Naperville · DuPage County · IL
Homes for sale in
Baileywood.
- Active listings
- 1
- Median list
- $415K
- Avg time on market
- 163 days
- Sold · last year
- 9
Active listings
1 home on the market
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About the community
South Naperville's low-maintenance way into District 203.
Baileywood is a small attached-home community on the south side of Naperville, built between 1995 and 1998 on a handful of curving cul-de-sac streets: Harlowe Lane, Longbranch Court, Orchard Circle, Treeline Court, and Whitespire Court. The homes are townhomes, not detached houses, with attached two-car garages and full basements underneath. Plans run from roughly 1,600 to 2,900 finished square feet, and several are ranch layouts with the primary bedroom, a second bedroom, both baths, and the laundry all on one floor. The neighborhood is unusual on two counts: the association fee absorbs the water bill along with the usual exterior work, and a Naperville Park District park with ponds sits inside the community rather than being something the association has to fund itself.
At a glance
Attached townhomes
Roughly 1,600 to 2,900 finished sqft with attached two-car garages and full basements.
Naperville District 203
Maplebrook Elementary, Lincoln Junior High, then Naperville Central. Confirm the assignment for the specific unit.
Water is in the fee
The monthly assessment covers water along with exterior maintenance, lawn, snow, insurance, and trash.
Baileywood Park on-site
A Naperville Park District park with ponds and permitted fishing sits inside the neighborhood.
One-level ranch plans
Several floor plans put both bedrooms, both baths, and the laundry on a single level.
Built 1995 to 1998
A settled, fully built-out community. Every sale today is a resale.
Shopping across 75th
Market Meadows and Fox Run Square, both grocery-anchored, sit just north at Naper Boulevard.
I-355 at 75th Street
The closest tollway ramp is about four miles, and the Metra BNSF station is roughly three and a half.
No pool or clubhouse
This is a maintenance community, not an amenity community. The fee buys upkeep, not recreation.
What’s close
Baileywood sits in south Naperville near 75th Street and Naper Boulevard, close enough to downtown Naperville and the BNSF station to make either an easy drive.
- Schools
- Naperville CUSD 203: Maplebrook Elementary, Lincoln Junior High, and Naperville Central High School. Verify with the district for a specific address.
- Shopping
- Market Meadows and Fox Run Square at 75th and Naper Boulevard, both grocery-anchored, plus Mariano's and Trader Joe's within a couple of miles.
- Hospital
- Edward Hospital on South Washington Street in Naperville, roughly three miles.
- Highway
- I-355 at the 75th Street interchange is the closest tollway access, with I-88 reachable via Naperville Road.
- Train
- Metra BNSF from the Naperville station into Chicago Union Station, roughly three and a half miles away.
- Parks
- Baileywood Park inside the community, Winding Creek Park about a mile west, and the Riverwalk and Centennial Beach downtown.
What it’s actually like to live here
Baileywood is built for people who want the Naperville 203 address without the Naperville 203 yard. The association handles the lawn, the landscaping, the snow, the trash, the exterior, and the water bill, which makes the monthly cost of ownership more predictable here than in a detached house of similar value. The floor plans reflect who actually buys in: two and three bedroom layouts, several of them true one-level ranches. That draws downsizers leaving larger Naperville homes, professionals who want the express train and the tollway ramp without a mortgage on 3,500 square feet, and buyers who need a main-level bedroom. Full basements, many unfinished and some pre-plumbed for a third bath, give owners room to expand without touching the exterior.
The setting is the quiet advantage. Baileywood Park, with its ponds and permitted fishing, is a Naperville Park District facility sitting inside the neighborhood rather than a private amenity the association has to maintain. Winding Creek Park is about a mile away with ball fields and trails. Maplebrook Elementary is a short walk and Lincoln Junior High is under a mile. Two grocery-anchored centers sit directly across 75th Street, so a lot of the weekly errands never require a long drive, and downtown Naperville, the Riverwalk, and the BNSF station are all under ten minutes by car.
The honest tradeoffs are worth hearing before you tour. This is not an amenity community: there is no pool, no clubhouse, and no fitness room, so what the assessment buys is maintenance and insurance, not recreation. The fee itself is not small, and while it includes water it is a fixed line item that can rise, which makes the reserve study and the budget worth a careful read on buildings whose roofs, siding, and pavement date to the late 1990s. Some ranch units sit on the upper level of a two-unit building, so one-level living can still mean a flight of stairs to the front door, and you should confirm the entry configuration unit by unit. And at roughly 1,600 to 2,900 square feet with two bedrooms as the norm, this is a right-sizing community rather than a growing-family one.
Market trends
Why this market moves the way it does
Baileywood is a small, tightly held townhome association inside one of the most competitive school attendance areas in DuPage County, so the market here is driven less by price swings and more by how rarely units come up. Buyers are usually choosing between Baileywood and a detached house in the same schools, and the comparison turns on the assessment, the level of interior updating, and whether the specific unit is a ground-level entry or an upper-level ranch.
What holds value
The fundamentals matter more than the cosmetics here. Buyers want floor plan, lot, and basement, in that order. Cosmetics are the tiebreaker.
- The District 203 attendance area
- Being in Naperville 203 rather than District 204 is the single most durable demand driver on these streets, and it is what keeps a small association liquid.
- Entry level and floor plan
- Ground-level entries and true one-level ranch layouts draw a wider buyer pool than upper-level units, and that shows up in both price and time on market.
- Interior updating
- The buildings are late 1990s, so kitchens, baths, flooring, and mechanicals separate the units that sell fast from the ones that sit.
- The water-inclusive fee
- Because the assessment absorbs the water bill, Baileywood's monthly cost compares better against nearby associations than the headline number suggests, once buyers understand it.
- Basement finish
- Full basements are standard, so a finished lower level meaningfully expands usable space and separates otherwise identical plans.
- Association health
- On buildings this age, a funded reserve and a clean special-assessment history support value more than any cosmetic upgrade.
Real talk
Who shouldn’t buy here
Here is the honest version before you tour.
This is attached housing with everything that implies. You share walls, you answer to an association, and the board makes decisions you will not always agree with. If you want to park a boat in the driveway or repaint the trim on a whim, this is the wrong product. What you get in exchange is that nobody calls you about the roof.
The buildings are approaching thirty years old, which is exactly the window where roofs, siding, pavement, and common mechanicals all come due at once. That is not a reason to walk away, it is a reason to read the reserve study and the last few years of board minutes before you remove your attorney review contingency. Ask specifically what capital projects are scheduled and how they are being funded.
DuPage County property taxes in Naperville run high by national standards, and District 203 is by far the largest component of the bill. The schools are the reason people pay it, but the number still lands in the monthly payment alongside the assessment. Pull the actual parcel bill from the DuPage County Treasurer rather than estimating, because exemption status on the seller's bill may not carry over to you.
One piece of advice
“Baileywood is one of the more attainable ways into the Naperville 203 attendance area, and for a downsizer or a buyer who wants a main-level bedroom it is a genuinely good fit. Just confirm the school assignment in writing, check whether the specific unit is a ground-level or upper-level entry before you fall for the ranch floor plan, and read the reserve study on buildings this age. Do that and the maintenance-free trade is a fair one.”
The questions buyers actually ask
Baileywood FAQ
The questions I get most from buyers shopping Baileywood. If yours isn't here, text 224-385-8779, same-day reply.
- How much is the HOA?
- townhomes and condos are $403 per month.
- What does the HOA actually cover?
- Monthly assessments on recent Baileywood listings have run roughly $400 to $540, and the fee covers exterior maintenance, lawn care, snow removal, master insurance, scavenger (trash), water, and parking on some units. The water inclusion is the part buyers miss when they compare Baileywood to nearby associations that bill it separately, so the headline number is not apples to apples. Electricity, gas, internet, and your own HO-6 unit policy are not included. Ask for the current budget, the reserve study, and the 22.1 disclosure before you release attorney review.
- What's the typical closing timeline?
- 30 to 60 days from accepted offer to keys. Cash deals can close in two weeks. Conventional financing is usually closer to 60.
- Is Baileywood townhomes or detached single-family homes?
- Attached townhomes. MLS records classify the homes here as townhomes, and the assessment covers exterior maintenance and master insurance, which only happens with attached ownership. Buildings include both one-level ranch plans and multi-level plans, with attached two-car garages and full basements underneath.
- Is Baileywood in Naperville District 203 or Indian Prairie District 204?
- District 203. ZIP 60565 straddles both districts, so this is a real question rather than a formality. District 203's published attendance map places these streets with Maplebrook Elementary, Lincoln Junior High, and Naperville Central High School, and MLS records on closed sales here agree. Boundaries can be redrawn, so confirm the assignment for your specific address with the District 203 enrollment office before you write an offer.
- What does the assessment cover, and why does it look high?
- It covers exterior maintenance, lawn care, snow removal, master insurance, scavenger (trash), water, and on some units parking. The water inclusion is why the number looks high next to nearby associations that bill water separately. Electricity, gas, internet, and your own HO-6 policy are not included. Ask for the current budget, the reserve study, and the 22.1 disclosure during attorney review.
- Can I get true one-level living here?
- Often yes, but check the specific unit. Several plans are ranches with the primary bedroom, a second bedroom, both baths, and the laundry all on one floor. However, some of those ranch units sit on the upper level of a two-unit building, so you may still climb stairs to reach your front door. If step-free entry is a requirement, make it an explicit search criterion.
- Is there a pool or a clubhouse?
- No. Baileywood is a maintenance-free community rather than an amenity community, so there is no pool, clubhouse, or fitness room. What the neighborhood has instead is Baileywood Park, a Naperville Park District park with ponds and permitted fishing that sits inside the community, plus Winding Creek Park about a mile west and full Naperville Park District access with the address.
- What do homes here cost and how fast is the market moving?
- Pricing and pace change constantly, so this page pulls those figures live rather than freezing a number into a sentence. Check the Market snapshot above for current inventory, recent sale prices, and days on market in Baileywood. In general terms, attached homes here price below comparable detached houses in the same District 203 schools, which is the whole reason buyers look at the community.
- Who is the real estate agent for Baileywood?
- Joe Keegan is the local licensed Illinois real estate broker who covers Baileywood in Naperville, IL through Subdiview, a neighborhood-first home search for the Chicago suburbs and collar counties. Joe prices and negotiates from the live MRED sold comps for Baileywood specifically, not national averages, and can help you buy or sell here. Reach Joe at 224-385-8779 or joe@joekeeganhomes.com.
Your local agent
Joe knows Baileywood
Most agents will list anything. I focus on the places I actually know, and the things that move value here don't show up in the MLS write-up: which streets and buildings hold demand, what the HOA or assessments really cover, how the comps read once you account for condition and location, and where buyers consistently want to be.
When you're ready to tour or list, you want someone who has read the last 50 closed comps in this specific market, not a national average, and can tell you what they actually mean for your price. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Licensed Illinois broker
- Comp-driven pricing
- Naperville specialist
- Honest local market take
- Brokerocity
Market snapshot
Baileywood, by the numbers
Live MRED data, refreshed daily. The numbers below tell you what this market is doing today, not what Zillow's algorithm thinks it might be doing six weeks from now.
Typical list price
$415,000
Typical sale price · last 90 days
$470,000
Homes for sale right now
1
Avg time on market
163 days
Sold in the last year
9
This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC for the period August 16, 2025 through August 16, 2026. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.
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Not a Zestimate. A real CMA from someone who's sold this neighborhood, knows the floor plan premiums, and can tell you which upgrades the buyer pool here actually pays for.
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Schools serving Baileywood
Where Baileywood homes go to school
Homes in Baileywood are most often zoned to Naperville Central HS. Open a school to see its area, the district, and every home for sale that feeds it.
School assignment is derived from the school the MRED listing agent entered and is not a guarantee. Always verify current attendance boundaries with the district before writing an offer.
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