • 78 % Say streets are well-lit

  • 78 % Say kids play outside

  • 77 % Say it's quiet

  • 73 % Say yards are well-kept

  • 60 % Say there's wildlife

  • 59 % Say they plan to stay for at least 5 years

  • 55 % Say it's walkable to restaurants

  • 55 % Say neighbors are friendly

  • 45 % Say it's walkable to grocery stores

  • 42 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Nikki
    "The amount of stores and shops but it’s expensive "
    0
    Flag
  • Rick.slavin
    "Great place. Amazing people, shops, dining, etc. very family friendly and great public schools. Wish everyone could live here. Amazing in every way."
    0
    Flag
  • AP
    "Lived here 10 years. Great proximity to train station, restaurants and retail. Great schools! Friendly neighborhoods. Safety and security is strong. Access to highways is good! "
    0
    Flag
  • Rick.slavin
    "It’s awesome. One of the best places I have ever lived. Naperville has the best schools, downtown area, shopping and restaurants. Family friendly and professional. Why live anywhere else?! "
    0
    Flag
  • Megan DeAngelis
    "Very dog and family friendly town with ample sidewalks, bike paths, incredibly dog friendly downtown area with shopping and restaurants, as well as parks. "
    0
    Flag
  • Debbylu24
    "Naperville offers excellent schooling, a safe environment, and convenient access to stores. It boasts beautiful parks and a diverse culinary scene with great restaurants and grocery stores. The community is incredibly friendly, making it a wonderful place to live. "
    0
    Flag
  • Debbylu24
    "Naperville offers excellent schooling, a safe environment, and convenient access to stores. It boasts beautiful parks and a diverse culinary scene with great restaurants and grocery stores. The community is incredibly friendly, making it a wonderful place to live. "
    0
    Flag
  • Megan DeAngelis
    "Nice area, clean landscaping, walking distance from grocery stores, gas stations, walking trails, and restaurants."
    0
    Flag
  • Astrid Romero
    "The dream Downtown, is magic, like an American movie. There are everything like excellents restaurants and bars, stores, entertainment, etc"
    1
    Flag
  • Emily Hallenbeck
    "Too far from the highway, and there is scarce work opportunity around naperville from my experience "
    0
    Flag
  • Shontel Johnson
    "Commute is ok. Live by major highway and right off busy street with great shopping area. No public transportation but close to train station. "
    0
    Flag
  • Ilara Bestel
    "I think dog owners would like here to have More sidewalks connecting places. Maybe they like the fact that here we have a lot of families and kids, it give us a sense of safety. "
    0
    Flag
  • Edgar.bolanos
    "Friendly neighbors and great schools nearby. Very close to the shopping areas and downtown. Bicycle tracks nearby."
    0
    Flag
  • Scott Robison
    "I moved to Naperville in 2019 from the Lakeview neighborhood in the city. I love this town! Huge variety of restaurants and bars. There is great shopping and all the public spaces are well maintained . I wish I had moved here sooner."
    2
    Flag
  • Ilara Bestel
    "Here at Benedetti drive in Naperville I know that has a lot of babies and little kids, but people barely go outside. I know because I see sometimes those families in the parking lot going out with their cars; but they don’t walk with their kids. "
    0
    Flag
  • Ilara Bestel
    "It’s a quite, safe and nice neighborhood. But nobody talks to each other. Neighbors are not so friendly. "
    0
    Flag
  • Bigcordo
    "Amazing schools with a outstanding reputation for special needs families. Naperville is safe, and has a wonderfully population. "
    0
    Flag
  • Kathleen Brennan
    "Great schools and park district also excellent library programs. Taxes high due to school district costs"
    0
    Flag
  • Aj.winter77
    "This area has Good schools, great nature possibilities. Wonderful parks. Great downtown area with lots to do. "
    1
    Flag
  • Kathleen Brennan
    "Plenty of neighbors walk dogs daily including on bike path with mutt bags for dog waste. The wolf crossing park has water fountain fitted for dogs to participate"
    0
    Flag
  • Kathleen Brennan
    " Commuter train runs express at rush hours and trip less than one hour. If you miss the express then trip about 90 minutes"
    0
    Flag
  • Carly
    "We drive everywhere, we’re close to route 59 and 88 so traveling is pretty easy. The train station isn’t too far either "
    0
    Flag
  • Amani.bakush
    "Diversity and good school district, quiet, all shopping centers near by. Everything the community needs from schools, college, university, hospitals are in this city and the best."
    1
    Flag
  • Lindsey.samawi
    "The perfect place to raise a family. It’s very family centered and many kid friendly activities held year round. "
    2
    Flag
  • Ahutchison116
    "Farmers Market, Annual Block Party, close walk to downtown Naperville and train to Chicago. Naperville River Walk and local parks are beautiful."
    0
    Flag
  • Ana S.
    "Very safe neighborhood, never had any problems, and we live to live here... we don’t know schools and don’t ha e pets "
    0
    Flag
  • Dana M. D.
    "Local dog park, dog friendly atmosphere, lots of trails, downtown Naperville is dog friendly. Lots of shops gave treats for dogs. "
    0
    Flag
  • Kori O.
    "Block parties , kids scheduled activities , friendly , safe , conveniently located close to shops and downtown. And schools. "
    1
    Flag
  • Mikayla M.
    "Quiet neighborhoods, people are nice and helpful. Naperville school system is one of the top twenty schools for learning. "
    0
    Flag
  • Jay2222
    "People enjoy walking their dogs and picking up behind them as they walk . Good neighborhood and nice neighbors . There are dog walkers available in the neighborhood "
    5
    Flag
  • Christine B.
    "Great access to downtown Chicago. 10 minutes from train. "
    2
    Flag
  • Charmayne S.
    "You have easy access to the metro train that runs into the city. Makes local stops along the way. You also have the local buses that travel into the city. We have lift, Uber and cabs. I would say we have a very good transit system "
    0
    Flag
  • Christine B.
    "Rib fest Last Fling Oktoberfest Naperville Settlement Art Fair Carillon concerts Triathlons Naperville Riverwalk Canoeing the river "
    5
    Flag
  • Justjen0676
    "There are many many dogs in the area and people are always out walking them. They usually are friendly and almost always pick up after their dogs. "
    0
    Flag
  • Venkat R.
    "Its a community of educated professionals. It’s diverse community, many are middle class immigrants to US."
    3
    Flag
  • Ariee31
    "Ribfest is usually really nice and has gained popularity over the years. There’s also a few firework displays for the fourth as well! "
    1
    Flag
  • Mrss66
    "Neighborhood is good with dog / owners, it seems that everyone has one so dogs are accepted and welcomed. "
    0
    Flag
  • P.B.
    "Great place, but realty taxes are exorbitant, and home values since the recession (of 2008) have not come back."
    0
    Flag
  • Catmandu513
    "My husband drives to one of the local commuter lots and commutes by train into the city. So much faster than driving! Tip: try to get an express train for the fastest trip to the city. "
    0
    Flag
  • Gretchen P.
    "Patio Crawls, Holiday Light Trolleys, Adult Halloween parties , winter pool parties, block party, so much fun"
    7
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

109 pet-friendly rentals in Naperville, IL

Explore by feature - Garage

153 rentals with a garage in Naperville, IL

Explore by feature - Air Conditioning

172 rentals with air conditioning in Naperville, IL

Explore by feature - Pool

46 rentals with a pool in Naperville, IL

Explore by feature - Washer/dryer

140 rentals with a washer/dryer in Naperville, IL

Explore by feature - Outdoor Space

29 rentals with an outdoor space in Naperville, IL

Homes for sale near 258 E Bailey Rd

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Off Market Homes Near 258 E Bailey Rd

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Frequently asked questions about 258 E Bailey Rd

  • What is 258 E Bailey Rd estimated to be worth?
    Trulia's estimated value for 258 E Bailey Rd in Naperville, IL is $203,600.
  • What is the price history for 258 E Bailey Rd?
    258 E Bailey Rd in Naperville, IL last sold for $60,000 in June 1993.
  • Is Naperville a buyer's or seller's market?
    Naperville is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Naperville?
    The median sale price in Naperville is $575K. That is up $11.67K from the prior month.
  • Does 258 E Bailey Rd have air conditioning?
    Yes, 258 E Bailey Rd in Naperville, IL has air conditioning.
  • Does 258 E Bailey Rd have a pool?
    Yes, 258 E Bailey Rd in Naperville, IL has a pool.