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    1 home
      1 home available
      289 Winding Creek Drive, Naperville, IL 60565
      NEW 3 hrs ago
      289 Winding Creek Drive, Naperville, IL 60565
      $959,900
      5beds
      3.5bath
      3,552sqft
      0.23acres
      House for Sale

      289 Winding Creek Drive, Naperville, IL 60565

      Listing by: Re/Max 10
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      © 2026 Mainstreet REALTORS® All Rights Reserved.
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      289 Winding Creek Drive, Naperville, IL 60565
      NEW 3 hrs ago
      $959,900
      5beds
      3full,1half bath
      3,552sqft
      0.23acres

      289 Winding Creek Drive, Naperville, IL 60565

      House for Sale by Cara DulaitisRe/Max 10.

      Data checked -. Listing last updated 2 hours ago.
      1. Overview
      2. Details
      3. More 

      HIGHLY DESIRABLE WINDING CREEK NEIGHBORHOOD - HEATED IN GROUND POOL - DISTRICT 203 SCHOOLS! This gorgeous 5 BR 3.5 bath Georgian offers the best of both worlds; loaded with updates & in a prime location in one of the most sought after neighborhoods & school districts around. With nearby community pool, tennis & volleyball, & close proximity to schools, parks & the DuPage River Trail, this location is IDEAL. If you prefer to entertain at home, spend summers in your FENCED IN YARD by the in-ground HEATED POOL w/newer liner (2022) & new programmable heater (2023) extending your pool season! Featuring TWO primary suites (one on the main floor & one upstairs), the main floor ADDITION w/vaulted ceilings, skylights & floor to ceiling windows, serves as a wonderful private guest suite with private bathroom; home office or even potential for related living. Real HARDWOOD FLOORS throughout the main level & a cozy wood burning fireplace. Modern kitchen is a chef's dream with stainless steel appliance package, granite counters, large island & walk in pantry. Convenient main floor laundry/mud room just off the kitchen, plus a formal living room, dining room & family room on the main level. Upstairs, retreat to the massive primary suite; with new sliding barn door to the walk in closet, ensuite bathroom with double sinks, jacuzzi tub, separate shower & skylight! Three additional good sized bedrooms & another full bath round out the upstairs floorplan. Still looking for more space? Head down to the FINISHED BASEMENT for movie night in the Rec Room or squeeze in a quick workout in the finished exercise room; which could also double as a quiet home office. TONS OF RECENT UPDATES including a NEW ROOF in 2020, new main furnace & AC in 2022, new guest room furnace/AC in 2024 (zoned) both with convenient WIFI thermostats. Nearly all windows replaced in 2021; except 3 bay windows & office; plus new blown-in R-60 attic insulation; lowering your utility costs! This home has been lovingly maintained & is sure to move quickly in one of the most desirable neighborhoods around!

      Internet Serviceability
      Details
        Property type
      Residential
        Year built
      1987
        Heating
      Natural Gas, Forced Air, Sep Heating Systems - 2+
        Cooling
      Central Air
        Total rooms
      12
        Garage
      Yes (2 space)
        Parking spots
      2
      MRD12545369
      MLS ID
      Active
      Status
      02-20-2026
      On market date
        Laundry features
      Main Level
        Fireplace
      Yes
        Pets allowed
        Architectural Style
      Georgian
        Basement
      Finished, Crawl Space, Rec/Family Area, Storage Space, Partial
      Interior features
      Cathedral Ceiling(s), In-Law Floorplan, 1st Floor Full Bath
      Exterior features
      Fire Pit
      Lot features
      Landscaped
      Appliances included
      Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal, Stainless Steel Appliance(s), Cooktop, Humidifier
      Construction materials
      Brick, Cedar
      Monthly taxes
      $1,147
      Yearly taxes
      $13,764.3
      School district
      Naperville C U Dist 203
      Schools
      Maplebrook Elementary School, Lincoln Junior High School, Naperville Central High School
      Senior community
      No
      Common Charges
      $75/Annually
      Maintenance
      -
      Additional Fees
      -
      HOA Fees Include
      None
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      Cara Dulaitis
      Cara Dulaitis
      REALTOR®, Re/Max 10
      Direct 
       
      Location
      Modaff to Bailey (E) to Terrance Dr (N) to Winding Creek Dr (E) to home on left
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      289 Winding Creek Drive, Naperville, IL 60565, is a 5 bedroom, 3 bathroom, 3552 sqft. Single Family Residence built in 1987. This property is currently available for sale and was listed on Mainstreet REALTORS® on 2-20-2026. The MLS# for this Single Family Residence is MLS# MRD12545369.
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
      Copyright ©2026 Mainstreet REALTORS®